What I Have Learned from the Leaders Who Failed — and the Ones Who Did Not

By Ton de Graaf  |  Quest Coaching International

Twenty years of coaching senior leaders across thirty countries produces a particular kind of education. Not the kind that comes from reading research or attending conferences, but the kind that comes from sitting very close to real people making real decisions with real consequences, over sustained periods of time. You begin to notice patterns. Not theories, patterns. Things that repeat with enough consistency that they stop being coincidences and start being signal.

This article is an attempt to describe what I have actually seen. Not what leadership literature says should distinguish successful leaders from derailing ones, but what, in my direct observation, actually does. The distinction matters, because the two lists overlap less than most people expect.

I want to be clear about what this is not. It is not a study. It is not a dataset. It is the distilled pattern-recognition of two decades of close-range observation, offered as a set of propositions for you to test against your own experience. Some of what follows will be familiar. The parts that feel slightly uncomfortable are probably the parts worth sitting with longest.

What failing leaders have in common

The leaders I have watched derail, lose their role, lose the confidence of their organisation, or simply plateau well below their actual capability, almost never fail for the reasons they believe they failed. They attribute it to politics, to timing, to a board that did not understand the strategy, to a peer who undermined them, to circumstances that were genuinely outside their control. Some of those things are partially true. None of them are usually the main cause.

The main cause, in the overwhelming majority of cases I have observed, is a pattern that became visible years before the failure itself. And it is always some version of the same thing: the leader stopped being honest with themselves.

Not dishonest in the obvious, ethical sense. Dishonest in the quieter, more common sense of having developed a set of explanations for their own behaviour that were comfortable but not accurate. The manager who believes they are direct when their team experiences them as unpredictable. The executive who believes they are strategic thinkers when they are, in practice, operational controllers who have learned to use strategic language. The leader who believes they develop people when they are, in the judgment of those people, someone who takes credit and gives blame.

The gap between self-perception and reality at senior level is not unusual. What distinguishes those who fail from those who do not is not the existence of the gap, almost everyone has one, but what they do when that gap is pointed out to them. The leaders who eventually derail almost invariably respond to honest feedback with one of three moves: they dismiss it as the other person’s problem, they acknowledge it briefly and then revert to exactly the same pattern within weeks, or they manage the messenger in a way that ensures the message is not delivered again. The feedback loop closes. The gap widens, invisibly, until something breaks it open from the outside.

“The leaders who eventually derail almost invariably respond to honest feedback with one of three moves: dismiss it, briefly acknowledge and revert, or manage the messenger so the message stops arriving.”

There is a second pattern that appears almost as consistently: an inability to distinguish between being effective and being liked. This sounds like a psychological observation, and it is, but its practical consequences are organisational. Leaders who need to be liked tend to avoid the decisions that require them to be temporarily unpopular. They promote for loyalty rather than capability. They manage upward with exceptional skill while managing downward with inconsistency. They produce organisations that look well-aligned from the outside and are, in reality, structured around not upsetting the person at the top.

This pattern, in my experience, is almost invisible to the leader themselves. The most reliable signal is the absence of genuine internal disagreement. When I am coaching a senior leader and I ask who in their organisation would disagree with them directly in a meeting, and the honest answer is very few people, that is not a sign of exceptional alignment. It is a warning.

What enduring leaders have in common

The leaders I have watched sustain high performance across many years, across different organisations and contexts, share a set of qualities that differ from what most leadership development programmes try to build. They are not necessarily the most intelligent, the most charismatic, or the most technically skilled leaders I have worked with. But they share something that the ones who fail almost never do: they have a settled relationship with their own limitations.

By this I do not mean they are comfortable being mediocre. The leaders I am describing are almost universally demanding of themselves and of the people around them. What I mean is that they know, accurately and without defensiveness, where their judgment is reliable and where it is not. They know which kinds of problems they solve well and which they tend to make worse. They have learned, often through experience that was genuinely painful, that the areas where they are most confident are sometimes the areas where they are most blind.

This self-knowledge has a specific quality that distinguishes it from ordinary self-awareness: it is actionable. It does not just sit as an interesting fact about themselves. It shapes who they put around them, what they delegate, what decisions they slow down on, and which advisors they actually listen to rather than merely consult.

“They know, accurately and without defensiveness, where their judgment is reliable and where it is not. And that self-knowledge is actionable, it shapes who they put around them, what they delegate, and which advisors they actually listen to.”

The second quality enduring leaders share is what I would describe as a long relationship with discomfort. Not suffering for its own sake, but a genuine tolerance for the kinds of discomfort that most people organise their professional lives to avoid. The discomfort of hearing something about themselves that does not fit their self-image. The discomfort of a decision that needs to be made before the evidence is complete. The discomfort of a conversation that will change a relationship in ways they cannot fully control. The discomfort of being publicly wrong and having to say so without constructing an elaborate explanation for why it was not entirely their fault.

Leaders who have developed this tolerance are significantly harder to destabilise than those who have not. They can move through uncertainty without transmitting it catastrophically to their teams. They can absorb feedback without either dismissing it or collapsing under it. They can sit in the gap between what they know and what they need to decide without either waiting too long or acting too fast. These are not personality traits. They are capacities, and they are built through repeated exposure, which is why the leaders who have them are almost always leaders who have genuinely failed at something significant earlier in their careers and used it well.

The role of failure itself

This last point deserves its own space, because it runs counter to what most organisations actually do with leadership failure.

In almost every senior leader I would describe as truly exceptional, there is a chapter in their career that they describe, now, as the thing that formed them. It is almost always a failure of some kind, a role that ended badly, a decision that cost the organisation significantly, a team they misread, a situation they handled in a way they are not proud of. And the quality that distinguishes those who became exceptional from those who were merely resilient is what happened in the period immediately after.

The leaders who used failure well did three things. They looked at it honestly, without either catastrophising it into evidence of their fundamental inadequacy or rationalising it into something that was mostly outside their control. They extracted something specific, not a vague lesson about humility but a precise understanding of what they had misjudged, overlooked, or avoided. And they changed something specific as a result, something that was visible in their behaviour afterward.

The leaders who did not use failure well did the opposite: they narrated their way through it. They developed a version of events that was coherent and defensible and allowed them to emerge from the experience with their self-image intact. Which meant they emerged with the same blind spots they went in with, slightly better concealed.

Organisations are largely complicit in this. The cultures that most reliably produce excellent long-term leadership are those that create conditions in which failure is named directly, examined honestly, and treated as information rather than verdict. These cultures are rare. Most organisations are far more comfortable with the narrated version, because it is less painful for everyone in the short term and produces exactly the kind of leadership it deserves in the long one.

One question worth asking yourself

After twenty years, the single most diagnostic question I know for assessing a leader’s trajectory is not about their strategy, their team, or their results. It is this: when did you last change your mind about something significant, as a direct result of someone else’s input?

Not the experience of hearing a good point and agreeing with it on a topic where you had no prior strong view. A genuine reversal. Something you believed, or planned to do, or had already started, that you stopped or changed because someone showed you something you had not seen.

Leaders who can answer that question with a specific, recent example are, in my experience, almost always on a trajectory of continued development. Leaders who find the question slightly irritating, or who can only produce examples from several years ago, are almost always protecting a version of themselves that stopped updating at some point, and have not yet noticed.

This is not a comfortable question to answer honestly. That is precisely why it is worth asking.

Ton de Graaf is the founder of Quest Coaching International and a Chartered Business Coach™ with over 20 years of experience coaching senior leaders in Fortune 500 and FTSE 100 organisations across 30+ countries. His background in the Royal Dutch Military Police and Royal Dutch Airforce informs a coaching practice built on precision, directness, and accountability.

To explore working together: coachton@qci-coaching.com  |  www.qci-coaching.com