Stop Relying on Experience to Make Better Decisions. It Is Not Doing What You Think It Is.

Picture a leader you respect. Someone who reads a room well, who stays composed when everything is moving at once, who seems to reach the right call faster than anyone else in the room. What separates them is not experience. It is a structured internal practice for examining assumptions and patterns before the decision arrives, the kind of personal leadership development that most frameworks describe but few provide a concrete mechanism for.

Now consider this: research covering more than 1,000 decision-makers found that leaders make wrong business decisions 40 percent of the time.

That number probably does not match the leader you just pictured. Which is precisely the point.

The leaders who consistently make sound decisions are not making fewer mistakes because they are smarter, more experienced, or better informed. They are making fewer mistakes because they have built something most leaders never deliberately build: a structured internal practice that does the real work before the decision ever arrives.

The gap between a good decision and a poor one is almost never in the moment. It is in the preparation that did or did not happen beforehand.

What Is the Belief Most Leaders Carry Into Every Decision?

There is a deeply held assumption running through most leadership culture: that better decisions come from better analysis. More data. More deliberation. More rigour applied to the options in front of you.

It is a reasonable belief. It is also wrong, or at least incomplete.

The quality of a decision is not primarily determined by what happens when the options are on the table. It is determined by the quality of the thinking that frames those options, by what the leader assumes to be true before the analysis begins, by which cognitive patterns are operating in the background, and by how much genuine reasoning capacity is available in the moment.

Daniel Kahneman's research on fast and slow thinking showed that humans do not default to careful deliberation under pressure. They default to pattern recognition. To the familiar framework. To the decision that resembles the last one. This is efficient and often wrong, particularly when the situation is genuinely new and the familiar framework is borrowed from a context that no longer applies.

Michael Watkins's decades of research on leadership transitions found that when leaders derail, the failures can almost always be traced to cycles that formed in the first few months. Not from catastrophic misjudgments. From the quiet, uncritical application of patterns that worked before, to a context where they no longer did.

The assumption that experience prevents poor decisions is one of the most expensive beliefs in leadership.

What Is Actually Happening When a Decision Goes Wrong?

Sit with a decision you made that you later wished you had made differently. Not a crisis. An ordinary one. A hire, a strategic direction, a conversation that went sideways.

In most cases, looking back, the information that would have changed the decision was available. The signals were there. What was absent was the structure for surfacing them before the decision was made.

Three things are almost always present when a leadership decision misses the mark.

Unexamined assumptions arrive as instincts. A framework that worked in a previous context gets imported into the new one without being tested. It does not feel like an assumption. It feels like judgment. The difference is only visible in retrospect.

Reactive patterns activate before conscious reasoning can intervene. Schema Therapy frameworks applied to leadership identify emotional and cognitive modes that switch on automatically under pressure: over-control that wants to own every decision point, detachment that retreats from the discomfort of the situation, appeasement that calibrates the response to what will be most socially acceptable rather than most accurate. Leaders who experience these patterns often describe the resulting decisions as unlike them. They were not unlike them. They were exactly like them, under a specific set of conditions that had not been examined.

Cognitive load quietly degrades the quality of reasoning. The prefrontal cortex, responsible for planning, complex reasoning, and self-regulation, operates under metabolic constraint. Research by Arnsten confirmed that sustained high cognitive demand shifts processing toward structures involved in emotional reactivity. The leader appears to be thinking carefully. Internally, the quality of the thinking has already changed. The decisions keep coming. The output continues. What changes, invisibly, is what is driving them.

Arnsten, A.F.T. (2009). Under sustained cognitive demand, processing shifts away from the frontal lobe, where judgment lives, toward more reactive brain structures. The leader appears to be deciding carefully. The quality of the reasoning has already changed. Image is AI generated.

None of this is visible from inside the decision. That is what makes it expensive.

Why Does Experience Alone Fail to Build Leadership Judgment?

Here is the part that runs against most of what leadership development has taught: experience does not automatically produce better decision-making.

David Kolb's foundational research established that experience is only the raw material of development. The mechanism that converts experience into capability is the structured processing of that experience: reflecting on what happened, examining what assumptions drove it, identifying what patterns were operating, and extracting what the equivalent situation requires in the future.

Without that processing, experience accumulates. It does not compound. A leader who has navigated thirty high-stakes decisions without a structured reflection practice has not necessarily built thirty units of judgment. They may have reinforced the same pattern thirty times.

Kolb, D.A. (1984). Experiential Learning. Experience is the entry point, not the outcome. Without reflective observation and conceptualisation, the cycle does not complete and capability does not compound. Image is AI generated.

This is the uncomfortable truth sitting underneath the "I've seen this before" confidence that can make experienced leaders more vulnerable to certain categories of poor decisions, not less. Familiarity that has not been examined is not wisdom. It is habit.

What Changes When Leaders Build Self-Awareness Into Their Practice?

Self-awareness is the upstream variable that most leadership development misses because it is harder to teach than any skill.

Tasha Eurich's research found that only 10 to 15 percent of leaders are genuinely self-aware despite 95 percent believing they are. And the gap widens with seniority. The higher a leader rises, the fewer people are positioned to offer honest calibration, the more the professional norm rewards decisiveness over reflection, and the more the performance of composure requires managing internal states without naming them.

The result is a leader making decisions from a model of themselves that is increasingly less accurate.

A structured internal practice closes this gap. Not by slowing down decision-making. By building the self-knowledge that makes the first reading of a situation more reliable: surfacing the assumption before it drives the analysis, naming the reactive pattern before it determines the response, distinguishing genuine urgency from the internal discomfort of an unresolved question.

The leaders who appear to decide faster and better are not doing less thinking. They have done the thinking in advance of the moment that requires it. They review their decisions consistently, examining what drove them and what the outcome revealed, and they convert that examination into the calibrated judgment that looks, from the outside, like intuition.

It is not intuition. It is a practice.

What Does the Practice Actually Look Like?

Before any significant decision: What am I actually deciding, distinct from what feels like the decision? What do I know? What am I assuming? What pattern am I defaulting to? What does the evidence actually say, separated from what I need it to say?

Those questions, applied consistently in fifteen to twenty minutes, do more to improve decision quality than any amount of post-hoc analysis.

And after: What drove the decision? What did the outcome reveal about the quality of the reasoning? What would a more calibrated version of that call have looked like?

That review, repeated consistently, is what converts experience into compounding judgment rather than reinforced habit.

Most leadership development has invested heavily in the presentation layer: how to communicate a decision, how to align stakeholders, how to hold the room. These skills matter. They are also downstream of the actual problem. Before a leader can communicate with clarity, they need to have reached clarity. The process of reaching it is where most frameworks go quiet.

The Within Pages Leadership Series addresses this layer directly, providing leaders with the structured internal practice that most leadership development points toward and few provide a concrete tool for.

Explore the full series at withinpagesjournal.com. The complete Leadership Series, Step In, Move Through, and Lead On, is available as a bundle at USD $349. Individual volumes from USD $159. For consulting and coaching practices, the framework is available to license at withinpagesjournal.com.

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This article was prepared by the Within Pages® editorial team, dedicated to making leadership and professional growth accessible worldwide. © 2026 Within Pages®. The Reflective Edge. All rights reserved. Follow Within Pages® on LinkedIn or visit https://withinpagesjournal.com/ for more reflections on leadership and professional growth. This article was originally published on The Reflective Edge – Within Pages® (https://withinpagesjournal.com/blogs/the-reflective-edge)

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Sources:

• Nutt, P.C. (2002). Why Decisions Fail. Berrett-Koehler.
• Arnsten, A.F.T. (2009). Stress signalling pathways that impair prefrontal cortex structure and function. Nature Reviews Neuroscience.
• Kahneman, D. (2011). Thinking, Fast and Slow. Farrar, Straus and Giroux.
• Kolb, D.A. (1984). Experiential Learning. Prentice Hall.
• Watkins, M.D. (2003). The First 90 Days. Harvard Business School Press.
• Eurich, T. (2018). What Self-Awareness Really Is. Harvard Business Review.
• Young, J.E., Klosko, J.S., & Weishaar, M.E. (2003). Schema Therapy: A Practitioner's Guide. Guilford Press.