Leadership

What Leaders Get Wrong About Uncertainty — And What the Data Says to Do Instead

Journalist Simone Stolzoff's new book reframes uncertainty not as a leadership failure to be managed away, but as the operating condition every executive is already in.

Written by Elena Brooks · Bureau Business · Jun 2, 2026

The Uncertainty Problem Leaders Won't Admit

Most leadership frameworks are built around the premise that good leaders reduce uncertainty. They forecast, they plan, they communicate confidence. Simone Stolzoff's new book, *How to Not Know: The Value of Uncertainty in a World That Demands Answers*, challenges that premise directly — and the evidence he marshals is harder to dismiss than the usual business-book fare.

Stolzoff is a journalist whose work has appeared in *The New York Times* and *The Atlantic*. His argument isn't that uncertainty is fine. It's that the instinct to eliminate it is both biologically understandable and operationally counterproductive.

Why the Brain Is a Bad Uncertainty Manager

Researchers at University College London ran a study in which one group of participants had a 50% chance of receiving a painful electric shock, and another group had a 100% certainty of receiving one. The certain group was less stressed. The ambiguity itself — not the outcome — was the primary driver of distress.

A separate body of research found that professional uncertainty produces health effects comparable to actually losing a job. These aren't soft findings. They have direct implications for how organizations communicate during restructuring, strategic pivots, or leadership transitions — moments when executives often default to vague reassurance rather than honest framing.

Anchors, Not Answers

Stolzoff's most operationally useful concept is what he calls anchors: the fixed commitments that allow an organization to move through uncertainty without requiring certainty first.

The Airbnb case is instructive. When the pandemic eliminated roughly 80% of the company's business, CEO Brian Chesky didn't build a new forecast. He wrote six principles — including "be decisive," "preserve cash," and "be the hero, not the villain" — and used them as the decision framework for the crisis period. "A principle decision is irrespective of the outcome," Chesky said. That's a meaningful distinction for any operator facing a situation where the outcome genuinely cannot be known.

Sequencing as a Crisis Tool

Stolzoff profiles a crisis management consultant named Meredith who works with organizations after serious incidents. Her method is low-tech and high-leverage: she rolls out butcher paper, lists every outstanding task, and forces the executive team to sequence rather than swarm. The act of externalizing the unknown — moving it from anxious mental loops onto a physical surface — converts paralysis into prioritization.

This is what Stolzoff calls "the next right action," a concept borrowed from Buddhist practice. The operational logic is sound: when the full picture is unavailable, the question isn't *what's the plan* but *what's the next move*.

The Slack Case Study

The book's most striking example is Stuart Butterfield's decision to shut down Glitch, a gaming startup that had raised $17 million, attracted international press coverage, and built tens of thousands of active users — and then pivot to an internal collaboration tool the team had built for themselves. That tool became Slack. Salesforce acquired it for nearly $27 billion.

Butterfield's own account is notable for its honesty: "We discovered our product and opportunity, rather than planning for it." That's not a story about visionary foresight. It's a story about staying operational under uncertainty long enough for the real opportunity to become visible.

What This Means for Leadership Practice

Stolzoff's framework won't satisfy executives who want a prediction model. But it offers something more durable: a set of practices — written principles, externalized task lists, sequenced action, reframed threat perception — that hold up precisely when prediction fails.

The leaders who navigate uncertainty best, the evidence suggests, aren't the ones who project the most confidence. They're the ones who've built the clearest internal architecture for moving without it.

Key takeaways

University College London research found people are more stressed by a 50% chance of a bad outcome than a 100% certainty of one — meaning ambiguity itself is the stressor, not the outcome.
Brian Chesky's pandemic response at Airbnb centered on six written principles, not forecasts — a deliberate shift from outcome-based decisions to values-based ones.
Crisis management practice shows that externalizing unknowns — getting them out of executives' heads and onto paper — converts anxiety into sequenced, actionable priorities.
Stuart Butterfield shut down Glitch, a game with tens of thousands of active users and millions in the bank, to pursue an internal tool his team had built. That tool became Slack, which sold to Salesforce for nearly $27 billion.
Psychological research distinguishes 'threat mode' from 'approach mode': framing uncertainty as a threat reduces cognitive function, while framing it as information-gathering increases it.

FAQ

What is Simone Stolzoff's main argument in 'How to Not Know'?

Stolzoff argues that uncertainty is not a leadership failure to be eliminated but an operating condition to be navigated. He presents research and case studies showing that leaders who build systems — values, principles, sequenced priorities — for moving through uncertainty outperform those who try to resolve it before acting.

What did Brian Chesky actually do differently during the pandemic?

Rather than building new financial forecasts, Chesky wrote six guiding principles and used them as the decision framework for the crisis. He distinguished between 'business decisions,' which optimize for predicted outcomes, and 'principle decisions,' which hold regardless of outcome — and committed to the latter.

How does the Slack origin story illustrate Stolzoff's thesis?

Stuart Butterfield shut down Glitch — a funded, covered, user-acquiring game — to pursue an internal tool his team had built while making it. Slack became one of the fastest-growing enterprise software companies ever and sold to Salesforce for nearly $27 billion. Butterfield's own account credits discovery over planning, which is Stolzoff's central point.

What does the UCL shock study tell us about how to communicate during organizational uncertainty?

The study found that ambiguity — a 50% chance of a bad outcome — was more stressful than certainty of the same bad outcome. For leaders, this suggests that vague reassurance during restructuring or strategic change may be more damaging to employee wellbeing than honest, direct communication about what is and isn't known.

What is 'approach mode' and why does it matter for decision-making?

Psychologists use 'approach mode' to describe the cognitive state that occurs when uncertainty is framed as an opportunity to gather information rather than a threat. In threat mode, blood flow shifts away from the brain; in approach mode, it increases. The practical implication is that how leaders frame uncertainty — internally and externally — has measurable effects on the quality of thinking that follows.

Citations

A guide to navigating uncertainty head-onSimone Stolzoff shares five key insights from 'How to Not Know: The Value of Uncertainty in a World That Demands Answers,' including the UCL shock study, Brian Chesky's pandemic principles, and the Slack origin story.
University College London study on uncertainty and stressParticipants with a 50% chance of receiving a painful electric shock reported more stress than those with a 100% certainty of receiving one, per UCL researchers cited in Stolzoff's book.
Brian Chesky's six pandemic principles — AirbnbChesky created six guiding principles at the start of the pandemic after Airbnb lost approximately 80% of its business, framing them as principle decisions rather than business decisions.
Slack's origin from Tiny Speck's Glitch shutdownStuart Butterfield shut down Glitch in the early 2010s despite $17 million raised and tens of thousands of active users, pivoting to an internal messaging tool that became Slack, later acquired by Salesforce for nearly $27 billion.