The Conversation Factory

Welcome to the conversation factory. I'm investigating how we create change through changing conversations. Each episode I'll talk to an amazing conversation designer to try to distill insights we can all bring into our work and lives.

Join or Die: Behind the Scenes of Creative Collaboration 05/22/2025

Founder-Led Sales and Building Co-founder Relationships 04/03/2025

Founder-Led Sales and Building Co-founder Relationships Get free chapters of my book, Good Talk, and master the art of conversations big and small: Please support the podcast! 💌 : https://spoti.fi/3QzcPAW 💌 : or with : : Check out for the full transcript and video highlights. We break down: The Importance of Deep and Authentic Conversations and unpack how Natalise fosters honest and open conversations and has worked to build a company culture that reflects these values. Intentional Co-founder Relationship Building: We talk about how Natalise and her co-founder, Nathan Brown, approached building a strong relationship intentionally by having regular in-depth conversations and retreats together in some of their favorite spots. She shares some of her favorite questions to bring into these co-founder conversations. Founder-Led Sales and CEO as Science Translator: Both Natalise and her co-founder Nathan are actively involved in explaining their product to both investors and consumers. We talk about how she approaches adapting her message for different audiences, always striving to put the science ahead of marketing. Highlighting the Potential of Phage Therapy: We dive into some of the science behind phage therapy and its potential as a precise and sustainable alternative to antibiotics. The Value of Open Feedback and Continuous Evolution: Natalise encourages feedback from all levels within her company and believes that good ideas can come from anywhere. She also emphasizes the importance of ongoing communication and alignment between co-founders. Key Chapters 00:00 Exploring the Depth of Conversations 03:01 The Ambivert Spectrum: Understanding Social Dynamics 06:06 Creating Safe Spaces for Honest Conversations 09:01 Feedback Culture: The Art of Positive Feedback 11:57 Building Authentic Relationships in Business 14:57 The Journey of Co-Founders: Nathan and Natalise 21:01 Navigating Vulnerability in Professional Relationships 24:17 Navigating Co-Founder Relationships 30:14 The Art of Communication in Business 37:45 Understanding Phage Technology and Its Impact 46:02 Building Strong Co-Founder Foundations Links : Video Highlight Links 👀 https://youtube.com/shorts/5zwdVyJr_mc 👀 https://youtube.com/shorts/MjeDjSIUeDM 👀 https://youtube.com/shorts/fp6oKVhq-FQ /episode/index/show/theconversationfactory/id/35912690

The Inner Work of Leadership with Carole Robin, PhD 03/14/2025

The Inner Work of Leadership with Carole Robin, PhD Master the art of conversations big and small - both inside yourself and in your teams and organization. Get free chapters of my book, Good Talk: Please support the podcast! 💌 Subscribe on Spotify: 💌 iTunes: or with a monthly contribution here: or make a one-time donation here: For the full transcript, video highlights, and more show links, check out the episode page here: Every conversation - especially the hard ones - is an opportunity to learn more about yourself, to learn about another person and to learn about interpersonal dynamics - if you can set aside judgment and be open to curiosity. I’m SO excited to share this epic podcast conversation with the "queen of Touchy Feely" - Carole Robin, PhD. Carole taught the most popular elective at Stanford Graduate School of Business, Interpersonal Dynamics (mostly known affectionately as "Touchy Feely"!) for nearly 20 years and is co-author (with co-teacher David Bradford) of the excellent book Connect: Building Exceptional Relationships with Family, Friends and Colleagues. She has a vast reserve of wisdom to share. We discuss the importance of navigating vulnerability and intentional connection as an essential leadership skill and unpack some of her most powerful principles of effective communication. We also talk about Carole’s conversations with her own personal AI, trained on all of her past writings and course notes…and how it helped her evolve how she tells her own story! Building exceptional relationships is work that’s done one conversation at a time. Carole’s insights can help you unlock the potential in each conversation. Key Moments 00:00 The Art of Greeting with Interpersonal Dynamics in mind 03:00 AI and Personal Narratives: The Evolution of Carole’s Story in collaboration with her personal AI 06:01 Leadership Lessons: Emotions in Business 09:06 Vulnerability vs. Strength: The Leadership Paradox 12:04 Transparency in Leadership: The Balance of Sharing 14:58 Strategic Authenticity: Navigating Vulnerability 18:01 True and Kind: The Principles of Effective Communication 20:50 The Importance of Self-Care for Leaders 21:59 Navigating Emotions in Leadership 23:49 Vulnerability and Authenticity in Leadership 30:07 Self-Management and Emotional Discipline 32:59 Curiosity as Leadership superpower 37:57 The Work of Building Relationships /episode/index/show/theconversationfactory/id/35611810

Your Brain on Beautiful Conversations with Anjan Chatterjee 02/26/2025

Changing the Political Conversation with Nick Troiano 10/30/2024

Changing the Political Conversation with Nick Troiano If you want to change the game, changing the rules and incentives of the game is a powerful approach. Few people who watch the news - or those folks who avoid watching the news! - would say the political system in the United States is going according to plan. The founding fathers, if they were alive today, would be aghast at the unbridgeable chasm that seems to have developed in our political culture, making dialogue, compromise and progress nearly impossible on some of our most pressing issues. In fact, our founding fathers warned against the rise of what they called factions in their time, and what we today call political parties. All of this is happening at a time when the majority of Americans agree that common-sense laws for guns, healthcare and other issues are badly needed. If you look at the numbers, we’re closer together on more issues than you’d think. Research shows that our leaders are often much more polarized than we as a people are. Meanwhile, the US and local governments get less done, eroding our confidence in our democracy. What can we do to change the game? Some people say “let’s get rid of the electoral college!” but such large scale changes are hard. My guest today has a simple solution that starts at the local level to change the political conversation. Nick Troiano is a civic entrepreneur based in Denver, Colorado, and is the Executive Director of Unite America –– a non-partisan organization that seeks to foster a more functional and representative government. Nick has been a leader in the political reform movement over the last decade, beginning as a founding staff member of Americans Elect in 2010. Nick ran for Congress in Pennsylvania’s 10th District in 2014 and drew national attention as both the youngest candidate that cycle and the most competitive independent U.S. House candidate in nearly two decades. He subsequently worked for Change.org to launch a mobile application to help voters cast informed ballots. In 2016, Nick was named to the "Forbes 30 Under 30" for Law & Policy. He earned a Master’s degree in American Government from Georgetown University. He has spoken on the topics of political and fiscal reform to dozens of groups across the country, including along three national bus tours that collectively visited over 40 states. Nick is the author of an *excellent* book that explains the challenge and a viable set of solutions to political division in America, and a producer on the 2024 film which lets you watch political change unfold in real-time. I highly recommend watching Majority Rules - you can rent it on Youtube now! You will see partisan politicians learn to navigate a different political game as the rules are changed - and become more issues-focused instead of attacking personalities, and more inclusive than divisive. I also highly recommend supporting primary reform in your region - it’s a non-partisan issue that can help us become less partisan! Listen to the end where Nick and I discuss how he leads his organization and builds coalitions while living his leadership and political values. Head over to 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 . /episode/index/show/theconversationfactory/id/33450232

The Secrets of Motivation and Systems Change with Becca Block, PhD 08/19/2024

The Secrets of Motivation and Systems Change with Becca Block, PhD Warning - this episode uses a specific curse word - a lot. And once we started using one, we started using more of them. So…if f-bombs, sprinkled like salt are not your cup of tea, this is a good episode to skip! My guest today is Rebecca R Block, PhD, who is an expert in helping organizations build programs, services and products that equip young people to develop the confidence and skills they need to enter adulthood as thriving and adaptable lifelong learners. She has spent the last 14 years leading the design, improvement, and evaluation of educational programs and services to make them more impactful and learner-centered. She has built R&D departments from scratch and managed large and small teams responsible for creating, measuring, and improving learning experiences. She also wrote a book with the word “Shit” in the title…or Shit, with an asterisk where the “I” goes, which actually makes her book a bit hard to google! The book is titled “Can You Help Me Give a Sh*t? Unlocking Teen Motivation in School and Life,” and she teamed up with Grace L Edwards, a current undergraduate student, to talk to young people across the country and gather their stories about what truly makes for engaging learning environments. In the process, she learned a lot about how motivation works for everyone, not just teens, and has taken those lessons learned into her work as a leader, parent, and educator. In the opening quote Becca outlines the ABCs of Motivation. These ABCs are true for children and adults - we’re basically the same species. And the work of luminaries such as Peter Senge and Amy Edmondson make it clear that great working environments are great learning environments - places where we can create and sustain positive feedback learning loops with ourselves and others. So it’s essential for anyone leading or managing others (or themselves!) to understand how motivation really works. We also talk about Becca’s essential values when it comes to co-creation - that is, making a systems change along with the people in that system who will be affected by that change. Co-creation is not just a good idea… it leverages the truths about motivation that Becca shared in her opening quote. People are much more likely to want to participate in change that they’ve taken part in forming, rather than going along with something forced on them. Two Levels of Systems Change We also talk about the need to work on at least two levels when engaging in systems change: Helping people, now Helping make a bigger shift, over time. Given that Becca knows how challenging it can be to transform a system as complex as education, she focuses her work in this book on helping people, now, to work to create change for themselves, within the current system. This perspective is helpful for anyone leading a team in a larger organization or anyone leading an organization within a larger industry they are hoping to transform. Listen in for Becca’s deeper breakdown of the ABC’s of motivation, as well, summarized here! The ABCs of Motivation Ability Belonging Choices Ability: In any situation where you want someone (or even yourself!) to have sustained motivation, you need the Ability to do (or learn how to do) the things you want to do. Indeed, whenever you find that someone isn’t doing something you have asked them to do, it’s important to ask - is this an issue of Will or Skill? In other words, can they do the thing? If they can’t yet, do they have the confidence in their ability to learn the thing? Belonging: Real relationships help us accomplish things. I show up for my Spanish lessons (partly) because I’ve paid for them, and partly because I’d feel bad for standing up my tutor, even though the classes are online. Ditto for my exercise classes. Real relationships create real motivation. who talked about how his relationship with his Co-Founder Josh David kept him going through a difficult decade of bringing their dream to reality - talk about Relationships = Motivation! Choices: Having real choices means you have the autonomy to determine for yourself what you are going to do. “Liberty or Death” isn’t much of a choice - although it is one many have taken. Becca suggests that dysfunctional workplaces create crappy or fake choices, and functional ones enable everyone to see how the work fits into their own personal why. , author of “Nine Lies about Work” and most recently “The Problem with Change." Ashley says, “The ultimate job of leadership is not disruption and it is not to create change; it is to create a platform for human contribution, to create the conditions in which people can do the best work of their lives.” This is what every human (and teenager!) actually really wants, if they can connect to the ABCs of motivation. Head over to 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 . If you want to be on her podcast: /episode/index/show/theconversationfactory/id/32594637

How to Turn a Conversation into a Public Park 07/22/2024

How to Turn a Conversation into a Public Park Sometimes the bold goals we set out to achieve actually happen, and sometimes something even more amazing happens - something better than we can imagine. Usually that happens because of the people we meet along the way, the conversations we have, the unexpected connections we make that open up new doors - in a word, Serendipity. I had always wondered about what amazing, powerful and sustained conversations led to the High Line Park in New York City becoming a reality. Have you walked the High Line? Literally millions of people a year walk some of its 1.45 mile length, enjoying expansive views of the city and hundreds of local plantings, as well as amazing art installations. But it was slated for demolition and considered an eyesore and a relic, as long ago as the 1980s. Built in 1933, it was at the time a revolutionary elevated train line that was colloquially called the Lifeline of New York City since it was regularly bringing millions of tons of meat, dairy and produce by rail, directly into the warehouses and factories of lower manhattan for preparation and distribution. The rail line wasn’t just a lifeline because of the food it brought, it also moved the rail lines safely above the city’s growing traffic - in the 1910s, hundreds of people were killed by the ground-level trains that ran in the middle of the bustling 10th avenue! By the 1960s the line was growing obsolete due to the rise of trucking, and by the 1980s, it was a hulking relic of the past. In 1999, Robbie Hammond, my guest for this conversation, co-founded the Friends of the High Line along with Joshua David. The two met at a local community board meeting where the High Line’s future was being discussed. Rudy Guliani, NYC’s mayor at the time, had signed an executive order for its demolition - many property owners wanted it gone so they could take back the land occupied by the tracks and build bigger buildings - a dream of greater square footage and increased rent rolls. Currently Robbie is the President & Chief Strategy Officer for , where he is leading an initiative to bring large scale bathing facilities to the United States. He also currently serves on the boards for Little Island, Sauna Aid, Grounded Solutions Network, and the San Antonio Museum of Art. When I was a little kid in NYC in the 80s, I looked up at the hulking tracks and thought “what the hell is that doing in the middle of the city?!” Many adults thought the same thing. Robbie and Josh looked at the tracks and thought “we should really do something cool with that instead of tearing it down.” In 2009 the first section of the high line opened to the public. In 2019 and 2023 new sections were completed. Against all odds, “two neighborhood nobodies” (as one writer described them!) created a coalition, learned to raise money and garner the favorable attention of local politicians, and persisted and succeeded. The park is maintained, operated, and programmed by Friends of the High Line in partnership with the NYC Department of Parks & Recreation and is run on donations. There are many amazing angles to the story of the Highline: Maybe you DON’T need a coherent or complete Vision or Mission?! Robbie makes it clear that they didn’t even have a clear vision or strategic plan for some time…just the idea that the elevated line was worth saving and doing something with…they discovered what they wanted to create along the way. He actually credits the vagueness of the mission with creating a “big tent” that attracted more people to the organization. From a conventional dream to something better than anyone could imagine One surprising insight is that the property owners had a rather conventional dream - tear the elevated tracks down so they could build bigger. Turning the High Line into a park seemed like a low-value, impossible pipedream - sex workers and drug users congregated under the overpasses, after all! But the High Line’s millions of visitors have transformed the value of the area far beyond the addition of a few extra square feet. The High Line as a symbol for dreamers of impossible dreams One of Robbie’s greatest points of pride is that the High Line now stands as a symbol to many “crazy dreamers” who find inspiration in the story of outsiders persisting and accomplishing more than they ever dreamed possible. The High Line is now a global inspiration for cities to transform unused industrial zones into dynamic public spaces. But Robbie loves the personal stories of folks who come up to him at talks, who are working on all sorts of projects and who find inspiration in Robbie and Josh’s “keep going against all odds” story. The importance of Talking to People Robbie talks about how he was always willing to pick up the phone and talk to anyone - the fearlessness of someone raised in sales. But the Friends of the High Line were also willing to host conversations with community groups and listen to them, and learn from them and communicate with them about why they were listening to their ideas and why, in some cases, they weren’t going to. Open lines of consistent communication made the High Line possible. The Alchemy of the Co-Founder Relationship In this conversation, Robbie is bracingly reflective and shines a sometimes harsh light on himself. Here at the 15th anniversary of the opening of the Highline and the 25th anniversary of the start of the project, the founding of the Friends of the High Line, Robbie looks back and is refreshingly honest about his own challenges and shortcomings, as well as missed opportunities along the way to do things differently. What was truly surprising to me in this conversation is that Robbie was so open about his challenges as a co-founder, and is so open-eyed about how essential this most intimate of relationships can be…and how much he and Josh were willing to invest (in time, energy and resources) in that relationship to keep it intact, functional and flourishing. The Energy and Anxiety of Creation Robbie suggests that it is common for creative people (which includes entrepreneurs, and anyone that starts anything) to have a drive to accomplish their dream - that is what keeps them going… but that there is often “an undercurrent of anxiety”. Meditation helped Robbie reclaim a higher level of happiness as the High Line approached realization, but it took him years to undo the deep grooves anxiety etched in his psyche. It's a worthwhile lesson for anyone listening out there who's creating something, start taking care of yourself sooner rather than later. You can follow Robbie on Instagram at and stay in the loop on Therme’s projects at . Head over to 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 Early documents from the highline: Talks: /episode/index/show/theconversationfactory/id/32216262

Art that Changes the Conversation 07/01/2024

Art that Changes the Conversation Art has the power to change and even lead the conversation, to spark curiosity and fuel real engagement. But what comes first in a powerful creative project? The idea and the message? The tools and the talent? Or The Funding, that can make or break it all? My guest today is , who creates art on a grand scale that goes beyond awe. He is an Artist focused on amplifying positive impact. He does that both in the process of how he creates his art, through community, and in the images it produces, finding visual metaphors that stick with people, long after they’ve seen the work. His mission is to help make positive impact unforgettable. For the last seven years, Von Wong and his team, under the banner of ” have generated over a billion organic views on topics like Ocean Plastics, Fast Fashion, and Electronic Waste for organizations like Dell, Greenpeace, Nike, Starbucks and Kiehl's. In this opening quote you can hear him wrangle with the dance between art and marketing, and his new mission to find ways to create sustainable funding streams that allow him to create message-shaping art in times and places where the world is gathered to solve some of our most pressing challenges. It’s a move that can make his work more deeply sustainable - for himself and for his team. Von Wong’s leverages the collective power of philanthropy to help build broader campaigns around environmentally net-positive innovations worth spotlighting - instead of waiting for corporations that are seeking eyeballs and leveraging their funding for good, he’s building a funding source that actively seeks the next project that needs to go viral. which used trash from the slums of Kibera, in Nairobi, Kenya, to demand that corporations #TurnOffThePlasticTap. The Giant Tap was displayed prominently when to discuss what was then termed the “Paris Agreement For Plastics” and was eventually used in the United Nations official Plastics Report while raising over $100,000 for the Human Needs Project. in collaboration with Kiehl’s to raise awareness and drive adoption of refillable products in the beauty world. Von Wong, along with a large community of volunteers, collected and assembled 2 tons of plastic bottles into a “single-use hydra”, seen by nearly 300-thousand visitors and close to 3 million social impressions for their message of #DontRebuyJustRefill…but as he points out in this conversation, most of the people on the High Line don’t have the leverage to change the system - which is why he seeks to place his epic art in places where the system changers meet. I learned about Benjamin's work through at (a global, IRL community of creatives that hosts monthly talks all around the world). His presentation spoke to some beautiful topics - like the importance of nurturing the conditions of success (like inner narratives and cultivating community) vs chasing success, and the notion of sifting your feelings from reality when it comes to deciding what is enough - personally, financially, and in the work - ie, is my work having enough impact? Von Wong shared the ways in which he’s rewriting his inner narrative to balance his personhood and his purpose or impact. I found the talk profoundly moving and beautiful and highly recommend watching it. In this conversation, you’ll find: Ruminations on Creationships - relationships that exist to co-create something wonderful together (4:09) The Importance of an Interface or a Container to foster Conversation (7:47) Benjamin’s perspectives on going to where the conversations are already happening to have the deepest impacts. This is certainly true for the large scale work that he creates, but it is also true for anyone looking to change a big conversation. Making people come to you vs going to them means the activation energy of change is that much lower. (13:18) Benjamin’s thoughts on Community Building and Co-creating art with a community (16:43) The polarity Benjamin is threading right now: Balancing Speeding Up (to do more work and have more impact) and Slowing Down (in order to build deeper creationships) (26:21) The difference between an Audience and a Community (32:44) The power of creating a word that summarizes and defines an idea that people flock to (which we might term the or (as she famously wrote in A Wizard of Earthsea “To weave the magic of a thing, you see, one must find its true name out.” (33:39) Head over to 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 /episode/index/show/theconversationfactory/id/31934192

Leadership is Designing Moments of Impact 05/15/2024

Leadership is Designing Moments of Impact Today my guests are Lisa Kay Solomon and Chris Ertel, the co-authors of the powerhouse 2014 book Moments of Impact: How to Design Strategic Conversations That Accelerate Change, which celebrates its 10th anniversary this year! I devoured this book 10 years ago and I think you might enjoy it, too! Lisa Kay Solomon is currently a Designer in Residence at the Stanford d. school, where she teaches classes such as Inventing the Future where students imagine, debate and analyze the 50-year futures of emerging tech, and works closely with the K12 community to make futures thinking a mainstay of 21c core curriculum. She has also been named to the Thinkers50 2022 Radar List and is one of ixDA’s Women of Design 2020. Chris Ertel is a managing director of Deloitte Consulting LLP with a specialist role designing and providing high-stakes strategic conversations for clients and priority firm initiatives, in the Deloitte Greenhouse® signature environments. Chris is an innovation strategist with 18 years of experience advising leading organizations. He holds a PhD in demography from UC-Berkeley. We talk about What it really means to be a facilitative leader, and why it’s so impactful. As Lisa and Chris say in MOI: “At these critical moments, everyone will be looking at you, not for all the answers, but to help them unearth the answers together” The Five Core Principles of Moments of Impact, which can form a Design Process 1. Define your purpose (your design intent!) 2. Engage multiple perspectives (with your facilitation skills!) 3. Frame the issues 4. Set the Scene 5. Make it an experience (even an intense or challenging one!) How designing conversations is different from facilitating them: Lisa makes it clear that Conversation Design is about intent and purpose while Facilitation skills are the tool that helps orchestrate those Moments of Impact. Why Conversation Design isn’t taught to leaders but should be (Lisa also tells us why it’s so hard to teach, since it brings together strategy, psychology and emotional intelligence) Why Chris always coaches leaders to condense and delete content from their strategic meetings (to 10 slides!) instead of making what communications expert calls a “Procument” (something that’s neither an easy to use and digest presentation or a leave-behind document!) How crucial discussing decision-making rights are - as Chris suggests many leaders want to keep their options open and wind up creating an “air of democracy without the reality of it” Why You should start becoming a junkie of learning theories The importance of balancing humor and levity with challenging-ness and sparkiness to create productive environments The importance of knowing that the “yeah buts” will come when we’re hosting challenging conversations as in: yeah, but, that won’t work here! or… yeah, but, what will we be able to report next quarter? Or… yeah, but who’s budget is going to cover that? And so much more! If you have Moments of Impact that you need to shape, design, and lead and you *don’t* have Moments of Impact on your desk - get it! Head over to 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 Get A plan is not a strategy: we were talking about! /episode/index/show/theconversationfactory/id/31328317

The Problem with Change and the Power of Stability, Humanity and Praise with Ashley Goodall 05/07/2024

The Problem with Change and the Power of Stability, Humanity and Praise with Ashley Goodall My guest today is Ashley Goodall, a leadership expert who has spent his career exploring large organizations from the inside, most recently as an executive at Cisco. He is the co-author of Nine Lies About Work, which was selected as the best management book of 2019 by Strategy + Business and as one of Amazon’s best business and leadership books of 2019. It is an awesome book - highly recommended. If, after listening to this conversation you want to hear more (and I think you will!), take a listen to him and his co-author, Marcus Buckingham, talking on the HBR Idea Cast about lie #5 - - which is also an idea we dive into later in our conversation today. Prior to Cisco, Ashley spent fourteen years at Deloitte as a consultant and as the Chief Learning Officer for Leadership and Professional development. His book, "The Problem with Change: and the Essential Nature of Human Performance" is about what we might call lie number 10: the idea that change is good and that leaders must lead change in order to be good leaders. Wholesale belief in this lie has created what Ashley calls “Life in the Blender” - driven by what I’ve heard some folks refer to as “The Reorg of the Day”. I love love love the musical analogies Ashley uses to describe leadership - not as the lead guitar or first violin, but as the . The Leader can help teams navigate change by playing a backbeat of stability and consistency, supporting a range of free expression and variation. Find a link to and (which he mentions in the extended version of the analogy, later on in the conversation). What is that Ground Bass? For Ashley it’s about helping people feel seen, connected, celebrated and clear on the story of the meaning of their contributions to the work. Bree is a Partner at SYPartners and shared her framework around the challenges of designing organizational change - that most change can easily result in one or more of the Six Types of Loss she identified: Loss of Control Loss of Pride Loss of Narrative Loss of Time Loss of Competence Loss of Familiarity All of which Ashley suggests leaders can deflect or reduce through 9 key leadership skills that he outlines in depth in his book: Make space Forge undeniable competence Share secrets Be predictable Speak real words Honor ritual Focus most on teams Radicalize HR Pave the way Prior to releasing the book, and is an even more succinct, poignant and straight-on condemnation of modern corporate leadership - it is also highly worth reading. This book feels a bit like a Burn Book - Ashley is pointing out fundamental misconceptions at the heart of corporate life in a direct and unvarnished manner - in the hope that some leaders will listen and start doing things differently - Leading in a way that takes into account how humans really are and what we really need to thrive at work. Ashley is very clear: companies need to look beyond wellness initiatives and corporate cheerleading and shift their focus to the fundamental environment of daily work. The effects of a corporate life caught in constant change are more than clear to anyone who’s been through it: uncertainty, a lack of control, a sense of unbelonging and of displacement, and a loss of meaning As Goodall says, “The ultimate job of leadership is not disruption and it is not to create change; it is to create a platform for human contribution, to create the conditions in which people can do the best work of their lives.” Also - do listen for an extended exchange around minute 40 where we talk about the power of praise and the Paul Hollywood handshake - if you’re not a Great British Bake off fan, there’s still time to watch a few episodes to get in the mood - Head over to 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 Find a link to and Take a listen to Ashley and his co-author, Marcus Buckingham, talking on the HBR Idea Cast about lie #5 - Canon in D Major by Kevin MacLeod is licensed under a Creative Commons Attribution license () Source: Artist: /episode/index/show/theconversationfactory/id/31173397

Reunion: Leadership and Creating a Culture of Belonging 04/29/2024

Reunion: Leadership and Creating a Culture of Belonging Rabbi Tarfon said: The day is short, and the work is plentiful…It is not your duty to finish the work, but neither are you at liberty to neglect it. (Pirkei Avot 2:15-16) My conversation today with Jerry Colonna closes with him paraphrasing this powerful notion - and the work we are discussing is the work on yourself and the work to create a better world - one where everyone feels like they truly belong. In a world where many organizations are retreating from Diversity, Equity, Inclusion and Belonging initiatives, I’m grateful that Jerry is leaning into this conversation. I see the work of antiracism as firmly in the realm of what my peoples call It’s absolutely essential that men in positions of power and especially men who present as White, do not neglect this work. Jerry is a graduate of Queens College and a Brooklyn native. Jerry helps people lead with humanity and equanimity. His unique blend of Buddhism, Jungian therapy, and entrepreneurial know-how has made him a sought-after coach and leader, working with some of the largest firms in the country. In his work as a coach, he draws on his experience in Venture Capital as Co-founder of Flatiron Partners, one of the most successful early-stage investment programs. Later, he was a partner with J.P. Morgan Partners, the private equity arm of J.P. Morgan Chase. As a partner with J.P. Morgan Chase, Jerry launched the Financial Recovery Fund with The Partnership for the City of New York, a $10 million-plus program aimed at creating grants for small businesses impacted by the attacks on the World Trade Center. Along with a strong commitment to the nonprofit sector, Jerry is the author of two books: REBOOT: Leadership and the Art of Growing Up (2019) and REUNION: Leadership and the Longing to Belong. (2023) Reboot was met with critical acclaim, stirring up a big question in the hearts and minds of people: “How have I been complicit in creating the conditions I say I don’t want?” Jerry’s second book builds on this question, asking us what benefit we get from the conditions we say we don’t want - the systems of oppression that those who have eyes to see, can see. Reunion is a highly personal book that asks us all to examine our history of longing to belong - and the ways in which we have been excluded or excluded others. Key Threads in the Conversation We discuss Jerry’s Journaling practice and how it is an essential conversation he has with himself, each morning. We explore what it means to be a “good man” - and how in his first book, REBOOT, he questioned whether he was a good man, while in REUNION, he built upon the assumption that he is a good man and explored (and expanded) what it means to be a good man in a world where there is division and polarization. And I get Jerry to coach me on one of my favorite questions: understanding the disowned parts of ourselves, exploring the reasons behind disconnecting from them, and the importance of integrating them back without denying them - very much in line with the process of REUNION. All while working to authentically grow in ways that matter, without self-abuse or denial. Those parts of ourselves we wrestle with wrestle back at us. Many leaders I coach want to be feel or been seen as more or less of some quality or another - they, like so many of us, feel they must be other than they are in order to belong. In my experience, fighting against our parts without understanding and loving them is a losing battle. Jerry asks us to understand the stories behind our self doubt, and to honor the ways that part of us has sought to care for and protect us in the past. I find great empathy and lovingkindness in spending time nurturing my denied parts and my clients do, too. I’m so grateful to absorb Jerry’s approach to self-integration, and to expand our inner work towards creating not just a life we love, but a world we want to live in. Head over to 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 Some other solid interviews with Jerry: /episode/index/show/theconversationfactory/id/30999608

The Intentional Conversations that Build Powerful CoFounder Relationships 04/15/2024

The Intentional Conversations that Build Powerful CoFounder Relationships My guests today are Rei Wang and Anita Hossain, Co-founders of coaching platform The Grand, which was seed funded by Alexis Ohanian’s firm Seven Seven Six in 2023. Rei is the Chief Product Officer and Anita is the CEO. I met Rei ages ago, in her early days in NYC at General Assembly, where she worked as a Product Manager and Global Community Lead, developing educational opportunities for students. And I was excited to interview her about her work as the CEO of the Dorm Room fund at First Round Capital a few years back to get her perspectives around the intersection of community and product design…especially when the community IS the product. . Rei cultivated a vibrant startup ecosystem, mentoring over 250 entrepreneurs on various aspects of business management and fundraising. Their leadership garnered recognition, including the Forbes 30 under 30 award. Rei and Anita met during their time at First Round Capital, where Anita was the Head of Knowledge. While there, she helped hundreds of entrepreneurs connect deeply and vulnerably, to share their concerns and to learn from each other. Anita was also an executive coach with the renowned coaching firm, Reboot, and is a certified Neuro-Linguistic Programming Practitioner. Key Advice for Working Through Challenges Prevention is first and foremost! Speak early and often to reduce buildup, bottling up and boiling over of tensions Make feedback about actions and behaviors, not about the person or their personality Rei suggests that using a simple framework like SBIO is a great way to frame feedback. (Situation or data, the Behavior you see, the Impact it has on you, and the Opportunity for improvement or transformation) Make sure feedback conversations are two-sided, with both partners regularly asking for and offering feedback Anita underscores the importance of Co-Creation of resolutions to challenges instead of telling someone to be different. Working on these tensions with a sense of collaboration can lead to reduced defensiveness. Head over to 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 /episode/index/show/theconversationfactory/id/30586988

From Transaction to Participation 02/20/2024

From Transaction to Participation My guest today is James Rutter, Chief Creative Officer at COOK, the pioneering frozen food company, where he oversees internal and external branding and communications. COOK is a founding UK B Corp, committed to using its business as a force for good in society, and has been ranked in the top 100 Best Companies To Work For every year since 2013. COOK’s award-winning frozen meals and puddings (which are desserts, btw) are made by hand in Kent and Somerset, and sold from 98 of its own shops nationwide, in 950 concessions and through its own home delivery service. James joined COOK in 2010 after 15 years as a financial journalist and editor, and he speaks and writes regularly about purpose-driven business and brands. James and I talk about the glory that is a proper Fish Pie, and about citizenship and participation. James’ leadership philosophy for his internal team is grounded in a sense of play and a recognition of community. He shares some of his favorite insights from and the deep value he’s found in working with Jon Alexander on Citizenship and Participation. James references Jon Alexander’s Participation Premium Equation in the opening quote. There is so much goodness in this episode! At Minute 27 James shares his community and transformation insights from Peter Block, including the essential idea that a small group, a community, is the fundamental unit of change, especially when that group is grounded in possibility. He also goes to share the impact that Block’s ideas of Inversion have had on him: As James says, summarizing Block: “It's not the performer who creates the performance, but the audience… And again, in a conversation sense… it's the listener who creates the conversation whereas we often think it's the speaker who creates the conversation… it's the child who creates the parent, not the parent who creates… this is (not) some kind of answer, but… a thought to play with. What if that's the way it works? How would you approach it differently? If the audience creates the performance, then how are you seeking to bring the audience into it? How are you giving them the power?” At Minute 42 we discuss the importance of Connection over content: “...you've got to seek to build the human bonds first before you seek to do whatever the worky thing is you want to do.” In essence, we are marinating in Danny Meyer’s ideas of an Employee-First workplace, which is why we talk, at the end of the episode, about how Happy Cooks make Happy Food, referencing an earlier conversation we had. And James insisted on talking about my Mom being on the Mike Douglas show with John Lennon, Yoko Ono and Chuck Berry in 1972, hosting a historical cooking segment - this episode is famous because it’s the and You can see (most of them seem to get pulled down). At a crucial moment in the cooking segment, my mother, just 22 and not actually my mother yet (or anyone’s!) realized that the studio band was playing chaotic music, and that everyone was in a chaotic space, and she announced that unless we had a calm, peaceful environment, the food would taste chaotic - our intention and our energy would flow into the food. The Host, Mike Douglas, asked the band to play something quieter and more mellow, and John Lennon, assigned to cut cabbage, began reciting the mantra he wanted to suffuse the food: “Rock n Roll…Rock n Roll…Rock n Roll” What do YOU want to suffuse your work with? Head over to 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 Agency = Purpose + Belonging + Power Agency: the ability to shape the context of one’s life Purpose: the belief that there is something beyond your immediate self that matters Belonging: the belief that there is a context to which you matter in turn Power: practical access to genuine opportunities to shape that context : An essential book on people and organizations Finding flourishing and play at work - inspiration in Quotes no one said: “Teach Them to Yearn for the Vast and Endless Sea” Via quote investigator: Happy Cooks make happy food: On Daniel’s Mom being on the Mike Douglas show with John Lennon, Yoko Ono and Chuck Berry Hosting a cooking segment: Why this episode is famous - it’s the and (most of them seem to get pulled down) /episode/index/show/theconversationfactory/id/29967743

Divorce by Design - Shifting the Default Conversation with Suzanne Vickberg 02/05/2024

Divorce by Design - Shifting the Default Conversation with Suzanne Vickberg Today I share my conversation with Suzanne Vickberg, aka Dr. Suz. She is a social-personality psychologist and a Research Lead at Deloitte Greenhouse. Along with her Deloitte Greenhouse colleague Kim Christfort, Suzanne co-authored the best-selling book Business Chemistry. But there’s another type of Chemistry - or Alchemistry - that I sat down to talk to Dr. Suz about - shifting the default track of a conversation from protection and opposition to collaboration, , a Professor of Social Interaction at Loughborough University, who speaks in her book Talk about conversations as having a landscape or a “track” that participants asses and orient to rather quickly…and that we glide down that track, while we monitor the texture of that landscape, and navigate the bumps in the road…so that we can keep things on safely on track. and In the opening quote to this podcast, you can hear Dr. Suz describing this process of “landscape orienting” happening very rapidly in a divorce context. Knowing the default path is very helpful when navigating a “hello, how are you?” kind of “small talk” conversation in a non-wierdo-way. Knowing the default track can help make things smooth and easy…when you’re visiting the store, or a bowling alley. And when you don’t know the basics of the track, things can be hard - Doing simple things in a different culture can be surprisingly slippery to navigate when you don’t know the basics of the track. But sometimes the default path can be extremely detrimental - especially when the default is ineffectual or becomes unconscious and habitual - we keep doing things out of rote, not intent. In business, a common default/habitual conversational path is looking at an underperformer and putting them on a Performance Improvement Plan in order to be able to fire them more easily, A non-default, more conscious conversation is taking the time to learn *why* they are underperforming and helping them actually transform themselves, their work performance and their lives….and in the process deeply benefiting the company and even the community. Seems impossible, right? Or grandiose? talks about an organization that did just this… a manager discovered that a chronically underperforming and late employee was just functionally illiterate. That employee, once they felt safe to share more, helped that manager learn that many of their employees were facing similar issues. Instead of a PIP, this employee got literacy training, and became an advisor to a new literacy program developed inside the organization, which spread out to the larger community, in ripples of growth and transformation. That is a *non* default conversation - turning a PIP conversation into a community-transformation conversation. On a micro-scale, Dr. Suz’s book tells the story of rethinking or re-designing the “default track” for a very, very common conversation - Divorce. When that word gets said out loud, people find lawyers, put up a shield, and start digging trenches. There is a better way! It takes effort to deeply empathize with your “opponent” in a difficult conversation. It takes patience and imagination to collaborate with your “opponent” to design a win-win scenario. But the default design for divorce doesn’t usually create ideal outcomes…just conventional ones. It’s possible to create something better than you can imagine if you create the space for a transformational conversation. Dr. Suz helps break down how “design” in these situations just means really understanding the REAL problem we’re solving and what our IDEAL outcome really could look like… BEFORE we jump to solutions. Also check out my , author of, among many other amazing books, the book Collaborating with the Enemy - which is what I know a divorce can feel like. Some of his perspectives take this “divorce by design” mindset into the broader business and strategy arena. Enjoy this conversation as much as I did…and think about how you might transform the most challenging conversations in your life and work. With more conscious creativity and intention, with empathy and collaboration…with more design you can create more of what you really want, just like Dr. Suz did for her own divorce and for her own life. Head over to 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 /episode/index/show/theconversationfactory/id/29633443

Conversation Wisdom from an AI-savvy CEO 11/07/2023

Conversation Wisdom from an AI-savvy CEO My guest today is , co-founder and CEO of , a Voice-AI company empowering restaurants to leverage AI and automate food ordering using natural language voice ordering at drive-thrus, over the phone, websites, and mobile apps. VOICEplug's technology integrates with existing systems and apps, allowing customers to interact with the restaurant using natural voice commands, in multiple languages and be serviced seamlessly. I wanted to sit down with Jay to unpack what he has learned about how conversations are structured (for computer-to-human interaction) that he brings into his CEO (human-to-human) conversations - crucial conversations, with his senior leadership team and his broader organization - does an AI-savvy conversation-aware CEO approach conversations and interactions with a different eye? We also focused on a few questions of deep concern for our culture today: the responsible and ethical use of AI and how it might impact the future of work. Through our conversation, it became clear that: AI is great for: Repetitive or highly similar and constrained tasks. Ordering fast food at a drive-in, VOICEplug’s use case, is a perfect context for AI. In these kinds of conversations, there are boundaries on the scope of the interaction and a clear set of intents and possible goals. Jay also points out that his AI is trained on many, many different instances of people ordering food from other people. So,the voice-driven bot can get better and better at these kinds of conversations, all the time. Humans are best for: High-risk and high-complexity conversations with no clear comparables or no clear scope. For Jay’s conversations with key industry stakeholders, at company-all-hands, and with his leadership team, AI can give him ideas or first drafts, but ultimately, he needs to navigate nuance with his human conversational intelligence ++++++++++++ AI is great for: Crunching lots of data (which is always from the past) and summarizing it. Humans are best for: Deciding what kind of future they want to create. Jay points out in the opening quote that the Human mind can think, reflect, envision and CHOOSE an ideal future, creatively. AI can do a lot of that…but it can’t choose the future it wants. That is still a uniquely human strength - to dream and to choose to create that dream. Jay dreams of a future where work is a deeper and deeper collaboration between humans and AI, where humans focus on higher-value activities while AI takes over repetitive tasks. Jay goes on to suggest that curiosity and powerful questions are THE most critical of human skills. When I asked Jay to share his favorite ways of designing conversations, he shared three tips: Take just a few minutes before a meeting to be very clear about your key one or two objectives for the conversation. In other words, start the end in mind. Another way of putting it is to take time to set an intention. If Jay is meeting with folks he doesn’t know as well, from outside the company, like new clients or stakeholders, he’ll deliberately slow down the conversation and delay getting to the core objective. Instead, he’ll spend 20-30% of the meeting time getting to know them, talking about other things, all in service of trying to understand them as people, and their conversational style Jay consciously chooses some conversational areas to NOT be highly scalable or automated - he shares a story about being offered an AI tool that would send automated and personalized birthday emails to his employees. As he says “What is the point of me having to use that as the CEO (when)…that relationship, that wishing someone on their birthday as a personalized conversation means so much to me. That's the last thing I would want to ever automate.” Not all conversations, even ones that can seem small and inconsequential SHOULD be automated. It is possible that a real, human touch will be the ultimate in luxury in the future. Head over to 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 /episode/index/show/theconversationfactory/id/28501256

Designing Conversations to Unlock Strategic Foresight and Innovation with Kevin Bethune 10/31/2023

Designing Conversations to Unlock Strategic Foresight and Innovation with Kevin Bethune I’m excited to share my conversation with Kevin Bethune, a multidisciplinary design executive, entrepreneur, best-selling author and keynote speaker based in Redondo Beach, California. He’s been a VP of Strategic design at BCG Digital, A global process product manager at Nike and a Nuclear Engineer at Westinghouse. He currently leads his own firm, One of his key ideas is “Open your aperture.” -ie, shifting the lens that you are looking at a problem from or through. Design and Design Thinking has so many tools to help us do just that, and find creative approaches to our biggest challenges. In our conversation, we discussed the importance of embracing creative approaches (since our habitual approaches most likely can’t solve them!) and the need for bold leadership to optimize for curiosity and creativity - because going with business as usual is usually a lot easier than spending time on curiosity. It takes a willingness to slow down to optimize for curiosity in a business environment that is often so focused on quarterly capitalism. We also highlight the lack of diversity in design and innovation, particularly in black representation, and the cognitive dissonance of claiming to serve certain communities without actually representing them - an unresolved critique of many innovation firms. The S-Curve and the Cone of Possibility Kevin’s book, Reimagining Design: Unlocking Strategic Innovation, is CHOCK A BLOCK with diagrams (and I love diagrams!) that will stretch your thinking, but we spent some time on one diagram in particular that combines two classic models of thinking: The cone of possibility and the s-curve. The Cone of possibility is a cone on its side, with the tip at the present, and the sides of the cone stretching out like rays of sunshine to the right. The rays represent possible futures along the timeline. There are many versions of this diagram online. Kevin’s version calls the center of the cone the “most likely” or projected future. The cone of possibility invites us to consider widening edges - future scenarios that are plausible and even impossible or preposterous futures, not just the projected or ideal future. Opening our aperture to consider multiple possible futures means that our plans can be more resilient, adaptable and even antifragile. The S-curve is a visual representation of one of my favorite Shakespeare Sonnets. #15: When I consider everything that grows Holds in perfection but a little moment, That this huge stage presenteth nought but shows Whereon the stars in secret influence comment; When I perceive that men as plants increase, Cheered and check'd even by the selfsame sky, Vaunt in their youthful sap, at height decrease, And wear their brave state out of memory; Things are born (or emerge), they grow, mature and then fade away. Kevin’s version of the S-curve includes more detail: Emergence A dip - the trough of disillusionment A hyper-growth phase that slows into.. Maturity and then… Decline, or retirement. Kevin overlays the cone of possibility with a set of cascading s-curves, representing a host of possible trends rising and cresting as we look out into the possible futures. As Kevin describes this diagram in our conversation, his hands are making waves of opening and closing, diverging and converging. That's what he’s seeing when he looks along the cone of possibility: all of these different trends, multiple pathways. It’s this complex, undulating space that he tries to illustrate for the teams that he works with to help them see a bigger aperture to think inside of. These diagrams, these mental models, help redesign the conversation about strategy and innovation. We’re not designing for a single, simple, ideal future. We’re looking out at a complex landscape with multiple possible twists and turns. That is how you unlock strategic innovation - step back, widen the aperture and change the conversation. In short - creative visualization facilitates dialogue and widens perspectives. Head over to 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 /episode/index/show/theconversationfactory/id/28466858

A Leader's Guide to Managing Organizational Emotions During Layoffs and Beyond with Emily Levada 10/17/2023

A Leader's Guide to Managing Organizational Emotions During Layoffs and Beyond with Emily Levada My guest today, Emily Levada, is a seasoned Chief Product & Technology Officer. Currently, she is the Chief Product Officer and Interim co-CEO at Embark Veterinary, a company dedicated to leveraging genetics to enhance the health and longevity of dogs. During her tenure, the company has achieved notable recognition, ranking as the #3 fastest-growing private company in Massachusetts and earning a spot on Forbes' list of promising venture-backed startups. She also serves as a Board Member at JCC Greater Boston, bringing her expertise to contribute to the organization's growth and development and holds a significant role as a Member of the Customer Advisory Board at UserTesting, where she actively engages in guiding and advising the company. Emily is also a two-time podcast guest, my first ever! Emily was also gracious enough to be a guest mentor for the Innovation Leadership Accelerator cohort I co-ran with my friend Jay Melone from the product innovation consultancy New Haircut some years back. In this conversation, we sat down to talk about managing organizational emotions, especially negative emotions, and especially during critical junctures, like layoffs - something that many folks have been through, and many folks in the past year. I knew that Emily had some experience with this in the past and had some great thinking to share around this crucial leadership topic. There’s no *good* side to be on in a downsizing event - the people who are losing their jobs and income are also losing a sense of identity and need to navigate an uncertain future. But the loss of identity and the need to face an uncertain future is also true for the folks who are still with the company - both the “rank and file” and the leadership. Layoffs done poorly can dent a company culture. Emily emphasized the importance of transparency in the period leading up to a layoff, as it builds trust and can mitigate negative emotions. On the other hand, leaders often have a desire to protect people from such difficult conversations until the last possible moment, so the whole team can focus on their day-to-day jobs. I explored this polar tension between these two fundamental values, transparency and protection, with Emily using a tool called Polarity Mapping, developed by Barry Johnson Ph.D., the creator (and registered trademark holder!) of The Polarity Map®! and IMHO, Stephen’s version of Barry’s diagram (below) is a bit clearer! The basic idea of Polarity mapping is that often we feel pulled by two values, like: Should we focus on Innovation or Efficiency? Should we prioritize Deadlines or Quality? Growth vs. Consolidation? Short-term Gains vs. Long-term Organic Growth? Centralization vs. Decentralization? (thanks for these examples, Stephen!) In my own coaching work, I’ve found leaders can struggle to navigate conflicting parts of themselves, forming inner polar tensions that leave them feeling stuck, like: “I need to be flexible vs I need to be firm” “I need to lead the conversation vs I need to let the conversation flow” “I need to be aggressive or I have to be more passive” “I need to listen more vs I feel the need to fix challenges” “I want to be authentically myself vs I need to be a chameleon to get by” And because we get pulled between them, and feel the polarity to be an unwinnable double bind of “damned if I do,” we kind of flub the balancing act. Polarity mapping asks us to be ultra-specific about the positives of both values AND to be very clear on the downsides of over-indexing on one value to the detriment of the other. Doing a mapping like this can help us thread the needle of polarity, and look out for the early warning signs of over-indexing in one direction or another. Below is a version of a polarity map for the tension Emily describes in our conversation, between Transparency and Protection. Emily points out that these polarities pop up, not just at crucial moments in a business like layoffs, but in day-to-day operations, too. Leaders can feel that Emotions are Inconvenient, but Team Emotions have real impact Emily shares the top three negative organizational emotions she finds can deeply impact a team’s ability to learn (ie, be willing to experiment), be creative (ie, being able to innovate) and be fundamentally effective: Anxiety (Fear)BoredomApathy Fear, anxiety, and boredom are detrimental to creativity and productivity in knowledge work. Leaders need to address these emotions and create an environment that fosters engagement and challenge - and ultimately, create a learning organization. “People cannot do creative knowledge work when they feel fear and anxiety and boredom. Those things are just incompatible.” Emily suggests that well-run one-on-one meetings are crucial for understanding how team members are feeling and detecting signs of overwhelm, underwhelm, or “whelm” in their job. One-on-ones can help build a foundation of trust and safety, on which we can build honest and productive conversations. Emily also shares some straightforward approaches for shifting these key negative emotions: Anxiety: focus on building psychological safety for teams experiencing anxiety, and provide more transparency and context. Boredom: create relevant challenges Apathy: create accountability and challenge for teams experiencing apathy Head over to 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 , by Stephen Anderson /episode/index/show/theconversationfactory/id/28308182

Unpacking Mentoring with Jason Knight and Sandra Monteiro 09/14/2023

Unpacking Mentoring with Jason Knight and Sandra Monteiro My guest today is Jason Knight, the creator, host, producer, editor and promoter of the podcast, a , 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 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 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 /episode/index/show/theconversationfactory/id/27982791

When the Mission Drives the Tech: Co-Founder Conversations 09/05/2023

When the Mission Drives the Tech: Co-Founder Conversations It’s not every day that a patient-doctor relationship turns into a Techstars-Funded medical innovation startup. In this episode I sit down with Dr. Onyinye Balogun and Eve McDavid, the co-founders of Mission-Driven Tech, a women's health venture in collaboration with Weill Cornell Medicine dedicated to the transformation of cervical cancer care with modern technology. Onyi, as her friends call her, is the CMO of Mission Driven Tech and also an Assistant Professor of Radiation Oncology at Weill Cornell Medicine specializing in the treatment of breast and gynecologic malignancies and does research into improving cancer care in low and middle income countries. Eve, the CEO, is a former Google executive who is also a Stage IIB Cervical Cancer survivor. Eve and Onyi met during the pandemic, when Eve was undergoing cancer treatment under Onyi’s care. I heard Eve and Onyi’s presentation at the 2023 Techstars Demo day in New York and was stunned by the fundamental disparities in historical improvement in gynecological cancer outcomes - as they point out in this conversation, in recent years, Prostate cancer treatment has achieved a nearly 100% five year survival rate. In the same period, cervical and uterine cancer mortality has gotten worse, while cancer treatment for all other cancers has improved exponentially. Their company exists to change that story. Co-Founder Communication Insights This conversation is one of a series on co-founder communication. Check out my interviews with the co-founders of online gaming start-up Artie on (the secret - have a coach and a therapist!), a conversation with , the co-authors of the 2015 bestseller, Wired to Create, on navigating Paired Creativity, and One key that Beth Bayouth and Mario Fedelin, the COO and CEO (respectively) of Changeist, a non-profit organization dedicated to youth empowerment, so that they can be sure to not fall apart at the same time, a sentiment that Eve and Onyi echoed. I also discussed the with Jane Portman and Benedikt Deicke, co-founders of Userlist - and they helped me see that the healthiest companies have partners that have worked together in some capacity - and indeed, in this interview, Onyi and Eve called Eve’s cancer treatment their “first collaboration”. Know yourself and each other The start of a startup journey can be optimistic, so we explore what they have learned about each other that has helped them to better communicate and collaborate together since they started the project. Accelerators can’t do it all for you Eve and Onyi share how the accelerators can help with structure, mentorship, capital and community, but that ultimately you need to have something worth accelerating - a key customer insight or a core technology - both of which Mission-Driven Tech has! Have multiple modes and frequencies of communication Eve and Onyi have a weekly meeting just focused on their flagship product, the Blossom device, and another meeting weekly for other issues, and to simply connect. Meanwhile, they have a Whatsapp thread that enables them to constantly stay connected and in touch with each other. Balancing always-on connectivity and scheduled connectivity is key. A partnership is a marriage and reflective listening is key! Onyi shared their perspective that being in a co-founder relationship is like marriage, and that communication is key for any marriage to work. As she says, “The future of this company rests partly in how well we're able to communicate. So we tell each other the good, the bad and the ugly.” She shared their simple and effective approach to communication - making specific time for it, and using active listening intentionally: “I hear what you're saying, I reflect it back to you. You hear what I'm saying and you reflect it back to me.” Know who your real audience is We discuss user-driven product development, which Eve and Onyi, as a former patient and doctor, are a unique example of…but we also discuss how in their current stage, investors are their actual “buyers”. Onyi discussed how she’s developed a keen sense of “push vs pull” when they are making their investment pitch - some investors just get the commitment required to make a startup like this successful, and those people are their real audience. It’s not about convincing the wrong people, it’s about finding the right people. Balance Now and Next Every startup needs to balance managing their current challenges and opportunities with putting energy into strategic vision and planning. Eve points out that this is a particular challenge for medical and device companies - the rate of change can be slow, due to fundamentals of the problem space. So, there needs to be more patience and intention put into planning and hypothesis testing. As Eve pointed out, There is immense pressure to achieve immediate results, but real impact takes time. Head over to 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 LinkedIn: Onyi: Eve: /episode/index/show/theconversationfactory/id/27902070

Give First: The Long Conversation of Being a Co-Founder 08/28/2023

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 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 /episode/index/show/theconversationfactory/id/27849948

Cofounder Conversations: Pivoting while Staying Sane 08/21/2023

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 /episode/index/show/theconversationfactory/id/27712212

The Power of Intention 08/10/2023

Leaders as Humble, Audacious, Z-Shaped Coaches 07/20/2023

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! 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 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 /episode/index/show/theconversationfactory/id/27518844

A Company Must be a Community of Practice 06/26/2023

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 and his more general . Head over to 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 /episode/index/show/theconversationfactory/id/27278724

Coaching from Essence, Creating from the Future 05/16/2023

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. 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 , by Robert Ellis /episode/index/show/theconversationfactory/id/26805855

How to Think Strategically about Funding for Founders and Investors 05/09/2023

How to Think Strategically about Funding for Founders and Investors I first met , 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 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 Avantika's Tedx Talk: Daniel’s , highlighting key questions and perspectives from Avantika, including the “base camp/summit” metaphor. /episode/index/show/theconversationfactory/id/26732787

A Recipe for Team Agility: One Page, One Hour 04/10/2023

A Recipe for Team Agility: One Page, One Hour Today my conversation partner is Matt LeMay! Matt is an internationally recognized product leader, author, and consultant. He is the author of Agile for Everybody (O’Reilly Media, 2018) and Product Management in Practice (Second Edition O'Reilly Media, 2022), and has helped build and scale product management practices at companies ranging from early-stage startups to Fortune 500 enterprises. Matt and I met at UX Lisbon last year where he gave a talk that included him describing his extremely actionable recipe for team agility: the One Page / One Hour Pledge, a powerful commitment to minimize busywork and maximize collaboration that has been adopted by individuals and teams at Amazon, Walmart, CNN, and more. I was excited to bring Matt into a conversation about this pledge, because I know how easy it is to get caught in a rabbit-hole of perfectionism before sharing my work with others. Teams can work more fluidly if we reduce the cycle time between solo work and team work. Matt is an advocate for the power of focus, subtraction and feedback loops over perfection - I mean, would you rather ride a bike you can only aim once or one that you get to steer continuously? I never dreamed I’d get to have a podcast conversation that includes references to Alan Watts and the power of Ego Death to accelerate your team’s success and ultimately, one’s own success…but glad that we are! Matt and unpack how TIMEBOXING (ie, Tight-and-almost-thoughtless constraints ) helps shift the relationship between thought and action in teams and organizations…and can help move the conversation forward. Head over to 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 “When we attempt to exercise power or control over someone else, we cannot avoid giving that person the very same power or control over us” Alan Watts /episode/index/show/theconversationfactory/id/26426583

The Surprising Power of Two Hour Mid-week Cocktail Parties 02/28/2023

The Surprising Power of Two Hour Mid-week Cocktail Parties In 2019 My friend Philip invited me to a 2-hour cocktail party at his tiny apartment in the Lower East side. True to his word, the gathering, which was on a Tuesday night, started at 7 PM sharp, and at 9 PM he kicked us out onto Orchard Street to enjoy the rest of our night and/or to get to bed on time (since it was a weeknight, after all!) I met a whole bunch of awesome people, and if I’m honest, I thought Phil was super cool for bringing such a lovely group of people together. The food and drinks were nothing to write home about, but no one cared. Phil stopped the party two or three times to get us to circle up and introduce ourselves and respond to an icebreaker prompt. It was pretty fun. He mentioned during the party that he was following an early draft agenda, a recipe if you will, for such gatherings, that was being developed by his friend Nick Gray, who I knew of through other friends. Nick had started a company called Museum Hack that had blown up - in the good sense. They were leading creative tours in Museums around the city, so I guessed this guy Nick knew a thing or two about getting people together. Cut to 2022 when Nick Gray’s book “The Two Hour Cocktail Party: How to Build Big Relationships with small gatherings” came out. Here it was, four years later! I was fascinated to talk to Nick because I thought “How much could there be to this? Isn’t it all in the title!?” How much could the form have evolved over 4 years of prototyping and testing?! I’ll tell you folks…this is a polished gem of a book. If you’ve followed my work, you know that I’m a bit of a nerd when it comes to gathering/facilitation/conversation design. I love card decks about it, books, diagrams, narrative metaphors to fuel creative innovation in gathering science for skilled facilitators to bring diverse stakeholders together to tackle wicked problems. I have coached leaders on this skill, all over the world. I hosted many, many cohorts of my 3-month Masterclass on Facilitation that people lovingly described as “drinking from a firehose” of facilitation while somehow being spacious and deeply mindful of how we gather. Managing complex gatherings is a crucial skill! Companies that can’t come together to discuss and decide on actions for their biggest challenges will not survive! And I love these types of gatherings - they are never the same, they have to be absolutely customized, and deeply considered. Nick, on the other hand, has designed the “CheckList Manifesto”, the “Design Sprint” or the “Joy of Cooking”...not for any and all types of gatherings - but for one, single, Life-changing, surprisingly powerful gathering - a 2-hour, midweek cocktail party. Nick’s book is designed with absolute beginners, or those hesitant or nervous to lead gatherings in mind…but masters of gathering will be pulled in too…I was. Nick designed this insanely in-depth book to cover everything from snacks to drinks to how to write an invitation to…everything. Where to put name tags. How big those tags should be. You get the idea. While I am a nerd in the sense of being an omnivorous gathering nerd, Nick is an obsessive-compulsive nerd of this one form…and for good reason. Nick believes, and I now do, too, that if more people felt more comfortable with having more gatherings we would all be more connected. The midweek 2-hour cocktail party just might save the world. You can get the gist of the form from this conversation (I mean, even from the title!), but if you’re a gathering nerd like me, you'll absolutely enjoy Nick’s insanely thorough guide, which I found myself flipping through regularly as my wife and I prototyped our own first midweek, 2-hour cocktail party, which we titled a “Serendipity Salon”. I think we all need more serendipity in our lives, and that’s why I loved the opening quote I pulled from my conversation with Nick - the ability to take a short conversation with someone and turn it into a deeper one, to create a space where your old and new friends can connect with each other…only good things can happen from creating more of that type of serendipity in our lives. My wife and I have hosted two parties like this already and, as Nick has advised, we have our next one in the books! I hope you will, too. Head over to 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 /episode/index/show/theconversationfactory/id/26069304

Launching a Remote, Asynchronous Venture Studio 02/13/2023

Conscious Collaboration: Co-founder Conversations 12/15/2022

Conscious Collaboration: Co-founder Conversations In this conversation, I sat down with Beth Bayouth and Mario Fedelin, the COO and CEO (respectively) of Changeist, a non-profit organization dedicated to youth empowerment. They are building a community of young people that utilize their personal agency to create a more just society. Changeist’s programs help 11-26 year olds learn a common civic language, engage in dialogue, and build community to investigate local and global social justice issues. Participants also work with other local community-based organizations to implement local solutions to local problems. Together, Mario and Beth explore how they met, built a relationship and decided to work on this project together…and how they continue to manage themselves and each other in the entrepreneurship journey. A few insights we’ll unpack about conscious co-founder relationships: The key to a great co-founder relationship is that both of you do not fall apart at the same time! Fighting Well and how Cofounder Intimacy can help: With cofounder intimacy, there is an understanding that often there’s something else behind a conflict or a mood. Because when you're close, you tend to know about what’s going on or that it’s safe to ask. Knowing yourself and your skills The Power of working with someone with a Different Skill Set but Similar Values On Knowing yourself and your skills, and finding compliments on your core team: A great leadership team requires Comfort with yourself and your skills and Respect for the skills of others... and it takes Balance - but Balance of what?! On a leadership team you need: + Architects and Visionaries + Multipliers - someone who brings something you do not have to the table, who is also committed to the vision and the journey Another way to think about this is that you need: + A Balance of Openers and Closers on the team. This is the essence of conscious collaboration - knowing if you are more comfortable in a generative or divergent mode, ie, opening, or are more natural in the “Synthesizer” role - organizing, closing, or planning towards action. Mario owns his limitations as a “closer” and intentionally chose Beth as a COO for her natural “shark” skills - her ability to move things forward with clarity. Mario and Beth also talked about their balanced styles in “Speeding up” and “Slowing Down” creative conversations - Beth will pump the brakes and ground ideas in reality when the time is right. Feeling that balance between creativity and clarity, speed and thoughtfully slowing things down, is the essence of conscious creativity and conscious collaboration…being comfortable with both opening and closing modes is critical, but collaborating with others who complement your natural approaches is powerful. Be sure to check out my other co-founder conversations. I discussed building an Integrity Culture with the , and investigated prototyping partnerships with , co-founders of Userlist. (Which Mario and Beth absolutely did, as well!) I also sat down with Conflict and collisions will inevitably happen in relationships, so you might as well learn to lean into it! , the co-authors of the 2015 bestseller, Wired to Create, where we unpack how they managed their working relationship and discuss Paired creativity, which is totally a thing! And if you really want to dive deep into the idea of being a conscious co-founder, make sure to , the Senior Vice President of Entrepreneurial Development at EDAWN, the Economic Development Authority of Western Nevada. Head over to 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 On Healthy Conflict: /episode/index/show/theconversationfactory/id/25331625

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