The Conversation Factory Daniel Stillman

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 theconversati

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

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. You should really follow him on LinkedIn!
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 Peter Block’s book, "Community: The Structure of Belonging" and the deep value he’s found in working with Jon Alexander on Citizenship and Participation. Jon Alexander is the author of the bestselling book, "Citizens." 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 first time John and Chuck met and Played together. You can see A Tiny Video Clip of my mom on TV here (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 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 exc

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

My guest today is Jay Ruparel, co-founder and CEO of VOICEplug AI, 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. You might enjoy my conversation with Leah Smart, the host of one of LinkedIn’s top podcasts, on just this idea.
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 incon

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, https://dreamsdesignandlife.com/
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 c