3 Essential leadership conversations for creative transformation

Start with drawing a circle

Daniel Stillman
8 min readJun 23, 2021

This essay first appeared on my blog.

Some of these ideas are extracted from my recent book, Good Talk: How to Design Conversations that Matter. You can find free chapters and downloads here.


“A dialogue is a conversation with a center, not with sides.”

William Issacs

Being able to facilitate and lead such a conversation is no trivial task.

Conversations can easily become what Philippa Perry, in The Book You Wish Your Parents Had Read, calls fact tennis: Each side lobs their own facts back and forth trying to score points…what those points can be later cashed in for, no one knows.

Our teams and organizations are defined by the conversations that they can and can’t have. And fact tennis doesn’t help us solve the biggest challenges we face.

What we need more of are leaders who can get groups to face those challenges and face each other in deeper dialog — to sit in a circle (or a grid on zoom) and talk these issues out.

At the center of the circle of a conversation is the question — the central question — a group of people are considering. To go more deeply into that question, to find a real solution, is the goal of a facilitative leader.


Why is facilitative leadership so important? One leader I coach had this struggle: She was very excited about the innovation project she was leading and the possibilities for transformation the mission implied…but the team assigned to this special project was a little less enthusiastic. Cue the flashback to high school group projects, right?

Also, when I say leading…she was the driver for the project, but many folks on the team were near-peers of hers. Some were more senior, even. So, leading this project was a delicate affair.

Many projects are like this: a group of people, all with their own motivations, levels of dedication to the project and levels of seniority. She couldn’t put her foot down and order folks around. Consensus was the order of the day…and that kind of teamwork takes facilitative leadership, not command-and-control leadership. Even if she had positional authority, force doesn’t get the best out of people.

How do you bring a group of folks together who aren’t actually sure that the challenge is even worth solving?

The team knew the core business model of the mid-size pharmaceutical concern they worked for all too well. They knew what kinds of work would get them bonuses or promotions. Innovation projects, with their long horizons and likely chance of failure, were not the stuff of amazing performance reviews.

So, this leader had a tide pushing against her. How, with the organization sending mixed signals, could she get her team inspired? Inspired, when conventional thinking easily proved that what they were doing would very likely not work? Why bother even thinking of ideas?


Modern brainstorming best practices have actually not evolved that much since their first formulation by Alex Osborn in the 1950s.

These basic rules like deferring judgement and encouraging wild ideas are really hard to use on a group of rational cynics with low motivation.

The question my coachee and I sat with was this: How should she show up to get the group to be creative when suspending disbelief (deferring judgement- first rule!) was an unlikely possibility? What were her options?

Three Essential Leadership Conversations for Creative Transformation

Getting to a “center with no sides” state is great. This is where my coachee was trying to get her team to — thinking of solutions to their central, big hairy goal. But it doesn’t come for free…you have to build up to that conversation. First she had to get them to locate themselves as *in* vs outside the circle of the question. Once they were aligned with the goals…that’s where the magic of the third conversation comes in.

Leading powerful, transformational change requires the ability to facilitate three essential conversations, to answer three key questions:

  1. What is in and what is out? Ie, what are we talking about and what are we not going to talk about? Who is in and who’s out? Are we all in?
  2. What is our center with no sides? Ie, what is the most central question we are hoping to solve together?
  3. How can we dance on the edge of possibility? Once we know what we are talking about, and our most central question, how can we look past what’s possible to solve this challenge?


As we talked, I drew a circle for her. Her team, although they didn’t know it, had such a circle in their minds. The inside of the circle was what’s IN (or possible) and the outside of the circle being OUT (or what’s impossible). We’ve all been taught to color inside the lines and to play inside the playground…don’t go running in the street!

Making this sort of a circle explicit instead of implicit is powerful. Anytime you’ve used a “parking lot” in a meeting you’re basically doing this. My first suggestion was that she get the team to draw their own circles, list what was “in” and “out” and compare them. She might find out that some folks differed, even slightly, about what they thought was impossible. This could be a crack in the fortress, and a tremendous opportunity for conversation.

It’s also helpful to draw an in and out circle and ask people: “why is this challenge important to you?” …ie, what would make you want to be “in” this circle of conversation and problem solving?

We’re often afraid to hear that people are not fully committed to a challenge…it triggers feelings of being broken up with or picked last for a team or pushed to the outside of a tribe. But finding out -explicitly- that people are out instead of in can be a relief.

Facilitating the in/out conversation as a co-created exploration is different and powerful from telling people what is in and out.

In fact, this in/out circle must be established at the start of any and every meeting, conversation, workshop. Even if you have some positional authority, pausing for additions and amendments to your proposed in/out agenda can be highly motivating for your team.


What does it mean to have a conversation with a center, but no sides? Issacs cites an example from the public stage: resolving the violence in Northern Ireland. John Hulme, a Nobel-prize winning politician from Ulster, spent years behind the scenes in deep conversation with Gerry Adams, who was the leader of Sinn fein, the political arm of the Irish Republican Army.

Their central question: How do we stop the violence?

Hulme is quoted as saying

“Twenty-Five years we’ve been fighting violence. Five governments have failed to stop it. Twenty Five thousand troops and fifteen thousand policemen failed to stop it. So I thought it was time to try something else. Dialogue.”

With that question at the heart of their conversations, the two leaders were able to talk to that central issue. That they were on two sides of the issue didn’t matter. They could agree on a central question to look at, together.

In her business context, as in any business, the best center with no sides is a Human-Centered outcome. Which human? Ideally someone outside the company! But as long as you are clear about what human(s) you are centering a challenge around, the conversation will be much, much smoother. Positive patient outcomes on a larger scale was the point of her project, after all. Putting that conversation in the center can make the questions of possible vs impossible easier to approach.


Now that we have a group of people who are IN, and we’ve established a central question…how do we break the rules?

My coachee was stuck. The team would barely have ideas. They would shoot anything remotely risky down.

Zoom way in

I made a suggestion: Zooming as close as possible into the boundary between the possible and impossible, she might help folks examine their assumptions and shift ideas, ever so slightly, from the impossible to the barely possible. The closer you look at a line, the more fuzzy it becomes.

This visual metaphor helped her with a flash of insight. Her job was to get the team to “dance on the edge of possibility” — that was her phrase, and I loved it. It’s why I’m writing this essay.

This allowed us to start brainstorming: In what ways could she inspire them to dive into the razor’s thin edge of what they knew could work, and what they were sure could not. Not to shy away from it…but to make it very, very explicit. This is the opposite of “encourage wild ideas”…this approach is about rigidly defining constraints until they become harder to explain or defend. It’s 5 Whys on rocket fuel, zoomed in.

This phrase “Dance on the edge of the possible” was enough of a spark. She could imagine herself putting on her “Dancing on the Edge of the Possible” Hat and working to get her team to do the same. She would explicitly invite them into the conversation of what was possible and impossible and explicitly get them to look at that border, ever more closely.

Her opinions about what was in and out of the circle were not, ultimately, critical. Selling the team on what she thought was possible wasn’t the point. She wanted the whole team bought in and aligned. And so she had her clear vision and plan about how she wanted to show up for her team.


The other way we decided she could get her team to be creative was to think of bad ideas and to slowly nudge them back into the circle. In the pharma context where she works it took some careful planning for folks to feel safe to say, out loud, things that were illegal or unethical. Saying “we can’t do this…but what if we could?” is a delicate matter.

Her job was to create a safe space for the conversation…a larger circle of trust. The goal, the central question, was still how to create better patient outcomes…and maybe bend some international regulations in the process.

Everyone knows how to turn bad, immoral and illegal ideas into good, human and legal ideas…as long as you can create the environment to have bad ideas first.

Slowly but surely, she was able to get her team to have “wild” ideas and to slowly turn them into ideas that they could use.

It was an act of heroic innovation leadership.

For the next tough crowd you have to lead into wildness, start the conversation with a circle.

Learn more about these ideas in my book Good Talk: How To Design Conversations That Matter. You can download a few free chapters here and find links to buy the audio book and physical books online.