Decision Making Under Uncertainty: How Leaders Assess Risk and Decide Anyway

DorWay

Sandor Kovacs

February 19, 2026

Editorial photograph illustrating: Assessing Risks In Leadership Decisions: A Guide To Effective Leadership
How leaders make decisions under uncertainty: risk vs uncertainty, diagnosing the situation, matching speed to reversibility, and a practical process.

Decision making under uncertainty is choosing a course of action when you cannot know the outcome in advance, because key information is missing, the situation is changing, or the probabilities themselves are unknown. For leaders, the goal is not to remove uncertainty but to size it, decide at the right speed, and build in ways to adjust.

Risk vs uncertainty

The two words are often used interchangeably, but the difference matters for how you decide.

Situation What you know Example Useful approach
Certainty The outcome Renewing a contract at agreed terms Decide and execute
Risk The possible outcomes and roughly how likely each is Expected default rates on a loan portfolio Expected value, insurance, diversification
Uncertainty Some possible outcomes, but not their likelihood Demand for a product in a new market Scenarios, small bets, staged commitments
Deep uncertainty or chaos Very little; even the options are unclear The first days of a crisis Act to stabilize, then sense and adjust

Diagnose the situation first

The Cynefin framework is a practical way to tell which kind of uncertainty you face. In their Harvard Business Review article, David Snowden and Mary Boone recommend different responses for each context: in complicated situations, where experts can find the answer, sense, analyze, and respond; in complex situations, where answers emerge only through action, probe, sense, and respond with safe-to-fail experiments; and in chaotic situations, act first to establish order, then sense and respond. The most common leadership failure under uncertainty is treating a complex situation as merely complicated and waiting for analysis that cannot settle it.

Match speed to reversibility

Uncertainty is far less dangerous when a decision can be undone. Jeff Bezos’s 2015 shareholder letter distinguishes irreversible “one-way door” decisions, which deserve careful deliberation, from reversible “two-way door” decisions, which should be made quickly by individuals or small groups. Many organizations apply one-way-door caution to two-way-door choices, and lose more to delay than they would ever lose to a reversible mistake.

A practical process for deciding under uncertainty

  1. Name what you do not know. List the key unknowns and which ones would actually change the decision.
  2. Check reversibility. If it is a two-way door, decide quickly and plan to learn.
  3. Build scenarios, not a single forecast. Test each option against three or four plausible futures.
  4. Run a pre-mortem. Imagine the decision has failed a year from now and list why. It surfaces risks people hesitate to raise.
  5. Stage the commitment. Where possible, make a smaller first commitment that buys information, with a clear point to expand or stop.
  6. Set trigger points in advance. Agree on the signals that will cause the team to revisit the decision, so changes of course are planned rather than panicked.
  7. Decide, and say how confident you are. Stating “we are about 60% confident” invites the right level of monitoring.

Assessing risk in leadership decisions

A simple risk assessment for a significant decision covers four questions: What could go badly? How likely is it, roughly? How severe would it be? What would we do if it happened? Score the biggest risks on likelihood and impact, assign an owner to each, and agree on the early warning signs. Keep this light for reversible decisions; reserve full analysis for one-way doors. For broader frameworks, see our guide to decision-making frameworks.

Common mistakes under uncertainty

  • Waiting for certainty that will not come. Delay is itself a decision, often a costly one.
  • False precision. Detailed forecasts that hide how uncertain the inputs are.
  • Overconfidence. Treating the most likely scenario as the only one.
  • Judging by outcome alone. A sound decision can still turn out badly. Evaluate the process, as we explain in decision quality.
  • Vague commitments. Under uncertainty, plans must change. Teams that never agreed on who decides when to adjust end up drifting.

That last point is where DorWay’s work begins. Uncertainty makes broken commitments more likely, so the leader’s job is to make commitments that include how they will be renegotiated. In an organization run as a Network of Agreements™, changing course is not a failure; failing to renegotiate openly is. That is the practical meaning of accountability in leadership.

FAQ

What is decision making under uncertainty?

It is making a choice when the outcome cannot be known in advance because information is incomplete, conditions are changing, or the probabilities are unknown.

What is the difference between risk and uncertainty in decision making?

Under risk, you know the possible outcomes and roughly how likely they are. Under uncertainty, you may know some outcomes but cannot reliably estimate their likelihood.

How do leaders make decisions under uncertainty?

They diagnose the type of situation, match speed to reversibility, use scenarios and pre-mortems, stage commitments to buy information, and agree in advance on the signals that would trigger a change.

How do you assess the risks of a leadership decision?

List what could go badly, estimate likelihood and impact, assign owners to the biggest risks, and agree on early warning signs and responses.

Tracy Vasaturo

Head of Sales

Tracy Vasaturo has spent the better part of two decades in rooms where the stakes are high and the sell is real. Medical devices. SaaS. ERP. High-ticket coaching programs. Live events. She has sold millions across her career — but the throughline has always been the same: finding the bridge between a technology or a transformation and the person who needs it. She’s sold to Fortune 500 executives and to entrepreneurs rebuilding their lives from scratch. She’s worked corporate sales floors and grassroots stages.

She understands that people don’t just buy a product — they buy into a belief that something can change.

At DorWay, Tracy works with individuals, entrepreneurs, executives, and organizational teams who are ready to lead and operate differently. If you’re exploring whether DorWay is right for you, there’s a good chance Tracy is who you’ll talk to first. That’s very much by design.

Thyme Francis

Chief Client Experience and Creative Officer | Co-Founder
Thyme Francis is the architect of how every client experiences DorWay, from the first moment of contact through the full arc of their transformation journey.
 

Her background spans creative direction and financial services, an unusual combination that turns out to be exactly the right one for her role. The creative lens means she understands how people experience brands, communications, and environments emotionally, not just functionally. The financial services background means she understands precision, accountability, and the weight of decisions that actually matter.

What Thyme does at DorWay is ensure that the quality of the client experience matches the quality of the transformation the programs are designed to create. That every touchpoint (every communication, every program delivery, every interaction with the DorWay team) reflects the same integrity and intentionality that DorWay teaches.

She brings to every client relationship the same thing she brings to every aspect of her work: genuine attention to the specific person in front of her. Their story. Their goals. What they actually need versus what they think they need. The ability to hold both the detail and the larger vision simultaneously.

In an organization built on the conviction that leadership is fundamentally relational, Thyme ensures that DorWay practices that conviction in every interaction it has.