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by Daniel Stillman
Welcome to The Conversation Factory, where I investigate how to create change through changing conversations. Each episode I'll talk to an amazing conversation designer about how to Amplify, Shift or Transform conversations in Organizations, Teams, Communities and our own lives.
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- Aug 18, 202653 min
Meet Your Members Where They Are with TightKnit CEO Zach Hawtof
My guest is Zach Hawtof, CEO and Co-founder of TightKnit.AI, a platform for businesses that run their communities on Slack. He is also a community builder for people who do or who could potentially use his company's product. He and I are both members of Fabrik, where I host a Founder's Forum that Zack often joins. In this conversation, we discuss community building, the difference between an audience and community, and how to introduce yourself (and get people to introduce themselves) at events. Zach also shares his philosophy on building and selling B2B SaaS products in the AI era. One of my favorite moments in this conversation is this question: What if you built your second company first — the one you actually believe in, instead of the one you'd build just to prove you could, or the rational play? The one that might create real impact, rather than just another zero on the balance sheet? Zach's metaphors for this kind of business are just as human as he is: the Costco of B2B SaaS or the Corner Deli of Startups - a place you work with because you like working with them, and you get great service! We also get into why you can't vibe-code your way to a real community or a real product. Since the tech is the "easy" part now, the actual moat is understanding why people don't do things. The founders who win are the ones who understand a problem so deeply that people trust them to solve it for them today and in the future. I'm also grateful for Zach being willing and able to unpack his relationship with his co-founder Stephen, who he's known and worked with for 10 years. AI can't be your co-founder. Zach makes the case for something AI can't replace: a person who can actually say "in my experience, I think you should do this," and mean it. A real human co-founder, who will disagree with him, but can trust his gut and back him 100% anyway. Zach describes his "butterfly" thinking style and contrasts it with Stephen's "thinker" mode, and believes that their different styles give them more surface area for problem solving. I think that's still core, in all the co-founder interviews I've hosted - respecting and even admiring your co-founders' different way of thinking and approaching the world. I've been able to piece together an interesting checklist for how to navigate co-founder disagreements from this conversation - especially when the conversation is about what to do now vs what to do later or what not to do - what I've heard described as the Woodstock Paradox: When the organizers of the first Woodstock concert were running out of time and money, they had to make a hard choice: Build a stage and bathrooms so that they could actually have one of the best concerts ever Finish building a fence so that they could charge admission to every person who showed up They chose experience over profit and created a moment that defined a decade. How to disagree (well) with your co-founder in Four Easy Steps: Zach leads with the most essential check: When you feel friction, slow down first. Tension is evidence of difference. Slow down so you can notice it - like walking to a location vs taking a bike or a car. Slowing down just a bit can make all the difference in the quality of the decision and the quality of the relationship after the decision. The second is a simple idea that's hard to apply in practice: the reversibility check. If it's an irreversible decision, slow down even more and think a little harder. If it's a two-way, easily reversible decision, it's best to optimize for speed. The third is a strategic check, a set of questions to suss out ROI: will solving this meaningfully move things forward for our customers? If we don't solve it, is it going to become our biggest problem later? This comes down to really being able to define the return on investment and work through the trade-offs with your co-founder. The final check, which he doesn't mention in the opening clip - it comes up later in the conversation - is that the real challenge after feeling the friction, having the reversibility and strategy conversations…is that sometimes, if your co-founder still feels strongly about something, to trust that there's a real reason behind it, even if they can't fully explain it. Making low-signal gut decisions is sometimes necessary, and trusting someone else's gut over your own is part of being in a good relationship. Links Zach on LinkedIn: <a href= "https://www.linkedin.com/in/zhawtof/"
- Aug 18, 20261h 12m
The Science of How Small Talk Can Add Up to a Big Life with Dr. Gillian Sandstrom
Welcome to the Conversation Factory, conversation designers. My guest today is Dr. Gillian Sandstrom, a psychologist at the University of Sussex who studies what happens when we talk to people we don't know. She is a scientist of Small Talk. Her book, Once Upon a Stranger, is all about the science of how small talk can add up to a big life. And I know exactly what you're thinking. I hate small talk. I hear this all the time from plenty of senior leaders. "It's dumb, it's a waste of time!" they say. "Let's just get on with the real stuff. Big Talk!" The research does not support your aversion. Your brain is telling you that you dislike small talk because it feels hard. That hardness is the resistance we feel toward any new skill, not evidence that it isn't worth doing. Small talk is a learnable skill, and it is far better for us than we think. It's like medicine we don't want to take that can heal us tremendously. Dr. Sandstrom's data is clear: small talk is a life skill. My anecdotal data shows that small talk is also a leadership skill. A leader who says "I hate small talk" is missing out on opportunities to intentionally create connection and community, to learn what's really going on with their team, to build a little psychological safety into every meeting and interaction. Some of the leaders I coach, and the leaders in the forums I facilitate, have made their peace with this by telling themselves, "Small talk isn't for me, it's for them." And they're right that it's an act of service, creating a moment of connection for everyone else in the room. But here's what I think they're missing: how much they themselves might come to enjoy it, and how much they will learn from it. In fact, the ones who've been willing to do the experiment, to lean into small talk, have found it has made their professional lives more enjoyable and surprised their spouses to boot. Now, maybe you're thinking: but Daniel, I'm an introvert. That's fair. But here's one of the most surprising things in Gillian's research: Introverts enjoy social interaction just as much as extroverts, and they're just as good at it. And across the board, these conversations that sometimes we feel resistance to and anxiety about usually go far better than we expect. And here's the part that surprises people most: even when efficiency feels like the whole point — getting your coffee, getting through the line — taking a moment to actually connect leaves you happier and more connected. And you're still waiting for that coffee either way. I've seen this efficiency work against leaders in meetings because I find that a meeting that starts cold stays cold, while a meeting where someone takes those first few minutes to actually welcome people in comes alive and leads to better work. So let's review: Efficiency is overrated. Creating micro-spacious moments to connect with people is nearly always more enjoyable and beneficial than we think Even if you're an introvert, you can be good at talking to people AND enjoy it as much as an extrovert Talking to people is a learnable skill. We reference one of my favorite Pride and Prejudice moments where Mr. Darcy and Elizabeth Bennet discuss how talking to strangers is a learnable skill like playing the pianoforte, not a fixed personality trait. Gillian has a framework in her book, the acronym QUICK. I refer to it in the interview, but we don't break it down. How to QUICK-ly break down talking to people into manageable skills and mindsets QU is for Questions, and her favorite is as simple as "whatcha doing?" You see someone photographing a fence, or fiddling with something in the park — "whatcha doing?" — coming from a place of real curiosity. I've discovered that in meetings, you can ask almost anything at the beginning to get people talking and to create a moment of spaciousness. One CEO I coached loved asking icebreaker questions. On a day when I was observing the executive leadership team, he asked everyone, "What is your favorite sandwich?" One amazing thing was that everybody answered the question differently. Each person's answer was a micro-manual to understanding more about that person, because the CTO answered differently than the COO, who a
- Jun 29, 20261h 16m
Founder Unfriendly - Under the Hood with Charlie O'Donnell
Welcome to The Conversation Factory, the podcast where we explore the deep mental models that turn difficult conversations into opportunities for clarity and alignment. Founding a company is often viewed as a binary choice: win big or fail completely. But what if success isn't about total victory (what would that even mean?) but about mastering the long game, the infinite game, and the quality of the relationships you make along the way? In this episode, I sit down with seasoned venture capitalist and author of Founder Unfriendly, Charlie O'Donnell, to explore the communication strategies and clear thinking that fuel successful entrepreneurship. Charlie is a 20-year VC veteran, a Partner at Brooklyn Bridge Ventures, and an active presence in the NYC Startup scene…and his recent book is a very helpful guide for the 99% of founders who will struggle to fundraise. We dive deep into the essential, often-avoided conversations that make or break a startup. Charlie explains why your co-founder is your most important hire—they provide the deep trust, honesty, and pushback that AI really can't - you can't walk away from a real person like you can from your laptop - and a real partner will want to be real honest with you in a way an employee just can't. He also explains why key documents, such as a structured financial plan and weekly hypothesis-and-progress conversations rooted in OKR thinking, are not "fiction" but an essential anchor for strategic conversations, even at an early stage. We also talk about the power of a "conversational judo" approach to tricky investor conversations and how to marshal the inner resources to steer difficult questions towards your strengths. One thing I really loved about this conversation was the moment I chose for the opening quote - Charlie was pointing to an idea near and dear to my heart that I've been noodling about - Emotional Metabolism. As he says, you can't tell someone to feel differently than they feel. No one has an emotional metabolism that is that fast! If you don't believe me, reflect back on what happened the last time you told someone to calm down - I'm guessing the opposite happened? I often deal with difficult emotions on coaching calls - even leaders in the C-Suite or C-minus suite sometimes feel impostor syndrome, struggle to step into boisterous team debates, or feel like they don't belong or don't have anything worth hearing at networking events. And telling them NOT to feel those emotions and to do something different is not an effective way to change their outcomes. While I'm not a therapist, I sometimes have to create a therapeutic experience for my clients, based on what I understand is best practice, to create a space to process those emotions. Accepting that they feel their feelings is an essential first step. Feeling these difficult feelings fully can help you metabolize them…and for certain, avoiding feeling our feelings doesn't make them go away, it just stuffs them down - metastasizes them, more than metabolizes them. But feeling our feelings is only one step towards fully metabolizing them into something useful. Eventually, we have to learn to calm those feelings when they return - which they very well might. We can calm those feelings through meditation, journaling, and breathing, but we can also calm those feelings by stepping outside of ourselves and focusing on others instead. Charlie suggests a healthy coping mechanism for our anxieties, which is not to pretend that we don't experience them but to think more about what another person needs to hear than what we feel - we could call it the "get out of my head and get into their head" approach - in this case, focusing on an investor's desire to, as Charlie describes it, buy a "ticket to a very large outcome" and focus on how to craft our messaging towards that goal. And we dive into a very worthwhile and very likely conversation founders will face - how to strategically design the conversation after a startup failure, where Charlie argues that avoiding investors and ghosting them is an (understandable) mistake, but one that surrenders control of your narrative. Instead, Charlie shares how to lean into hard conversations with some clear 2 X 2 thinking! This episode is jam-packed with actionable advice for navigating the complexities of raising and running an impactful company. Links https://www.thisisgoingtobebig.com/ What's next after you lose someone's money? https://www.thisisgoingtobebig.com/blog/2025/11/29/whats-next-after-you-lose-someones-money <a href= "https://www.brooklynbridg
- Apr 20, 202654 min
The Power of Nature to Fuel Creativity with Warren Berger
Get free chapters of my book, Good Talk, and master the art of conversations big and small: https://www.danielstillman.com/good-talk Please support the podcast! 💌 subscribe on Spotify: https://spoti.fi/3QzcPAW 💌 iTunes: https://apple.co/4ifh6pb or with a monthly contribution here: https://bit.ly/support-tcf-monthly one-time donation here: https://bit.ly/support-tcf-once Check out https://theconversationfactory.com/podcast/the-power-of-nature-to-fuel-creativity-with-warren-berger for the full transcript and video highlights. Warren Berger, a bestselling author and "Questionologist," advocates for reconnecting with deep, purposeful questioning by taking our most important questions into nature—specifically, a 2-hour walk in the woods followed by 3 hours of focused work. He argues that in the digital age, our creativity is being eroded by constant connectivity and AI-generated "good-enough" answers, which prevent us from wrestling with truly meaningful problems. Drawing on Henry David Thoreau's philosophy, Berger promotes this practice as a way to reclaim breakthrough thinking and move beyond surface-level solutions. Beyond the woods-and-work framework, Berger emphasizes the craft of questioning itself—encouraging people to root their questions in deep empathy, design them for maximum impact, and sequence them thoughtfully within conversations. His "Question sandwich" approach demonstrates how context and framing shape how questions land with others, ultimately enabling more powerful and authentic dialogue. Key Moments 00:00 Exploring Creativity and Nature 07:32 The Role of Questions in Organizations 11:23 The Power of Collaborative Inquiry 18:54 Designing Beautiful Questions 23:21 Empathy in Questioning 24:50 The Outside-In Method for Creativity 28:22 Nature's Impact on Creative Thinking 30:30 Balancing Structure and Flexibility in Creativity 34:15 The Commitment to Creativity 39:31 The Role of Companionship in Focus 42:57 Defining Creativity and Its Broad Applications Links Here's a recent NYT article from Warren talking about his experiences with nature's effects on creativity - specifically, an area in Ireland called the Burren. https://archive.ph/tgnrG You can find more information about the Burren Creativity Experiment here. https://www.burrencreativityjournal.com/creative-experiment Here's a NYT article talking about my cousin's company, Caveday, that we mentioned. https://archive.ph/sC7pX
- Sep 10, 202557 min
Leading with Respect with Marcy Syms
Marcy Syms is a pioneering businesswoman and advocate for respect in leadership. She's seen leadership fads come and go. She was a CEO when people still thought "women shouldn't do that sort of thing" And she's done something many folks have never had to endure - shuttering her family's business while making her key creditors whole - an act deeply in line with her core value of respect. Marcy shares insights from her journey in the retail industry, her experiences with leadership dynamics and her advocacy for the Equal Rights Amendment - something she hopes to see made part of the constitution while she's still around to enjoy it! Why Respect? 🗝️Respect drives sustainable growth - respect for your team allows them to feel empowered to be the face of your business and to build the processes and systems that make growth sustainable. 🗝️Giving respect helps you get respect - starting first, leading the conversation with respect at the core helps get things done, especially in times of stress and turbulence. 🗝️Respect is outer behavior and inner work - to make it a core habit and your default behavior takes strategic reflection and personal growth. Check out the full conversation 👇 🎙️ Spotify: https://spoti.fi/3QzcPAW 🍎 Apple: https://apple.co/4ifh6pb 📺YouTube: https://www.youtube.com/@danielstillman-TCF-podcast 🌐more episodes at https://theconversationfactory.com/listen And please subscribe on Spotify or iTunes! Also! support the podcast with a monthly contribution here: https://theconversationfactory.com/conversation-factory-insider or a one-time donation here.: https://dastillman.gumroad.com/l/dscoffee Don't have time to watch or listen to the full episode? To learn more about leading conversations more powerfully and beautifully, watch these short clips 👇 👀make respect a habit and start from within https://youtu.be/tmURMgvcnIs 👀How to Respond to Disrespect with Dignity and Strategy https://youtu.be/f21aAalKGLU 👀To Scale you need to Respect your team https://youtube.com/shorts/HczFY9-ASFw 👀Leadership Balances Top Down Strategy and Bottom up Insights https://youtube.com/shorts/57yWfiQtykw 👀Know your board as humans https://youtu.be/eH5Mv95iunE One Takeaway to not forget: Fight for the ERA! Marcy shares how she sees the ERA as the ultimate sign of respect and continues to fight for women's full inclusion in the constitution. Watch here: https://youtu.be/YAbEAqIVxzU Key Links: Marcy's book: Leading with the Respect Marcy's website
- Aug 25, 202557 min
The Seven Everyday Habits for Transforming Systems
Download free chapters from Good Talk and master the art of conversations big and small: https://www.danielstillman.com/good-talk Listen now 👇 🎙️ Spotify: https://spoti.fi/3QzcPAW 🍎 Apple: https://apple.co/4ifh6pb And please subscribe on Spotify or iTunes! Also! support the podcast with a monthly contribution here: https://theconversationfactory.com/conversation-factory-insider or a one-time donation here: https://dastillman.gumroad.com/l/dscoffee Full show notes: https://theconversationfactory.com/listen SUMMARY In this conversation, Adam Kahane discusses the complexities of transforming systems, emphasizing the importance of understanding systems thinking, collaboration, and the role of individual contributions. He shares insights from urban transformation examples, the significance of culture, and the necessity of engaging with systems responsibly. Kahane introduces seven habits for transforming systems, highlighting the importance of finding cracks as opportunities for change and the balance between closeness and distance in understanding systems. KEY TAKEAWAYS Systems can't be transformed without understanding them. Transformation requires many people to do many things. You can't just change a system by force. Look for what's unseen in a system. Forget your perfect offering; there's a crack in everything. Acting responsibly is crucial for transformation. We all have bells we still can ring. Engaging with the system is a collective activity. You can make wiser decisions by understanding others. Change how you think, change how you are. CHAPTERS 00:00 Understanding Systems for Transformation 02:29 The Role of Collaboration in System Change 05:05 Insights from Global Examples 07:46 The Importance of Proximity in System Change 10:10 Cracks and Leverage Points in Systems 12:46 The Journey of Transformation in South Africa 24:31 The Journey of Collective Engagement 24:55 Radical Engagement: Understanding System Transformation 26:13 The Role of Outsiders vs. Insiders 27:41 Spotting Cracks: Micro Interactions in Systems 28:46 The Art of Persuasion vs. Convincing 30:29 Granular Habits for System Transformation 31:41 Relating in Three Dimensions 33:43 Understanding the Seven Habits 39:32 Acting Responsibly in Systems 43:21 Finding Light in the Cracks LINKS Learn more about Adam's work at www.reospartners.com , www.reospartners.com/adamkahane and find him on twitter/X at @adamkahane
- Aug 6, 202549 min
Innovation, Connection, and Conscious Leadership with Othership CEO Robbie Bent
Get free chapters of my book, Good Talk, and master the art of conversations big and small: https://www.danielstillman.com/good-talk Please support the podcast! 💌 subscribe on Spotify: https://spoti.fi/3QzcPAW 💌 iTunes: https://apple.co/4ifh6pb or with a monthly contribution here: https://bit.ly/support-tcf-monthly one-time donation here: https://bit.ly/support-tcf-once Check out the episode page for the full transcript and video highlights. Episode page: https://theconversationfactory.com/podcast/innovation-connection-and-conscious-leadership-with-othership-ceo-robbie-bent AI Summary: Introduction and Connection: Daniel Stillman introduces Robbie Bent, highlighting the connection through mutual acquaintance Robbie Hammond. Inception of OtherShip: Robbie shares the story of starting with a backyard ice bath, fostering community connections without the influence of alcohol. Innovative Experiences: Discussion on unique offerings at OtherShip, such as comedy nights and men's work sessions, blending wellness with entertainment. Creativity and Experimentation: Robbie emphasizes the importance of allowing creativity to emerge through testing and iteration. Challenges and Growth: Insights into the challenges faced in expanding OtherShip, including managing stress and maintaining personal well-being. Community and Relationships: The role of community in personal and business growth, with Robbie working closely with his wife and friends. Facilitating Conversations: The significance of open communication and addressing conflicts early in both personal and professional settings. Future Aspirations: Robbie's excitement about expanding OtherShip and continuing to innovate in the wellness space. Links Othership - https://www.othership.us/ Follow Robbie Bent on Instagram | LinkedIn IG: https://www.instagram.com/robbiebent/?hl=en LI: https://www.linkedin.com/in/robbiebent/
- Jul 24, 202558 min
The Founder's Financial Compass: Navigating Emotions and Assumptions with Fractional CFO Lauren Pearl
Get free chapters of my book, Good Talk, and master the art of conversations big and small: https://www.danielstillman.com/good-talk Please support the podcast! 💌 subscribe on Spotify: https://spoti.fi/3QzcPAW 💌 iTunes: https://apple.co/4ifh6pb or with a monthly contribution here: https://bit.ly/support-tcf-monthly one-time donation here: https://bit.ly/support-tcf-once Check out https://theconversationfactory.com/podcast/the-founders-financial-compass-navigating-emotions-and-assumptions-with-fractional-cfo-lauren-pearl for the full transcript and video highlights. Money! It can be an emotional topic. But, as my guest on today's podcast, fractional CFO Lauren Pearl says, it's emotional for everyone in different ways! In this episode, Lauren reveals her perspectives on how to approach these difficult conversations. Given how many leaders she's worked with, we also explore her thinking about effective leadership, intentional decision-making, and how it's crucial for founders to be endlessly unafraid to ask why. She makes an excellent point in the opening quote: we often listen to respond. And when we respond from that place we're missing a lot of crucial information. It's hard to do but it's so important to take the risk to slow down, to ask why and to be a little bit more vulnerable with what you don't know - it's that inner willingness to face your blind spots that separates the best from the rest. We talk about the life experiences that taught her how to adapt her communication styles for diverse audiences, how she approaches talking with founders about triggering money topics, and we unpack some insights from her course on Business Modelling - how she helps founders turn their core understanding of their business into plain-English business math. I particularly enjoyed Lauren's insights around reframing tough decisions not as losses but as opportunities. We unpacked how shutting down a "pet project" can be reframed not as a loss or a mistake but as a day one decision - ie, we made a choice and a decision one day with the information and the knowledge and insights that we had and today with different knowledge, different insights and different information we're making another decision. We linked this notion back to one of the key ideas in Annie Duke's classic "thinking in bets" - the idea of "resulting", or judging a decision based on its outcome. A good bet is one that a reasonable person with the amount of information we had would have made at that moment, not necessarily one that works out exactly as you'd hoped. And Lauren urges founders to start admiring business leaders who didn't just get lucky once…but ones who repeatedly make smart bets - and can explain why they made them. Strap in! We also unpack some common financial misconceptions, discuss how to be a founder whose advisors can help them, and we unpack some interesting case studies in strategic decision making. Lauren's on-the-fly explanation of some key financial assumptions was dizzying in the best way possible. Links https://www.laurenpearlconsulting.com/ https://www.laurenpearlconsulting.com/newsletter Thinking in Bets by Annie Duke - A Visual Summary: https://www.youtube.com/watch?v=H49lFODYp7g Video Highlights Adapting your communication style on the fly - https://youtu.be/rWtSvkoMkiw The Founder Finance Gap: Managing Emotions and Unearthing Assumptions - https://youtu.be/Dfc8r9BBtyY Using Clear Language to define your Critical Business Math - https://youtu.be/l7oosTdqTLo Admiring Founders
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About The Conversation Factory
Welcome to The Conversation Factory, where I investigate how to create change through changing conversations. Each episode I'll talk to an amazing conversation designer about how to Amplify, Shift or Transform conversations in Organizations, Teams, Communities and our own lives.
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