Leading When You Cannot Know

In my coaching conversations with senior executives, one theme has moved to the center over the past two years: the difficulty of committing to decisions while the ground keeps shifting. This is not a private anxiety. The Conference Board's 2026 C-Suite Outlook, drawing on more than 1,700 executives and board members worldwide, identified uncertainty itself as the greatest challenge facing business, driven by a convergence of geopolitical tension, regulatory fragmentation, rapid advances in AI, and shifting labor markets. The leaders I work with are not struggling because they lack intelligence or information. They are struggling because the operating assumption underneath their training, that enough analysis eventually produces the right answer, no longer holds.

The ache for certainty

Most executives were formed in a world that rewarded a specific sequence: gather the data, analyze rigorously, decide, execute. That sequence works beautifully when the environment is stable enough for the past to predict the future. It fails when the environment shifts faster than the analysis can be completed. In The End of Leadership As We Know It, Steve Garcia and I argued that data can become a trap in disruptive contexts. It feels wonderfully precise and scientific, which is exactly why leaders desperate for an anchor over-rely on it. But data describes the past. When the future stops resembling the past, more data mostly produces more confident descriptions of a world that no longer exists.

The same is true of best practices. Borrowed frameworks make sense when your situation resembles the situations they were derived from. In genuinely complex circumstances, every situation is unique, and the general framework will either mislead you or push you to do exactly what your competitors are doing.

Sensemaking is the alternative

The alternative to waiting for certainty is not guessing. It is sensemaking: building your own working theory of the situation. Sensemaking means identifying the factors that matter, mapping the relationships between them, forming hypotheses, and testing them against reality. It is as much an act of creativity as analysis, because you must choose what to pay attention to and how to represent what you see.

My favorite illustration comes from Steve Jobs. When he returned to a struggling Apple in 1997, the company was supporting roughly 350 products. He could have hired consultants and applied a standard portfolio framework. Instead he made sense of the situation himself, sketching a simple two by two: consumer versus professional, desktop versus portable. Anything that did not fit was cut. Apple went from 350 products to 10, and the clarity that came from Jobs's own theory of the business freed the company to build what came next. The framework was not sophisticated. It was his, built from direct engagement with the specifics of his situation. That is what made it powerful.

There is a second pressure worth naming, because it compounds the first. The margin for error has narrowed. Decisions at senior levels now face more scrutiny from boards, investors, employees, and the public than at any point I can remember. Leaders feel simultaneously pushed to act boldly and punished for acting wrongly, which makes the temptation to wait for certainty even stronger at exactly the moment waiting is most costly.

And here is what rarely gets said in strategy discussions: the barrier to leading differently is less intellectual than emotional. The heroic model taught us to project confidence and appear invincible, and many executives privately fear that saying I do not know yet will read as weakness. In my experience the opposite is true. Teams can tell when certainty is performed. A leader who says here is my current theory, here is what would change my mind, and here is how we will find out builds far more confidence than one who pronounces answers that events keep contradicting.

Five practices for deciding without certainty

Hold your plan as a hypothesis. Instead of asking whether the plan is right, ask what would have to be true for it to work, and what evidence would tell you it is failing. Leaders who frame plans as hypotheses update faster and defend their egos less, because changing your mind stops being an admission of error and becomes the point of the exercise.

Experiment before you commit. In complex environments, analysis cannot tell you what will work. Only reality can. Run small, cheap probes before large, expensive commitments. The question is not how do we get this right the first time, but how do we learn the most for the least cost.

Know which kind of problem you are facing. Complicated problems, like engineering a bridge, yield to expertise and analysis. Complex problems, like shifting a culture or entering an unpredictable market, do not, because cause and effect only become clear in hindsight. Applying complicated-problem tools to complex problems is one of the most common and expensive mistakes I see senior teams make.

Ground yourself when the map fails. When the external environment offers no reliable guide, your internal one matters more. Leaders with a clear sense of purpose and values make faster, more consistent decisions under uncertainty, because not everything is up for grabs. The destination can stay fixed while the route changes constantly.

Think out loud with people who owe you nothing. Sensemaking done alone recycles your own assumptions. The executives I see navigate uncertainty best all have some version of the same asset: trusted peers outside their reporting lines, and often outside their companies, who will challenge their theory of the situation before the market does.

Trading the answer for the question

Certainty is not coming back. The convergence of forces the Conference Board describes is not a storm to be waited out; it is the climate. What strikes me most about the leaders I admire is that they have stopped waiting. They have traded the comfort of the answer for the discipline of the question, and they have discovered something the rest of us need to learn: confidence under uncertainty does not come from knowing you are right. It comes from knowing you will find out quickly, and adjust.