100 episodes

Welcome to The Conversation Factory, where I investigate how to create change through changing conversations. Each episode I'll talk to an amazing conversation designer about how to Amplify, Shift or Transform conversations in Organizations, Teams, Communities and our own lives. Visit www.theconversationfactory.com where I distill these insights we can bring into our work and lives.

The Conversation Factory Daniel Stillman

    • Business
    • 4.9 • 38 Ratings

Welcome to The Conversation Factory, where I investigate how to create change through changing conversations. Each episode I'll talk to an amazing conversation designer about how to Amplify, Shift or Transform conversations in Organizations, Teams, Communities and our own lives. Visit www.theconversationfactory.com where I distill these insights we can bring into our work and lives.

    How to Turn a Conversation into a Public Park

    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 Therme Group US, 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

    • 1 hr 3 min
    Art that Changes the Conversation

    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 Benjamin Von Wong, 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 “Unforgettable Labs” 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 The Unforgettable Project 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.
    Some of his notable work includes the Giant Plastic Tap which used trash from the slums of Kibera, in Nairobi, Kenya, to demand that corporations #TurnOffThePlasticTap. The Giant Tap was displayed prominently when 193 different countries and 1,500 delegates came together at UNEA 5.2 in 2022 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.
    Recently he installed a grand sculpture at the Highline in New York City 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 his wonderful talk at Creative Mornings (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 crea

    • 52 min
    Leadership is Designing Moments of Impact

    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 Nancy Duarte 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 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.
    Get Moments of Impact! 
    A plan is not a strategy: The short video from Roger Martin we were talking about!

    • 1 hr 5 min
    The Problem with Change and the Power of Stability, Humanity and Praise with Ashley Goodall

    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 - the idea that people need feedback - and how most managers think about giving feedback in an utterly wrong way - 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 Ground Bass - the principal structural element of a musical piece. 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 Pachelbel's Canon here and listen to the Goldberg variations here (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. 
    This perspective aligns very well with the message Bree Larson offered here some years back. 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, Ashley wrote a New York Times Op-Ed piece which is a blockbuster 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

    • 1 hr 8 min
    Reunion: Leadership and Creating a Culture of Belonging

    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 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

    • 57 min
    The Intentional Conversations that Build Powerful CoFounder Relationships

    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. 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.
    The Grand
    My previous conversation with Rei Wang

    • 48 min

Customer Reviews

4.9 out of 5
38 Ratings

38 Ratings

ryarianne ,

Will change the way you think of conversations

I’m also a fan of Daniel Stillman’s book, Good Talk, and I appreciate how he both explains and models what intentional and interesting conversation design looks like. He has interesting guests and I always get a new idea from any episode.

jamessjohnson001 ,

Thought Provoking and Inspiring

After 10 years in the UX design and strategy space, the techniques, frameworks and conversations that Daniel shares have fundamentally shifted the way I show up. The podcast is a treasure trove of ways to not only excel in your career but to show up and be a better person for/with others. Daniel is the best!

thisisandrewyoung ,

Daniel is amazing and the podcast exposes me great things!

First off, if you ever get the chance to have a 1:1 conversation with Daniel - DO IT!

I use The Conversation Factory podcast as my go to source for finding interesting inspiration. I was exposed to “Coaching From Essence” from Daniel and the podcast. I picked up the book and could not put it down. His chat with Matt LeMay - “A Recipe for Team Agility: One Page, One Hour” was like listening to my people talk!

Please do yourself a favor, listen to this, and find yourself in growth mode!

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