Living the Questions: A Leadership Practice for Uncertain Times

‍“Be patient toward all that is unsolved in your heart and try to love the questions themselves… Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”

— Rainer Maria Rilke

In my last post, I wrote about the difference between problems to solve and tensions to manage — and why so much of what leaders face in complex and uncertain environments belongs in the second category, not the first. I suggested that managing tensions is a core leadership capacity. In this post I’ll explore another leadership capacity that can serve us in times of uncertainty—asking powerful questions and, at times, slowing down the process of finding answers.

Years ago, I read Marilee Adams’ Change Your Questions, Change Your Life. (In fact, I made everyone in my household read it.) I was so inspired that I did something I’d never done before — I reached out to Marilee! I discovered that authors appreciate it when people tell them how much their work means to them. I ended up on the phone with her and went on to take part in several workshops, including a class on “Question-Storming.”

Marilee taught that behind everything we do is a question — and that the question is often implicit. We wake up and ask ourselves how we want to start the day: What will I wear? What’s on my calendar? What will I do first, second, and third? Do I get out of bed immediately or take some time? She also taught that the quality and direction of our questions shape us. “Judger” questions (e.g., Who is to blame for this mistake?) shape us in very different ways than “learner” or curious questions (e.g., What can we learn from this mistake?). Since encountering her work, I’ve become far more aware of the questions I’m asking — of myself and of others. Not whether it’s the “right” question, but whether it’s the “right kind” of question.

The Question Beneath the Topic

Perhaps the most important thing I learned from Marilee’s work — and the thing that most changed how I work with clients — is that we don’t spend enough time making our questions explicit. We jump into problem-solving before we’ve gathered and chosen our questions. Her Question-Storming method is all about giving that step real time and attention.

So, often, at the start of an engagement or a session, I ask my client: “What’s the question you’re coming to coaching with?” Not the topic. Not the problem to solve. The question. It sounds subtle, but it changes everything. It slows things down. It opens something up. And often, the question that surfaces is far more interesting — and far more honest — than the agenda item they walked in with.

I want to share an example of how this works that I’ll return to throughout this post. Recently, a client came into a session, frustrated almost to the breaking point with her boss. The session began with venting about how difficult she was and how hard it was to do her job as a result. When there was a break in the venting, I asked her to take a breath and tell me the question that she was bringing to this session. At first I got a blank stare. She realized she really didn’t know. The time we then spent exploring possible questions allowed us to shift from venting to exploring. It was a mini Question-Storming session. Her questions ranged from “Can I stay in this job?” to “How can I communicate my experience to my boss?” to “What can I do now to feel better about my work and my team?”

Together, we chose to work together on the last question—strategies for navigating the moment. She also decided to hold the first question in mind—recognizing that answering it was premature.  It could sit in the background for now.

Why Questions, Why Now ‍

What drew me back to the topic of questions was Elizabeth Weingarten’s How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty. I couldn’t resist the title when it showed up as a recommendation on my Kindle — questions and uncertainty, two of the things I think about most. And, as you’ll see, her work sheds light on the conversation with my client and what we did together.

While Marilee’s work sharpened my attention to the kinds of questions I was asking, Weingarten’s pulled me toward something else: how long I’m willing to stay in a question before reaching for an answer. Using the example of my client, can she just sit with, or in Rilke’s language, “live” the question of whether she’s in the right job now? And how can “living the question” support our capacity to navigate uncertainty?

A brief word about navigating uncertainty. It seems hard to argue that the level of uncertainty we’re facing right now is high—perhaps higher than at any point in our collective history. It’s everywhere — in our political moment, in businesses, in nonprofits. I’m convinced the alternative to building the capacity to navigate uncertainty is exhaustion and burnout for individual leaders as well as poor decisions and outcomes for their organizations. Moreover, we are navigating, often simultaneously, both “micro” uncertainties (e.g., my client’s relationship with her boss) and “macro” uncertainties (e.g., the impact of AI on our work and society). It’s genuinely a lot.

Why We Rush to Answers

Weingarten begins with the deep discomfort most of us feel around questions that don’t have immediate answers. We’ve been trained — by school, by organizations, by the relentless pace of work — to move from question to answer as fast as we can. It’s likely one of those instincts that gave us an evolutionary advantage at some point and, in an era of complexity and uncertainty, may serve us less well.

She describes how the need for cognitive closure creates a sense of urgency: we seize on an answer, then freeze on it, closing ourselves off to other possibilities. In other words, when we close in too fast — especially in complex situations — we lose our peripheral vision. Dave Snowden, in his work on anthro-complexity, calls this premature convergence — coming too quickly to a single solution rather than keeping our options open.

I’d add that our growing reliance on technology, and on AI in particular, is quietly raising the pressure for closure. Rather than helping us build a tolerance for the unknown, the reflex to reach for Claude or ChatGPT the moment we feel uncertain may be doing the opposite. Weingarten points to evidence that our intolerance for uncertainty is in fact growing, correlated with how habitually we reach for our phones, or our AI agent, eroding the small, everyday encounters with not-knowing that once made us more resilient to it.

Living the Question‍ ‍

Drawing on Rilke, Weingarten suggests that some of our most important questions are ones we’re meant to live with rather than rush past. Paradoxically, living with a question can help us move through uncertainty with more grace and ease — in our personal lives and in our organizations alike. Those who live the questions, she writes, “crave the experience of continuous discovery, rather than a specific outcome.”  What might look like wallowing — the discomfort of being unsure — she reframes as a kind of authoritative action.

Here’s the distinction I keep coming back to: living with the questions isn’t about reducing uncertainty — it’s about reducing our anxiety in the face of it. We can relax into uncertainty and give things the time and space to mature, rather than forcing the premature convergence Snowden warns about. In the short term, that means less anxiety. In the longer term, it means better, more thoughtful decisions.

This runs counter to what we’d expect. Researchers such as Nur Hani Zainal, at Harvard Medical School, suggest that anchoring ourselves in questions — rather than answers — can actually lower our anxiety, because curiosity keeps us from narrowing prematurely onto the single thought that’s generating our sense of stuck-ness. ‍

What my client discovered was that asking the big question about her future and letting that “breathe” helped her find a kind of peace in the midst of a challenging situation. It acknowledged the depth of the challenge she was facing and that answering this question was not something she had to do right now. Similarly, when organizations are facing strong headwinds, leaders must ask themselves whether the questions that they are asking—that could lead to disruptive actions—are ripe. Is the need to answer them NOW coming from a need for cognitive closure? What does the situation genuinely require?

Asking as Action

In the face of uncertainty, leaders who pause long enough to ask a better question — and give it time to ripen, resisting the pressure to move quickly and “decisively” in all situations— tend to be more effective, not less. The first client I worked with, almost thirty years ago, was a major cookie company. I watched an organization, under the guidance of a top consulting firm, make a drastic, rapid change in the way its retail organization operated. Reflecting on this over the years, I realized that the leadership team, with the encouragement of a powerful consultant, chose action over reflection, change over stability, and structures over people. Anyone who suggested that they slow down and think more deeply—ask different questions (or any questions at all)—was seen as “negative.” The results were catastrophic, and the business was ultimately sold. ‍

None of this means fast, decisive action is always wrong—at times it’s imperative. As the Cynefin framework, which you can read about here, suggests, quick decisions may be exactly what’s needed in times of chaos, when a leader needs to stabilize a situation that has spun out of control — think the early days of COVID. They’re also fitting when things are clear, and the right move is obvious. But in genuinely complex situations, the essential move is to step back, ask the less obvious questions, and give them room.

Weingarten offers the analogy of a fruit tree, distinguishing between peaches, pawpaws, heartwood, and dead leaves. Peaches are the questions that can be answered quickly, pawpaws are answerable, but only over time, and heartwood questions are the ones that remain with us through our lives, like “who am I?” Dead leaves are the questions that don’t ripen and need to be let go. These might be questions that Marilee Adams would consider “Judger” questions, or simply questions that no longer serve us. Taking the time to determine the nature of the question and treat it accordingly can be the difference between suffering and thriving. The more complex the context, the more likely we are to be in the land of “pawpaws” and “heartwood.”

Choosing to sit with a question, then, isn’t avoidance of action. It is an action — and a critical one at that.

An Invitation

I’d encourage you to take a moment and consider: What’s a challenge that you’re facing? Ask yourself about the questions behind that challenge. Which of these need an answer now and which would benefit from “ripening”? What other questions might you be sitting with that you haven’t fully named? Consider how you can make this inquiry a regular practice.

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