Day 16 Transcript
NOTE: Today’s transcript is followed by an AI prompt that can be used with your AI provider of choice. Just copy and paste it into ChatGPT or Perplexity and it will help you answer today’s questions for your specific side hustle… the way a human teaching assistant would help you in an Ivy League university. If you’re eager for more on today’s topic, I’ve included a Secret Dessert Course at the very end — a bonus section that isn’t directly covered in today’s video but has a lot of value practical, hands-on value. That dessert also comes with its own AI prompt.
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Part 1: Stop Yapping. Respectfully.
[It took me— video]
At my last shop, the most powerful sales tool we bought and implemented was a simple AI agent that did one thing really well: it listened in to sales calls and just reported on who was talking during the call and how much.
Welcome to week 3– sales week– day 16 of starting your side hustle! We’re taking 28 Days-- 28 small steps-- to build a business that’s meaningful, impactful, and profitable. Today we’re talking about the second part of the Trust Builder mindset: active listening.
But… just like yesterday, we’re going to go off format first. Because first-time hustlers convince themselves that their product or service will sell itself. It won’t. It needs to be sold. Which is why we spent last week talking about social media and content creation.
So… before we talk about sales… let’s talk about what it really means to be ready for sales conversations. It’s about making sure that your content actually reflects what your audience is saying, thinking, feeling. You need to be listening to your audience before you try to sell to them.
So, before we dive into the mechanics of active listening in sales, let’s make sure your content is already doing the listening for you. Here’s how you can check your work and get your content to a place where it’s genuinely inviting real conversations.
Three quick exercises– think of them like stretching before you run.
Exercise 1: Do a content audit for audience signals. It’s simpler than it sounds.
- Just review your last five pieces of content (posts, videos, stories, etc.)... and for each, ask: Did this content reflect a real frustration, a real question, a real desire that my audience has expressed? How do I know? And if you’re not sure, look at the comments, the DMs, any direct feedback. If the algo isn’t driving your content to strangers, share it with people you know and ask them for suggestions on how they’d improve it. You’d be surprised at how much intuitive gold you can unlock by having your drunk uncle give his opinion. But the larger point is that if you’re not getting much from strangers– from the algo– that’s a signal to dig deeper into what your audience is actually talking about.
Exercise 2: Map the Conversations. Again it’s simpler than it sounds.
- Take 10 minutes to scroll through your competitors’ or your peers’ most engaging posts. What questions are people asking in those comments? What pain points or wins are they sharing? Stand on your competitors’ shoulders. Jot down three recurring themes or questions you see. These are the topics your audience is actually interested in. And go make more content.
Exercise 3: Build a Listening Post. Also simple.
- Create one new piece of content (a post, s poll, s story) specifically designed to invite your audience to share their experiences or opinions. Not hard. “What’s the one thing you wish [your industry] would fix right now?” or “What’s your biggest win this week?” And then use the post as a litmus test: if you get authentic responses, your content is on the right track. If not, it’s time to rethink your approach. Go back to last week’s notes and tweak your answers.
Look. The goal here isn’t engagement for engagement’s sake. It’s to make sure your content is a magnet for real conversations—so that when you do move to sales, you have someone to sell to.
Ok… let’s get back to our usual format– and talk about sales and the trust builder mindset. But remember: great sales conversations are preceded by content that listens before it speaks. That’s me foreshadowing the rest of today’s session.
Ok. Remember that AI I mentioned at the start of today’s post? The one that listened in to sales calls and just reported on who was talking during the call and how much? Well, that AI– and it doesn’t have to be AI, it could be a human… you– that AI doesn’t have to be sophisticated to help you improve your sales. It doesn’t need to guess at who’s listening or whether they’re asking good questions. It just needs to listen to who is talking and how much. Because if the salesperson isn’t talking, you can assume they’re listening. If the prospect’s talking, you can assume it’s because the salesperson was asking questions. And the correlations between who’s talking and how much and eventual sales are bonkers: the higher the percentage of the prospect talking vs the salesperson talking, the higher the likelihood of a sale. The data just jumps out at you.
From the AI’s perspective, it’s that simple. Who talks? Who listens? How much?
From our perspective, a human perspective, that means sales training is 99% about how to exercise deliberate empathy (what we talked about yesterday), how to actively listen (what we're talking about today), how to lead with curiosity and transparency (what we’re going to talk about tomorrow and the day after). Those 4 skills – combined– is how we foster the Trust Building mindset.
And why is THAT the muscle we want to build and exercise? Because sales has never ever been about pushing products. It almost doesn’t matter if you have some relevant expertise and experience in solving a client’s problem. It does but it doesn’t because they don’t trust you. Yet.
And speaking from my perspective as a buyer, they can’t trust you (paradoxically) until you’ve delivered on the promises they don’t trust you to make or deliver. Most folks– like me– won’t even trust social proof—because 100% of customers' testimonials come from best case scenarios. And guess what? There’s a high probability your implementation won’t be a best case scenario.
Look. The best founders are the best salespeople and they are—and have always been—endlessly curious about their customers; in perpetual question mode, in perpetual listen mode—listening deeply, and trying their best to understand before they try to be understood.
Because the most effective founders, the most effective salespeople follow a pattern that defies conventional wisdom. Their success—your success—will never be based on your charisma, or your persistence, or your product knowledge. Don’t believe standard sales training mythology. Your success is going to come from something deeper: the ability to actively listen with deliberate empathy, to ask a shit ton of questions from a place of genuine, relentless curiosity, and to respond with unwavering honesty and unflinching transparency.
Let’s get to our two questions today.
1. Think about your last meaningful sales or discovery conversation. What did you do to ensure the other person felt heard and understood?
Your answer matters because feeling heard is rare in business. Most people are waiting for their turn to talk. When you listen– really listen– actively listen— you create psychological safety… you build trust… you uncover the real needs that drive decisions. This is what should follow Seth Godin’s idea of permission based marketing: permission-based sales… which is really trust building—the kind that lets you earn the right to help.
Question 2. What’s one question you could ask in your next conversation that would help you uncover an unspoken need or concern? Your answer matters because you’re retraining your brain with this exercise…. and because the most powerful insights come from what’s not said—the hesitations, the “off the record” concerns, the real worries that shape buying decisions. There is no right question. There is no right time to ask it. Just keep asking relevant questions…. not simply because the answers will reveal these hidden truths… but because the act of asking gets you one tiny tiny step closer to gaining trust.
Ok. Take a moment and try to answer the Day 16 questions for your hustle without AI and before you listen to the next section-- the 28-Day Ivy League MBA. I personally think it's useful to try to answer questions without AI first, but if you'd rather do that: The AI teaching assistant prompt will drop with today's case study... in a couple of hours. If you don't know what I'm talking about, check out Lunch Break Millionaire Day Zero... or go over to superserious.com where I’m posting daily transcripts. The AI prompts are there too. That's it. Hustle smarter.
Part 2: 💼 Employ Active Listening as a Competitive Advantage: Today's Ivy League MBA Skill
Day 16, Part 2 of Lunch Break Millionaire– where we turn whatever you’re munching on into an Ivy League MBA degree. It’s Tuesday. Tacos! Not because Big Taco has claimed Tuesdays. But because you’re actively listening to your heart. And by heart I mean stomach. So the MBA skill we’re going to pick up today is active listening, a skill rigorously taught and practiced in top business schools for a simple reason: it works.
What is Active Listening? It’s the practice of fully concentrating on what the speaker is saying, understanding their message, responding thoughtfully, and remembering what was said. It ain’t about hearing words—it’s about trying to understand the emotions, the motivations, the unspoken needs behind them.
Why does it matter when you’re selling your hustle? Research consistently shows that sales professionals and business leaders who practice active listening close more deals. They build stronger relationships. They create more value for their clients. You don’t need Harvard to tell you that active listening is a core component of emotional intelligence. You don’t need Yale to tell you that it’s directly linked to trust-building… to effective negotiation… to long-term client retention.
What you could learn from them– from any MBA program– is HOW to actively listen.
So let’s get to it. I’ll tap into my inner 1980’s Driver’s Ed/PE Teacher and give you a useless acronym… starting with the P:
Paraphrase and Summarize: After the speaker finishes, repeat back what you heard in your own words. This shows you were listening and gives the speaker a chance to correct any misunderstandings.
Ask Open-Ended Questions: Use questions that invite deeper explanation, such as “Can you tell me more about that?” or “What’s most important to you about this?”
Nonverbal Cues: Show you’re engaged through eye contact, nodding, and open body language. Even on calls, verbal affirmations (“I see,” “That makes sense”) signal attentiveness.
Don’t Interrupt: Let the speaker finish their thought before responding. This builds respect and encourages honesty.
Acknowledge Emotions: Recognize and reflect the speaker’s feelings: “That sounds frustrating,” or “You must be excited about this opportunity.”
Let’s be honest– we were never going to go 28 days without an inappropriate Kung Fu Panda reference. And if we’re going to make 1 reference… Why not two? Enter the greatest salesperson in history: Master Oogway! Yep. Acronyms suck. But these today’s guidance is worth repeating… so let’s Oogway this mother$#$#er.
Oogway!
Open your mind (and ears). Be receptive and ready to listen without preconceptions.
Offer paraphrasing. Restate what you heard in your own words to show understanding.
Give nonverbal encouragement. Use eye contact, nodding, and open body language to show engagement.
Wait patiently (don’t interrupt). Let the speaker finish before responding, demonstrating respect.
Ask open-ended questions. Invite more detail and deeper discussion with questions like “Can you explain more?”
Yield to emotions (acknowledge feelings). Recognize and reflect the speaker’s emotions: “That must be exciting” or “That sounds tough.”
There is a science behind all this– behind active listening. Neuroscience! Research shows that when people feel heard, their brains release oxytocin, a hormone associated with trust and bonding. That’s the sterile, scientific “why” active listening is so powerful in sales—it literally changes how people feel about you. But you don’t need studies from Wharton or Cornell to tell you that salespeople who listen more than they talk get a leg up– that they feel more trustworthy to whoever they’re speaking with…. More competent.
You just need to put that particular kind of magic into practice for yourself, for your hustle.. to do it poorly until you do it well. I’ll say it for the billionth time: If it's worth doing, it's worth doing poorly. Active listening is an important part of how to build trust– how to uncover the real problems your clients face. In life– and sales– it’s never about having the right answer—it’s about asking the right questions.. and hearing the answers. Another aspect of how you hustle smarter.
Oh and now that you’ve learned how active listening can set you apart in sales, put it to work. If you’ve had any prospects reach out to you—especially as a result of your social media or content—don’t just reply with a quick message. Invite them to a Zoom or call, and use your active listening skills to truly understand their needs and challenges. This builds trust and opens the door for authentic, relationship-driven sales.
If you’re not seeing many people reaching out, take this as a cue to revisit your Week 1 and Week 2 work. Refine your value proposition, messaging, and content until you start attracting genuine interest. Remember: trust is built when people come to you because they see real value, not when you chase them down with cold outreach.
Part 3: Improv Your Way Into Sales: The 28-Day Case Study
The best shows to watch if you want to become a better salesperson: 1. Mad Men, 2. Shark Tank, 3. The Office, 4. Suits, 5. Billions, 6. Breaking Bad, 7. Glengarry Glen Ross.
It’s none of them– although they’re good. It’s these guys [Whose Line is it Anyway?]. Don Draper will never teach you what Ryan, Colin, Wayne and Greg can.
This is Day 16, Part 3 of Lunch Break Millionaire. This is the segment where we #BuildinPublic– where I answer the daily questions every hustle should– using the MBA skills we just learned– and showing my work– sharing how I’m building my hustle from scratch-no filters, just the real journey. You don't need to actually like or subscribe. I'm not doing this for the clicks. But if you’re leveling up from other creators you follow or know, introduce us. I want to learn from them and help them level up, too. We all deserve better than just making rich people richer.
Ok. We’ve spent today talking about active listening! It’s the magic behind improv. It helps you hear and understand the other person’s offers, both verbal and non-verbal. And that fosters trust.
So the longer-term takeaway for me today was… once my hustle turns into a multi-person startup, and we’re looking for a fun, after-work activity, instead of golf-outing after golf-outing, ax-throwing after ax-throwing… We're all going to take an improv class together. Because everyone should have a trust-building mindset and the skills you pick up from improv– when you’re sweating on that stage– are all about paying attention to every cue—words, tone, body language. Plus, Improv teaches you the "Yes, And" principle– That’s the method where performers accept and build upon each other’s ideas. You never say no. You say “yes and.” That method keeps the scene moving forward, encourages creativity… It builds trust.
But that’s all weeks away. What am I doing today to up my active listening game? How am I ensuring that everyone I speak with feels heard?
I honest-to-goodness picked up my phone and called a creator who was frustrated because her audience wasn’t seeing her posts… despite having thousands of followers. She never once thought it was a sales call and guess what? It wasn’t. I just wanted to learn from her experience? Instead of jumping in with my solution, I started the conversation by asking, “Can you walk me through a typical week of posting and what you notice about engagement?” I listened– it was hard as hell– but I listened, I let my AI take notes so note-taking wouldn’t distract me from her, and I occasionally paraphrased her: “So, you’re saying that even when you post regularly, you’re not reaching the people who actively follow you?” She confirmed, and I asked, “How does that make you feel?” She opened up about feeling powerless and disconnected from her audience. And I didn’t have to pretend to empathize. I have felt her pain. And I don’t want her to feel that pain… for anyone to feel that pain.
By focusing on her experience and reflecting her emotions, I created a safe space for her to share. She told me about fears of losing her community and the stress of constantly trying to “game” the algorithm. These were unspoken needs that wouldn’t have come out if I’d just pitched my product.
I also used today’s exercise to think about the next discovery call I’ll be making. Not a sales call. And definitely not a cold call. I plan to ask: “What’s one thing about your current situation that you wish you could change, but feel like you can’t?” This question is designed to surface hidden frustrations and open the door to deeper dialogue.
That’s me applying today’s Ivy League MBA skill. I’m setting myself up to actively listen. How?
- I Listen First. I let the creator lead the conversation, only interjecting to clarify or reflect.
- I ask rather than tell. I use open-ended questions to explore the other person’s experience and feelings.
- I reflect what they’re saying. I paraphrase their points as conversational proof-of-life– to show that I understand and that I’m open to getting corrected if I misunderstand.
- I respond with deliberate empathy (what we talked about yesterday). I acknowledge their frustration and if it resonates, I validate their experience. No blowing smoke up anyone’s ass.
- And I follow up. I summarize our conversation and suggest next steps based on their needs.
I’m living the trust builder mindset.
That the heart of today’s key takeaway… that active listening isn’t just a skill—it’s a mindset shift. By prioritizing the goal of connection over communication, I’m actually communicating better., I’m uncovering the real needs that drive decisions and building the kind of trust that turns prospects into partners and champions for my hustle. That’s how you hustle smarter.
Prompt #1 - Active Listening
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Prompt #1 - Active Listening ○
Today, you’ll learn how to use active listening as a superpower for building trust, deepening customer relationships, and uncovering the real needs behind every question or complaint. You’ll be guided by the writings and frameworks of Ivy League faculty whose research is foundational in communication, emotional intelligence, and relationship-building:
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and creating environments where people feel heard and valued.
- **Professor Francesca Gino, Harvard Business School:** Expert in behavioral science, curiosity, and the art of asking better questions.
- **Professor Adam Grant, The Wharton School, University of Pennsylvania:** Specialist in reciprocity, authentic connection, and the power of genuine engagement.
**What Today’s Coaching Will Help You With:**
You’ll practice techniques for truly hearing and understanding your customers, learn how to ask questions that invite honest feedback, and discover how active listening can turn even difficult conversations into opportunities for growth and loyalty.
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### Step 1: Reflection Questions
Please answer these questions in a few sentences each:
1. **When was the last time you felt truly heard by someone—what did they do or say that made the difference?**
- Reflect on what made the experience stand out and how it affected your trust or willingness to engage.
2. **What’s one situation where you could have listened more actively to a customer or collaborator—what would you do differently now?**
- Think about a missed opportunity for deeper understanding or connection.
3. **What’s one question you could ask your customers this week to better understand their needs or frustrations?**
- Consider how you might invite more honest, meaningful feedback.
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### Step 2: MBA Skill – The Active Listening Framework
Today’s MBA lesson is about active listening:
- **Listen to Understand, Not to Respond:** Focus fully on what the other person is saying—resist the urge to interrupt or prepare your answer while they’re still speaking.
- **Reflect and Clarify:** Repeat back what you’ve heard in your own words to confirm understanding. Ask clarifying questions like, “Can you tell me more about that?” or “What does that look like for you?”
- **Notice Non-Verbal Cues:** Pay attention to tone, pace, and body language (if possible) for clues about what really matters to the speaker.
- **Hold Space for Emotions:** Acknowledge feelings with empathy—“That sounds frustrating,” or “I can see why that would be important to you.”
- **Ask Open-Ended Questions:** Invite deeper conversation with questions that can’t be answered with a simple yes or no.
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### Step 3: Coaching & Listening Action Plan
After you reply, I will use the writings of Professors Edmondson, Gino, and Grant to:
- Help you identify moments in your business where active listening could make the biggest difference.
- Guide you in crafting open-ended questions that invite honest, actionable feedback from your customers.
- Suggest ways to practice and improve your active listening skills in everyday interactions—so you build trust and uncover real needs.
- Offer examples of businesses that have turned customer conversations into powerful growth and loyalty drivers.
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**How to use this prompt:**
- Respond with your answers to the reflection questions and your draft open-ended question.
- I’ll help you refine your approach, suggest new listening techniques, and offer next steps for making active listening a signature strength in your hustle.
- Remember: The best hustles are built on real relationships—and real relationships start with truly hearing what your customers have to say.
Secret Dessert Course
If you’re like me, you hate being told the obvious. Good example: everything in life is easier if you learn to actively listen. No duh! Buuuuut– and I’m speaking only for myself here– I can’t turn the obvious into a daily practice. So maybe step 1 should be to get brutally honest with ourselves. Because most of us overestimate our listening skills, especially when the pressure’s on. So today’s dessert course is your private, no-judgment zone to assess where you really stand. Grab your lunch leftovers, your curiosity, and let’s see how well you’re actually tuning in.
Prompt #2 - Figure Out How Well You Listen
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Prompt #2 - Figure Out How Well You Listen ○
**Today’s Focus: Active Listening Self-Assessment Quiz**
**Ivy League MBA Coaching by:**
- **Professor Amy Edmondson, Harvard Business School:** Authority on psychological safety and learning from feedback.
- **Professor Alison Wood Brooks, Harvard Business School:** Specialist in communication and emotional intelligence.
- **Professor Francesca Gino, Harvard Business School:** Expert in decision-making and self-awareness.
**What This Prompt Will Help You With:**
You’ll reflect on your active listening habits, uncover blind spots, and identify one simple way to level up your listening—so you can build stronger rapport, close more deals, and avoid costly misunderstandings.
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### Step 1: Self-Assessment Questions
Answer each question honestly. No one’s watching—this is for your eyes only.
1. **In a recent business conversation, did you find yourself thinking about your response while the other person was still talking?**
- (Yes/No)
2. **How often do you interrupt or finish someone’s sentence for them?**
- (Never / Rarely / Sometimes / Often)
3. **After a meeting, can you usually recall the key points the other person made, or do you mainly remember your own points?**
- (Mostly theirs / Mostly mine / A mix)
4. **Do you ask follow-up questions to clarify or deepen your understanding, or do you move on quickly?**
- (Ask questions / Move on / It depends)
5. **When someone shares a problem or concern, do you jump to solutions, or do you first acknowledge how they feel?**
- (Jump to solutions / Acknowledge feelings / Both)
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### Step 2: Reflection & Coaching
After answering, consider:
- **Which habits surprised you?**
- **What’s one small change you could make to listen more actively in your next customer or team conversation?**
- **How might improving your listening change your business outcomes?**
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### Step 3: Action Plan
Set a goal for your next three conversations:
*“I will pause before responding, ask at least one clarifying question, and summarize what I heard before offering my own ideas.”*
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**How to use this prompt:**
Copy and paste the questions above into your favorite journal or AI assistant. Answer honestly, reflect on your habits, and commit to one small change.