Stephen Sokoler on Designing Meditation and Coming to your Center

In episode I talk with Stephen Sokoler, the founder and CEO of Journey Meditation, a company dedicated to a world where more people meditate! I wanted to talk to Stephen because the inner conversation we need to foster is often forgotten completely. Instead, we focus on our teams, our organizations, our communities...all of the other critical conversations we've discussed in past episodes. But without going inward, the whole thing falls apart.

Meditation is like when an actor goes backstage to freshen their makeup, change costumes, look over the script... In life, we go from role to role without pause...and meditation is a way to step back and let it all chill.

I screwed this episode up! I'll be honest. I've done it before. When you're doing your own field recordings, it's easy to press the record button once, watch it blink, check your levels and then get into the interview. Oops! You actually need to press the button twice! The blinking stops and the seconds counter goes up. I messed up and lost about 30 minutes of sweet, sweet conversation with Stephen. Noticing it during our interview sent a cold chill through my whole body. I  just wasted this man's time, terribly. I had two options. Say nothing and try to "fix it in post" or cop to it and try again. I went for honesty...and since we're friends, Stephen humored me and we started over.

I mention this, not because I love honesty or vulnerability (although I do!) but because you might hear how the conversation with Stephen starts off a little stiff, a little mechanical. We are both *pushing* energy into the system to try to get the energy of the conversation back to where it was!  It's not tremendously noticeable...but you'll hear, once we get to the halfway point, things relax, we find a new thread for the conversation instead of trying to pull back towards the old one, and the conversation finds a more natural tone.

Meditation is like this, too. Being present has a gravity, but we can lose it, drift off to wherever. And we have to "bring ourselves back" in a way that isn't forced or artificial.  In the episode, Stephen and I discover another really interesting point, a connection between meditation and conversation that I hadn't noticed before.  Meditation is about coming back to your center. Recently, I was talking to a facilitator friend of mine who described his role as "holding the center" ...facilitating a great team conversation is about holding that space for real dialogue, open, at the center, and keeping people who drift off from getting too far. We just bring things back, as gently as we can, to the thread and keep things going.

Enjoy the episode! Stephen is a gentle and passionate soul, building an amazing company based on something he truly loves...I learned a lot from this episode, and I hope you do too!

Journey Meditation

Buddhism for Busy People

The Four Core Conversations: Medium Article coming soon!

The Costs of Burnout

Light Watkins

Sharon Salzberg

Why have a Coach

The benefits of Group Meditation

Open, Explore and Close: The Three Creative Conversations Medium Article coming soon

No Good or bad ideas: Episode two with Abby Covert

Stephen's Five MCs (in order mentioned, not ranked)

Biggie Smalls





Honorable mention:

Chance the Rapper

Elliot Felix of Brightspot Strategy on changing conversations through changing spaces

On this episode of the conversation factory, I talk with Elliot Felix, founder of Brightspot Strategy, a boutique consultancy. Elliot founded Brightspot almost seven years ago, and as a former founder of an even smaller design consultancy, I'm totally impressed by what he's built and grown. Elliot has a background in Architecture, which I tease him about (only an architect uses "sightline" in a sentence)...different types of designers talk about and see the world differently: we manage different materials. I studied Industrial Design, and so I often look at an idea and think "can this be made at scale?"...even if it's a service, I break it down and ask if it can be manufactured, reproduced. This tendency can annoy people! It's been recently suggested to me that when people tell me about their ideas I should just say "that sounds fun!" and leave it at that...

Brightspot officesL Check out those sightlines!


Elliot was kind enough to do our episode on site at Brightspot's offices in the Financial District here in NYC and as we walked around chatting about various artifacts in the office, Elliot's love of space as a primary material of design was clear. As he says in the opening quote: the right space can facilitate work, help express ideas, support and reinforce or make culture manifest.

I've seen this in my own facilitation work: I can't tell you how many times I've seen a group get stuck in rut, literally because they'd run out of wall space to work with. Just giving them a new wall to work on gave them a new space to have a conversation, got them unstuck. Walls help make work visible, and when work is visible we can have more productive conversations. Without it, we slow down. Designing the space work takes place in *is* conversation design. Change the space, change the conversation.

At Brightspot they frame challenges as a three conversation checklist: Examining the Spaces people are in, the services offered in those spaces, and how people are organized in that space. This checklist is, itself, a design for a productive client-consultant conversation. Trying to shift a system by approaching one of those conversations and not all of them is going to be harder. On the other hand, changing all three at once might be tough. But having the conversation about space, content and people is clearly crucial, that's why Brightspot designs their client conversations to include each of these three aspects of work.

When I teach facilitation I always tell people that they have to make the space they are facilitating in their own...and my favorite story of this is one of my first days working with Applegate Farms,  an organic food company, back in 2013. The room we were working in was large, cavernous, and had three big tables arranged in a "U" shape, with a screen projecting at the mouth of the U...the room had been designed for presentation, for the "sage on the stage"...but I wanted the group I was coaching on design thinking to collaborate, not focus on me! The U made everyone sit on the outside, facing me, not each other.

So during the break, I took the foot of the U and rotated it, so all three tables were parallel. The team walked in and was a little disoriented...the room was the same, but the energy was different. They sat in the chairs, facing each other, and we could get down to work in the style I was trying to cultivate.

Thinking about your own work: Is your space working for you or against you? Do you have the right variety of spaces, large, small, intimate, public, to do your work? In conversation design, we talk about the Q: the requisite variety of talent on your team, the right balance of familiar faces and fresh seems like, in talking to Elliot, that there's a similar quality of balance to be found in the spaces a truly functional company inhabits. If your space isn't working for you, shake it up!

Links and Notes

BrightSpot Strategy

Making a War Room for projects (but can we find a better name?!)

Expertise Audit: What do our people know? What knowledge aren't we tapping?

Vertical years and Horizontal years: Alternate Keeping the work the same and adding people with new skills and Evolving the offering.

Sightline - the most architectural word Elliott uses

Osmotic Communication

Leaders send signals whether they think are sending them or not: Semiotics

Idiosyncrasies of Leaders can be scaled unintentionally: Elliott over-analyzes, so his org tends to as well! Be intentional about communicating what's optional and what example you're setting, what aspects (quirks) of your personality you're transferring to the culture.

Focus and Time: Choosing our battles and having the time to fight them: Is there a better word: Where to learn and how to grow?

2X2: Size and Structure of conversations

Q of teams: New Yorker Article and Source, ie Requisite Variety in a System

Is your space working for you?

Larry Greiner:  The Greiner Curve


Alistair Cockburn on the Heart of Agile, Jazz Dialog and Guest Leadership

My conversation with Alistair Cockburn was Agile to the core! We revised our timeline and deliverable with a quick standup and got right into it: After all, Agile principle #2 is to welcome changing requirements, even late in development. To wit, I thought we had an hour, early on the call he asked for 20, tops! (Somehow I kept him on the line for 45, since I'm deft at conversational manipulation. And he was keen to keep it going, too.)

Alistair quite the nomad, teaching Advanced Agile workshops all over the world. When he's not teaching, he might be dancing Tango in Argentina or brushing up on his French in Nice. But sometimes the location is too distracting, so he was holed up in Florida where he found a town that was *just* boring enough to allow him some time to get some work done. He was moving house unexpectedly the day we were slated to chat. I saw on Facebook that his AirBnB had a shag carpet and the humidity and mustiness mixed with a thick carpet was making him sick! I tried to give him an out, but he was adamant we do our conversation, even for only 20 minutes. His motto: Now is better than the future.

One of the pleasures and inspirations of talking with Alistair is that he's a man who really lives his principles: Agile principle #10 is that "Simplicity--the art of maximizing the amount of work not done--is essential". You'll hear how Alistair tries to design his life to make this principle a reality!

As I mentioned two episodes back with Daniel Mezick, around Open Space Agile Transformations, Agile is kicked around a lot in the consulting world, but my sense is that all of those people haven't actually read the Agile Manifesto! Alistair was one of the originators and signatories back in 2001, and it was a response to a broken way of working. But just like any ideology, it's come to be interpreted in alot of ways by a lot of people. It was fun to go back to the source!

I really enjoyed Alistair disagreeing with my characterization of Agile as a Design for Conversations. But I see it that way: Agile designs for some conversations and  not for others. And in fact, Alistair has a lot in common with Dave Gray, who I interviewed a few months back: Dave wondered about who has the right to design a conversation and if it can be overdesigned! Alistair is a proponent of Guest Leadership...that making space for momentary, voluntary leadership can powerfully transform work and teams.

Alistair and I had what he would call a Jazz Dialogue: a conversation with a meta-conversation layered on top! I have listened to this episode a few times and it's a tough one to summarize or encapsulate. One thing that I'm left with is the idea that even the desire for agility or the hunger for no ideology is an ideology. Which leaves me reflecting on the ways that my own internal tendencies leads to my own ways of seeing things as "right". After all, designing a conversation is power and power should be exercised carefully...because I could be wrong!

Show Bullets and Links

Alistair Cockburn on the Web

Agile Manifesto

Crystal Clear

Improvisation in Dance: What's Fixed and What's Flexible?

"I expect people to decline my advice"

The Oath of Non-Allegiance

Precision vs. Looseness

Crystal Clear: The Sloppiest methodology that could possibly work (Martin Fowler)

"Arranging my life for the maximum amount of freedom"

Anchoring Sloppiness in Essential details. (the opposite of an Overdetermined System)

Cultural Invasion: Design as Cultural Imperialism

Assuming that people bring their whole adult self to work:

Agile Practitioners mentioned:

Daniel Mezick

Ken Schwaber

Nic Sementa

Kay Johansen

Guest Leadership

RE: When do people step forward and help: The Good Samaritan Experiment (hint: when they're not in a hurry)

Be the Change you want to See can backfire

Host Leadership

The Art of Hosting

Open Space Technology

Going Meta: Talking about how we talk

Jazz Dialogue

The Heart of Agile

Self Storytelling

Kokoro: The heart

Alistair's Poets: ee cummings and Emily Dickinson and a poem Alistair wrote in honor of ee:

Rei Wang of First Round Capital's Dorm Room Fund on Community *as* Product

One of the great pleasures of hosting this show is that I have an excuse to reach out to old friends and spend some quality time with them. And I get to double the quality time! I really love gettingto listen to the whole episode again. It's a time to dig in and figure out what the episode was really about, and write these essays. Originally I was going to have the episodes transcribed and then read them, but in episode 2, I heard a different perspective. Information Architect  Abby Covert  talked about how processing her own research transcriptswas essential to her work....I tried it, and she was right.

It can be hard to give oneself the time for reflection and learning, even though our internal conversation is  the most critical of all the conversations I've been researching (See David Whyte's The Three marriages for more on that!) In a few weeks I'll be sharing an episode I did on Meditation, one of the key tools to maintain (and silence, occasionally) a healthyinner conversation. Redesigning your inner conversation! Who wouldn't sign up for that from time to time?

In this episode I talk with Rei Wang, Director of the Dorm Room Fund. Rei and I connected way back in my Design Gym days: I think we were running an innovation day for GOOD magazine  where she was manager of GOOD Local. The workshop might have been  around connecting with your neighbors? We stayed connected as she moved to General Assembly (where I taught UX part time) as she rose up the ranks and managed their rapidly growing community efforts.

She now directs the Dorm Room fund for First Round Capital, and it's an amazing and unique organization. First Round does early investing in companies like Blue Apron, Birchbox and Warby Parker. And while the Dorm Room Fund is funded by First Round, it's run completely by college student volunteers, not professional VCs! This tight community of volunteers IS the Dorm Room Fund.

I think there is a lot talk about community: about building it and trying to monetize it...but few people treat their community as an living conversation to be designed.  In the opening quote I pulled, I was struck by Rei's perspective that companies develop better products in deep dialog with their communities. To some, this is obvious, but only those who cultivate their community consistently and with intentionality get to harvest insights and profit!

Community can be just for celebrating and marketing a product, it can be to have customers contribute to the product...but Rei sees her community *as* the product, which means she's very careful to orchestrate it's development and evolution. The volunteer students in the Dorm Room fund must have a high level of autonomy and drive, which means she has to pull the work out of them, not push it on them!

And her community is rapidly refreshing, by design: Each year they lose people as they graduate and gain students who come in: Capability leaks out of her community constantly! Rei's solution doesn't seem to have a name, so I'll call it Cohort Mixing. In her annual event, she makes sure incoming, current and outgoing groups all connect in significant ways, in large and small groups and over time. This helps keep traditions and institutional knowledge alive and constant, even as the community renews.

Thinking about your own company or can community transform how you develop and test ideas? And how can you empower people in the community of your company to share and pull their own work forward, without you pushing every day?

Enjoy the episode! Rei's insights are solid gold. No bonus tracks this time...Rei and I somehow got it all in under the bell!

Show notes:

Community as Product workshop at CMX East 2015

First Round Capital

Dorm Room Fund

Defining Community

GA Hub: Community Engagement through curation

CMX Community Professionals Organization

Good Magazine

Foursquare's Superuser Group

The Famous Designer who said internships should be paid!

Rei's totally venture backable card company based on her mother's tiger mom texts

Radical Candor

Level Mixing In Communities

CMX's excellent article on community Engagement

Mutualism in Pair Relationships

Tony Robbins - I am Not your Guru

Slow Goodbyes : The Post-Wedding brunch

Automation in Group Decision Making: Not what they use at DRF, but an interesting example of using automation to simplify group conversations at the close

Balancing Privacy and Openness in Community: An office perspective

Mashup Teams: The optimal density of connections in teams

Motivation in Volunteer Communities: Open Source Sustainability and community building

Rewarding your community Volunteers: The Creative Mornings Summit



Daniel Mezick on Agile as an Invitation to a Game

On today's episode I talk to Daniel Mezick, author of the Culture Game and the founder of Open Space Agility. Dan has a really unique perspective on culture, self management and how to make agile really work. At the core, agile believes that a team doing work is the authority on what needs to be done for that work, since they're closest to the work. This is self management at the team level.

In trying to make a switch to agile ways of working, organizations often dictate new frameworks, patterns and procedures. To dictate a new way for how work is to be done is basically the opposite of self management...and a clear limit on how an externally generated conversation design can really work: Change from the outside is going to get push back.

That Agile is implemented in a non-agile way is an irony not lost on Dan!

in Dan's view, culture is a game, how work is done is a game, meetings are games, with rules, ways progress is measured...some of the rules are implicit, some are explicit, but it's kind of annoying to play a game with no rules, or with rules unevenly applied, or with rules that change without notice. If you're a reader of "Calvin and Hobbes" you've heard of CalvinBall, and you know how frustrating it is!

Whoever *must* play, can't really play... (that's from james carse's excellent book on Finite and Infinite games)

Dan suggests that agile be *invite only*, pull, not push, and that that "pull" invitation be in the form of an Open Space meeting. People that opt in, step into the circle, decide what to talk about, and leave with proceedings, outputs. That starts a new game, with new rules, written by those who want to play.

 Dan's Open Space Agility process is an answer to the question of how to change the rules of a work culture in a clear and fair way, without hemorrhaging people in the process. Open Space dictates that whoever responds to the invitation are the right people, what conclusions they come to are the right conclusions, worthy of an experimental test, at the very least.

Open space meeting philosophy has infected my own conversation design practice. I feel particularly uneasy when a facilitator I'm working with tries to massage or shift the decisions a group is coming's one of the reasons I say a facilitator should ask better questions instead of giving answers. A great question is an invitation. An invitation is the start of a new conversation. This episode has me rethinking all the invitations I send out, for all my meetings, and all my conversations, moment by moment. Are my invitations inviting? Are people hearing an invitation to the game I want them to play?

Check out the a bonus track where Dan and I talk about Holocracy and his work with Zappos....enjoy the episode!

The Agile Manifesto: 12 values and 4 principles

Jeff Sutherland

Scrum: rules, roles, artifacts

Planning Poker

User Stories

The Alpha Geek and the pecking order

meetings as games

Open Space Agility

Open Space four principles and the law of two feet

Butterfly and the Bumblebee

Waterfall vs Agile Culture

Pull vs Push Culture

Triggering Self management

four variables in software development: cost, delivery date, features, quality

client's changing their mind is a feature, not a bug

Pareto's Principle is the opposite of what you think

90% syndrome

Code gets brittle

The Big Picture Diagram of Open Space Agility

Signal Events in Culture

Buying into a process vs. Authoring a process

Proceedings of an Open Space Meeting

Organizational Cadence

The Agile Imposition

Beware the man of one book

SaFE Framework



The Mandate of Holocracy at Zappos

Holocracy or Quit

Nandini Stocker on Google's Map for how to make conversations work

In this episode of the conversation factory I had the distinct pleasure of talking with Nandini Stocker, the head of conversation design advocacy and partnerships at Google. She's the rare individual who is more of a conversation design geek than me, to the point that she interrupted me just to make a point about how awkward interruptions are!

We cover a sprawling number of topics in conversation design, and you might enjoy downloading Google's PDF on "How Conversations Work" and read along! I think just knowing that threading, repair and turn taking are *things* means you can look for them in your own work and find ways to transform conversation experiences that you design.

David Bohm, the storied physicist, wrote a book called "on dialogue" and said "Conversation is a principled, mutual process of collaboration and negotiation." So I shouldn't be surprised when Google's map of how conversations work matches exactly to the process of opening, exploring and closing I teach groups to follow when designing a creative, collaborative process for design thinking and innovation. Opening a channel for conversation is like the invitation into a cooperative game, a world to explore and engage with, and every leader needs to think empathically to design these invitations to be...inviting! Finding places along a conversation journey where there is breakage leads us to think about how to repair the thread of conversation and keep things moving along towards closure: a desired action or agreement!

We've be conversing for thousands of years, and we've gotten pretty good at it. But being good at something doesn't mean you know how to teach someone else how. Nandini's work is specifically on how to help us talk to digital agents with more natural ease.  We spoke a few weeks ahead of Google's I/O conference, and she's since sent me a wealth of talks that happened there that you might enjoy digging into. One of my favorites is from James Giangola, who *literally* wrote the book on Voice Interfaces. He talks about Conversational Hacks and digs into the cooperative principle, a way of helping us think about how relevant, clear and helpful information is exchanged at a steady pace in a good conversation.

Compare two exchanges:

"How much did your shirt cost?"

"Don't you love it? I got it at Vinnie's Vintage Warehouse!"



"Don't you love it? Shirt has five letters and five is my favorite number!"

To a computer, both responses contain about the same "amount" of information, but only a human conversationalist can tell that the information is irrelevant and least for now!

If you want to hear Nandini tell one of the worst/best Harry Potter puns ever (She calls puns the earworms of the English language, check out this short outtake.


Show Notes and Links:

Grice's Maxims in brief and extended

Threading and building threads

Seven of Nine

Turn Taking and Yielding

Conversation Repair

conversation overlap

Personality in digital agents:

discourse markers

Google: How Conversations Work

Google's quick reference design principles for conversation design

Amplifying Women's Voices in Obama's oval office

Barge In capability

The Uncanny Valley

On Inner Dialogue

Clifford Nass on Multitasking and his Obit


Bonus: Core talks from the Google Team from IO17:

This one is my favorite: Applying Built-in Hacks of Conversation to Your Voice UI 

Building Apps for the Google Assistant 

Finding the Right Voice Interactions for Your App 

Defining Multimodal Interactions: One Size Does Not Fit All

In Conversation, There Are No Errors

Getting Your Assistant App Discovered

How Words Can Make Your Product Stand Out

PullString: Storytelling in the Age of Conversational Interfaces 

Google's VUI design codelab:

Crafting a Character: Design an engaging Assistant app

Some solid talks from IXD17 on chatbots and conversational UIs:

and the pun game

Sally McCutchion on Holacracy and Self Management at all levels of organization

Holacracy asks a big question: How can organizations be designed  in a way that really works, for everyone in the organization? Right now, orgs are often structured according to power from the top to the bottom, rather than self management distributed throughout the organization. This slows orgs down and demotivates some people.

In this episode, I talk to Sally McCutchion, a certified Holacracy coach based in the UK. Sally teaches public workshops on Holocracy and coaches orgs  in making the shift to working with Holacracy.  Sally and I had a seriously wide ranging conversation about Holacracy. We hit on some big topics towards the end that I've placed in the extras, which you can find here. Check those out, as they're really juicy, just scroll all the way down!

One conversation design principle of Holacracy is to allow information and knowledge to flow through the org. Too often, people at the "edges" of an org, the people closest to the users, know a lot about what's wrong and how to make it right...but those same people don't feel empowered or safe to speak up, or even to just do something to shift issues. One CEO who's organization I coached years back desperately wanted people to feel a sense of ownership: How, if you own your house, and the toilet is running, you fix it, if you know how, or talk to someone who can. You don't just let it run. Holacracy attempts to open regular channels of communication between areas of the organization and to allow sections of the organization to feel that they can solve problems that they see without asking permission, waiting for permission, identifying if permission is even possible.

Holacracy designs several meetings within orgs very rigidly, in order to break down power structures and allow all voices to be heard: People are expected to bring updates framed as needs, not just complaints. Other structures  are a lot more open and can be adapted to the unique company requirements. It is without a doubt a very interesting design for organizational conversations. I get into the weeds with Sally a bit, and if you follow the links in the show notes you might find some of the terminology and structures dizzying...but the forest and the trees of Holacracy are worth absorbing: That self managementand purpose are essential all scales: at the scale of the person, the team, and all throughout an organization.

Show Notes:



Apollonian Gasket

Glass Frog


Holacracy Tactical (triage) meeting

Rep Link

Lead Link


"If you want to go fast, go alone, if you want to go far, go together."


Another Interview with Sally: Punks in Suits





Donna Lichaw on Storymapping and Seeing With New Eyes

Today I talk with Donna Lichaw, a UX strategist, coach, teacher and author of The User's Journey: Storymapping Products That People Love.

What's awesome about Donn'a approach to storytelling is that it's practical. There are a lot of frameworks for storytelling: The Hero's journey, Aristotle's 2 or 3-ish act structure, the rising and falling action of "Freytag's pyramid". It really doesn't matter which framework you the end, when you see things as story, story becomes a doorway into a new way of working. Story becomes a material you can shape by design. For me, I've started to see conversation in the same way: a material that can be shaped to create better experiences for people.

Donna and I talk about story*telling* vs story*making* and story*doing*. Storymaking is not the act of enrapturing a group of people around a campfire or at a podium, in a's knowing how you want people to feel about an experience after it's over, what you want them to remember, to walk away with, to talk about. Storymaking isn't about manipulation, it's about intent, in this mindset. When you see experiences as a rising and falling arc, you want to make that arc smooth and incredible. You want to shape it well, with no jerks, gaps or least not unintentionally!

Designing with Story in mind and designing with Conversation in mind seem to me to be two sides of the same coin. You want the person experiencing your story to respond in some way. And the next story you guide them through continues that dialogue until...? I don't know. The next chapter?

Every Story has a hero, and we want to root for that hero, to see her win the day. In a great conversation you try to make the other person the hero, not's the empathy with the other person and their needs and goals that makes story a powerful tool in great conversation design.

Donna's Diagram of Rising and Falling Action

Coaching Conversation with Phil N on Shifting the Entry Point of Challenging Converstions

For this episode, I did a 30 minute coaching call with a friend of a friend that turned into a wonderful and transformational hour! Phil is a talented photographer and entrepreneur, and we spent a good section of our time looking at what conversations in this life are functional and which are missing something. He's part of solid men's group, so we could use design principles from that experience to reframe how his less functional patterns are working.

As he says in the opening, part of the change was using the tools of conversation design to map friction points in his conversations with women over relationships and work to shift that conversational pattern in three ways:

One, to have the conversation he's avoiding sooner. (time)

Two, to generate multiple ways to open up that conversation.  We talk about how to "Open up" a dialogue in the most conscious, empathetic and energizing way (not to force it) and to generate multiple openings for challenging conversations to find a space that feels authentic, empathetic and effective. (ideation)

Three, to find a way to continue to converse with as much comfort and regularity with women as he does with men. (pattern)

In essence, we're talking about Rhythm. Or the technical term is Prosody:

"the systematic study of metrical structure, the rhythmic and intonational aspect of language"

The one physical aspect of your central nervous system you can control is breath...the depth and frequency of your breathing. When you're in stress, regulating your breathing can transform that state. Just like the pace of breathing, pace and depth is an important part of a conversation that you can control: both the frequency of responses IN communication and speed OF communication.

One clear outcome of our conversation was that just like he'll go to his men's group every Monday, whether he feels like it or not, he has to make a *date* with himself to consider if he's being honest with himself and open with others. Can you make a date with yourself to consider whatever topics are critical to your own personal conversation?

At about the halfway point we shift to his ambitions in photography and his resistance to owning his ambition. We talk about incremental conversations versus a paradigm shifting conversation: Playing chess vs Sweeping the pieces of the board and creating your own type of greatness. Making the conversation on your own terms, rather than playing by the rules. (see episode 006 with Sara Holoubek where we talk about accepting/rejecting trends and I talk about non-complimentarity)

Enjoy the session! And it you'd like to have a conversation with me, just reach out on the coaching page. Show links are below.

Dave Bohm on Dialogue: Shared Pool of Meaning

" Participants [in a dialogue] find that they are involved in an ever changing and developing pool of common meaning."

Morning pages and journaling


Cave Day/Deep Work

Episode 006: Sara Holoubek on Human Companies and Solving Problems that Matter

Invisibilia: Flip the Script (non-complimentarity)


Natural Cycles Model of Creativity

Dave Gray on Drawing Conversations and Liminal Thinking

Today I talk with Dave Gray Author of Gamestorming and his new book,     Liminal Thinking. We kick things off with a Zen story and dig into why Dave wrote this new book. We hit on a wide range of topics from the nitty gritty of facilitating group conversations to organizational change being fueled more by emotion than reason. Dave's books have always opened new pathways in my brain, so I hope you enjoy unpacking some of the lessons inside with me.

One of the reasons I pulled the opening quote about drawing is that it's without a doubt the most powerful way to transform ANY conversation. Most conversations have one interface: the air. Once it's past your eardrums, I have *no* idea what's really going on inside someone's head! Drawing makes sure there's a tangible record...hell, a paper trail, of our conversation, what we've agreed to, what is in or out of the conversation. A few months ago now I helped my mom and dad work out some scenarios around selling their house and moving someplace else. Me and my brother, together with my folks, generated as many options as we could: They move, and rent out their big house, they sell it all and rent something else, they sell and buy and so on...we made a big poster for each option and then stuck up comments on each, using a format called "Rose, Thorn Bud"...which not to be too meta, is also a conversation design: We could have just done plusses and minuses, we could have done a SWOT analysis on each...but Rose Thorn Bud (which is from the boy scouts of america) is a kind of "friendly" design for conversational analysis.

We used different colors for Rose Thorn Bud, a trick I learned from teaching design thinking with the LUMA Institute...and after our meeting we had a visual heatmap of how the whole family felt about all the options on the table. It really helped my folks step back from the confusion of choice and get some clarity about the steps ahead. And it helped my mom realize that she and my dad haven't tried living in enough other places to make a choice about living somewhere else...and that they ought to figure that out before they sell.

That, in essence, is Dave's point about drawing making a series of triangulations for a conversation. Rather than one person trying to hold all those points in mind, we used color and space to do it for us...a board for each future for my parents, and a map of each future.

Another point Dave makes towards the end that I want to highlight about conversation design...when I'm designing a group workshop, the question of size and time comes up. He talks about watching people at parties, and how 3-5 people can "hold" together pretty naturally...but at 6-8 it splits, unless there's someone holding it together, someone famous, magnetic or especially entertaining. There's some math there, just like how paper increases the points of triangulation to give clarity. If 4 people generate 3-5 post-its that's about 20 stickies, and lot's of possible combinations as they try to discuss and organize them all...if you add just one more person, that's 25% increase in raw information...and increases the combination possibilities exponentially. To expect that group to process the increased information in the same period of time is just unfair! That's where a facilitator can help, by making a first action clearer (and taking some options off the table) or by giving more time, a clearer organizational framework, making the stickies all contain the same types or categories of content, or by making sure the group sizes are all consistent. On the face, conversation design for group work can seem so fuzzy, but I feel like there's a lot of quantitative thinking and actual MATH that goes on beneath it.

Show Links:



Liminal Thinking

LUMA Institute

zen flesh zen bones


Power in organizations


Finite and infinite games


Morning pages and journaling


Monkeys watching monkeys


Candid Camera Video of elevator conformity

Sara Holoubek on Human Companies and Solving Problems that Matter

Today I talk with Luminary Labs CEO and founder Sara Holoubek. Luminary Labs is a really unique company that both consults with companies on strategy and also helps run massive open innovation programs for organizations. We talk about working on problems that matter, on how humans have always been more nuanced than marketers and how companies need to be creating Intelligence Engines.

One of the things that Sara helped me think about is an idea i've been noodling with about Complimentarity vs. Non-Complimentarity. How in situations, you have really only these two choices: to go with or against the current tide. Sara helped me see that the conversation between a company and the culture it's in is very similar to the conversation two people might have! Companies face that choice, too. Only, too many companies choose to go along with trends or not...not intentionally, but mostly unintentionally.  And that's the thing about design: everything is designed,  either well, or poorly, intentionally or unintentionally. Sara clearly helps companies and the people in them be more intentional about their work.

 In trying to re-design a conversation you're in,  you can shift patterns by consciously pushing with or against them. David Bohm tells a great story  about this in "On Dialogue"...a psychologist was treating a young girl who wouldn't talk to anybody. After an hour of fruitless attempts, he was exasperated and said "why won't you talk to me?"

"because I hate you" she countered: She was pushing *back* on his energy, you see?

So he asked "how long will you hate me?"

she said "I'll hate you forever"

Then he kept with it, taking the logic further "how long will you hate me forever?"

Somehow, this broke the spell and the little girl laughed. He kept questioning her refusal... somehow, taking it seriously helped shift it.

What is that behavior? He somehow accepted what was happening with the little girl, but questioning it in the right way, shifted the conversation.

I learned about non-complimentarity from Invisibilia, an *awesome* podcast from NPR. I'll link the episode in the notes: in the show opening they talk about a group of people drinking wine in their back yard who get help up at gunpoint. They tell the robber they have nothing, so they offer him a glass of wine instead...which flips the whole script of getting robbed. Spoiler alert: it ends in a group hug. Enjoy that episode from Invisibilia and enjoy this episode, too! I hope you learn something about redesigning conversations for your own context...



Luminary labs


David Bohm on Dialoue:


Invisibilia: Flip the Script


Toothpaste Medium Article


Gartner Hype Cycle


The Human Company Playbook


Makers and Takers


Danny Meyer


EdSim Challenge


Avoiding the 20 Million Dollar Mistake:


Gabe Gloge on Reflection, Learning and Language as a Tool for Thought

Today's Episode is a bit...unusual. My friend Gabe Gloge is interviewing me, so I'll be yapping a lot more than normal! His company,, helps organizations become learning organizations by breaking jobs into skills...and we try to do this for some conversation design skills!  We talk about how to break down engagements into discrete steps, tools and triggers, how a reflective practice accumulates benefits over time and how mathematical reasoning figures in all this. Enjoy!


Show Links





Dave Grey


Liminal Thinking


Persona Profiles


Excel Timeline example


The Tick: On Counting Syllables Vs Writing a Haiku in action


Agile Story Estimation

Johari Window


The Learning Organization


David Whyte's 3 Marriages


Active Listening Script


LUMA Workplace


Inductive/Deductive/Abductive reasoning

Sarah Gallivan Mitchell on Not Listening to all your users at Once.

Today I talk with Sarah Gallivan Mitchell, Product Owner of in-car interfaces at Faraday Future, a company focused on the development of intelligent electric vehicles.

Sarah is an Ace product designer and it was a lot of fun to talk with her about her work through the lens of conversation design. We touch on some big questions, like “How can software be sincere?” and “What’s the difference between manipulation and Modulation?” And “Why you shouldn’t listen to all of your users all of the time”

Show Notes

Sarah’s IxD17 Talk:

Talk  slides are here:

And content is here:

Ixd17 link (video to come)

Faraday Futures

Discussing Design

Crossing the Chasm

Death Talk from IxD17

Agile Introduction

Active Listening


The Easy Hard Problems:

Paul Pangaro’s IxD17 Talk

Leland Maschmeyer on Negotiations and Hallucinations

I first met Leland when he was giving a talk at SVA’s Design Criticism Program back in 2010 and he referenced “Finite and Infinite Games” by James Carse...I knew, right then and there, that we had to be friends!


Lee is the Chief Creative officer at a food company which will not be named (for reasons...but linked here), which Fast Company rated in the top 10 most innovative companies in the world. When I met him, he was one of the Founders of Collins, an agency that Forbes tapped in 2016 as an agency defining the future of brand building.

We had a wide ranging conversation where we tried to find a theory of change: can you only harness trends and follow patterns, or can you create the future? We also discuss how companies need to digest chaos and turn it into Creativity and Action through balancing volume of ideas captured, velocity of ideas turned into opportunities and maintaining a Variety of ideas in the mix. I hope you enjoy listening to Lee as much as i enjoy talking with him!

Links and Notes:

Eight Flavors, by Sarah Lohman

Innovation through features vs The Jobs to be Done Framework

Finite and Infinite Games

IxD17 Users versus Owners (video not posted yet!)

Sketch notes at

Reinventing Instagram:

Harvard Negotiation Project and classes

Other book mentioned:

On Improv:

Rejection vs Acceptance vs. Creation


On cherry blossoms and cradle-to-cradle-design

My whole life is waiting for the questions to which I have prepared answers.

Abby Covert on Collaboration and Listening

This episode was fun! I love Abby Covert, she’s a delight to talk with. It was interesting editing this episode because I could see it was more of a *conversation* than an *interview* opposed to episode one with Phil McKenzie, just from the waveforms.
Abby is an Information Architecture rock star, and you’ll learn more about her inside the episode.
We talk about How much my mother loves her book “How to make sense of any mess”, how to really plan research to reduce bias and how to hold the space for problem framing versus problem solving.

Visit her at and check out her book

Phil McKenzie on Authenticity and Impermanence

My Guest today is Philip McKenzie, the co-host of 2 Dope Boys and a Podcast, a biweeekly podcast on trends and cultural insight. Philip is best described as a polymath.He’s a former Domestic Equity Trader for Goldman Sachs and He is a writer, rabid music fan and…. an accomplished DJ

Today We talk about Consistency and Authenticity in Conversations between brands and the fans they seek to connect with, how companies need focus on long-term thinking, not short term gains and on growth as a false model for our times.

Phillip’s Podcast can be found at:

A critique of mindfulness:

On rethinking everything currently made by Ursula Le Guin:

Timestamp where it gets interesting: