First 30 Days as a New CIO

I journaled my first 30 days as a CIO on TikTok. I also compiled the videos weekly and published them to YouTube. So to round this out for the readers among us, here’s the transcript for the whole shebang— minus the ums and uhs.

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SERIES PREFACE: Good mornin’!   Day zero. My name doesn’t matter. What’s important is that I was (and am) a CIO– and I’d like to help you build the skills and mindset that will eventually land you in the C-suite.  I don’t know how to do that.  Because it’s different for everyone. And nurturing a career is more art than science.  So instead of telling you what to do, I’m going to share how I prep myself for my CIO gig every day.  

The format is simple.  I’ll do a kind of daily standup with myself– one topic per day– for the next several weeks… wildly useful to me… because it allows me to narrow my focus.  Which is a key part of getting any job right.  And I’m hoping that it’ll be useful to you.  Won’t know until we try.

I haven’t seen a ton of content where you can get into the mind of an operator (as opposed to a consultant).  Most people at “the top of their game” are afraid to put themselves out there– it’s good risk management not to.  Why?  Because if you’re sharing at the same time as being in a C-suite or being a senior executive or just being a leader, you’ll get sniped with seemingly innocent comments like “Where do they find the time?”  That’s someone who doesn’t understand that better time management– more effective execution– comes from slow thinking… a deliberate approach to problem-solving that starts with a daily (almost spiritual) commitment to reflecting on what you’ve done in the past 24, thinking through the next 24, what’s around each corner, and figuring out the underlying WHY(!) at the core of whatever it is you plan to get done every day.  It’s not just a narrowing of focus (useful!) but intentional mindfulness. Combine that with the practice of active listening-- and you’ll inevitably succeed at work… at life… at learning.

If I were you, I wouldn’t wait on any of the steers you hear me giving myself or any of the ideas I’m going to talk about for “when you eventually become a CIO or COO.”  I wouldn’t even do what I do, paint what I paint.  I’d do your version.  Informed by all the questions you’ve asked of life and all the answers it’s given.  That’s how I got here. A playful,  curiosity-driven, artful life.  I’ve been operating with these principles– with this mindset– for the last half-century.  They’re how I landed in my senior roles: these ideas, some small amount of hard work, and a whole lotta luck.

The good news is that I have nothing to sell and I don’t plan to have anything to sell on any of my channels.  If you have more time to learn and want to get into the details of the business of banking technology or healthcare technology, I have a channel on YouTube called Educating Squirrels.  Obviously.  Or if you learn by reading, join me at superserious.com– where I’ve been blogging for… ever. We start with Day 1, Week 1 - Tomorrow.

Day Zero Bibliography:  Hi BookTok… CareerTok. I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 0 Reading List:

Thinking Fast and Slow by Daniel Kahneman... every new CIO should read this if they haven't already.  It's not a tech book but it can help you avoid the pitfalls of overconfidence and confirmation bias in your decision-making.  The more senior you are in an organization, the more you need to exercise humility. This book helps the more cerebral among us to get over ourselves. Here's the science behind arrogance-- our tendency to overestimate our own abilities and the accuracy of our judgments. Reading “Thinking Fast and Slow” probably won't make you humble but recognizing and correcting your biases is a start.

The second book is The Creative Act: A Way of Being by Rick Rubin. Again, not a tech book. But a good meditation on how to cultivate a mindset of openness and curiosity... which along with humility... puts you in a decent position to foster innovation and collaboration in your organization.  I love Rick’s idea that creativity is not a talent or a skill that some people have and others don’t, but a way of being that anyone can access and develop. 

Book numbers 3 and 4 are industry-specific and are meant to be interesting reads that ground you in the language and culture of that sector.  For instance, if you're in Finance, read The Lords of Easy Money by Christopher Leonard.  It’s a fun read.  Or if you're in Healthcare, read Healthcare Insurance and Managed Care by Peter Kongstvidt.  It’s a textbook so less fun but important because it gives you depth.

Finally, if you're more of a podcast person, try Simplifying Complexity.  I was drawn to it because that title– Simplifying Complexity– is a great description of what most of us do for a living.

That’s it for day zero.

Day 1 (Part 1). Your first 6 months as the incoming CIO of an established company-- is NOT about drinking from the firehose.  If it feels that way, that’s a signal that you might not be asking the right questions or asking it of the right people.  

Your honeymoon needs to be spent understanding the business end-to-end.  And that starts with relationship building– talking with people.  On day 1, fill your calendar with equal parts: 1) key internal stakeholders, 2) with your team, and 3) with your company’s clients. 

That last one is not about kissing babies.  You’re doing it from a place of humility and with the intent to serve.  With your stakeholders, it’s about understanding their expectations and establishing a cadence for information sharing.  With your directs, it’s about understanding their skills, their ambitions, the rocks that they’re expecting to move, and together, mapping their path for delivery and growth.  And with your clients, it’s about learning their end-to-end– the reasons they think your product or service solves their problems.

That last third– the client meetings– are the ones that rather unfortunately tend to be pushed out on your calendar for months if not indefinitely… the rationale being that you need to first understand your business.  Welcome to your first paradox as a CIO: you can’t understand your business’s end-to-end without radical client-centricity… without understanding how your clients run their business end-to-end.  Because your business processes don’t start when a request from a client lands at your institutional boundaries.  Your processes start in your client’s shop. So… not talking to clients until you’re ready– until you understand your business end-to-end– means that you’ll never be ready.  [Sooo…]

Day 1 (Part 2).  Meetings don’t have to suck the life out of you.  The best way to navigate them during your honeymoon is to be deliberately curious and document what you’re learning.  

Why?  To learn and to establish credibility and trust.  How? Continuously share what you’re learning from these meetings with all the people who are on your calendar.  I don’t mean “share your meeting notes from the Bob meeting with Bob.”  I mean: use those notes as your agenda for all non-Bob meetings.  

Every stakeholder needs to understand what your other stakeholders need.  Your directs and skip levels will always appreciate the breadth of your information sharing because most of the leaders before you put them into functional boxes– sharing what the previous leader thought their directs needed to know to do their specific role but not what they need to know to grow beyond their current role. 

And… your clients need to understand that their needs are at the center of your universe… they keep you up at night… the driving force behind every activity in your company.

So Day 1 is not “drinking from a firehose.”  It’s focused relationship building.  Yes, you’re learning– and facilitating learning– (exercising a learning mindset is huge). And just as importantly, you’re demonstrating that you care about the people around you, that you care about the details, and that you’re open and transparent, collaborative and inclusive, that your goal is not to tell people what to do, but to listen and to find ways to serve them. [Follow that &]

Day 1 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 1 Reading List:

"Deep Work" by Cal Newport.  One of your top three most important tools is focus.  And this book lets you think about how to resist the temptation of multitasking and distraction in the age of information overload.  A lot of it is obvious so you’re not reading to learn so much as use it to meditate on how to work and think deeply.  It’s not going to teach you how to prioritize and protect your time and attention… but it might encourage you to give yourself structured blocks of time for deep work… and it’s always good as a reminder– an affirmation– that focus should remain a focus.

Next book: "Give and Take" by Adam Grant.  The message here is that we’re all more successful when we’re more generous and less selfish in our interactions with others.  A little preachy but in a business culture that looks down on spiritual texts, -you have to fall back on social science. No judgement there.  Just read what you need to as long as it gets you to adopt what Adam calls a giver mindset and behavior.  It’s the right framework for building better relationships at work.  Adam’s work tends to read like Malcolm Gladwell’s.  It's more of a popcorn read-- fun storytelling-- interesting mostly because of the case studies, and meta-research.  So worth it for entertainment alone.

And finally, if you're more of a podcast person, start with the HBR IdeaCast.  It’s HBR so it’s not rocket science.  But a lot of executives listen to it– which doesn’t make it good– but does make an opportunity for connecting with your peers.  A common ground.

That’s it for day 1.

Day 2 (Part 1). As I said yesterday, you’ll want to meet with your direct reports and skip levels and figure out how you can serve them.  But most people have their work armor on when talking to someone they don’t yet trust… so they’ll be hesitant to take you up on some high-level “how can I help” kind of question.  Especially if they’re stuck in a more traditional “my boss is going to tell me what to do” mindset.

So you need business context… functional context before you can figure out how to help them.  This is a good point to remind yourself that before your first 6 months are up as the incoming CIO, there will be unrealistic expectations about the speed with which you need to articulate and own tech strategy.  But… that expectation can serve you well because it gives you an excuse to go deep, to assess the current state of technology, to identify areas for improvement. 

So your agenda for the meetings with your directs and skips– can be driven by what will be a thorough, multi-month technology audit– reviewing existing systems, infrastructure, architecture, security, applications, processes… everything. And we’re going to get into each of those domains as we go day by day on this journey.  The key to all of it is that you’re going to want to get into the details– well past the usual PowerPoints– because how else will you find ways to help your people? To help them grow? [Soooo…]

Day 2 (Part 2).  Understand the business end-to-end.  Dig well past the PowerPoints everyone already has and is eager to show you.  Because those slides assume business depth or worse, they’re not rooted in an end-to-end understanding of the business.  They’re a reflection of siloed thinking.

Plus, most decks are upward-facing.  They’re designed to inform and calm… to send the message “Hey, we got this.” which… might be right, but is not useful if your goal as a leader is to find a way to serve.  Plus, upward-facing decks mean that the only person in the org with a mountain-top view is the person at the top.  The last CIO for instance.  Not cool.

When everyone in an org walks up the same mountain, explains their little part of the scenery to the person above them, and walks back to their cube– the one that intentionally blocks their view of the mountain, the business loses the value of diversity… the value of perspective.  And just as bad, when the leader at the top moves on— just like all the leaders before them— they take that mountaintop view with them.  No one else had it.  The business loses continuity. 

So… don’t make that mistake. Break the cycle. Apply your learning mindset to the thorough technology audit you have to do.  Use your need to educate yourself— to learn the business end-to-end— as a path to serve others.  To educate them. Everyone on the mountain.

Set your bar higher, and then ask the org– not just your directs, but the entire org– to learn with you. As you humbly walk down the mountain to learn, record that experience… not the decks… the interactions between you and the experts. And share. That’s compelling content for everyone. When you share it broadly, it opens up everyone’s path… up the mountain… to their next role.  The final point here: encouraging others to continuously learn isn’t enough. It has to be “do as I do.”  The goal: as I audit, we all learn.  We all grow.  [That’s your goal…]

Day 2 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 2 Reading List:

“Atomic Habits” by James Clear.  In the early days of any new gig, you want to be thinking about the systems and processes that make up your business.  The natural and unnatural incentives that are at play.  What James adds is the idea that systems are really a collection of habits. So you can think of change management both as a design exercise for systems/processes… and in terms of the intractable habits that chain us to the old ways of doing things.  That’s a powerful idea when the common enterprise approach to change management is mostly a comms and training plan… which usually doesn’t change behavior– it just expects it to be changed.  

Next book: The Power of Servant-Leadership by Robert Greenleaf— the guy who coined the phrase in 1970. Open yourself up to this one because when you sit on top of a large org, you’re ideally placed to challenge the conventional wisdom of the hierarchical and authoritarian leadership styles that you grew up with.  It’s about living your values.  Our Day 0 reading list emphasized the importance of humility.  Day 1 made the case for generosity.  Today– day 2– the spotlight is on service– the intersection of humility and generosity. That’s what serving others demands.  Whether those others are your employees, your customers, or your community.

And finally, if you're more of a podcast person, try The Gartner Talent Angle. This one is also popular with a lot of executives because it’s so broad in scope– covering psychology, economics, music, sports… anything really… that gives you an edge in how to manage and develop talent and how to lead through change and uncertainty.

That’s it for day 2.

Day 3 (Part 1). How do you— as an incoming CIO— develop a strategic IT roadmap that is aligned with your company's goals? I know this is going to sound obvious but step 1 is to understand your new company's goals— their mission and vision. Most companies have that written beautifully somewhere and it's too broad and too high-level to be any kind of useful.

So after you’ve read it, and you’ve interrogated this year’s budget through the lens of how it aligns with that mission…, and you’ve used your regular stakeholder meetings to get their perspective (which hopefully informs yours)– then ask yourself one, counterintuitive question: why are so many potential clients using your competitors, not you? 

Be careful because the answer is rarely price… or features… or even quality of service.  Usually, the answer is the intersection of trust and the human aversion to change. I know that’s “high level.” So keep peeling the onion on “What is it about your competitors that build trust with their customers?”  What is it about your company, your tech— the onboarding of your products or services— that makes the cost of change management too high for your potential customers to switch?

This means that the strategic IT roadmap you’re developing needs to increase… you guessed it— trust… I don’t care what industry you’re in. That’s your company's goal: increase trust.  It’s your goal too: increase trust internally with stakeholders and with your team… and obviously, increase trust externally with clients and potential clients. [So keep asking yourself…]

Day 3 (Part 2)  Building your IT roadmap is an exercise in building trust– on multiple levels. You can and should recast the relationship building we talked about on Day 1.  Your roadmap is what you want to do– but not you by yourself.  Trust tells you how you need to partner, to jointly come up with that list… how you trust others and trust yourself.

An example of trust-building with internal stakeholders is better governance and better program execution— they’ll tell ya– it’s the how of delivering their business priorities and tech initiatives better, faster… cheaper.

An example of trust-building with your team is doing more listening than talking.  And being genuinely thankful that they’re on the team.  It’s really that simple.

An example of trust-building with external stakeholders is to improve their customer experience— how you sell, how you onboard, how you deliver value.  

Just remember that trust is measurable. So always inspect what you expect.  

Nothing should land on your roadmap unless you’ve established clear metrics around it and you have a path to monitoring them.  KPRs for instance.  Why? Because you should regularly evaluate the roadmap’s impact on the company's explicit business goals.  [I’ll say it again…]

Day 3 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 3 Reading List:

Net Positive by Tom Parks, Paul Polman and Andrew Winston.  I usually can’t stomach books that read like a CEO patting his own back… buuut, Paul did do something amazing things at Unilever. So he kinda deserves the mic.  The good news is that the book and message don’t come across as overbearing… just some executives living their values… contributing more to the world than they use or take.  If your politics doesn’t align with a climate change agenda or a social justice agenda, it’s still worth a read… because you stand for something and that something is worth some corporate courage, vision, and action.

Next book: Thinking in Systems: A Primer By: Donella Meadows. This one’s about how to manage VUCA… volatility, uncertainty, complexity, ambiguity.  It’s about how to understand and improve the complex and dynamic systems. That’s your job.  Systems thinking is a way of doing your job– of seeing the world as a network of interconnected and interdependent elements that influence each other through feedback loops and nonlinear relationships. If none of that made sense, read the book.  It might help you avoid the common traps and mistakes that often lead to the unintended consequences of system failures.

And finally, if you're more of a podcast person, try a16z. It’ll help you stay ahead of the curve, anticipate future trends… that kinda thing.  It’s a good commute listen.  Way more interesting than subway noise.

That’s it for day 3.

Day 4 (Part 1). While it’s still your first week of being the new CIO, you’ll want to start getting your arms around your IT infrastructure.  Building trust means getting to the 4 9s of availability– having your servers up 99.99% of the time. Facilitating business continuity, digital continuity, scalability, resiliency.  Infrastructure trust.  Wait time: zero. Downtime: zero. Kinda thing. If trust is your north star– and it is– it starts with your infrastructure. 

There are a ton of docs that you’ll want to study: from your network architecture to your operational runbooks; from info about your formal and informal data centers to any cloud providers you’re using or plan to use.  

Just like with your software inventory: No judgment.  Always assume that the people before you were smarter than you: not just well-intentioned but doing their best… given legacy business priorities and budget constraints.

The other reason to hold off any quick judgment on your infrastructure is that you need to first understand your larger software stack– all the tools that your folks use to build and operate their applications, systems, platforms (whether they’re bought, built… or more likely, integrated).  You need context. Just like all businesses need a client context, software needs a business context, and infrastructure needs a software context. That’s the right way to think about scalability, resiliency, security…  and ultimately, trust.  [Sooo…]

Day 4 (Part 2).  It’s important to apply the two ideas we talked about yesterday to infrastructure: 1) your IT roadmap is all about building trust and 2) trust is measurable…. Ask a simple question about production support: how many of your outages over the last year were reported by your users vs your monitoring?  How many times did users complain about an application being slow or inaccessible– even if it didn’t become a major incident?  How often did you find after an incident was resolved… that it was a hardware issue, a network issue, storage, an expired cert, an unannounced security patch?  

Your first chance to serve all your stakeholders– internal and external– is to help your infrastructure team prioritize the virtuous work they’ve always wanted to do.  World-class monitoring. There are a ton of good reasons that “that work” isn’t being done or done fast.  

The answer– many times– again not just in infrastructure– is governance– a common framework for prioritization.  It’s usually more acute in infrastructure because governance tends to prioritize itself to first focus on the outer shell– the clients, sales activity— or the next layer down– business operation– or the layer after that software… in that order… and… in theory, they’ll eventually get to infrastructure… but in practice, there’s enough yummy goodness in that outer candy shell that they’ll never get to the gummy center.  Are Tootsie Pops still a thing?  

Anywho… your goal for infrastructure– day 4– is to start the conversation about how to find production issues before your users and clients do.  Make it a game.  That’ll start threads about governance, but also about how *you* can help your team by engaging the business, ops, your software development teams, security.  Connect those dots. Grease the wheels of collaboration. [That’s why…]

Day 4 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 4 Reading List: 

The Phoenix Project by Gene Kim.  This one’s worth reading because every other book about tech is either a biography or something meant to scare you.  Plus, there’s nothing like fiction to teach you about the principles and practices of DevOps.  That came out wrong.  If you don’t have the time to find real-world, business school case studies, this is a decent proxy to reflect on managing technical debt, dealing with conflicting priorities, aligning IT with business goals.

Next book: The Cloud Adoption Playbook by Moe Abdula and 6 other authors. Cloud adoption used to be about complexity and uncertainty but now that it’s matured, it’s bearable. You still need a primer because cloud adoption is not a one-size-fits-all.  A better place to learn about the cloud is directly on AWS or GCP or Azure but their training give you theoretical example.  Moe’s book give some real-world case studies from various industries and organizations.

And finally, if you're more of a podcast person, try the platform-specific podcasts from Amazon, Google and Microsoft.

That’s it for day 4.

Day 5 (Part 1). It’s the end of week one as the CIO, and all your conversations– all the demands you’re fielding across your stakeholder discussions– internal and external– are questions of prioritization.  That’s because of two potential dysfunctions. 

The first is that hierarchical organizations tend to keep pushing the decision-making buck up the management chain. And leadership– not just at the CIO level but throughout the org… leadership means the buck stops with you.  That doesn’t mean you have to solve the problem alone. It just means you are the recruiter-in-chief for the team that’ll tackle the issue.  

That team can include anyone to your left or right and/or people above you.  You– as a leader at any level– can delegate up.  Don’t be the person who says something is above your pay grade because that’s simply validating why you’re not paid more.

The second reason everything sounds like a prioritization discussion is that your PMO– your project management office– is either missing as a practice or it exists but lacks real authority and autonomy.  If it’s missing, then tribal prioritization is already in place for all your projects… which means there are organically-grown power brokers and processes in the org.  That might be effective for project delivery but the lack of transparency is not healthy.  It leaves the business– even those who are plugged into the informal delivery networks, the informal prioritization networks– with legit feelings of learned helplessness. [Important to note…]  

Day 5 (Part 2). You need an empowered PMO– and I don’t just mean people.  I mean a process, a framework– agreed to by all your stakeholders– that gets the larger org to commit to the relative value and impact of every project, of all potential IT spend. Project prioritization needs to be stack-ranked– what’s the first priority, what’s the second priority, all the way down to the last priority– with no two projects sharing the same priority– so no ties. That’ll set the stage for proper capacity planning.  How? Through the principle of single-threaded ownership.  

Simple thought exercise.  Take your priority one project and list the names of every person who needs to contribute… the PM (Project Manager), the BA (Business Analyst), the SME (Subject Matter Expert), the engineers, etc.  Be exhaustive.  Then, move to project priority two and do the same.  But as soon as you list a name that’s already been attached to a higher priority project… stop, defer that project to the next quarter, and move to the next priority… keep attaching names until there’s a repeat… stop, defer, move down.  Keep doing that for the whole project list.

The projects you didn’t defer– the few that are fully staffed with real names, not TBDs– are the ones that exemplify single-threaded execution.  They’re the ones that will get delivered first.  Why?  Because humans stink at multitasking.  A team of multitaskers is adding months– perhaps years– to the project’s delivery.  Welcome to your second paradox as a CIO: If you can’t wait, you’ll wait longer. Single-threaded ownership, leadership, contributorship….  single-threaded execution radically speed up your velocity for a small set of prioritized projects.  It also– counterintuitively– increases your chance of delivering your deferred priorities.  If you can wait, you’ll wait less.  [Make it a mantra:]

Day 5 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 5 Reading List: 

The ONE Thing by Gary Keller and Jay Papasan.  This is the second book on the list about focus… the first one being Deep Work. It sounds obvious but the way to avoid the trap of multitasking is to radically narrow your focus. Single-threaded leadership– the Amazon version of this– sounds obvious but management continues to operate like everyone in the org is an effective multi-tasker.  The reality?  No one is.  

Next book was going to be about Amazon but all of the authors fawn over Bezos.  Except one.  The honeybadger himself: Scott Gallaway.  The book is called The Four: The Hidden DNA of Amazon, Apple, Facebook, and Google. And it’ll help you understand and compete with the four most influential and dominant entities on the planet. How’d they become so powerful? I love Scott’s take on it: By manipulating the fundamental emotional needs that we have as humans.

I’d also recommend a book on Amazon’s practice of single-threaded leadership but I don’t know of one… so just google it.  There’s a good implementation focused article by Jade Rubick.  Worth a read.

And finally, if you're more of a podcast person, try The Prof G Pod with… Scott Galloway.

That’s it for day 5.

Week 1 Recap.  First weekend in.  I just watched my Day 1 through Day 5 shorts… and all I keep thinking is:

Being a CIO is more art than science.  It's both what you do and who you are.  It’s rooted in a daily practice that starts with listening and asking hard questions. If your practice asks questions that are easily answered, you’re not improving the work. That’s why management is an art, not a craft. If you know what you want to do and you do it, you’re a craftsman. If you start with a question– a really hard question– and let it map your journey, you’re an artist.

Anywho… I’m meeting a lot of new people. Doing a lot of listening.  Asking questions that help me put together the puzzle that is the end-to-end business.  That’s goal one.  It doesn’t feel like drinking through a firehose.  It feels focused.

Everyone I’ve met exudes warmth.  That’s priceless.  I still have to build trust… because I’m the unknown.  I still have to demonstrate humility because I’m the one learning. 

New executives tend to signal their worth during their honeymoon with statements like “This is an opportunity-rich environment. [wink, wink]”  I’d say the same but not because of what I’m bringing to the game.  The quality of the team on the ground makes it an “opportunity-rich environment.”  

Reasons to be grateful I suppose. And to be fair, it’s not enough to be grateful for the opportunity.  I am.  I have to turn that gratitude into action, into service to my team and to our clients.  Looking forward to week 2.

Day 6 (Part 1).  Software is WD-40.  It’s not the engine of transformation, it’s the grease. So figure out how much you have in the can.  How? You’ll want to get demos of all your digital channels– portal, mobile, internal platforms– 1) to understand your business– end-to-end (their commercial ambitions) and 2) to assess whether the grease you inherited will remove that creaking sound everyone hears. Plus, demos get you a sneak peek into your client’s digital experience. You can’t or shouldn’t influence digital direction until you know the business at least as well as your business partners.  What you can or should influence– as early as week 2– is the software development lifecycle (SDLC).  Every shop is a unique snowflake and now is the time to understand how your different pockets of engineers code, build, test, release, and monitor.  The question is always how do you pull up the rear– those groups who haven’t yet focused on improving their practice– without slowing down the teams in forward positions?

I’ll tell you how you don’t do it: from the outside in.  You don’t create an SDLC office– filled with people who no longer code– who maybe never-ever coded– to set standards and policies for people who do code.  And before I get an amen from engineers everywhere, you also don’t leave it to the engineering community to solve on their own– because that requires them to change the business (again from the outside in– because engineers are not the business).  Outside-in transformation never works in any sustainable way.   So one of your jobs as CIO is to work with your business counterparts, to help them understand that the SDLC starts with a business transformation… Agile– for instance– won’t stick if it’s inflicted on the business by tech.  It might stick if it’s being led by the business for the business. The point here is that tech’s goal is to grease the process of continuous, business-led, business transformation…[!]

Day 6 (Part 2).  Understand how your engineers– from team to team to team– how they build, test, release, and monitor today.  And I say “team to team” because each one is a precious snowflake– a reflection of their unique skills, workloads, deadlines, incentive structures… their maturity… and ultimately, how all those factors influence the way the team engages their business partners… who themselves– their business partners– also sit on a complex spectrum.  When someone above that detail– like an SDLC office– asks engineers to skate to an enterprise standard SDLC, they’re not doing the Firm any favors.

Teams– like individuals– have different levels of maturity.  If you’re a parent like I am, you’ve already learned that you don’t make the same demands of your toddler as you do of your teenager… as you do of your adult children.  Each requires a different set of challenges and supports.  Structure is needed at one end of the maturity spectrum but at the other end, that same structure is overly rigid and inflexible.  Yet another CIO paradox– paradox #3– what’s good for the goose is not good for the gander. So you need a path to get into the details at the team level.  That sets you up to celebrate those who are ahead, and to empathize with those who are a little overwhelmed– the ones who know what’s been blocking them all along… and have never been empowered to change it  You’ll want to quickly get to a common definition of better.  The north star– that you set jointly between your engineering community and your business partners.  And you’ll want to set some bounties– financial incentives and/or social, statusy ones– for every team– tech and biz– to get better. Just remember that each snowflake has a different path to better… [So it’s critical that you understand your snowflakes.]

Day 6 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 6 Reading List: 

The Mythical Man-Month by Fred Brooks. This one’s the classic on the topic.  If you haven’t read it, you didn’t major in software engineering in college. It’s accessible and compellingly cautionary.  Covers project planning, design process, team organization, system testing. It’s an old book by tech standards but the ideas are still widely relevant today.

What else?  Google the Agile Manifesto if you never have.

And if you’re looking for something more recent, try Clean Code by Robert Martin or Code Complete by Steve McConnell.

And finally, if you're more of a podcast person… I’m not a fan of any engineering audio experiences.  I’d redirect you to three different SubStacks– one by Kent Beck called Software Design: Tidy First, one called Platformers by Casey Newton and one called Digital Native by Rex Woodbury.

That’s it for day 6.

Day 7 (Part 1).  There’s an implicit expectation that you– as the new executive– will be evaluating your leadership team– and the broader IT org– to determine if any changes are needed on the talent front.  That includes adding to or subtracting from the team and/or building out functions that seem to be missing from the org.  The usual exec response during their honeymoon period is to say something smarmy like “We’ll need to upskill”… which is code for “I’ll need to replace some people”... which is a red flag on two fronts… three if you consider how fast they came to that conclusion.   

Red flag one: it’s tech.  It’s constantly changing.  So by its very nature– it requires everyone to be constantly upskilling.  So if your engineers haven’t learned their way out of mainframe skills– I picked that randomly– that’s not the engineer’s failure to upskill.  That’s the organization’s failure to modernize, to set an ambitious strategic Northstar– that will demand engineers stay current.  Trust me, they all want to stay current.  Most want to be in a forward position.

The second red flag if a new exec is eager to “replace existing talent” is that they’re signaling their need for a ‘command and control' culture.  And usually, that’s not because command and control is faster or easier– it is– but because the exec doesn’t know how to influence.  They have no choice but to exercise authority.  And that’s not just a problem that robs good tech people of their autonomy.

It’s a signal that the new executive won’t be able to influence their business partners.  Because those business partners will never report to them.  So “upskilling”-- comically– is not what the org needs.  It’s what the new exec needs.  And that missing skill is the skill to influence. []

Day 7 (Part 2).  There are two good ways to determine if you have the right people in the right seats.  The first is their stakeholders.  Not their managers, who they’re probably managing.  But the people they serve every day.  And built into that is the business partner’s ambitions… their business’s trajectory for growth and/or change.  The business context for that employee’s future.

The second source on the talent front– and I know this will sound even more obvious– is to spend some quality time with your HR partner.  Not to get their read on who’s going to be a problem or who is a hidden gem.  I’m sure that *will* be useful.  But more importantly, you’ll want to mine your organization’s history of assessments– you’ll want to read older performance reviews, to learn from the history of feedback that HR (and only HR) has been privy to.  

There’s a school of thought– even in HR– that says don’t immediately ask HR.  Form your own opinions first.  That’s like saying, the only way to avoid burns is to stick your hand in the fire. Your HR partners have charred blackened hands– so they’ll have a pretty good sense of team dynamics… skills gaps (soft and hard) and areas for improvement.  Plus they’ve already thought about how to restructure roles and responsibilities, provide training, and invest in employee development.  All the conclusions that you’d come to *after* you stuck your hand in the fire.

That’s the fourth paradox of being a CIO… when they tell you to form your own opinions first: Don’t listen to HR.  Listen to HR. []

Day 7 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 7 Reading List: 

The Lean Startup by Eric Ries.  It’s a much better read if you have no intentions of ever starting your own company.  The larger the company, the more it needs everyone working there to read this… to understand the value of validated learning, rapid experimentation, and customer feedback.  Figure out what the customer wants, without asking them first, which can help create products that are more innovative and better suited to the needs of the market.  

Book #2: Not directly related but try Awakening You Ikigai by Ken Mogi.  A great to noodle on "a sense of purpose”-- finding meaning in your work and personal life. 

And finally, if you're more of a podcast person, try The Engineering Leadership Podcast.

That’s it for day 7.

Day 8 (Part 1).  It’s never too early… as a new CIO… to be thinking about risk management. The big three these days are cybersecurity– how to protect the organization from bad actors– external mostly but internal too.  Data breaches: how to safeguard sensitive information from unauthorized access.  And tech obsolescence: ensuring that the legacy tech plant remains up-to-date with continuous investments in modernization.

It’s not some wild overstatement though to say that the CIO’s primary job is risk management.  Everything in tech (and the business) has a risk context.  We talked about a PMO last week– that’s the risk of poor governance– the need to establish proper frameworks and processes to guide decision-making. It’s a fiduciary responsibility to spend your company’s money wisely.

And in the coming weeks, we might or might not talk about vendor management– effectively managing relationships with external suppliers.  Business continuity: ensuring uninterrupted operations and minimizing the impact of disruptions. We’ll definitely talk regulatory compliance– making sure you don’t end up in an orange jumpsuit. 

Change management. Talent acquisition. Budget. Everything has an important risk context.  Everyone’s job is risk management.  But if it’s everyone’s job, it also tends to be no one’s job.  So the question to ask in week 2 is: who– outside of you– owns the practice?  Whose job is it to think exclusively about all the risks in your operating discipline and how to mitigate them? []

Day 8 (Part 2).  You need someone fully dedicated to establishing and improving a risk management practice.  Someone who will operationalize proper frameworks and processes to identify risks– to regularly conduct thorough assessments of potential issues.  To work with the company’s leadership to prioritize risks. To develop mitigation strategies and action plans to eliminate what they identified and prioritized.  To implement risk controls… like cyber protocols, data backup strategies, disaster recovery plans. It’s a full-time gig.  Or if your company is large enough, it’s a team’s worth of work.  

There’s also a communications angle to it– business-facing, client-facing– and that’s going to plug into the incident management practice we talked about in week one.  Thursday last week.

There’s a training angle to it which bleeds into an awareness angle.  Because as you’re training, you’re creating awareness… and establishing ways to make risk an active, ongoing discussion.

And all that leads to the fifth paradox of being a CIO:  the more risk you uncover, the less risky your org.  There will be a bump in identified risks when you first establish the practice or when you put some muscle being an aging practice.  But that’s good.  If you have a comprehensive risk management practice and you get past that initial bump of identified issues and your risks start to trend down, that actually means you’re failing.  A maturing risk practice demands that you broaden and deepen your search for potential threats so your steady state should be flat… and mildly trending up…  not trending down.  Your mitigating controls should be getting more mature over time… getting more and more proactive.  Risk is never once and done.  [That’s why…]

Day 8 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 8 Reading List: 

Instead of some textbook on risk management, read  The Alchemist by Paulo Coelho. Without spoiling it, let’s just say that its about a shepherd boy who explores themes of risk-taking.

Alright fine.  Read a textbook too.  The Essentials of Risk Management by Michel Crouhy et al. Or A Practitioner’s Guide to Managing Market and Credit Risk by Steve McConnell. 

And finally, if you're more of a podcast person, sorry… nothing.  But if you’re in SubStack, try Exponential View by Azeem Azhar.

That’s it for day 8.

Day 9 (Part 1).  We talked last week– day 1– about filling your calendar with equal parts: 1) internal stakeholders, 2) with your leadership, and 3) with clients. But it’s worth calling out that having regular conversations with seniors is not enough in terms of a communications strategy. You need to establish clear communication channels with the broader org.  And you need to start to churn out content that’s worth reading, watching, and listening to… because email alone or email newsletters are very 2005.

You should consider a three-pronged comms strategy.  The first revolves around how you communicate with your team.  Instead of doing the occasional town hall, you should invite everyone in tech to your weekly staff meetings with your directs.  The meeting should be completely optional if the employee is not a direct report, but they have to be cool with turning off their camera, listening in, and only participating via chat.  Otherwise, the meeting will be hard to manage.  If your employees do that, they get more transparency than they ever imagined.  You should also record all of those sessions and post them for anyone who couldn’t make it.  From my experience over the last 5 years of doing this, not everyone will make it but everyone will benefit from knowing that they’re being treated like adults.

There are two side benefits to this kind of radical openness: first, you– as a leader– get to practice mindfulness, thoughtfulness in your message and tone– because everyone is always listening… not metaphorically.  They’re actually listening.  And more importantly: when your juniors understand how dull the practice of senior management really is, they’ll hopefully aspire to more than just having their boss’s job.  They’ll aspire to remain hands-on.

Day 9 (Part 2). The next piece of the three-pronged comms strategy is showing up at other people’s staff meetings.  Outside tech.  Not to present.  But to listen and participate.  Why would they invite you?  Because you asked to be invited.  Because you intend to serve them.  Because you genuinely care about their needs and want to understand their perspectives. Not once and done.  But continuously. The key is to just live where they live.

By attending their meetings– or having someone in your org attend them and write up notes– you gain valuable insights into themes across groups– common challenges, goals, and prioritization issues… which will help you tailor not just your communication approach but your IT strategy– to better meet everyone’s needs.  

Also, by actively participating and offering your support or expertise when relevant, you build trust– your strategic Northstar.  You build credibility and you’re living the idea that effective communication is a two-way street that requires active listening and genuine collaboration. So, seize every opportunity to engage and connect with your colleagues across the organization.

The final piece of the three-pronged comms strategy is client-facing and that should be rooted in cross-selling new functionality.  If you look at IT’s backlog of committed work, there’s a very good chance that most of it is for a specific client.  When that work is completed, the new functionality is socialized with that specific client and only that specific client.  Just recognize that a lot of your clients are similar and have similar needs.  So every feature, function, and business capability that you deliver for one client needs to be socialized with all similar clients.

Day 9 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 9 Reading List: 

Instead of some textbook on communications planning, read On Writing: A Memoir of the Craft by Stephen King.  It’s a more interesting way of learning how to communicate effectively– how to develop/nurture creativity.  Read it like he’s a CEO you respect– a business leader with a unique perspective on communications, innovation and the creative process. 

Book #2: I should probably recommend something by Seth Godin or Simon Sinek but I can’t stomach their writing.  I do think they’re brilliant speakers though.  So Google their Ted Talks and/or any keynotes… and if you want to generate some royalties for them, gift their books to people you don’t like.

And finally, if you're more of a podcast person– or would rather listen than read– try the audiobook version of The Power of Myth with Joseph Campbell.  It was a Bill Moyers TV special a long time ago.  And it’s still amazing 35 years later.

That’s it for day 9.

Day 10 (Part 1).  Finishing off week 2 by focusing on regulatory compliance.  I now have experience in 3 regulated sectors– Banking, Healthcare, Insurance–  but this is a universal challenge.  You could be in pharma, energy, telecom, manufacturing….  You’re going to need to educate yourself– and your organization– on the framework of rules and laws for your industry at the federal, state, and sometimes even local levels.  And if you operate, internationally… the global reg landscape.

Regulatory compliance means that it’s not just your job to adhere to laws and regulations to protect customers' interests and the stability of the financial/healthcare system itself, it’s your job to prioritize that activity– to give it equal if not more weight than your company’s commercial ambitions.  And that’s tricky and paradoxical so I’ll come back to that.

Companies get fined– large numbers.  Why?  Because the regulatory system is saying “Hey, you didn’t prioritize our work. You prioritized making more money.  So the fine we’ll impose will be so large as to overshadow the money you made by not focusing on us.  Large enough that next time, you’ll remember.  Large enough that your competitors will be sent a message about their focus.  So what do you need to focus on?

The good news is that all the big consultancies constantly publish what you need to be thinking about.  For instance, in 2024, according to E&Y, if you’re in banking, you’ll want to prioritize consumer impact, ESG, digital assets, the use of AI, financial crime, and operational resilience.  So… easy high-level learning that can start a lot of the right conversation with your leadership.

Day 10 (Part 2).  If you want to get regulatory compliance really(!) right, you need to establish an auditable prioritization process– one that proves to any supervisory body that reasonable investments in compliance were priority 1.  Think audit trail.  Another reason you need a PMO.  It’ll will help you document that budget and resource allocations for all business change activity came second to reg.  Because compliance is part of how you keep your lights on.  You fund “run” first… in its entirety. Then change. That’s a good start.  Then what?

Well, you treat compliance as a strategic initiative… as a differentiating, commercial investment. And here lies the sixth paradox. Yes, you need to stitch compliance into the fabric of your culture with clear accountability and ownership.  But if you stop there, you miss the bigger picture. Two huge opportunities. 1) Regulatory compliance builds trust– IT’s strategic Northstar. And 2) a robust compliance framework can and should be executed through a commercial lens, with commercial imagination.  I did a walk on this where I talked about how something as boring as KYC – Know Your Customers (KYC)– a regulation– can be executed to check the box, or it can be delivered with commercial intent. If you’re a crusty old bank, you’re doing it begrudgingly.  If you’re a Meta or a Google, you “know your clients” (KYC), not for regulatory reasons but for commercial reasons– because there are trillions to be made in knowing your clients. 

So that sixth paradox? What I call the AWS paradox.  Amazon Web Services.  If you keep the lights on better than everyone else– if you can scale up that business capability– then compliance is a commercial opportunity– a strategic lever for topline growth.  Do it right and you’re satisfying your regulatory obligations and(!) building trust and(!) making more money.

Day 10 Bibliography:  Hi BookTok… CareerTok.  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily standup session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.

Day 10 Reading List: 

Instead of some textbook on regulatory compliance, read some books about companies who failed spectacularly at doing the right thing. “The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron” by Bethany McLean and Peter Elkind.  “Bad Blood: Secrets and Lies in a Silicon Valley Startup” by John Carreyrou.

If Enron and Theranos aren’t cautionary enough, try “The Wizard of Lies: Bernie Madoff and the Death of Trust” by Diana B. Henriques. 

And finally, if you're more of a podcast person, try FINRA Unscripted.  Yes, that FINRA.  The Financial Industry Regulatory Authority (FINRA). They’re an independent, nongovernmental organization that writes and enforces the rules governing registered brokers and broker-dealer firms in the United States.  

That’s it for day 10.

Week 2 Recap.  Second weekend in.  I just rewatched my Day 6 through Day 10 shorts… and all I keep thinking is:

I’m already getting restless with the amount of meetings I’m having.  Not because they’re me drinking through a firehose.  But because meetings tend to be confused with work.  

They’re not work.  They’re a tax.  You pay the tax with the hope that you’re getting an underlying service: better comms, more efficient work.

How do you reduce that tax?   A transformed SDLC. Day 6. A better comms strategy.  Day 9. 

Meetings are funny.  What’s said in them is not what’s heard.  And worse, what’s said is not what’s meant.  They’re multi-layered comms failures. They’re risk.

So maybe we frame meetings as risk.  Day 8. 

Cutting down the number of meetings we all have is a universal complaint.  That’s why everyone has at least toyed with the idea of “no meeting Fridays.”  

The problem is not meetings.  At a human level, the problem is people feeling compelled to join them.  Being unable to say no.  Knowing that their alternative to meetings is to change everyone’s digital habits– to live in Teams or Slack, to be locked into in a virtual conference room with a multi-disciplinary, single-threaded team.

So maybe we frame meetings as the first real opportunity to upskill our workforce.  Day 7.  Not to replace them but to transform how they work. 

Looking forward to week 3.

Day 11 (Part 1).  This is week #3 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… 

Unlike most new CIOs I just switched industries with this last move.  From banking to healthcare/insurance. In banking– where I spent 20+ years– I took for granted that I understood the specific role of technology and how it creates value for that industry.  In retrospect, I think I was wrong… too heavily influenced by the functional bubbles I’d grown up in.  And that becomes crystal clear when you have to start from scratch in a new industry.

In my new world which is driven by tasks like claims adjudication and customer service, and functions like workflow and document management, the conventional role of technology is to automate and digitize.  As with banking, healthcare tech creates value mostly by delivering efficiencies in ops (think back-office) and in theory by improving the customer experience (think digital portal).  On the Ops side, an example of the universal problem to solve is the need for a single pane of glass. So users don’t have to juggle a dozen legacy apps simultaneously.  And on the client experience side, the universal problem to solve is getting the client all their transactional data through digital channels– portals, mobile– instead of snail mail or call centers.  

The challenge with “universal problems to solve” is that they lack commercial imagination.  That’s why I think I got the question wrong– about the role and value of tech– while I was in banking.  Because convention leans towards what everyone else is doing– minimizing the power of tech as a differentiator.  The comparison most businesses make when they’re thinking tech is peer-relative– what are our competitors doing that we aren’t?  Good to know but everyone(!) has that mindset… including the leader in a space… ensuring that tech operates in a regressive, non-commercial bubble.  That’s an opportunity.

Day 11 (Part 2).  So I’m starting from the counterintuitive position that the primary role of technology and how it creates value for a company– is to advance topline growth.  Not through some 6 degrees of separation exercise– where you can rationalize any tech investment as eventually improving sales– but directly.  Think about how hard that is.  Outside of your CRM investments– which are mostly client note-taking apps– and your marketing platforms– which are multi-channel content management systems… how else is tech impacting topline growth?

Those are the questions I’m asking in month 1.  Maybe we focus on sales automation? Tools that streamline the sales process?  Better lead scoring systems?  Better sales analytics?  You can see how I’m immediately falling into the path of convention. When all else fails, tech tries to make it– whatever “it” is– more efficient and effective.  But how often do we focus that attention on prospecting and nurturing clients (for sales), focusing on better closing efforts? That’s a good start. Let’s make that more efficient and effective.

Or maybe we focus on better insights into customer behavior, preferences, and buying patterns? Use tech to tailor our sales strategy itself.  Or maybe we change our core offerings? Whatever it takes to accelerate revenue generation, to drive sustainable growth.

Tech has to become a business contributor, beyond efficiency creation.  Tech success has to be measured by its commercial contributions.  Not just productivity but performance. If you can’t draw direct lines between your tech investments and revenue growth, you can do better.

Day 11 Bibliography:  This is week #3 as a new CIO and after documenting how I prep myself for the role each day, I share books to read for that day’s topic.  So... Lets get to it.

Day 11 Reading List:

“Zero To One” by Peter Thiel.  I don’t appreciate his politics but he has a steel trap of a business brain.  My guess is that most of the folks who read him religiously are inspired by his success.  They’re either sitting in a startup or aspire to sit in one.  The people who really should be reading him are the ones in large, faceless enterprises.  The folks who don’t yet understand the value of embracing a monopolist, top-line mindset.  While conventional wisdom often warns against monopolies because of all the inequities that come with market dominance and the lack of competition, Thiel’s whole thing is about aiming for monopoly. How it can drive innovation, efficiency, and long-term growth.  

Second book is really a counterweight to any ick you get from Thiel.  Read “Abundance: The Future Is Better Than You Think” by Peter Diamandis and Steven Kotler.  This second book is just a reminder of how much better off we are today than in previous generations… the critical role that tech has played in getting us here and how likely it is that humanity is going to have a bright, bright future… very likely by the way… despite what you read in the news. 

And finally, if you're more of a podcast person, I’d listen to some sales-specific channels.  I’m not going to name any because they all try to sell you on their own sales university or sales masterclass or some other nonsense.  You can take the salesperson out of the sale…. Bu whatever.   Just ignore them.  Listen to the podcasts though– not because you need to be a master salesperson but because they think differently than you do and that empathetic exercise opens up all kinds of tech possibilities.

That’s it for day 11.

Day 12 (Part 1).  This is week #3 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… 

During your honeymoon period, how often should you check in with your boss?  Wrong question.  1) Because you don’t have a boss.  You own the company you work for.  Not because you’re a senior executive but because that’s the right mindset if you want to get stuff done.  And 2) That question is anchored in 200-year-old hierarchical thinking.  It made sense when you rode a horse to work but it’s BS in the modern workplace.  You don’t have a boss. You have a multiverse of bosses. Your job is one of influence and service.  The people to your left and right… your peers are your bosses.  The people who report to you are there to be served by you.  They’re your bosses.  Your clients.  Your bosses. 

Leadership demands that you reframe the “check-in” question.  How can I best steward this company– my company?  How can I best influence those I serve?  How often can I be “of service” to those I serve?  That depends on the size of the organization– and how long it takes you to compile information worth sharing, to process what you’re learning into questions– hard questions– that can help those you serve… improve their game and yours.

For your external client meetings, your check-in cadence depends on the number of clients you have and the state of their relationship with your company.  Start with quarterly and this is important, don’t just focus on clients with strained relationships.  The escalations.  They’re important from a client retention standpoint.  But if the only client engagements in your calendar are problem clients, that’ll skew your tech strategy towards the past as opposed to the future. 

Day 12 (Part 2). For your internal stakeholder meetings, start with weekly check-ins and then transition to bi-weekly.  Fight the urge later to transition to monthly because if you can get by with monthlies, you don’t need the meeting.  You need a quarterly lunch.

Remember the mantra: You can’t outsource relationships.  Every CIO I’ve ever worked with assigned some of their direct reports to own key relationships.  For instance, if the CIO had 10 peers– the heads of businesses 1 through 5, the CFO, the Head of Ops, Risk, HR, Sales– some of those relationships were managed by the CIO’s directs… at the CIO’s behest.  Usually, this is done as a time management technique.  Because the most effective people are the ones who narrow their focus to the most important challenges that the business faces.

The thinking goes: you can’t be everything to everyone.  But(!) as effective as that might be– I’ll say it again– you can’t outsource relationships. 

If you’re tempted to organize your directs to own some of your relationships, at least do one thing, attend their weekly 1-on1s or monthly 1-on-1s.  Make it a 2-on-1: you and your direct and your peer.  

Why?  Because your peers are smart.  They know that you’re narrowing your focus– like they are… and they understand that your no-show is a prioritization signal.  That their priorities don’t matter as much to you as their peers’ priorities.  And you… and all your peers are judged by the business (explicitly) on your peer-relative contribution.  Implicitly?  On the strength of your relationships– the trust you garner.  That larger dynamic always makes me think of a quote by President Johnson: “Never tell a man to go to hell unless you can send him there.”

Day 12 Bibliography:  This is week #3 as a new CIO and after documenting how I prep myself for the role each day, I share books to read for that day’s topic.  So... Lets get to it.

Day 12 Reading List: 

Crucial Conversations by Kerry Patterson.

Last week I recommended that you read Stephen King’s on writing to improve your corporate communications skills.  So here’s the flip side. Read Kerry’s corp comm book is to improve your fictional dialogue writing skills. While her book primarily focuses on real-life communication, its principles can be applied to crafting compelling and authentic conversations between characters in novels, screenplays, whatever else tickles your creative fancy.  Your executive need to better understand how to navigate high-stakes discussions (superserious) can lead to an artful,  playful skill: writing engaging and realistic dialogue that resonates with readers or viewers.

Second book:  Doris Kearns Goodwin’s “Team of Rivals: The Political Genius of Abraham Lincoln.” It’s a cool meditation on strategic leadership and coalition-building.  How should you navigate diverse perspectives at work?  Why should you commit to inclusive decision-making? What can Abraham Lincoln teach you about conflict resolution? What can he teach you about strategic alliances? A surprising metric ton.

And finally, if you're more of a podcast person, you’re outa luck.  I just cringe when I listen to or read anything about how to build winning teams.  They’re just exercises in confirmation bias.  That’s why I loved Doris’ book.  She’s a historian.  Couldn’t care less about business.

Not very satisfying.  So… take 2: if you're more of a podcast person, and you want to become a better leader, find a decent podcast about Buddhism or Goat Yoga and use that time to meditate on the power of kindness.  And if you find a good one, tell me about it. 

That’s it for day 12.

Day 13 (Part 1). This is week #3 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… Budgeting is a four-letter word.  An unusually large amount of your time will go to monitoring and optimizing your budgets and expenses. Capex.  Opex.  That’s normal, unfortunately, because budgets are tangible indicators of your priorities (your alignment with business objectives and strategies) and budgets are tangible indicators of your ability to execute (your performance).

Budgeting is how seniors guide roadmaps, guide planning, guide decision-making.  Senior management isn’t what most juniors think. It’s mostly an accounting job, with a little relationship management thrown in, a little talent management, and a little risk management.  But mostly, you’re an accountant with a fiduciary responsibility for your company. 

You’re monitoring your spending and ensuring that you are getting the most value out of all investments– tech, ops, people, process, innovation.  You’re regularly reviewing and adjusting your budget because that’s how you optimize. 

You’ll hear the word transparency as a stakeholder demand.  And what it mostly means is budget-related.  Are you spending the way you said?  The way we all agreed?

With a well-structured IT budget– and continuous governance process throughout the year– you have a real chance at real financial transparency that demonstrates responsible management while showcasing the value that IT brings to the table– not just features and function but collaborative governance.

Day 13 (Part 2).  Almost everyone budgets on an annual basis and the exercise has little to nothing to do with money.  It has everything to do with getting everyone on the same page.  Are we all looking at the same Northstar?  Given that the business changes every day, are we all still aligned with the company’s strategy and financial objectives?  And do they align with everyone’s day-to-day priorities? 

Does that sound like something you should do once a year?  No. This is why when anyone asks me how Tech can get more Agile, I say… step 1 is Agile Finance. We have to first address the limitations of traditional annual budgeting.  We need quarterly responsiveness to real-time changes. Because staying focused on what was agreed to last November does not help with next November.  

We need shorter planning cycles to allow for more frequent adjustments based on market conditions, business priorities, new client opportunities.  If finance is more flexible, the business is more resilient, more cross-functional, more collaborative, and transparent. It’s even more inclusive because it encourages more regular input from all relevant stakeholders.  And that(!) fosters a sense of shared ownership and accountability, as everyone has a voice in the financial planning process.

Budgeting does not have to be a four-letter word. It doesn’t have to reinforce the traditional hierarchical structure.  It can and should encourage a more decentralized decision-making process, that empowers teams at all levels of the organization to take ownership of the company… and how it runs every day.

Day 13 Bibliography: This is week #3 as a new CIO and after documenting how I prep myself for the role each day, I share books to read for that day’s topic.  So... Lets get to it.

Day 13 Reading List: The Innovator’s Solution by Clayton Christensen.  I’m actually surprised it took me three weeks to get to him.  Now, this isn’t his best known book– The Innovator’s Dilemma– or his most useful book– The Innovator’s Prescription– but he’s smart enough to keep selling tickets to innovationville… the business world’s most elusive “job to be done” – what I call corporate Disneyland.  I want to be mad at the guy for resuing his hook but I’ve read everything he’s done.  And it was written well.  Fun to read.  And it totally helps that he’s cross-disciplinary… that he uses familiar examples… he writes for regular people, not his fellow professors.  Read him.  Worth the time.

Book 2: Deep Finance by Glenn Hopper.  I should have recommended this last week when I was talking about how business transformation can’t happen from the outside in.  It needs to start in the business.  Agile– for instance.  As a CIO, you’re at the intersection of technology and business strategy.  Deep Finance tries to do the same as a CFO.  It delves into how technology, analytics, and data science are key to finance operations. Key to drivign digital transformation.  Key to innovation.  Glenn should partner with Clayton–  book 1– because the title would be easy: The Innovator’s Budget.

And finally, if you're more of a podcast person, I’m sorry. I’d stay the heck away from any podcast with the word money in the title.  Also the word financial.  And it’s for the same reason that I hate podcasts about how to improve sales:  every podcaster is in it to monetize people who lack self-confidence.  

That wasn’t satisfying.  I got it.  Listen the to audiobook of “Moby-Dick” by Herman Melville. It’s not just about obsession.  It’s about risk-taking, and the pursuit of goals.  It’ll help you get into the mind of the CFO because it’s a great parallels to managing financial risks.

That’s it for day 13.

Day 14 (Part 1).  This is week #3 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok…  As I said yesterday, senior management is– rather unfortunately– mostly an accounting job…  which is why you need to understand CAPEX and OPEX.  Shortest possible tutorial: CAPEX– which is short for capital expenses– are investments in assets that provide long-term benefits. So think: equipment, property, infrastructure, and software. CAPEX is generally a one-time expense but has a lasting impact on the company so its treatment in accounting terms provides your CFO multi-year flexibility… to hit financial expectations. OPEX on the other hand– which is short for operating expenses– are recurring costs from regular, daily operations. Think: employee salaries, rent, utility bills, maintenance costs. OPEX for a given year is use-it-or-lose-it in terms of accounting flexibility.  It’s only useful– from an accounting perspective– in the year that it was spent.

The other difference between CAPEX and OPEX is that your company’s governing body– usually your company’s Board– has much stricter oversight over CAPEX.  They treat your CAPEX budget as flexible– not fixed– and definitely not “always increasing.”  So you need to influence the Board for increases in CAPEX.  And influence is always hard work.

If you're working out of your garage, going all OPEX will get you out the gate quickly- but once you start making money, the expenses you incurred before you were flush won't be deductible (in the future) when you’ll need those deductions.  Once you move out of the garage– CAPEX will be more valuable because it helps you keep more of the money that you’re making.  Think tax benefits. To you and your investors.

Day 14 (Part 2). So how do CAPEX and OPEX play into the first 100 days as a CIO?  Your non-tech peers– and your board– understand the CAPEX-OPEX distinction but they might not understand its dynamic with software development. From the outside in, it’ll always look like investments in software– especially big marquee programs– are once-and-done… with minimal, post-delivery, “ongoing maintenance” that’s some small fixed amount.  That’s wrong!  Software maintenance is necessarily a small snowball, rolling down a snowy CAPEX mountain that will need everyone’s attention and focus to keep it manageable. 

You’re going to need to educate your stakeholders to understand that the CAPEX you invest in software will– over time– break down into two buckets: run and change. Run the business (RTB) and change the business (CTB).  

The problem is that any(!) software– post-delivery– that’s actually being used will require more development– more run (RTB CAPEX).  Why? Because the use of software (static) in a business (dynamic) means new requirements will sneak into your CAPEX spend as RTB… causing you to spend less and less of your overall yearly CAPEX on big marquee CTB.  If your stakeholders don’t understand that… tech will look increasingly incompetent every year.  

So– as a new CIO you need to help reframe the CAPEX and OPEX discussion. They need to know that what’s really happening is CAPEX– that snowball (as a run cost) is rolling down a snowy mountain.  Everyone– you, your stakeholders, your PMO– need to operate differently;  to better manage expectations and as your org matures– to refocus everyone on how to reduce RTB as a recurring cost.  Minor paradox: reducing RTB spend is CTB… at a structural level.

Day 14 Bibliography: This is week #3 as a new CIO and after documenting how I prep myself for the role each day, I share books to read for that day’s topic.  So... Lets get to it.

Day 14 Reading List: You’re going to have to Google today’s topic because no one’s crazy enough to write an entire book on Capex and Opex. So Google those two words and read the entire article on Investopedia.  

If you’d rather watch something on the significance of financial statements, one my hour long walks on YouTube is called “How to Read and Understand Earnings Reports.”  And here’s the scariest part: that’s not even the most boring hour I’ve recorded on YouTube.  You’re welcome.

What else can you read?  If you have kids in High School, borrow their copy of “The Great Gatsby” by F. Scott Fitzgerald or “The Count of Monte Cristo” by Alexandre Dumas (which is how my son pronounces it).  Gatsby can be reflection on financial ethics, wealth accumulation, and the impact of materialism on society.  And despite what they teach you in High School, The Count of Monte Cristo is about strategic planning and resource allocation… and all the themes that will let you thrive in corporate America: revenge, resilience, sneaky maneuvering.

Turned that one around!

That’s it for Day 14.

Day 15 (Part 1).  This is week #3 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… If the people in your company aren’t sharing news articles– every day– along with their commentary on those articles– about your industry, your clients, your competitors, and all the emerging technologies that could drive innovation and keep your company competitive, then… one of two things is broken.  Either the expectation is that everyone’s doing it on their own… which is deeply problematic for all the reasons that we tend to value diversity and inclusion… because not everyone comes to the same conclusion given the same input. And those who process differently tend to better represent the art of the possible.

So either the expectation is that everyone’s doing it on their own… or there is no expectation in your culture to be continuously learning from the outside, from one another… continuously exploring, engaging, and growing.  In my experience, cultures like that become fixated exclusively on project and program reporting.  Statuses.  RAGs. This project is amber.  That project is red.  This culture is dead.

And to be fair, in most companies, culture happens at the team level.  So it’s super easy to evaluate if you and your team are succeeding on this front.  Just count up all the threads– email, Slack, texts– over the last week where you or someone on your team shared some external news. For extra credit, count how many times that sharing led to a real conversation… beyond a thumbs up.

Why? Because that behavior is helping demonstrate the power of diversity– the value of a culture of continuous learning and engagement. It’s letting new perspectives rise to the surface. 

Day 15 (Part 2).  So… like with SDLC– the software development lifecycle… which we talked about last week… each team in your org will be on a spectrum… in this case… from passive to active learning… from intermittent to continuous learning.  And as with SDLC, there is no single solution that will mature every practice.  You need a case-by-case run book.

Let’s start with the most positive case. If a team is already sharing external news organically/regularly… awesome.  Arm them with a great curation tool– like Morning Latte.  It’s a mobile app– that lets your team curate the news for each other… and helps them build shared reading lists for when they find the time.  That’s just adding structure to healthy behavior.

If the team is mid-range sharing… sometimes sharing… then start real conversations on the articles that they’re sharing.  Don’t just thumbs up or reply with “Interesting. Thanks for sharing!” Create social capital around that behavior through positive reinforcement.  Your reply should demonstrate that you read it… that it helped you connect some dots. Share what those dots are… even if they seem obvious to you… because not everyone comes to the same conclusion given the same input. You might be the diversity– the value– in this thread.

If the team is challenged on the sharing front– well– Be the change that you wish to see in the world.  You can’t mandate a growth mindset.  You can’t teach a growth mindset in a classroom.  The best you can do is to model the behavior yourself… as a leader.  Share articles worth reading.  If someone replies with any kind of hint that they’ve read it… engage them. And thank them.  Not just for sharing but for championing diversity and continuous learning.

Day 15 Bibliography: This is the end of week #3 as a new CIO and after documenting how I prep myself for the role each day, I share books to read for that day’s topic.  So... Lets get to it.

Day 15 Reading List: It’s going to be a hard one today because it’s like the movie Inception– a dream within a dream within a dream.  Because I have to recommend stuff to read about sharing stuff to read while reading about reading.  You get the point.

So instead of books this week… my three favorite podcasts of all time.  In no particular order: 99% Invisible.  There’s no better example of a podcast that encourages life-long learning.  Plus the host’s voice is like browned butter: everything that’s baked in it, tastes better.

Podcast #2: Stuff the British Stole.  It’s not just that they stole. A lot.  And for a long time.  It’s that they did it intentionally in a way that they could tell a really cool story when they got back to the pub.  It’s the best kind of evil: entertaining.

And podcast #3: Revisionist History with Malcolm Gladwell.  Like all his narratives, these stories are a little too neatly packaged.  And I get why.  He’s shaping him them for a broad audience.  Making them digestible and in the process, maybe oversimplifying them a bit.  But honestly, who cares?  It’s like complaining about your popcorn having too much butter.  Please.

Why these 3 podcasts?  For the same reason that every third or fourth book I read, I force myself to pick a book I would never pick.  A book about the history of Cancer?  One of the best books I ever read.  These three podcasts feed your curiosity. They pick that third book for you. And that’s priceless.

Week 3 Recap.  Week three.  Haven’t even finished a month yet.  It’s a new organization.  And hopefully, a new you.

How quickly should you start to oversee the implementation of technology solutions? It’s a little bit of a trick question. Because that expectation started three weeks ago.  Day 1. 

But… projects were in motion long before you joined. Even the ones that are kicking off after your start date.

So how quickly you start to “oversee” really depends on how you define the word oversee. 

You’re still in the assessment phase— you’re still learning about what the business needs, the technology landscape; you’re still identifying areas where the intersection of all that learning will let you add immediate value.  The word “immediate” in “immediate value” haunts you.

This is where humility should play an outsized role. 

You don’t have answers yet. You might never have answers. Your only real value are the questions you bring, based on your experience… and how you ask them. 

Just beware of the assumption that the path you took that got you success— that got you here— is the same path that will get you to your next success.

Repeat the mantra: if you're walking through the woods and you find the same tree, you’re lost.

Day 16 (Part 1).  This is week #4 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… 

Let’s talk data.  Every person in the business intuitively understands the power and potential of data and analytics.  I say intuitively because that’s not enough for the business to get value out of data as a tech investment.  And I’ll come back to that.  On the other hand, every technologist seems to think that their data job is to build a lake or warehouse, put some self-service reporting tool on top of it, aaaaand they’re done.  When the business inevitably goes on and on about needing data, that engineering brain just points them to the general-use lake where “all the data lives.”  And no one wins.

I’m not saying there aren’t data specialists in tech– people who master and govern data.  People who use fancy words like data lineage and metadata and who actually care about data quality and consistency.  There are.  And their work is usually disconnected from business value.  

Because business value comes from changing business processes.  Not from having a warehouse or lake.  Not from having Tableau or PowerBI on top of it.  Business value comes from imbedding the entire data life-cycle as a workflow– end-to-end– in your company’s operational workflow– its data supply chain… that starts with sales and ends with Ops.  

So the usual tools we in tech focus on– our master data repositories, our consolidated analytics platforms– our fancy warehouses and lakes– they’re all half answers.  At best.  Until data is a ubiquitous part of the daily business workflow– not the tech workflow– the daily business workflow end to end.

As a CIO, it’s never enough to invest in a system that allows the business– theoretically– to ask any question they need of all the data in the company.  If tech builds that field of dreams, the business will not come.  Why? The problem is rooted in senior leadership (in both tech and biz) defining data and analytics as a technical/talent/governance problem that tech owns, rather than a process problem– an operating model problem– that the business owns.  Most business users ask for data like it's a tool.  It is and it’s not.  For that tool to be effective, you need to change business process– you need to change the operating model of the business– in a way that fundamentally redefines the way the business works.  

Day 16 (Part 2).  As much as every new CIO would love to invest heavily in data platforms and people, to build out data infrastructure and to staff with it expensive engineers and data scientists… that’s trying to change a process– the business’s– from the outside in.  It never works.  Tech is left on the hook for major spends that consistently fail to deliver measurable business benefits.  Even when that CIO delivered exactly what was asked of them… they still failed because it was the wrong ask.

The right ask with regard to data?  Business ownership of a business transformation.  You need business partners– relationships– who you can help educate– who will change their operating discipline to be data-centric– who will ask different questions of their people and processes– that will make different demands of tech– that will drive real business outcomes.

I can’t say this enough. Data problems are never (at their core) about implementing technology or managing data infrastructure. They're about building relationships with business leaders, understanding their business goals, and then guiding them in how to own data, not delegate it to tech.  

How?  Practically? Listening is important but active listening demands that you ask hard questions. So ask your business partners to define the top 10 questions that they can’t answer today… not high-level… ground-level… questions that if answered would change commercial outcomes.  10’s a small number.  But it's 10 more questions than most data warehouse projects have.  Prioritize those 10 and build your execution plan around them– not around answering ANY potential question… which is how most warehouses are built.  Then, help your partners change the business processes that have relied on that data being out of reach.  Automate that workflow.  And build your infrastructure and governance iteratively around those processes. 

Look.  It’s necessarily virtuous work to establish strong data governance practices– to ensure data quality and security for your entire data supply chain– to have thoughtful end-to-end processes for data collection, storage, and access– to define roles and responsibilities for data management… but I said this in week one and it’s worth saying again.  You don’t transform a business from the outside in.  So you need to help your business develop a business framework for making data-driven decisions; to drive business success from the inside.  That’s an operating model transformation.  That’s how data transforms.

Day 16 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 16 Reading List: 

I’m going to be cautious on this one because pointing you to a book about Python or R… or pointing you to a book about Data Science (which I’m about to do) or Data Governance… I’ll unintentionally narrow your focus and lead you down the path of being a data specialist.  And what the business needs is a data generalist– someone who is equal parts data nerd and business process specialist (different kind of nerd).  That said, book 1: “Data Science for Business” by Foster Provost and Tom Fawcett. This one emphasizes the importance of understanding the data supply chain. It’s still a bit narrow– because it focuses on data collection, cleaning, integration, transformation– which are all part of the tech end of data supply chain… so you need to supplement it with a book about operating model transformation.

That’s book 2: “The Business Transformation Playbook” by Heath Gascoigne.  You can also sub that out if there’s a book or white paper about your specific industry’s Target Operating Model.

And finally, on the multimedia front. Check out a YouTube walk I did called Data and Analytics: Questions to Ask as a Business Stakeholder. That’s it for day 16.

Day 17 (Part 1).  This is week #4 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… what’s the difference between a CIO and a Chief Digital Officer (CDO)?  And what’s the CIO’s role in driving digital transformation? First, if your company has both a CIO and a CDO, someone at the top didn’t fully understand the role of a CIO. Or there was some political garbage going on.   Think about the word digital in Chief Digital Officer.  Everything in tech is digital.  So if you’re going to have a chief digital officer, the CIO’s title should be changed to Chief Analog Officer.  If your company has both roles, it usually means that the CIO narrowed their focus so much as to crowd out the company’s client experience– client voice– and/or the company’s employee experience.  Luckily that’s not the case with my current company.  Yay!  So second question: what’s CIO’s role in driving digital transformation?

Step 1 is never tech.  Because before you automate processes– before you  digitize them end-to-end, you need an inventory of existing business processes and a detailed view of how they connect end-to-end.  There’s a very good chance they don’t connect or do… through semi-automated, non-documented, tribal processes.  And even if you have that list, it’s still not enough to get the build started. 

You also need business buy-in on tomorrow’s model– one of the books-to-read from yesterday.

The difference between your current inventory of processes to digitzie and tomorrow’s operating model is that the latter is a smaller, thoughtful, rationalized inventory for what ought to be… not what is… but how process ought to connect end-to-end, fully automated.  Plus that list needs to be prioritized– based on risk and ROI– in 2 separate buckets: processes that a central automation group should automate top-down and processes where you expect citizen development– decentralized teams– to automate their processes themselves, bottom-up.

If those lists don’t exist, tech is at least a year to 18 months from starting.  At least.  And that pre-work could mismanage everyone's expectations about how soon digital transformation will deliver results.  Tech will inevitably get comments like “This transformation started two years ago and all we have is an inventory.  Everything is still manual.  Nothing has changed.”  In those orgs, tech just did a poor job of continuously educating stakeholders on what to expect.  And who to expect it from.  Because– like the data discussion from yesterday– producing a future state operating model– is something the business should own and drive.  Tech should be in the car, helping… guiding.  Just not driving.

Day 17 (Part 2).  Tech is not sitting idle during the business-driven step 1 of a digital transformation.  While the business is focused on mapping the future-state operating model end-to-end, tech should be actively preparing the teams and the tools for step 2.  That’s where my two favorite three-letter acronyms come into play: BPM and RPA. 

BPM, or business process management– think workflow– helps organizations visualize their end-to-end process– step one to optimizing and automating them. RPA, or robotic process automation, takes it a step further by using software robots (think: old school macros on crack) to automate repetitive tasks. Together, these technologies enable businesses to streamline operations, increase productivity, and improve customer experiences.

The questions to ask are: do you have the self-service versions of these? Do you have the kind of culture within the larger organization to expect citizen development?  Do the non-tech people you expect to self-service have the time to do it?  Will they ever have the time?  When companies talk about leadership and the need to foster a digital mindset and encourage employees to embrace change, there is a training and upskilling dimension to it but the less obvious NEED is free time.  If you’ve spent the last 10 years optimizing your operations– and your workforce has been shrinking with each uptick in productivity, then the business folks who you expect to be mapping and automating processes with self-service tools won’t have the time… even if it’s a mandate from above.  One of the many reasons mandates don’t work. 

So yeah, there will be a buy/build/integrate dimension to BPM and RPA but equally important is the need to equip business teams with the necessary digital skills… and to work with their leadership to find them time to do the actual work.

Day 17 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 17 Reading List: 

Book 1: Google "HBR’s 10 Must Reads on Leading Digital Transformation." If you have the $25, buy it.  If you don't, just read the extract-- which mentions the authors of the 10 pieces and the titles... and then google them. Full disclosure: I'm not a fan of HBR for a lot of reasons but if you’re not going to tap one of the big consultancies, HBR’s the fastest path to figuring out the essential principles and practices that lead to successful digital transformations.  Also… when you read any HBR piece just know that the author probably published a book on the same topic.  So treat HBR as a book tasting menu.  If you like the taste, go to the author’s site and buy the book.

Book 2: “American Prometheus: The Triumph and Tragedy of J. Robert Oppenheimer” by Kai Bird and Martin Sherwin.  While the book is not directly about tech modernization, read it for inspiration and caution. It highlights the joys and challenges of pursuing enormous goals with the best minds.

And ditto on the multimedia front. Can’t go wrong with Christopher Nolan.  So watch Oppenheimer and then if you have time, his Batman trilogy.  Because every CIO is Batman.

That’s it for Day 17.

Day 18 (Part 1).  This is week #4 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok…  How does your moral compass play into your first 100 days?  The answer actually starts before you take the job… while you’re still looking. I purposefully switched from banking to healthcare because I needed to connect my personal values (to fight for the underdog) with what I do professionally (which in banking, my previous gig, was always an uphill battle).  

As cliche as it sounds, I am(!) defined by my career.  I don’t know any working professional who isn’t.   But my career doesn’t give me my sense of direction.  It shouldn’t.  It’s the other way around.  So before you switch jobs, recognize that when the company you work for isn’t helping shape the world in a way that aligns with your values, you’ve made the wrong trade-offs.  When meaning doesn’t drive your job search– when it’s about money or status– you’ll be forced into buying ideas like work-life balance because there will necessarily be a disconnect between work and life.  For me, because my values align with my new gig, my work is meaningful, I’m energized by it… even when it’s rough.  

And I realize how privileged a life I lead.  Because if you have the privilege of having a white-collar job that aligns with your definition of purpose and your values, you can easily blur work and life.  That’s much harder if you’re in a blue-collar role.  It’s privilege that allows me to  sustainably find motivation, productivity, job satisfaction.   So it’s critical– when you have that privilege– exercise it with an ambition to improve the world– to serve the less privileged.

Day 18 (Part 2).  Once you’re in the job– hopefully a purposeful job– then your moral compass should serve as a guiding tool for making ethical decisions– for being kind– and taking actions that align with your company’s (hopefully) shared values.

Look.  I don’t know of any leader I respect who doesn’t live their values… who doesn’t understand the impact of purpose.  But… I do know a lot of us that let our company’s mission become our purpose.  We bought the BS because it paid well.  

Those leaders talk a mean game on topics like courage but they remain silent on important topics that will impact their company’s short-term commercial ambitions.  I can’t tell you how disheartened you can become when your senior leadership sees injustice (as they define it) and chooses to stay silent to keep some clients.  That’s not a purposeful company.  

I recommend a book– I think it was week 1– called Net Positive by former Unilever CEO Paul Polman.  It makes a powerful case for how and why purposeful companies– led by courageous leadership teams– do better in the long term… because(!) they help change the world for the better. 

So… your moral compass is something you never expected it to be: a commercial boon.  It should inform your organizational culture, your employee engagement, decision-making, strategic planning, goal-setting.  Everything.  It’s the most meaningful thing you bring to the game.  So find a place where you can live your values… and then live your values through your daily actions.

Day 18 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 18 Reading List: 

Book 1 is one of my favorite business books of all time: Manifesto for a Moral Revolution by Jacqueline Novogratz. Here’s what sets this one apart for me.  No other business book has ever made me ugly cry.  ‘Nuf said.  TMI.

Book #2: Winners Take All by Anand Giridharadas. If you’re going to be a part of capitalism, it’s kinda on you to help shape capitalism. What this book adds is the idea that corporate philanthropy ain’t the answer.  This guy’s playing chess with corporate social responsibilities when most well meaning companies are investing a lot in checkers.

And finally, on the multimedia front– even though its not Christmas, watch “It’s A Wonderful Life.”  The reason we all kinda lost it at the end is not because of Christmas.  It’s because we all value community, kindness, selflessness.  We just need to bring that to the office… the way George did.

That’s it for Day 18.

Day 19 (Part 1). This is week #4 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok…  Been thinking a lot about professional development– my team’s and my own. Let’s start with what I’m doing– for me(!)-- to stay current with the industry and to always be in a tech-forward position.

Three things: I’m reaching out to my peers– the people who do my job– at my company’s competitors– the obvious ones and the digital newcomers.  I get the list off the web, jump to LinkedIn, and send invites with a simple message: “We’re playing in the same space.  Let’s play together.  It’ll improve both our games.”  I get 70% acceptance rates.  The other 30% probably did the worst thing possible for themselves and their companies– they stopped checking LinkedIn after they landed.  Bad move.

Second thing I do– I reach out to the experts– people who are explicitly paid to read themselves into a forward position.  The big consultancies. And I mean alphabetically: Accenture, Bain, BCG, Deloitte, McKinsey, Oliver Wyman, PWC… and throw in Gartner and Forrester.  I send a message to relationships I’ve grown over the years: “Hey.  Got a new gig.  What can you teach me about it?  Who can you introduce me to?”  Response rate: 100%... 1) because I’m a relationship and 2) because relationships are how they make money… eventually.

Third thing I do: I read everything I can get my hands on.  That’s an ask in every conversation with my peers, consultants, direct reports, my clients… strangers… really anyone I speak with.  It’s become a subtle indicator for me:  If a person can’t recommend a book that’s improving their game, their game’s not improving.    

Day 19 (Part 2).  How do I think about professional development for my teams?  I think about all the continuous education that I’m forcing on myself… and I think… share.  Set the bar high for yourself and find ways for your learning to influence others to learn.

Super obvious answer– especially when you’re always asking people what books you should read– a book club.  Publicize that you have one.  Make sure it’s optional, not mandatory.  Because the worst kind of mandates are the well-intentioned ones.  And steer towards books that will deepen everyone’s understanding of the business (end-to-end), of emerging trends (tech and biz), and this is important if you’re in a big company– books about how small companies succeed. Trust me on that one.

Second way I think about professional development for my teams: intentionally ask them for something that you know they can’t currently do and then ask them how you can support that kind of growth in them.  You’ll be surprised with their answers. 

Most people aren’t growing because their management is asking them to be heads down 100% of the time. That doesn’t help anyone in the long run.  

I’ve said this a million times: all cognitive growth comes from the right mix of challenge and support.  The challenge comes through an explicit ask: do something that you don’t know how to do.  The support comes from you(!) creating safe spaces for others to learn, to fail.  That’s the ultimate stretch goal: fail as you learn to fly.  It’s the only real path to flight. 

Day 19 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 19 Reading List: 

This first one needs a disclaimer.  I took one class with this Harvard professor when I was a grad student at MIT– a real school– and this dude changed how I think about everything.  His name if Robert Kegan and back in the 1990s, his book– called  In Over Our Heads: Mental Demands of Modern Life– wasn’t particularly accessible to the people in corporate America.  He’d probably disagree with that.  Since then though, he’s become an essential read for anyone who cares about their people.  If you haven’t read “An Everyone Culture: Becoming a Deliberately Developmental Organization”-- just stop scrolling and order it.  

Book 2: “Quiet: The Power of Introverts in a World That Can’t Stop Talking” by Susan Cain.  Nuf said on that one.

And finally, if you’re more of a podcast person– Google “coaches rising Robert Kegan” and you’ll find an episode where Bob talks about that book you should read.

That’s it for Day 19.

Day 20 (Part 1). This is week #4 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok…  Let’s talk skills assessment and gearing ratios because that’s one of the two strongest determinants of how fast you can run.  In tech, skills can be boiled down to 5 broad categories: software developer, hardware engineer, business analyst, program manager, and senior manager.  I just offended about a million of you,  What about architects?  What about cyber? What about risk? Look. You’re all important.  But in the larger clockwork, you’re smaller gears.  A CIO has to tune before they fine-tune.

Now I’d normally say: go talk to HR to get the skills assessment but I know they won’t have it.  No fault of their own.  HR never gets the budget to climb past the critical stuff: recruiting, payroll, benefits, and performance management.  Would every HR person on the planet immediately invest in training (beyond compliance training) and development (real cognitive development)?  Absolutely.  And that day will never come.

So instead of asking for skills data, ask your HR partner for help with a skill assessment survey.  Mine’s going to be simple and focused on what I value most– end-to-end business knowledge.  So question 1: Which of these 5 roles do you play? Question 2: Which internal system or tech process do you better than everyone else?  And question 3: On a scale of zero to 5– zero being you know nothing and 5 being you’re a deep expert, how would you rate yourself on the following business processes?  And then you list as many business processes as you can… which will also be a problem because process inventories don’t grow on trees.  We talked about that as a challenge earlier this week. It’s a prerequisite for digital transformation. If you don’t have a process inventory, keep the skills assessment high level for round 1.

Day 20 (Part 2). So what do you do with skills assessment data?  You figure out 1) Gearing ratios, 2) Single Person Risk, 3) What we talked about yesterday– professional development… because everyone’s career can improve the more they understand the business end-to-end.

Jumping back to 1. The term gearing ratios is borrowed from finance and over there, it’s a comparison of a company's equity to its debt. In tech, it’s the ratio– on a project-by-project basis– of software engineers (the equity) to business analysts and program managers (the debt).  Most BAs and PMs hear that and think: “Hey, wait a minute.  I’m just as valuable as an engineer!” You are. Maybe even more so.   

So why would a CIO need to understand the ratio?  Because in most orgs, that’s an excellent indicator– not just of how efficient tech is– but more importantly, how mature the business is… and whether its operating model has been optimized to be good partners with– and good stewards for– technology spend.  That’s a fundamental CIO paradox: tech is only as effective as the business operating model that it supports.  So one of the CIO’s unspoken roles is to help mature the business– an operating model transformation– that leads the business to be better consumers of tech.

The other benefit to getting skills assessment data?  Single Person Risk.  It’s why you ask everyone “Which internal system or tech process do you better than everyone else?”  Just sort on unique, snowflake answers and you’re looking at your next multi-day outage.  That’s the best kind of investment opportunity in professional development.

Day 20 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 20 Reading List: 

Earlier this week– I think Tuesday– I recommended an HBR compilation.  I’m going to do that again today.  And just like I said before, if you want to buy them as compilations and make Harvard even riched, great.  If you don't, just read the extrac-- which will mention the authors of the 10 pieces and the titles... and then google them. Treat HBR as a book tasting menu.  If you like the taste, go to the author’s site and buy their book.  So… which HBR compilations today?

The first– google “HBR’s 10 Must Reads on Mental Toughness.” Or just pick up Angela Duckworth’s book “Grit.”

Second– google “HBR’s 10 Must Reads on Emotional Intelligence.” Or just pick up any fawning biography of Elon Mush and do the opposite he would do in every situation.

And finally, if you’re more of a podcast person– Angela Duckworth has a podcast called No Stupid Questions.  In full disclosure, I stopped listening to it on principle.  The principle being that my favorite questions in life are stupid questions– mine usually– and I don’t need someone telling me its not stupid when I’m comfortable that it is.  If someone wants to start a podcast called “Ask only stupid questions… so we all know how little we know”...  I’d subscribe.

That’s it for Day 20.

Week 4 Recap.  This is the end of week #4 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. 

Ok… End of month 1.  I just sent out 6 boxes of cookies to some top performers and I haven’t even met 5 of them.  Each box had a personalized note that was me being grateful in a human way (not corporate speak) for some recent outperforming results… (all three words there are important– recent… outperforming… results) with me being a coach– explicitly calling out the behavior that led the person to be recognized…. And filled with cookie!  

Plus, I’m feeling grateful for the people I manage.  So it’s a good time to talk about what it means to lead and motivate.

Gratitude is hard– mostly because it needs to be done in real-time, with authenticity, with a deliberately developmental mindset (remember Bob Kegan from earlier in the week), and gratitude need to be done in the context of explicit company goals and values. 

The people who get it right– who create a positive and motivating work environment where employees feel valued– maybe even inspired– to perform their best… those people work on it. It’s a skill, a muscle. It gets stronger as you exercise it.

I personally struggle with it. Thanking individuals publicly has always struck me as disingenuous. I do it but it doesn’t feel right. It feels like a TV ad– people are too sophisticated, too jaded to be moved by ads. So it takes real effort (for me) to provide meaningful feedback, to pick out rewards and incentives that aren’t transactional (Amazon gift card!) that build a culture that fosters a sense of belonging, boosts morale, and strengthens relationships within the team. That’s hard and despite what Hallmark will sell you– not particularly rewarding… if you’re not a warm and fuzzy kind of person.  

But gratitude is one of the two most important parts of the job. More important than setting a strategy… or executing with speed… or managing a budget.  Because you’re sitting in a seat that others aspire to sit in. Modeling gratitude respects the seat. It keeps you humble. And when you’re humble, you’re open to learning and growing from others.  

That uncomfortable feeling is you leading, growing.

Looking forward to week 5.

Day 21 (Part 1):  This is week #5 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… Cyber security.  It’s like watching an eclipse.  You don’t look straight at the sun. Well, you hire the smartest person you can afford– who stares directly at it for you– or better yet, builds a team that does.  But you as the CIO, need to think in terms of business impact. 

I promised on day zero to focus on 1 issue a day but talking cyber will break that promise because its business impact needs you to think about everything.  Business continuity.  Disaster recovery.  Third-Party Risk Management.  Incident management.  Client communications.  Regulatory impact.  Reputation management.  Literally everything your company does.

Let’s do a speed run thru the first three because they’re the most important. 1) Business Continuity: you need detailed plans that outline how your company– not just tech– will continue operating during and after an incident.  You need to conduct realistic simulations to test your firm-wide response. You need to ensure that everyone in the company– not just tech– knows how to stop, drop, and roll during a fire.  You need to focus on every dimension of your operational resilience and that of your partners and vendors.  And that just business continuity– one tiny piece of the cyber puzzle.

2. Disaster Recovery (which sounds a lot like business continuity but is a field unto itself.  If I’m speaking Klingon, business continuity is about people, processes, and facilities, while disaster recover– DR– is about tech: data, systems, platforms).  For DR, you need up-to-date recovery plans written in plain English so the poor guy who joined last week can actually help next week when something happens. You need to automate everything because every minute counts during an incident.  You need to regularly test those DR procedures and automation to ensure they work effectively because your platforms– like your business– is constantly changing.  You need to consider the systems and services that you should move to the cloud for scalability, redundancy, resiliency… and then move them (a ton of work)… and then make sure the cloud is constantly monitored and safe.  You need to prioritize data backup and restoration and anything else that will block your business from getting back on its feet in a reasonable timefrme.  

What else? 

3. Third-Party Risk Management:  You need to care about the security practices of your vendors and partners because lightening might not strike your house put it’s going to hit critical business infrastructure in your industry.  That’s actually the most likely negative impact– cyber impact– to your company.  Business people intuitively understand the idea of a physical supply chain… what happens when the ships can’t dock, when the trucks stop running, when the shelves are empty.  But most people don’t apply that to the larger data supply chain. Because if they did, they’d realize how fragile their industry is… and they wouldn’t sleep at night.  They’d get these.

That’s 3 things I talked about.  Three things that you could spend your entire CIO tenure on and there are two dozen other bundles of complexity that cyber also forces you to focus on.  It’s white collar doomsday prepping… without all the mason jars.  And without having to apologize to anyone for the wild hair.  Because you’re doing it for your clients.

Day 21 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 21 Reading List: 

Fun fact before my first recommendation.  Did you know that companies that go thru high-profile, publicly-reported data breaches can actually improve their reputations by how they handle it.  Research has shown that an average firm's brand rises by 20+% following a data breach.  It’s human– an empathetic response.  You don’t hear about someone getting mugged and think “well it was their fault really.”  And that’s what cyber is: a digital mugging.  Ok.

Book #1: Spin Sucks: Communication and Reputation Management in the Digital Age by Gini Dietrich.  Do you know how to trigger that human, empathetic response I just mentioned?  Sound like a human. Be authentic.  Be ethical.  Be real.  Use contractions. Not enough corp comm uses the word ain’t.  If companies could just get over themselves and talk like people– not Chatbots– they’d realize that a well-handled breach response needs to demonstrate transparency, accountability, and an ongoing commitment to protecting customers. Investing in plain talk during and after a breach can enhance trust– our north star.

Book #2 is healthcare specific and actually another HBR article.  Google “HITRUST explained: One framework to rule them all.”  HITRUST is spelled HITRUST and I’ll spell it again in the post description. HITRUST is a framework that’s used to unify rules from various existing regulatory and industry frameworks, including HIPAA, GDPR, and PCI-DSS. It aims to simplify compliance efforts by consolidating requirements into a single-source solution. 

And finally, on the multimedia front, binge every episode of Mr. Robot.  It’s based on a true story. [Nod No]

That’s it for day 21.

Day 22 (Part 1): This is week #5 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… How do you navigate roles that shouldn’t sit in your organization but aren’t a priority for the organizations where they should sit?  For instance, when we were talking digital transformation, we mentioned the need for end-to-end process automation– the need to use tech to continuously evaluate and improve every operational process and procedure in the business end-to-end. We also talked about how that needs to be a living inventory of processes.  Maintaining that list isn’t just hard work– it’s a prerequisite for tech to do our job.

If that role exists on the business side, great.  If it doesn’t, it’s probably because Operations is busy keeping the lights on.  They’d love a BPM view of everything they do, end-to-end.  They just don’t have the time or the budget.

Two simple choices for you– neither good– and you need to pick the lesser of two evils.  Hire the role into tech.  Or slice off some tech budget for whoever outside tech needs to own it.  I’m not a fan of the first choice, because change should never happen from the outside in.  It won’t stick.  And I’m not a fan of the second choice because IF the role wasn’t a priority before getting the budget, it won’t be one after getting it.

What usually happens is option 1: the CIO hires the role into their org with some negotiation around the vague timeframe in which they’ll transfer the function to where it needs to live.   That’s command-and-control thinking… when it should be an exercise of influence.

Day 22 (Part 2): A role that shouldn’t sit in tech can’t start to be built in tech.  I’ve seen that happen multiple times with product functions, risk functions, even audit.  We’re talking roles which should fundamentally be challenge functions to tech.  They’re meant to improve tech by having an outside-in perspective.  

Regardless of how much or how well the leaders of that function speak truth to power, the integrity of those functions are necessarily compromised when they report in to the CIO.

So it’s important that you influence your way into having those roles created where they belong.  What are you giving up?  Speed of execution.  Because doing it right from the get go takes time.  Because influence takes time.  

You’re going to need a mitigation strategy until you successfully influence.  And as horrifying as it sounds, you personally are the mitigation strategy.  If your org is missing the product function, you personally need to play product. Same with risk, audit, compliance– whatever– is missing.

The only good news is that any organization that you just started leading already has tribal versions of the functions that are officially missing.  Because tech– before you– couldn’t have functioned without product, risk, audit, compliance– whatever– is missing.  There’ll be lots of clues: think informal roles– like “Who’s the tech product owner?”  That’s like asking “Who’s the amateur brain surgeon?”

You’ll be challenged on the sustainability front– because the secret to getting any job right is narrowing your focus… not picking up 2 or 3 extra roles.  So… influence, influence, influence.

Day 22 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 22 Reading List: 

Book 1: Range: Why Generalists Triumph in a Specialized World by David Epstein.  It’s one of these books that I should have recommended week 1.  Filled with valuable insights for CIOs.  It’s a meditation on embracing diverse perspectives… how to complex, multifaceted challenges… with an interdisciplinary mindset.   It’s a meditation on agility in a rapidly changing business landscape. It’s about creativity and problem-solving and I’m sorry it took me a month to recommend it. 

Book 2: Social Chemistry by Marissa King. Another book that I should have recommended week 1.  It’ll get you thinking about network dynamics– in human networks. How to influence organizational culture. How to build meaningful stakeholder relationships. How to navigate change management.  How to balance technical and social skills. Just all kinds of useful.

And finally, if you’re more into blogs, check out one that I wrote on superserious called “How to Manage Senior Stakeholders”... based on some really interesting research at MIT… which you should probably read before you read my take on it.  For that piece, Google “When Collaboration Fails and How to Fix It.”  Super interesting read.

That’s it for Day 22.

Day 23 (Part 1):  This is week #5 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… Let’s talk Help Desk and how to level it up.  You already have a ticketing system, a knowledge base… you couldn’t have survived COVID without remote support tools… a helpful staff.  When there’s a fire, they already flip the switch and become proactive– calling people, showing up at different offices, at people’s desks.  And they record the outcomes.

So leveling up is about what you do when there’s no fire.  You’re sitting on the greatest possible tool for proactively engaging the rest of the organization: empathetic people.

In the past, how many times– if ever– did you receive a call from your helpdesk saying “Hi.  This is Jane from the helpdesk.  You didn’t call us.  There are no fires.  So I thought I’d reach out, introduce myself, and see if there are any tech questions I can answer?  There’s a chance that I can’t answer your questions but if you give me time, I can do some learning and/or chase down the appropriate person.”

I know that if I had ever received that call, I’d probably hang up immediately because it’s gotta be a scam… right?  Some kind of vishing?  Because no one does that.  

Well, you can start.  Get your HelpDesk a list of employees to call.  Top of that list: new joiners.  But really, anyone can benefit from that call.

And you– as a CIO– scale the one thing that no one thinks you can scale: active listening.

Day 23 (Part 2): So… reboot your HelpDesk.  Have them proactively reach out to the organization– with earnest questions about how they might help– leads to two powerful results.  The first is trust– our North Star… because your users don’t expect that level of white glove service.  And even when your users speak, they don’t expect to be heard.  So… trust.

The second result is a learning path for the members of your helpdesk that’s rooted in customer demand.  Maybe they want to go into software development or robotic process automation (RPA).  Now they know where the demand sits. Maybe they want to go into training, ops, product, risk.  Careers– like the best businesses– can be shaped by just listening to what the market needs– answering the questions clients haven’t yet asked.

Look.  I don’t know of any CIO who does a victory lap with a story involving their HelpDesk.  They usually do laps for large, complicated deliveries– the new datacenter, the move to the cloud, the adoption of some innovative solution that enhances customer experience and drives business growth.  Cyber’s a good victory lap. These days, cost savings deserve a lap.  If you’re really hard up for success stories, maybe something in governance, compliance, risk management– stuff that should be water if you’re a fish.  

But no one focuses on the HelpDesk.  They might have during COVID.  But that was an anomaly. 

I think that’s a huge missed opportunity.   Don’t sit on people who know how to listen, who know how to learn, who know that most problems can be solved with a simple reboot.

Day 23 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 23 Reading List: 

Book 1: “The Nordstrom Way to Customer Experience Excellence: Creating a Values-Driven Service Culture” by Robert Spector and BreAnne Reeves.  There are a handful of companies that get mentioned over and over again in books about exceptional customer service.  Nordstrom is usually one of the top 5.  The others being Zappos, UPS, Chick-fil-A, REI, USAA (a bank for the military community), Trader Joe’s, etc, etc.

Actually… Trader Joe’s would be a good book #2.  Well there’s no book called Trader Joe’s but there is a really cool book called The Secret Life of Groceries by Benjamin Lorr.  It was on my list of favorite reads last year.  No spoilers.  Just read it.

And finally, if you’re more into podcasts, Try Creating Disney Magic: Lessons in Leadership, Management, and Customer Service.  The host is a former Walt Disney World EVP– which gives him instant cred when he talks about customer service.

That’s it for Day 23.

Day 24 (Part 1): This is week #5 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… The reason innovation is so hard is that it requires you to have a market leader mindset… not just business depth (super impotant!) but all the challenges associated with being *the* dominant player, *the* industry leader.  The point is that there’s a very good chance (always) that your company doesn’t have the largest market share, the highest sales volume, or the most die-hard customer-base in its industry.  

The literature on innovation talks a lot about focusing on a clear business strategy, a supportive culture… strong execution.. etc, etc, etc.  But the way most organizations– who aren’t #1– get there is by comparing themselves and their products and services to the market leader… which leads to commoditization and the death of competitive advantage. So how do you keep your tech-enabled innovation pipeline original and distinctive?  How do you stop playing catchup and start playing leap frog?  Well… remember that your core product is trust.  

That means you need to leverage tech to build a recognizable, client-centric, trust-centric business brand.  While competitors will always be able to copy the things you say or the services you provide, they can’t copy the way your customers feel about you.  By owning your digital footprint, you own your brand identity and it needs to be consistent across all your client touchpoints, from your website and mobile app to your social media to your IVR to your call centers. A strong brand identity– centered around your client and trust– is the only way to sustainably attract new customers, open new markets and/or to retain loyal customers in existing markets.  It’s the rock on which you build your church. 

Day 24 (Part 2): When the literature tells you to “always keep innovating,” to constantly monitor market trends and shiny tech, there’s a larger context that’s missed: customer needs. Your products and services aren’t going to differentiate on the bottom of Maslow’s pyramid.  It’s never about functionality, reliability, usability… you differentiate on the top of the pyramid in maslow's hierarchy of needs: business depth and trust.

When the literature says to focus on a specific vertical or niche… what it’s really saying is that it’s easier to build trust when you continuously narrow your potential audience. In other words, your job becomes easier when you target a specific segment of the market that has unmet or underserved needs— the narrower the niche the better.  

By focusing on a niche, you don’t just gain a deeper understanding of your customers, their pain points, their preferences– (all important!). You can also refine their trust in you… from some high-level general form of trust… to a more solid, sustainable, domain-focused business-expertise-driven specific form of trust.  That’s not gold. That’s platinum.

The companies who are failing at trust are the ones who continue to sell high-level generics… instead of narrowcasting.  The winners are tailoring their products – continuously narrowing their underserved personas… down to (if possible) an audience of one.  How do you scale that? Tech!  So ask yourself: How can tech help build a loyal and engaged customer base by seeing them each as an audience of one… by seeing their pain… by establishing your company as an authority and a leader in that experience?  How can tech be empathetic? To help understand that individual better?  Answer that and you’ll have a unique and competitive innovation pipeline.

Day 24 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 24 Reading List: 

A couple weeks back I plugged a bunch of Clayton Christensen’s books and I used the words “jobs to be done” without explaining the origin of that term.  Well, that’s book #1 today:  “Competing Against Luck: The Story of Innovation and Customer Choice” by Clayton Christensen.  If you want to save yourself the time, just read until you understand the significance of a milkshake during your morning commute.  I’d read the whole book though.  It’ll stay with you.

Book 2. Another classic worth reading.  But I’d read it skeptically.  Good to Great by Jim Collins.  Reason I found it interesting is that every great company was compared to a competitor that missed the mark.  Abbott (compared to Upjohn). Circuit City (compared to Silo). Fannie Mae (Great Western).  Gillette (Warner-Lambert). Kroger (A&P). Nucor (Bethlehem Steel). Philip Morris (R. J. Reynolds). Pitney Bowes (compared to Addressograph).  Walgreens (Eckerd). Wells Fargo (Bank of America).  Most of them weren’t “great” in the long view but the peer-analysis is worth your time.

And finally, if you’re more into blogs, google Hood– my first name– and The Innovation Game.  It’s one of my favorite pieces of my writing.  

That’s it for Day 24.

 Day 25 (Part 1): This is week #5 as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… A three year plan. Horizon scanning.  Future-casting.  When you first land in the CIO seat– especially if you’re new to the company– there is an expectation that you’ll either weigh in on or create a multi-year tech-forward roadmap.  That’s one of the initial values of reaching out to the big research firms and consultancies.  Talked about that last week.

One of the most important reasons that you spend your first 3 months understanding the business end-to-end is that three year tech planning really needs to be rooted in 3 year business planning.  Depending on the culture of your company, that business strategy could be anywhere on a spectrum from “dynamic and flexible” on one end to “rigid and structured” on the other.  It’s usually somewhere inbetween with a small handful of multi-year marquee transformations (the big rocks) and enough bandwidth and agility to skate to the ever-changing business landscape.

So your goal with a three year tech plan isn’t to be everything for every project.  It should be centered on improving the delivery of those multi-year marquee transformations. Create a grid that lists those big rock– one per column– across the top and in column zero you list the suggestions you got from talking to the consultancies– all the relevant tech from the current hype-cycle (Generative AI) and just for good measure, the tech from the last couple years of hype-cycles (Cloud, Cyber, Mesh Architecture, really depends on your industry).  Add to that a couple of lines of “how we work” improvements like Agile, Workflow Automation, Operating Model Transformation… and then ideate for every box in that grid… [and you have it…]

Day 25 (Part 2):  Horizon scanning and future-casting is a continuous activity, both because the business reinvents itself regularly and because tech– the business’s accelerant– recycles itself every 3 years. 

The question you’ll want to answer as you continuously scan the horizon is one of prioritization. What is the value proposition, feasibility, and risk assessment with each future-tech-vs- business-goal combination. And by value prop I mean aside from the marketing uptick you’ll get for announcing that you’re AI-this or Blockchain-that.  I’d leverage the same matrix we just created to score/rank the potential impact and effort of each combo. And then I’d select the ones that have the highest return on investment and alignment with business goals.

And if you’re going to continuously evaluate the horizon, I’d visit and revisit how you measure and communicate the progress and outcomes of your somewhat fluid three year tech plan.  Think key performance indicators (KPIs), dashboards, reports. Ideation might be fun but it’s real work to figure out how to define the metrics that will indicate the success with revenue growth, customer satisfaction, operational efficiency, or innovation. It’s real work to establish the frequency and format of reporting the results to your partners and stakeholders– the rest of executive team, the board, or even employees.

Fostering a culture of innovation and collaboration is one part ideation and 99 parts – iteration, repetition, communication, execution, adoption… and any other words that end with shon.  The principles and practices that will guide you innovation– customer-centricity, agility, experimentation, learning– are the hard part.  

Day 25 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 25 Reading List: 

Book 1 was going to be Sapiens by Yuval Noah Harari.  But there’s a similar book that’s infinitely better called The Dawn of Everything by David Graeber and David Wengrow. The book was so good that when David Graeber died in 2020, the world of people of love books lost something really special.

While I’m being a downer, book #2:  Man’s Search for Meaning by Viktor Frankl.  You’ve probably heard of it.  But until you read it, you’ll remain you.

And finally, if you’re more into multimedia, one of my followers on TikTok asked about future casting a couple weeks back so I shared a super-short blog on superserious called The Breakthrough.     

That’s it for Day 25.

Week 5 Recap.  Start of month 2.  You’re not playing to win (explicitly) (yet). You’re still playing to learn… which— when you’re playing the long game– is how you win: you lead with what makes play fun, what makes learning impactful.  You lead with curiosity.

This past week it was curiosity about how to farm trust… how to lead through change… how to tap the power of the curious in your larger org…   And we ended the week with curiosity about the future– the art of the possible.

There is a fundamental playfulness in 3 year planning.  Because… at the heart of experimenting with new technologies… with exploring different business scenarios… with creating new markets… is one of the most important keys to success.  It also happens to unlock how we adapt to changing circumstances.

Show me someone who wasn’t curious when they first interacted with generative AI.  Show me someone who didn’t ask an inappropriate question of chatGPT.  And I’ll show you someone limited by their lack of play… someone who would struggle (with or without cool tech) to provide data-driven insights, someone who’d struggle with creating operational efficiency.

Curiosity and playfulness are critical in 3 year planning.  God help you if you’re bored when you’re talking about strategic alignment, customer satisfaction, competitive advantage… because it doesn’t get better than that. 

So quick revision to what I said 2 minutes ago.  You’re not playing to win. You’re playing to play. That’s how you win. 

Day 26 (Part 1). This is the final week of my first 30 days– week 5– as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… Let’s get spicy.  The return to office.  I love going into the office.  There is no greater work-related joy than having a bowl of soup and breaking break with your co-workers.  So let me say this again: I LOVE going into the office. And I intentionally looked for and joined a company that is primarily Work-from-Home.  Why?  Because I value cultures that treat their employees as adults; that understand the importance of choice. Joining a work-from-home company isn’t and wasn’t a lifestyle decision.  It is and was a values-driven, purpose-driven choice.

Companies that force their employees back into the office– especially those that do it in the name of company culture… or collaboration… or innovation… those companies have lost touch with what those words mean.  Because you can do all of that… digitally… And employees did– digitally– for two years.  The executives who are driving RTO are well-meaning… AND falling back on their personal experiences, not the experiences of their employees.  If they built products that way, their companies would crumble.

So what’s a leader to do if their company is demanding return to office (RTO)?  My company isn’t– hallelujah– but my answer (to myself) is still relevant– because that answer speaks to the foundational problem at the heart of this– a problem that RTO companies fail to articulate: Management– as a discipline– doesn’t yet have its chips on trust (as a north star) and it doesn’t yet know or leverage the idea that all cognitive growth comes from the right mix of challenge and support.  Too much challenge: you burnout. Too much support:  you boreout. More in part 2. 

Day 26 (Part 2). Until management– as a discipline– changes from “I’m going to tell you what to do” to “I’m here to serve you”... or to say that in terms of trust and cognitive development– from “My job is to challenge you” to “My job is to both challenge and support you”... well, until that happens, the return to office is yet another failure of management… not the people… not the managers… the discipline of management.

Framing the institutional lack of empathy– of trust– of humble service– as a move based on values and culture… isn’t just disingenuous– it actively blocks you and your company from an earnest focus on culture… on growing your people… as they grow your business.  Framing the return to office as some path to purpose or engagement or collaboration or innovation… Well, we can all do better than that.  Because… the top of the house can’t mandate a sense of belonging or shared purpose; it can’t mandate creative expression or connection.  In my experience, mandates always have the exact opposite effect.  They’re culturally corrosive.

So let me ask again: what’s a leader– a CIO– to do if they’re unable to influence their company from demanding return to office (RTO)?  Two answers.  1) My favorite saying:  change your org or change your org.  Or 2) disagree but commit… Stay… AND make sure that everyone who actually shows up at the office has the benefit of an empathetic management framework that thoughtfully and intentionally challenges them and supports their growth as adults.  It’s as simple as: Treat employees like adults.  Give them agency and autonomy and this might be a little too spicy– dignity… give them that and they’ll commute to the moon.

Day 26 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 26 Reading List:

My first book was going to be  Measure What Matters by John Doerr.  But… we read it as an executive leadership team at a previous gig… and we engaged some really expensive consultants that specialized in OKRs (Objective and Key Results)-- that’s one of the ideas John talks about in the book...  and we did all that and nothing changed.  We just took what we were calling goals last year and called them OKRs the next year and checked that box.  It’s worth a read as a book but only to understand current, conventional thinking.

The alternative: Book #1– The Delicate Art of Bureaucracy by Mark Schwartz. I’ll even be more specific. Read Chapter 10: Bureaucracies of Metrics.  The rest of the book is worth a read but chapter 10 really hits home.  If you’ve watched this series, I resemble his remarks.  I realize (always) that I’m wrong in some fundamental beliefs I hold.  And I’m thinking through what to do about them.  Mark’s book helps.

Next book: Irresistible: The Seven Secrets of the World’s Most Enduring, Employee-Focused Organizations by Josh Bersin.  It talks about Purpose-Driven Culture and how– when employees feel connected to a meaningful purpose, they become more engaged and productive.  It talks about empowerment and autonomy… Continuous Learning and Development… Inclusive Leadership… Work-Life Integration… Prioritizing employee health and well-being… Recognition and Appreciation.  It’s one of the reasons I’ll never write a business book– I have nothing new to say.

And finally, on the multimedia front, read a piece I wrote at the height of the pandemic called “Our Post-Pandemic Return to the Office of the Future.”  So google “Hood” my first name and that title.  I’ll include it in the post description.

That’s it for day 26.

Day 27 (Part 1).  This is the final week of my first 30 days– week 5– as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… Quick story.  Once upon a time, a long long time ago, there was a Tibetan monastery that had a cat– a noisy cat– that wouldn’t stop mewing (I don’t mean this) during prayer time. The head monk loved that cat but needed some peace and quiet during prayer time so he asked a junior monk to put that cat into a closet during prayer time. 

And that junior monk did it every day.  Before prayer time began, cat– closet.  After prayer time, cat released and fed and cuddled.  

Quiet time during prayers was delightful so the practice continued for years.  Even after the head monk passed on….  Prayer time? Cat– closet.  Every day.  

When the cat eventually passed, the monks went out and got another cat… not a noisy cat… just a cat… you know… so they’d have a cat in the closet during prayer time.  And a thousand years later, we all put our cats in the closet.  Doesn’t matter if we’re praying or not.  That’s where they belong at sunrise, noon, and sunset.

Modern business has a lot of cats in the closet.  But today’s topic isn’t about them.  It’s about the power of storytelling.  The need to make whatever it is you care about… come to life… to be warm and to inspire.  For your narrative to stick.

The PowerPoint version of that cat story would be cold and uninspired and underwhelming.  

And do you know why we use PowerPoints at work?  Once upon a time, a long long time ago… 

Day 27 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 27 Reading List:

Book 1: “Bird by Bird: Some Instructions on Writing and Life” by Anne Lamott.  Here’s how you read it.  Every time she uses the word writer or writing, substitute the word leader or leadership. Every time she uses the word character, substitute employees.  Plot? Projects.  Do that– and some of the best writing advice will make you a better leader.  When she talks about taking Small Steps, think iteration and Agile. Apply it as a way to tackle complex projects… incrementally. When she says “bird by bird” think sprint by sprint.  When she suggests that you “Embrace Imperfection”... leave those words alone. Read them exactly that way.

Ok… Book #2. There is no book #2 when Ann’s book #1.  If you care about improving your storytelling practice, a better use of your time– given that you’re on TikTok– would be to think about content you find compelling.  I don’t mean all that generic stuff about reusing hooks… that leads to petabytes of recycled content.  Life and business– like good content– is never about what draws your attention. It’s about what keeps it.  It’s about what keeps you coming back.  Look at my last 30 days. It’s the opposite of viral– it’s a tiny step above watching paint peel.  And yet, here we are.  That’s it for day 27!

Day 28 (Part 1).  This is the final week of my first 30 days– week 5– as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… How do you pick vendors?  And I’m answering this because a sizeable chunk of you aren’t watching the series to one day become a CIO.  You’re watching them to try to improve your sales game.

So how do I– as a CIO– find and engage companies and products?  Three answers and let’s frame them like you’re trying to sell me something: 

1) Get your customers to rave about you and I don’t mean “put their positive feedback in your pitch deck.”  I mean delight them so completely that they actively rave about you.  Because those clients have people who trust them and when they rave, you get a call.  More than 50% of the companies I quietly check out come from recommendations from people I trust.  Influence them with your great product or service.

The second way to sell me on your value: invest in inbound marketing. Because that’s how my raging curiosity is going to land me on your page.  I’m trying to get something done, I’m looking for information (not about your company but about the job I’m trying to get done) and your site is hopefully sharing real expertise and depth about that thing– hopefully without jargon… so plain English– and…. hopefully without a hard sell tied to the content… AND the inbound marketing part– your site should offer a utility or a tool that adds value to my having landed there.  If you need examples, Google “inbounding marketing”  Hubspot. Or “inbounding marketing” Grammarly.  

The third and only other way that we’ll work together: be ready when my team (not me) starts to do its due diligence about your space.  If a CIO is interested in buying something, they’re not going to buy it without actively comparing and contrasting that offering– that vendor, that service– to the top products and players in the market.  There will necessarily be a bake-off.  How do you win it?

Understand our business.  Understand our requirements within the context of that business depth.  What else? Prove that you’re financially stable… that you have a world-class operational track record… that you’re continuously investing in trust, in your people.  And prove– through evidence– the 2 most important words– “through evidence” not spin– that you’re better than your competitors.

And some extra credit for the masterclass folks: sell to the people doing the work.  When you sell to their manager or worse to their seniors… or God help you when you try to sell to their CIO or CEO, your product or service will necessarily start with deep resentment.  There’s some hierarchy-worship in sales that instructs salespeople to “sell to the decision makers”… that nothing can happen without “aligning the leadership.”  Who do you think aligns that leadership?  It’s not you.  It’s the people doing the work.  Remember how I said I only check out stuff from recommendations from people I trust?  You know who I trust the most?  The people who do the work. Gain their trust because they have mine.

Day 28 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 28 Reading List:

Book #1 is old.  I was in college when it came out.  And back then, everywhere you looked: dinosaurs.  That’s how old I am.  Book #1: “Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers” by Geoffrey A. Moore.  It’s a weird recommendation if my goal is to arm you with how to evaluate and select technology vendors because it’s a book for salespeople.  But… knowing the principles outlined in the book will help you assess vendors.  It’ll also help you sell your initiatives internally by shining the light on “the-how” behind technology adoption cycles.

Book #2: The Challenger Customer by Matthew Dixon. I think it’s the second book of a series. It’s rooted in curiosity about how customers can buy better.  And it goes into how to build consensus– when you’re selling into an enterprise– how to build consensus among multiple decision-makers during their internal decision process. For a sales book, pretty insightful.  And it gets you thinking about how to help your future customers– your leadership– sell your solution internally.  Again, useful on two front– how to manage vendors selling to you and how to sell your internal agenda.

Oh and based on a recommendation from one of the subscribers to this channel, I’m half-way through Revenue Operations by Stephen Diorio.  It’s also the first book in my book club at work– see Day 19, part 2.

That’s it for day 28!

Day 29 (Part 1).  This is the final week of my first 30 days– week 5– as a new CIO and I’m documenting how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… How do you build a sense of urgency? And before speaking to the how, it’s important to reflect on– to think deeply about– the ethics of it because when it’s done poorly, you create unnecessary panic or stress… or worse, you eat into employee nights and weekends– which should be the rare exception, not the rule.  Without getting preachy, you need to think through how important it is to be transparent and honest… to balance urgency and impact… to avoid exaggeration and fear tactics… and to respect your employees’ autonomy. Why? Our north star – trust.   

Ok… on to the how.  Step one– the foundation– is constant situational awareness.  It’s about you understanding business context… being aware of the current environment and how it impacts or could impact the specific agenda you want to promote.  Quick example: if GETTING your contract management system prioritized by the business has always been a struggle, the minute Russia invades Ukraine– the minute sanctions are imposed– that’s when your agenda suddenly gets the context it needs.  

Step two is storytelling around impact… being able to spell out the consequences of delay or inaction.  When the world throws a pebble into your pond– in my new healthcare space the example would be the recent cyber attack on a company called Change Healthcare. When everyone else is focused on the pebble hitting the water, you need to be forecasting the waves.  Not just the first couple.  All the way to shore.  And you need to package that story in a way that’s consumable by everyone: stakeholders and disinterested others.  

Built into that story is step 3: a framing of timing that says “Right now. Action is needed right now.” Good recent example: COVID.  We either arm every employee with whatever they need to work from home… right now(!)... or we start losing employees.

Step 4: demand marketing. Yeah.  Marketing’s part of the gig.  You need to create demand for that urgently needed action.  If you’re doing that at the c-level, you’ll want to customize that campaign– because that’s what it is– based on how your different stakeholders perceive urgency.  The CFO needs a different spin than the CHRO or your Chief Revenue Officer.

And finally, narrow your focus.  If this urgent matter is really urgent, why would you be focused on anything else?  That perception– like all culture– doesn’t come from your words but your actions.

The larger takeaway?  Always monitor external events– the markets, politics, the regulatory landscape, your competitors… your clients.  Align what’s happening out there with what needs to happen in here.  And use this advice sparingly.  If everything is urgent, nothing is urgent. 

One last note: and this is for every level of leader.  The wrong way to create urgency is to name-drop.  Every time you frame something that needs urgency as being something someone else wants done urgently, you’re robbing yourself of agency.  You’re a leader.  Lead with that.

Day 29 Bibliography:  I just joined a new company as CIO.  And I’m documenting how I prep for each day.  Following that daily session… I do a quick bibliography segment (this one)-- where I share a book or two that would be a good pre-read for that day's topic.  So... Lets get to it.  Day 29 Reading List:

Over the past 30 days, I’ve suggested a handful of books that would apply here: most notably The Lean Startup by Eric Ries and Grit by Angela Duckworth.  

So let’s go with some classics that capture the essence of “never letting a good disaster go to waste.”

Book 1: “Les Misérables” by Victor Hugo:  Read it.  Watch it.  Have it sung to you.  Doesn’t matter.  

Book 2: “Great Expectations” by Charles Dickens.  You probably haven’t read it since high school but let me tell ya… as an adult, it hits differently.  

And book 3: “The Odyssey” by Homer.  Fun side fact, he wrote it while moonlighting at a nuclear power plant.

That’s it for day 29.

Day 30 (Part 1).  This is the final day of the final week of my first 30 days– week 5– as a new CIO. It is (or was) a series where I documented how I prep myself daily for the role. If you want a richer explanation watch Day Zero, my first TikTok. Ok… Last day: so let’s talk mentoring.  Not why you need a mentor but why you don’t deserve one until you’re completely oversubscribed as a mentor…  giving us our final paradox as a CIO: you don’t need a mentor if you’re rich with mentees.

How can I say this without sounding sappy?  I probably can’t.

Generosity is a muscle.  If you were to go to that gym– where people are all lining up to do reps on the generosity machines, you’d notice something about the freakishly muscled people: they’re happy.

That’s my wish for you– for the people I serve– for my kids… my actual kids. When parents say they want their kids to be happy, they don’t know it but what they really mean is that they want their kids to learn to be generous… and to live a generous life.

I hope you got something out of the series.  But I hope that if you did, you’ll go to that special gym and work on being freakishly happy.

Good luck in your journey…