

The Conversation Factory
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. Visit www.theconversationfactory.com where I distill these insights we can bring into our work and lives.
Episodes
Mentioned books

Oct 17, 2023 • 56min
A Leader's Guide to Managing Organizational Emotions During Layoffs and Beyond with Emily Levada
Emily Levada, Chief Product Officer at Embark Veterinary, discusses managing organizational emotions, particularly during layoffs. Topics include transparency and trust, polarity mapping, managing negative emotions, regular check-ins, driving resilience and creativity, and the value of challenge and psychological safety.

Sep 14, 2023 • 57min
Unpacking Mentoring with Jason Knight and Sandra Monteiro
My guest today is Jason Knight, the creator, host, producer, editor and promoter of the One Knight in Product podcast, a B2B SaaS product consultant, and fractional Chief Product Officer for companies that have gotten to product market fit and need help scaling their product team. Jason is also the founder of My Mentor Path, an inclusive, accessible and cloud-based mentorship service. Sandra Monteiro, a Product Manager at SAGE Publishing and a mentee of Jason’s, joined us halfway through to share her own experiences with mentoring, how she found her way to working with Jason as a mentor and what some of her learnings and insights from working with Jason as a mentor have been. She also shares her thoughts on what mentees should be thinking about as they search for and work with mentors. We explored Jason’s mentorship journey and why mentorship matters to him, the challenges of Industrializing mentorship pairing and productizing the matching of the lopsided mentorship marketplace. We also touch on how to measure the impact of the work and the subtle and important difference between Mentoring and Coaching. Jason suggests that many people who say they want coaching really want mentoring from someone who has “been there and done that”…and that great mentoring leverages coaching mindsets and skills in a practice he affectionately calls “centering”. Some fundamental questions we explored were the differences and relative merits of FORMAL vs INFORMAL mentorship as well as working with someone INTERNAL vs EXTERNAL to your Organization One of the big insights Sandra shared was shifting her expectations on the nature of the mentoring relationship from one centered around SOLVING vs conversations centered around TOOLS (ie, being offered relevant examples, learning materials and frameworks, holding space for emotional distance, and being offered broader context for challenges). Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Sandra Monteiro Jason Knight https://www.oneknightinproduct.com/bio/ https://www.oneknightconsulting.com/ My conversation on Unapologetic Eating and Living with Alissa Rumsey is here

Sep 5, 2023 • 59min
When the Mission Drives the Tech: Co-Founder Conversations
Dr. Onyinye Balogun and Eve McDavid, co-founders of Mission-Driven Tech, discuss the disparities in gynecological cancer outcomes and the importance of collaboration and communication in their co-founder relationship. They also emphasize the need for equity in healthcare, increasing awareness about gynecologic cancer, and finding the right connections and supporters for their mission.

Aug 28, 2023 • 47min
Give First: The Long Conversation of Being a Co-Founder
David Hoffman built and sold big-data and data analytics company Next Big Sound to Pandora in 2015. He's now building Beam, which helps people create shoppable mood boards for DTC brands. David reflects on his experience with mentorship and the long arc of the conversation that is being a co-founder and being in community. We unpack the Techstars motto "give first" and discuss the power of the Techstars community and the importance of community relationships in entrepreneurship. We talk through the complex evolution that is founding and scaling a startup, his experience doing just that with Next Big Sound, and the challenges of becoming a leader inside a growing company. One challenge is always scaling culture as a company scales, and David outlines some of the routines and structures that helped in defining his startup's culture. David also shares some insights on the post-startup-sale emotional roller coaster and the decision to build another company. Some of my other favorite insights from David: Living the “Give First” motto requires approaching everything with curiosity. “Grown ups” is a construct: When it is your idea and your company, you can make the decisions you need to make. Your Culture is made of your routines, whether it’s Friday bagels or snap-clapping after people share wins. Your MVP product can be much, much more simple than you think if it creates value for your customers. David’s nuanced reflections are a gift, and I’m so glad he sat down for this conversation. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Beam

Aug 21, 2023 • 1h
Cofounder Conversations: Pivoting while Staying Sane
My guests today, Ryan Horrigan and Armando Kirwin, bonded over their mutual fascination with the future of entertainment and their desire to do something innovative, which led to the creation of their current company, Artie. We talk about pivots and micro pivots and staying sane through the million tiny conversations Cofounders need to navigate. Ryan, the CEO, and Armando, President and co-founder of Artie have a pretty radical vision for the future of social media— namely, to make TikTok, Instagram, Twitter and other social media apps the gaming consoles of the future. Before co-founding Artie, Ryan served as Chief Content Officer of the Comcast-backed VR & AR startup Felix & Paul Studios. He oversaw the development and production of feature films, including Academy Award Best Picture Winner “12 Years A Slave.” at Fox/New Regency, and is a two-time Emmy Award winner for immersive entertainment projects he produced with President Barack Obama and NASA, as well as a Peabody Award winner. Armando has been in the VFX world for over fifteen years, working with numerous award-winning directors, including two-time Academy Award nominee Lucy Walker, Sundance Grand Jury prize nominee Sandy Smolan on The Click Effect, which was nominated for an Emmy; and Imraan Ismail on The Displaced, which won the Grand Prix at Cannes. He also produced Take Flight, starring Benicio del Toro, Michael Fassbender, and Charlize Theron. His most recent VR film, Nothing is Safe (2022), was an official selection of the Cannes Marché du Film. While movies are a wonderful industry, they both saw the power and potential of gaming as a storytelling platform - and a financial juggernaut. If you didn’t know: According to a report by SuperData Research, the global gaming market was valued at $159.3 billion in 2020. This includes revenue from console games, PC games, mobile games, and esports. Let’s put that into perspective: the music industry was valued at $19.1 billion in 2020, and the movie industry at $41.7 billion. That means the gaming industry is more than three times the size of the music industry and almost four times the size of the movie industry. TikTok used to be where people just watched videos (as of this writing, TikTok and Netflix are nearly tied for eyeball-hours). Now, hundreds of thousands of people are playing games on TikTok thanks to Artie and the technology breakthroughs that make streaming app-quality games from within social media apps possible. But how did they get here? Through a million micro conversations about data, signals, stakeholders and what it all means. Artie is where are are today not because of one big pivot, but many, many micro-pivots over the course of years. Pivots impact the team - who you needed on staff when you were focused on one path isn’t always who you need when you’ve decided to shift directions. Communication between departments and involving the team more is important - which means being intentional about regular check-ins and interdepartmental communication, but eventually, it comes down to the co-founder conversation - owning the choices that need to be made and moving forward, all while making sure you stay healthy and sane. Pivots vs Shaping Clay I loved this metaphor from Ryan, where he suggested that, from the outside, to investors, bloggers and customers, a company may have pivoted once, or a few times. From the inside, there are daily conversations, where the product is being shaped like clay, remade, refocused, almost constantly. “Listen to your body, have a Coach and a Therapist” This was one of my favorite insights from this conversation. It’s not often that men talk openly about mental health and needing support. Ryan and Armando both have a coach (although they meet with that coach separately) and Armando advocated for having a therapist, while Ryan discussed how they got much much more intentional about listening to their bodies and taking down time. Armando suggests that therapy focuses on self-awareness, learning about yourself and your patterns, while his coaching focuses on future outcomes and goals. “You have to care deeply about your people, but at the same time, you can't care about what they think of you” Ryan quotes what he describes as a harsh-sounding notion from Dick Costello when he was at Twitter: In Ryan’s experience, when you make a tough decision, you can't worry about everyone's collective feelings (even though you DO care about them as people and teammates). You have to make the decision that you, as the leader, believe needs to be made. As a founder, you have to make and own tough decisions. Ryan points out that, at the end of the day, you can't ignore tough decisions. You can’t have someone else do it for you. He suggests that while these moments are hard, it’s helpful to focus on the people who are still with you and the ultimate goals you’re trying to achieve. Links https://www.artie.com/

Aug 10, 2023 • 48min
The Power of Intention
Leah Smart from the LinkedIn Editorial team discusses intention, design of conversations, and personal mantras. They explore self-awareness in authentic dialogues, the value of spirituality in connections, and manifesting desires. Topics include spacewalk parallels, recipes for self-discovery, and iterative personal growth.

Jul 20, 2023 • 52min
Leaders as Humble, Audacious, Z-Shaped Coaches
I am excited to share my conversation with AJ Thomas, who I had the pleasure of meeting at the Culture Summit where we were both giving talks. AJ was sharing her perspectives on being a Chaos Pilot at Google’s Moonshot Factory, Called “X”. At the time of this conversation, she’s been with Google for nearly four years, starting as Head of People. AJ is also A CxO in Residence at A.Team AND an Advisor at Magic Eden and SemperVirens Capital. She is also an Executive coach on the side. She’s got a full calendar. X, A.Team, CxO. This is starting to sound like the credit roll on Sesame Street! That is a lot of letters, but we’ll add a few more, like T, I and Z. You may have heard of being T-shaped, as in having breadth of knowledge in general and having depth in one particular area…versus being “I” shaped - having just depth, but no breadth. Breadth is important in any position, because having some breadth means you can more readily engage a broad swath of people in productive dialog, partially because you “get” their inside language enough to collaborate with them. This breadth of collaborative potential is especially important for Leaders. AJ is a fan of being a Z-shaped-leader, which for her means having depth across many different areas, over time, and the ability to connect the dots between them. But while being able to connect the dots, to scan the horizon for innovation and emergent opportunities, to be able to see an Audacious and almost-impossible future AND communicate that vision to others is a powerful leadership skill, AJ sees Humility as an equally powerful leadership value. This puts AJ in excellent company with Dr. Marilyn Gist, PhD, Professor Emerita of Executive Programs at the Center of Leadership Formation at Seattle University, author of "The Extraordinary Power of Leader Humility," and a past guest on this podcast! Check out our conversation here where Dr. Gist shares her Six Keys to Leadership Humility. I love AJ’s idea of keeping Audacity and Humility in dynamic tension - staying “Humbacious”! That balance, the ability to “sprinkle” one quality or another into a conversation, shows up as tremendously powerful and generative in AJ’s leadership and coaching work. Audacity holds space for people to explore potential - the biggest vision and possibility. And Humility drives us to assume that we might be wrong and to leverage the mind of a scientist to de-risk the road ahead with powerful questions and intentional experiments. Enjoy this powerful deep dive into these ideas and a lot more. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links https://www.couragetakesflight.com/ www.itsAJthomas.com

Jun 26, 2023 • 50min
A Company Must be a Community of Practice
In this episode I talk with my friend Chris Murchison, who is a coach, a facilitator and a talented artist, too! We talk about his Four principles of Communities of Practice and how building a positive culture within an organization requires, essentially, creating a community of practice. Your team, your organization, is already practicing something…and that practice is either mindful and intentional, or it’s habitual and haphazard. Communities of practice are groups of people who share a passion for something they do and so, have a shared purpose or goal for learning how to do it better…and so, they interact regularly with the intention of continuous improvement of that thing. An example of intentional practice that Chris shares in the opening quote is what he calls a “Sunset Meeting”, a special, extended, and deeper version of a Retrospective, that asks, not just how did the work go, but how did we do? Stopping to look back and look forward means that the space for continuous improvement is being created. But without fostering deep psychological safety for people to say what needs to be said, a leader and a team can never get the continuous relevant learning they need from the conversation. How to lead that kind of safety is a whole other conversation, but Chris and I do unpack some of the facilitation skills leaders need to master in order to be able to host these types of continuous improvement conversations. Communities of practice require ongoing conversations and intentional practices. Chris shares four key principles to help you architect an effective community of practice for your own context: Meaningful connection (In order to, as Chris says, plant the seeds of trust and safety) Relevant learning (So people want to be full there AND so the organization benefits) Purposeful practice (so we’re focused on what matters most) Sharing and reflection (slowing down to notice and share what we’re each practicing and learning) Make sure to check out the links and show notes which include Chris’ wonderful Community of Practice Guide and his more general Community Principles & Practices. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Chris's Website Community of Practice Guide Community Principles & Practices

May 16, 2023 • 1h 2min
Coaching from Essence, Creating from the Future
Today, I sit down for a conversation with *my coach* Robert Ellis, about his new book, Coaching From Essence. Robert has been described as “one of Silicon Valley’s best-kept secrets” and has been coaching leaders at startups, mid-stage companies, Fortune 500 giants, and nonprofits for over 30 years. Robert has taught leadership and coached entrepreneurs at Singularity University and developed Level UP, the leadership curriculum for the Global Startup Program, and taught leadership courses at Stanford University. We met through radical serendipity and I’m grateful for the generosity and grace Robert has coached me with. All of his teaching materials are now publicly available on his free circle community and on youtube. Robert’s book is like sitting in a fireside chat with Robert, absorbing his profoundly wise and profoundly simple approaches to coaching. Sometimes, a new idea can feel so true that it lands like common sense - all the pieces fitting together so seamlessly and effortlessly. Roberts’ metaphors, stories and models hit like that - like powerful truths you knew all along. Robert’s visual models help ground a coaching conversation, make it easy to follow along, and make the conversation incredibly sticky. And literally every time I’ve drawn one of these diagrams for a client, it lands with them and becomes a new metaphor for thinking about their challenge and their path forward. This book isn’t just for coaches who want a more effortless and human approach to doing this work, it’s for anyone who wants to be deeply helpful to their clients, their teams, their organization, and to lead conversations in a more impactful way. Coaching from Essence is based on the radical idea that everyone has an essence, and that, when we work from it, we can effortlessly create value and impact. Coaching from essence works both ways - the coach coaches from *their* essence, their natural approach…and the coachee is coached to work from their *own* essence - their own natural approach. We’re not telling people how to be. We are here to help them remove the obstacles that get in the way of them finding their own way. According to Bill Gates, everyone needs a coach. I would flip this suggestion on its head and say that at some point in everyone’s lives, accessing a Coaching from Essence mindset can be a generous, powerful and transformative way to help someone in our lives. Some of us choose to make coaching our life's work, but Coaching from Essence is a powerful, generous and transformative approach to helping people that everyone can (and should?) access at the right moment for the right person. Robert Ellis is the embodiment of what he teaches - he is a generous, powerful and transformative coach who I’ve had the pleasure of working under for several years. I’m so glad this book is finally out in the world so that everyone can have the experience of working with him. Links https://coachingfromessence.com/ https://www.futurosity.com/ Coaching from Essence, by Robert Ellis

May 9, 2023 • 1h 5min
How to Think Strategically about Funding for Founders and Investors
I first met Avantika Daing, a General Partner & Managing Partner at Plum Alley Investments (and Tedx Speaker!) while she was onstage at an Entrepreneurs Roundtable Accelerator event. She was there to share a bit about Plum Alley’s Investment thesis as well as unpack six pitches live from early-stage companies. Let’s level set a bit so you understand Avantika’s and Plum Alley’s mission, which revolves around an important number that hasn’t moved much in years, despite a lot of effort - 2%. According to Pitchbook, in 2022, companies founded solely by women garnered just 2% of the total capital invested in VC-backed startups in the United States. Plum Alley only funds gender-diverse companies and works to create an ecosystem to help them not just get funded, but to grow and succeed. That’s one of the reasons I wanted to bring Avantika on, to share some of her ways of thinking strategically about funding as an investor, how Plum Alley is working to create a more sustainable funding ecosystem for diverse founding teams, and how she coaches founders to be more strategic about funding, too. Watching Avantika on stage peel back the layers of the onion (one of her favorite metaphors!) on a company’s story in conversation with a founder and work to understand the company’s potential was fascinating - it’s a tremendous act of intellectual rigor and curiosity. Her questions also reminded me that founders can make an investor’s job a lot easier through more powerful and intentional storytelling. Another powerful metaphor that Avantika came back to in a number of pitches was the idea of a Basecamp. In other words, Avantika, as a funder, wants to know: Is your company building a core technology or defensible market position (a basecamp) that will provide you with multiple paths to success? Avantika acknowledged that a “single story” about how your company will “win” or “summit the mountain” is powerful, but she was clear that she prefers companies that are creating a powerful “basecamp”...why? Because: 🏒A “many shots on goal” strategy can help create longevity and increase options for success. I’m so grateful that she was willing to have a longer conversation with me on the record to explain her ideals about storytelling and the basecamp-summit metaphor. She also helped peel back some layers on another idea she loves to coach founders on: “Dressing their cap table” for sustainable success from seed to IPO and well beyond - since capital needs don’t stop at IPO. I love how Avantika’s metaphors shift, refocus and redesign the conversation about pitching, funding and sustainable success for startups. Enjoy this conversation as much as I did! Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Plum Alley Avantika's Tedx Talk: There is No Balance. There is Juggling Daniel’s LI post on Avantika’s Entrepreur’s Roundtable Session, highlighting key questions and perspectives from Avantika, including the “base camp/summit” metaphor.