Leadership as Sensemaking

Winston Churchill allegedly once joked that the most important quality of a leader is the ability to tell what will happen tomorrow, next week, and next year. And then explain why it didn’t happen.

There is more truth in that than most leaders would like to admit.

We tend to imagine leadership as certainty. The leader is supposed to have the answers, calm the fears, and point clearly toward the future. In periods of real change, that is almost never how leadership actually works.

One of the most important jobs of a leader is to help people make sense of what is happening around them.

If you are asking someone to do something difficult, they have to understand why. They need to know how it fits inside the larger story they are already living in.

Everybody’s in a story.

Václav Havel, the Czech playwright, dissident, and later president of the Czech Republic, once wrote that “hope is not the conviction that something will turn out well, but the certainty that something makes sense regardless of how it turns out.” I have always found that definition clarifying.

Today, hope is often misunderstood as a promise that things will turn out well. Most people know life offers no such guarantee. What people need is something more durable. They need a sense that what they are living through still makes sense.

For several decades, much of the Western world operated inside a shared story. There was a broad postwar narrative about globalization, institutional stability, economic growth, and expanding integration across nations and markets. The story was imperfect. The Cold War was hardly peaceful, and many people were left out of its benefits. But it was still a story most people understood. It gave shape to the era.

Today, that story is collapsing. Institutions are losing trust. Technology is moving faster than culture can absorb it. People consume entirely different versions of reality depending on where they get their information.

And no shared story has emerged to replace the old one.

That is the leadership challenge of our time.

Years ago, a friend of mine was head of equity research at one of the largest investment firms in the world. She is brilliant, a wonderful human, and very good at her job. When the financial crisis hit in 2008, she left. Not gradually, not for another firm. She walked away from finance entirely and enrolled in divinity school.

When I asked her what had happened, she said something I have not forgotten. She had been doing the same work for nearly twenty years, and she realized she was operating outside the map she knew. The maps she had been using were no longer an accurate description of reality, and she could not do her job without one

That is the experience more and more people are having right now. The facts have begun to outrun the playbook. The terrain has shifted, and the navigation tools people were handed do not match the ground anymore.

You can feel it in a room. There is a question hanging in the air, asked silently if not aloud: What is going on?

This is the essence of the cultural moment, and it is precisely when sensemaking becomes most important. Leadership matters in every era, but especially in moments like this, when the old story no longer holds and a new one has not yet arrived.

The mistake many leaders make in moments like this is to shout louder. Push harder. Project more confidence. But none of that restores orientation.

What people need first is honesty about the bearings being lost. Few things are more refreshing than a leader who, when asked a hard question, says, “I don’t know, but we’re working hard to find out.”

Audiences are often not used to that answer, which is one reason so few leaders give it.

Instead, they reach for reassurance and the comforting fiction that everything is under control. But deep down, people sense the dishonesty. That is why so much modern leadership produces cynicism rather than trust.

Saying nothing real is worse than saying nothing at all.

Churchill understood this when he told his country he had nothing to offer but “blood, toil, tears, and sweat.” That is what real leadership sounds like.

In 1990, Sweden’s economy collapsed. The crisis forced the country to rethink many of its assumptions, and the decades since have been among the most successful in its modern history.

It was in that environment that I stepped in to lead McDonald’s Sweden. In that kind of moment, you cannot keep asking people whether they want fries with that. The old scripts no longer work. You need new strategies, new ideas, and most of all a new sense of where you are going.

You cannot get from point A to point B unless you are clear about what point B actually is. People say they want change, but they are rarely specific about what they are trying to reach. So they take action without a destination, and the action ends up serving nothing.

The first task of leadership in a moment of disorientation is not to act. It is to pause. As my friend Dov Seidman, a leadership thinker and author, so often reminds us, when we hit pause on a machine, it stops. But when we hit pause on a human, we begin. In pausing, we can engage the people around us in an honest conversation about where we actually are, what is no longer working, and where we want to be in five years.

Only after you have framed that destination together can you begin to ask what the best first few steps look like.

And those first few steps have to be small enough to win.

Early wins matter enormously in situations like this. If the first thing a team attempts is impossible and everyone fails at it, cynicism deepens and the work gets harder from there. People need evidence that the new direction is viable.

Real change is built one credible step at a time, against a clear and shared sense of where it leads.

Why do some leaders calm a room in difficult moments while others make it worse?

Part of the answer is simple: managers underestimate the people in front of them. They treat the room as a crowd to be managed, a mood to be controlled, an audience that needs protecting from the truth.

Leaders treat people as adults who can metabolize bad news.

People can carry a great deal if they are trusted with the actual situation. What they cannot carry is the suspicion that they are being handled. Engage people honestly in the problem and they will engage with you in the solution. Hand them a polished narrative built for reassurance and they will eventually stop trusting anything you say.

Over the years, I have come to notice a small number of patterns in leaders who hold a room together when the ground is shifting.

The first is an obsessive grounding in the facts as they actually are today. Not how they might look next quarter. Not where the trend lines might extrapolate to. Not what the situation could mean if certain things go wrong.

What is the real situation right now? Where are we, exactly? How bad is it? Who is hurting? Which customers did we lose, and why?

They take a very precise inventory of the present.

The second is the willingness to name the unknown without dramatizing it.

“We don’t know yet. Here is what we are doing to find out. Here are the scenarios we are considering, the good, the bad, and the ugly.”

There is more leadership in a few sentences like that than in most of the speeches a CEO will give in a career. They are rare because most leaders cannot tolerate sitting inside a question long enough to say them out loud.

The third pattern is consistency. The leader who calms a room is the same person on Tuesday that she was on Friday. She does not drift. She does not change with the weather.

The leaders who amplify fear, by contrast, are emotional windsocks. One day they are harsh, the next they are giving everyone hugs, apologizing for how harsh they were the day before. People feel that volatility, and they learn to brace for it instead of trusting the work.

When you are setting strategy in difficult times, the most important things you can be are calm, collected, and consistent.

That kind of consistency is harder than it looks. It must be built within over time and cannot be performed.

The steadiness many leaders lack can be cultivated through inner work. It comes from having sat with what one fears, and from knowing those fears well enough that they no longer run the room.

Everyone carries insecurities and blind spots. The best leaders become conscious of as many as they can and develop enough discipline to keep the rest from running the show.

The most powerful illustration of that discipline comes from James Stockdale.

Stockdale was an American naval officer held as a prisoner of war in Vietnam for more than seven years, much of it in solitary confinement and much of it under torture. Jim Collins, the business researcher behind Good to Great, wrote about him, and the principle that emerged from his story has come to be known as the Stockdale Paradox.

When Collins asked him how he survived when so many others did not, Stockdale said the prisoners who died first were the optimists. They were the ones who told themselves the Americans would come by Christmas. When Christmas passed, they told themselves Easter. When Easter passed, they told themselves the end of summer.

Each unmet hope was a small death.

Stockdale survived because he held two truths at once. He never lost faith that they would prevail in the end, but he refused to confuse that faith with a prediction about when.

That paradox is one of the most important leadership traits a person can develop. You have to believe, at some deep level, that you will come through, while maintaining the most honest possible view of reality as it exists today.

Why is uncertainty so destabilizing in this moment?

Most people, when they try to explain it, reach for the language of information. They say they do not know what is happening. They cannot predict what comes next. They feel uncertain because they cannot see clearly.

That is not quite right.

What is actually happening is what I call the suspension of meaning.

People can carry an extraordinary amount of difficulty if they believe their suffering has a place inside some larger story. Anyone who has read Viktor Frankl’s Man’s Search for Meaning has felt the force of this insight. Frankl survived the camps and built his life’s work around the observation that a human being can endure almost anything if they can locate it inside a coherent why.

Take the story away, and every minor frustration starts to feel like new evidence that nothing holds together anymore.

The historian Yuval Noah Harari makes a related point from a different angle. He argues that human beings are narrative creatures. We live inside stories, from campfires to scriptures to the stories we read our children before bed. Story is how we orient ourselves in the world.

The challenge today is that many of the stories that once provided that orientation no longer fit the reality around us. We are navigating artificial intelligence, the reorganization of work, the fragmentation of media, and the loss of trust in institutions of every kind.

The new landscape has arrived. The new story has not.

This is where I would invert Havel. If hope is the certainty that something makes sense regardless of outcome, then despair is not the certainty that things will go badly. Despair is losing hope that anything makes sense at all.

That is why uncertainty is so corrosive right now.

A leader’s job in such a time is not to manufacture certainty. It is to restore the experience of coherence. The felt sense that the situation, even if it is hard, can be understood, even if it cannot yet be fixed.

People will accept difficulty inside a coherent story. They will not accept incoherence, even when the news is good.

Consider Ukraine.

The Ukrainian people are enduring something almost unimaginable, yet they continue to fight because they have a story that makes sense of their sacrifice. Whatever one’s view of the war, most Ukrainians know exactly why they are fighting.

The cost has been catastrophic, and the coherence has held.

That is what meaning can carry a people through. And it is what its absence makes impossible.

Data can tell you what happened. It cannot tell you what it means.

The moment a leader begins explaining what the numbers mean, another challenge appears: how do you know you are interpreting them honestly?

One test I return to often is simple: does my framing leave room for me to be wrong?

If I have constructed a story that cannot be contradicted, if every counterargument has already been dismissed before it is heard, I am probably no longer making sense of reality. I am defending a position.

The best protection against this is exposure to multiple perspectives.

I read people I disagree with. Voices from the left and the right. Philosophy and religion. Every perspective reveals something the others miss. Podcasts have become my favorite medium because they allow me to listen to thoughtful conversations between people with very different views. It’s a simple way to broaden your perspective.

One of the easiest ways to become dishonest is to stop listening to anyone who challenges your assumptions. People surround themselves with confirming information and gradually lose the ability to understand how anyone else sees the world. A leader cannot afford that luxury.

Another test is paying attention to dissonance.

In meetings, I often find myself watching the reactions around the table as much as listening to the words being spoken. When an idea lands badly, when someone becomes uncomfortable, when a room suddenly grows quiet, something important is often happening.

The temptation is to move on.

The better instinct is to ask a question.

What just happened? What is the white elephant in the room that nobody is naming?

Sensemaking is teachable. The discipline of attention. The work of separating what you actually know from what you fear. The habit of testing your language against reality. The practice of writing the story before you tell it. All of that can be learned.

What cannot be taught in the same way are the deeper traits underneath the craft. Humility. The willingness to be wrong in public. The calm that comes from having actually faced something difficult and survived it. These are character qualities, and character is not built in a workshop. You cannot teach someone in a single session to be at peace with not knowing.

You can encourage them. You can model them. You can put people in situations that demand them. But there is no shortcut.

Sensemaking is one of the few leadership disciplines where the craft and the character cannot be cleanly separated. You can rehearse the words. You can practice the questions. But what people are actually listening for, in the moments that matter, is whether the person speaking has done the work underneath. Whether they have made peace with their own uncertainty, rather than asking everyone else to carry it for them.

The impulse to make sense of reality does not disappear when trustworthy leaders go missing. People construct meaning from whatever is available, and what is available is often whatever feels most emotionally satisfying, not most accurate.

The vacuum tends to fill in three ways.

The first is demagoguery. Someone offers a simple, foreclosing story, and a hungry audience accepts it because the alternative is the discomfort of not knowing.

The second is conspiracy. Loose threads get woven into intricate explanations because sinister coherence feels better than no coherence at all.

The third is cynicism. People stop believing anyone is telling the truth and withdraw from the conversation entirely.

All three abandon the slow work of figuring out together what is actually going on.

Of the three, demagoguery is the most dangerous because it borrows the form of sensemaking.

So how do you tell the difference?

Demagogue narratives foreclose. Sensemaker narratives open.

A demagogue’s story explains everything through blame. It was them. They did this to us. Here is who we will punish. Once the frame is accepted, inquiry ends and loyalty begins.

A sensemaker’s story leaves room for the next question. It provides enough orientation to act today while remaining open to revision tomorrow.

Demagogues make people feel certain. Sensemakers make people feel oriented.

The distinction has nothing to do with whether you agree with the narrative. It has everything to do with what the narrative leaves room for.

Populist narratives have not become powerful for no reason. Many institutions lost trust for reasons that were often earned. The danger is not that these stories identify nothing real. The danger is that they are too narrow to accommodate the full picture, leading people toward scapegoats rather than solutions.

A population that loses the experience of trustworthy sensemaking eventually forgets what it feels like. People stop looking for it. Stop expecting it. Stop demanding it.

We become, slowly, connoisseurs of suspicion. A culture trained to read every candid statement as a performance because genuine honesty has become so rare.

If that continues long enough, the ability to recognize good sensemaking begins to atrophy. Doing the right thing becomes harder, costlier, and less rewarded.

That is not a future any of us should accept.

Leadership does not need to manufacture certainty. It needs to restore coherence.

It asks for the discipline to interpret reality honestly in front of the people you lead. To say what you think is true without pretending you cannot be wrong. To stay calm when the news is bad. To leave room for questions.

The arc of the conversations worth guiding bends toward hope. Meaning can be rebuilt through honest conversations, difficult questions, and acts of sensemaking.

The map is unfinished. The terrain keeps shifting.

That is the work.

Have you ever watched a leader who helped people stay grounded during a period of uncertainty?

What did they do?

This essay is paired with a song I wrote called "Trying to Make Sense." Both explore the same central idea: that leadership is not the art of projecting certainty, but of helping people find coherence when the world no longer makes sense. As old assumptions fall away and familiar maps lose their meaning, the song reflects on what remains: the courage to keep walking, the humility to admit what we do not know, and the hope that making sense together is enough.

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