The Four Quadrants of Conversational Leadership

Leading through asking and framing

Daniel Stillman
The Conversation Factory
6 min readJun 17, 2019


“Leadership is not a person or a position. It is a complex moral relationship between people”

Joanna Ciulla

This is an excerpt of my upcoming book, How Conversations Work.

What does a leader do?

The legacy model of leadership is command and control: The CEO, with sleeves rolled, calling the shots. Behind this model was a quiet assumption that the hierarchy was a meritocracy: The people “at the top” directed the activities of their direct reports because the people at the top knew more, had more data, and were thinking of “the big picture.”

In the slower-moving world of the past, that scenario might have been the case. In today’s world, people at the edges of a company often know more and have more real-time data than the people at the “top” of a company. The people at the edges of a company are closer to the customer and closer to their real day-to-day challenges. Waiting for a directive from “on high” can mean that the window for meaningful action has vanished: the customer has already tweeted their dissatisfaction and their comments gone viral. Agile business philosophies suggest that these people at the edges of the company should be empowered to problem solve and co-create with their customers, quickly and efficiently.

— — a quick side note — —

my dear friend Peter Haasz pointed out a lovely reframe of the “edges” of a organization that I want to add here:

“The top of a company is one of its edges. As is the edge that faces customers or the edge that makes the products. The problem isn’t one of only one side knowing stuff. It’s that each edge only knows what it knows, so the org as a whole pulls in different directions and doesn’t respond as quickly or effectively to problems and opportunities as one might hope.”

— — end side note — —

In this fast-paced reality, leaders need to be asking instead of telling, leading through conversation instead of directives.

The Future of Work is Human Conversation

What is the “Future of Work?” For some, the future of work is Artificial Intelligence and automation. For others, it’s the gig economy, fluid workers moving from job to job in the blink of an eye.

The future of work is already here. People already stay in jobs for shorter and shorter spans. Computers and robots are better than people at more and more things, from reviewing legal precedents to logging trees. Soon, the jobs that will be left will be ones that ask more of us as humans, emotionally and intellectually, doing things robots can’t do well: feel and think. The future of work is in jobs where the outcomes are hard to measure and goals shift frequently. These jobs can only be done through conversation.

Legacy leadership can’t help with this work. Telling people the problem while directing them to a goal can be demotivating. Forcing people to work or think differently creates stress, activating the flight or flight responses of our brains. Stress is the opposite of creativity. Leading people to their own insights through conversation invites clarity, creativity and energy.

Telling people the solution to a problem feels strong and heroic. Conversational leaders empower others through thoughtful questions, framing the debate in a more subtle mode of power: making others feel powerful. This is leading through vulnerability.

Leading by Framing the Conversation

A conversational leader directs and deepens thinking through questions, being mindful of how their questions frame the conversation. The conversational leadership matrix, below, is a model to help guide your speech. Each quadrant of the matrix tracks different ways to lead through conversation. Do we lean into asking or telling? Are we focusing on problems or solutions?

Q1: What’s the problem? What parts have you thought about?

Q2: What solutions have you thought about to challenge [X]?

Q3: You seem to be having challenge [X].

Q4 : Have you tried solution [Y] to your challenge?

Staying in the Asking region is a gentle approach. Spending time there can earn us the trust to move into the Telling quadrants, if we can’t coach people into finding their own solutions.

Powerful questions can shift our focus through the quadrants, illustrated by the X and the question bubble. “Given the challenge you mentioned, which solutions could have the most impact?” is a question that thoughtfully shifts focus from problems to solutions, and sits squarely between asking and telling. It pushes towards solutioning — pushing someone in that direction before they “get there” themselves, which, in my book, is a kind of “telling”.

It’s also worth orienting this model in a larger context…Patrick Whitney’s four-quadrant model for Design Thinking and Ed Schein’s Humble Inquiry have all talked about worthwhile poles in the problem framing and solving conversation, but this framework owes the most to David Rock.

Unauthorized curiosity

Legacy leaders are anointed and appointed. They are given power through authority and that authority can be removed. Legacy leaders are not permanent–they can be stripped of their power by the authority that granted it.

Conversational leaders are different. Since we all have the power to speak (in writing or speech) anyone can be a conversational leader, no anointment or appointment required. These leaders appear in the moment, when they see a need and meet it. These leaders are also not permanent. They are more like waves in the ocean, swelling up and cresting in one moment and then disappearing back into the wide expanse of the sea the next.

All that’s required in order to be a conversational leader is the curiosity and willingness to ask powerful or interesting questions. The world needs conversational leaders, now, more than ever.

In 1867 John Stuart Mill suggested that, “Bad men need nothing more to compass their ends, than that good men should look on and do nothing.” Conversational leaders can look like whistleblowers reporting dangerous or harmful industry practices. Or they can be the person on the team willing to wonder out loud why things are the way they are and ask if we can do better.

Without anyone to ask and open the conversation up, no progress is possible.

Leader OS, Team OS

The Conversational Operating System of a leader interacts with the OS of a group, and of each member in the group. It’s a complex interaction. Some groups have been trained over time to be told what to do. They ask, the leader tells. These groups crave clearer goals, certainty, clarity. Other teams would rather be left alone to do what they see as best.

The leader’s OS interacts with the OS of the team. The work we do together is a conversation between our ways of working and seeing the world. The shift towards collaborative, conversational leadership requires significant patience with uncertainty.

The Conversation OS Canvas

For more on the Conversation Operating System Canvas below, you can check out my downloads page here or a webinar Mural hosted with me on this. And you can sign up to hear when my book on How Conversations Work comes out (link at the end)