The Conversation Factory

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 Tikkun Olam, repairing the world. 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 theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Reboot Jerry’s profile at Reboot Some other solid interviews with Jerry: On Being with Kista Tippett: Can you really bring your whole self to work? Noah Kagan, from AppSumo, interviewing Jerry on being a better human and a better leader

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. Check out that conversation here. 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 theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links The Grand My previous conversation with Rei Wang

James Rutter, CCO at COOK, talks about fish pie, citizenship, and participation. He emphasizes leadership grounded in play and community. Discusses insights from Peter Block's book and working with Jon Alexander. Highlights the importance of moving away from consumerism and fostering engagement for a meaningful collective vision.

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, Some years ago I interviewed Dr. Elizabeth Stokoe, 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. Check out our podcast conversation here and her TEDx talk here. 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? Carol Sandford, in her book about Regenerative Business 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 podcast conversation with Adam Kahane, 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 theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links https://www.divorcexdesign.com/ https://www.linkedin.com/in/suzannevickberg/ https://www2.deloitte.com/us/en/profiles/svickberg.html https://theconversationfactory.com/podcast/facilitating-breakthrough-with-adam-kahane

Jay Ruparel, Co-founder and CEO of VOICEplug AI, talks about using AI for natural language ordering in restaurants. He discusses the responsible use of AI, the benefits of AI in repetitive tasks like fast food ordering, and the importance of quality datasets for AI learning. Jay highlights the balance between AI tools and human connections, effective meeting strategies, and the power of asking insightful questions for team interactions and AI ethics.

Kevin Bethune, multidisciplinary design executive, discusses the importance of embracing creative approaches and the need for bold leadership to optimize curiosity and creativity. They also highlight the lack of diversity in design and innovation, particularly in black representation. Kevin's book, Reimagining Design: Unlocking Strategic Innovation, explores the cone of possibility and the S curve as models of thinking. They discuss rewiring organizations to embrace design thinking and the concept of opening the aperture in strategic foresight. Additionally, they emphasize the importance of diversity, intent, and belief in design, as well as handling ambiguity and navigating non-linearities.

Emily Levada, Chief Product Officer at Embark Veterinary, discusses managing organizational emotions, particularly during layoffs. Topics include transparency and trust, polarity mapping, managing negative emotions, regular check-ins, driving resilience and creativity, and the value of challenge and psychological safety.

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

Dr. Onyinye Balogun and Eve McDavid, co-founders of Mission-Driven Tech, discuss the disparities in gynecological cancer outcomes and the importance of collaboration and communication in their co-founder relationship. They also emphasize the need for equity in healthcare, increasing awareness about gynecologic cancer, and finding the right connections and supporters for their mission.

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