Questions

We expect leaders to have the answers. But the deeper truth is that leadership begins with questions.

A group can function for a long time on shared routines, inherited systems, or tacit understandings. But when the group encounters real difficulty — conflict, change, or crisis — the old answers no longer suffice. At such moments, leadership is not defined by decisiveness. The leader asks, What is really going on? What problem do we face? Questions flow forth. Have we explored deeply enough? What is the real problem? Some questions are sharply focused on the immediate problem.

Others are broader, seemingly not about the problem but about other things — the group’s core identity, its place in the world, the way people collaborate and interact, and what lies ahead in the future. These deep questions, psychically powerful and sense-making, are not often articulated, but they are always latent and ready to be activated. In times of crisis, they rise to the surface. Four questions, in particular, frame the group’s deep understanding of itself:

Who are we?

Where are we?

Where are we going?

How do we get there?

And since groups are made up of individuals, each with their own goals, interests, perceptions, and concerns, a fifth question, deeply personal and inward-turning, always hovers in the mind of each member of the group:

What about me?

The answers to these five questions, four of them social and the fifth private and almost anti-social, shape the life of the group. Answers that have become widely accepted guide people in what to do, what to notice, and how to work together. But at any moment, for any member of the group — especially when galvanized by change, failure, or restlessness — long-accepted answers can begin to feel wrong or lacking. When that happens, and especially when more and more people begin to feel the same thing, the group slows and stumbles; collaboration becomes difficult; the gravity pulling people to the group weakens. For many member of the group, re-establishing valid answers (or surfacing new ones) becomes the most urgent work. They grope, argue, and call out. And leaders — either prodded by that energy or moved by their own insight — must engage with the asking and answering of these deep questions.

At such moments, a particular kind of question becomes essential — not a request for a fact or a fix, but what we might call a generative prompt. These are questions that don’t close down thinking but open it up. They invite reflection, story, imagination, perspective. They create space for insight to emerge rather than forcing a quick solution. “Where have we grown complacent?” “What are we protecting?” “What future are we unconsciously building?” Good generative prompts don’t point to a single answer — they produce conversation, provoke meaning, and help a group sense what really matters now. Leaders who ask these kinds of questions aren’t drifting or avoiding decisions. They’re building the foundation for decisions to be real, grounded, and shared.

Thus, a leader who asks and encourages questions — not just the five existential ones, but all kinds, big and small — is not showing weakness, but modeling the curiosity, humility, and courage it takes to guide groups through change and challenge. A leader who works with questions creates space for reflection and perspective and invites others into the work of thinking and deciding together. And without that invitation, the conversation narrows. Trust fades. New insights dwindle.

Leadership, at its most vital, not only solves problems and answers questions — it asks them, and makes space for them. “One can lead,” as Ron Heifetz and Donald Laurie wrote in a classic Harvard Business Review article, “with no more than a question in hand.”