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Ton de Graaf, Executive Coach

LEADERSHIP INSIGHTS 

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By Ton de Graaf  |  Quest Coaching International


There is a particular type of senior leader that organisations find almost impossible to talk about clearly. They are not failing. Their results are adequate, sometimes genuinely good. They are experienced, technically credible, and widely regarded as decent people. They do not create the kind of obvious problems that trigger a board conversation or a formal review.


And yet, if you speak privately to the people who work around them, their direct reports, their peers, the people two levels below who watch how things actually operate, something consistent emerges. People respect this leader. They do not particularly want to follow them. They do what is asked, competently and without friction. But the discretionary effort, the creative engagement, the willingness to go beyond the requirement because they believe in where the leader is taking them, that is absent.


And in its absence, the organisation moves more slowly, achieves less, and loses its best people more frequently than anyone can quite account for.


This is one of the most common and least diagnosed leadership problems I encounter. It is common because it is easy to miss, the metrics do not obviously flag it, the leader does not obviously fail, and the people experiencing it rarely have a clear enough language to name what is missing. It is difficult to diagnose because the leader at the centre of it is usually the last person to see it, and the organisational conditions that would surface it, direct, honest upward feedback, are precisely the conditions that leaders who have lost genuine followership tend not to create.

 

The difference between compliance and commitment

Authority produces compliance. Influence produces commitment. Both look the same from a distance. They feel entirely different to the people inside them, and they produce entirely different results under pressure.


A team operating from compliance does what it is told, on time, to the standard required. It meets its targets in normal conditions. It does not volunteer what it has not been asked for. It does not raise problems early, because early problem-raising was not rewarded in the past. It does not adapt quickly to changing circumstances, because adaptation requires judgment calls, and judgment calls without explicit authorisation are not safe. When conditions become genuinely difficult, a compliance-based team waits. It waits for instruction. And while it waits, the situation gets worse.


A team operating from commitment behaves differently in every one of those situations. It raises problems before they become crises. It adapts without waiting to be asked. It brings energy to the work that is not contingent on the difficulty of the conditions, because the energy is not primarily about the conditions, it is about the belief that the direction is right and the leader can be trusted to navigate it.


The distinction sounds straightforward. The difficulty is that leaders who are producing compliance rather than commitment rarely know it. The compliance looks, from above, like a functional team. The leader reads the absence of complaints as evidence of effective management. The gap between what they are producing and what is possible does not appear on any report they receive, because it is defined precisely by what their organisation is not doing and not saying.


“Authority produces compliance. Influence produces commitment. Both look the same from a distance. They feel entirely different to the people inside them, and they produce entirely different results under pressure.”

 


How leaders lose influence without losing authority

Influence is not granted with the title. It is built, incrementally, through a specific set of behaviours, and it erodes in the same way it builds: gradually, through accumulated small moments, most of which the leader does not register as significant at the time.


The most common route to losing influence while retaining authority is consistency failure. Not dramatic inconsistency, the kind that generates a formal complaint or a notable incident. The quieter kind. The leader who says that candour is valued but whose expression shifts, almost imperceptibly, when they hear something they did not want to hear. The leader who endorses empowerment in a team meeting and then asks for updates on decisions that have already been delegated. The leader who agrees, in a one-to-one, to a course of action that they do not subsequently support when it becomes visible to others. None of these moments is individually significant. Accumulated, they teach people the actual rules, as opposed to the stated ones, with considerable precision.


The second route is the gradual withdrawal of genuine curiosity. Influence requires that the people around a leader believe, on some level, that the leader is actually interested in what they think. Early in a leader’s tenure, this is usually present. The leader is new, the learning curve is real, and the questions are genuine. Over time, many leaders replace genuine curiosity with managed consultation. They ask questions to which they have already decided the answer. They listen in a way that is visibly waiting for the other person to finish. They reference ideas from external sources, from strategy consultants, from books, from peers at other organisations, far more frequently than they reference ideas from the people in their own teams.


The people around them notice. They stop bringing their best thinking, because their best thinking is not what is required. What is required is endorsement of thinking that has already happened elsewhere. They shift from contributors to executors. The leader mistakes this for maturity in the relationship. It is actually atrophy.


“Over time, many leaders replace genuine curiosity with managed consultation. They ask questions to which they have already decided the answer. The people around them notice, and stop bringing their best thinking.”

The third route, and the one that is hardest to reverse, is the accumulation of unaddressed tension. Every team has conflict that is not being spoken about. Every senior relationship has dynamics that are felt but not named. When a leader consistently allows significant tension to exist without addressing it, between team members, between functions, between themselves and a key stakeholder, they are not keeping the peace. They are signalling that the peace is more important to them than the truth. People read this signal accurately. They conclude that this leader will not go to the difficult places. And a leader who people believe will not go to the difficult places is a leader they will not follow into difficult territory.

 

What rebuilding genuine influence actually requires

The leaders I have watched successfully rebuild influence after losing it share one characteristic that makes everything else possible: they stopped pretending they had not lost it.


This sounds simple. It is not. The identity of a senior leader is substantially built around the assumption of influence. To acknowledge, clearly and without excuse, that the people around you are complying rather than committing, that your team is functional but not genuinely engaged, that your peers manage you rather than confide in you, that the candour you believe you have created is performative rather than real, requires a degree of honesty about yourself that most senior leaders have never been asked to exercise.


Once that acknowledgment is genuine, the path forward is less mysterious than leaders tend to fear. It begins with a different quality of conversation, not the managed consultation described above, but questions that are open because the leader genuinely does not know the answer and is willing to be surprised by it. It continues with a different quality of consistency, not the performance of values but the slow, unglamorous work of making what you say and what you do the same thing, in small moments, over a sustained period. And it requires, almost invariably, at least one conversation that the leader has been avoiding, one place where the unaddressed tension is named directly, without the softening that has made it safe to ignore until now.


None of this happens quickly. Influence that has eroded over three years does not return in three months. But the trajectory changes faster than most leaders expect, once the direction is genuinely different, because people are watching for exactly the signals that the direction has changed, and they recognise them when they are real.

 

The question organisations rarely ask

There is a diagnostic question that most organisations never formally ask about their senior leaders, though the answer is almost always known informally by everyone around them: if this person were to leave tomorrow, what would the people who work with them actually lose?


Not the function. Not the institutional knowledge or the client relationships or the operational continuity. Those losses are real but replaceable. What would be irreplaceable is the thing that defines genuine influence: the specific quality of thinking, challenge, and permission that this particular leader creates in the people around them. The standard they set that people hold themselves to long after this leader has left the room. The questions they ask that nobody else thinks to ask. The conversations they were willing to have that nobody else would have.


Leaders with genuine influence leave that kind of trace. Leaders with authority alone leave a vacancy.

The distinction is worth knowing about yourself, clearly and honestly, while there is still time to change which one you are building.


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

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

Updated: Sep 8

Most senior leaders can tell you, without much hesitation, what the most important conversation in their organisation is right now. It might be about the underperforming business unit. Perhaps it’s regarding the executive who excels in their role but disrupts the team dynamic. It could also be about the strategy the board has approved, which half the leadership team privately believes is flawed. Or it may concern the relationship between two senior colleagues that everyone can see is broken, yet no one is addressing.


They can name it. They know exactly what needs to be said and to whom. Yet, in the vast majority of cases, they are not having it.


In my twenty years of coaching senior executives, I have come to believe that the single biggest constraint on leadership performance is not a lack of intelligence, strategic insight, or technical capability. It is the absence of courage in conversation. Not the dramatic, once-in-a-career kind of courage, but the quieter, more demanding kind required in ordinary working weeks, in ordinary meetings, with people who are not going anywhere. You will have to work with them tomorrow, regardless of what you say today.


This article explores what gets in the way of those conversations, the costs of avoidance, and what I have witnessed when leaders stop waiting for the right moment and simply engage.


Why the Conversation Does Not Happen


The most common explanation leaders give for avoiding a difficult conversation is timing. They believe it’s not the right moment. The person is under pressure. A major deliverable is looming. The relationship is already strained, and pushing now will only make it worse. While these reasons are often partially true, they are frequently used to delay indefinitely something that would be better done promptly.


Beneath the timing explanation, there are usually more honest reasons.


Fear of Damaging Relationships


The first is the fear of damaging the relationship. At a senior level, relationships are genuinely difficult to repair once they are significantly damaged. The stakes of a conversation going poorly are real. This is a legitimate concern. However, the unspoken version of the conversation is also damaging the relationship, slowly and invisibly, through distance, reduced trust, and the resentment that accumulates when important things go unsaid. The question is not whether to pay a relational cost. It is whether to pay it now, in a form you can manage, or later, in a form you cannot.


Fear of Being Wrong


The second reason is the fear of being wrong. Leaders who have built their identity around good judgment find it particularly challenging to raise a concern that the other person might credibly rebut. If I name this and they explain it away convincingly, what does that say about my read of the situation? This fear often produces silence or an overly aggressive version of the conversation, neither of which is what is actually needed.


Fear of Future Obligations


The third, and least often admitted, is the fear of what becomes required next. If I tell the underperforming executive directly and honestly that their performance is not good enough, I am then obligated to follow through, to support the change, to hold them accountable, and ultimately to act if nothing shifts. Raising the conversation closes the option of continuing to hope it resolves itself. Some leaders, at some level, are not yet ready for that obligation, and avoidance is a way of not having to meet it.


“The question is not whether to pay a relational cost. It is whether to pay it now, in a form you can manage, or later, in a form you cannot.”

What the Avoidance Costs


The costs of the avoided conversation are rarely invisible to the organisation, even when the leader believes they are being managed discreetly.


Cost to the Individual


The most immediate cost is to the person who needed to hear it. A senior leader who is underperforming and is not told directly is being failed by the organisation, not protected by it. They are denied the information they need to change, improve, or make a realistic decision about whether this role is the right fit. The compassionate instinct that drives the avoidance—wanting to protect someone—produces the opposite of a compassionate outcome. It leaves the person in a situation that is not working for them, without the honest feedback that would empower them to change it.


Cost to the Team


The second cost is to the team. People notice what their leader does not say. When an underperformance is not named, when a broken relationship is not addressed, or when a strategic concern is not raised, the people around the leader draw conclusions about what the leader is willing to do. Those conclusions tend to be limiting. The space for honesty in a team contracts to the size of the space that the leader is visibly willing to occupy.


Cost to the Leader


The third cost is to the leader themselves. Avoided conversations accumulate. Each one that is deferred adds a small but real cognitive and emotional load—the background awareness of something unresolved, the slight awkwardness in interactions that carry the weight of the unsaid. Leaders who carry a significant number of these tend to describe a sense of low-level depletion that they find difficult to account for. The connection between the depletion and the avoidance is almost never obvious from inside it.


“The space for honesty in a team contracts to the size of the space that the leader is visibly willing to occupy.”

What Gets in the Way Is Not What You Think


When I work with leaders on this, the instinct is almost always to focus on the mechanics of the conversation itself. How do I say it? What words do I use? How do I manage their reaction? These are not unimportant questions. However, in my experience, they are not usually the real obstacle.


The real obstacle is almost always internal. It is the story the leader is telling themselves about what will happen if they have the conversation. That story is often more catastrophic than what actually occurs. The person who will be devastated turns out to be uncomfortable but professional. The relationship that will be destroyed often becomes strengthened by the honesty. The strategic disagreement that will cause an irreparable rift is one the board has been waiting for someone to articulate.


This is not to say difficult conversations are not difficult. They are. But the difficulty that leaders anticipate is almost always significantly greater than the difficulty that materialises. The gap between the imagined conversation and the actual one is where most of the avoidance lives.


Perfectionism of Timing


The second internal obstacle is what I would call the perfectionism of timing. Leaders who are skilled communicators tend to hold out for ideal conditions—the perfect moment, the right setting, the version of themselves that is fully prepared and at their best. This is understandable but also self-defeating. The ideal conditions for a difficult conversation almost never arrive. The conversation that happens imperfectly, at a reasonable moment, is almost always more useful than the one postponed in pursuit of a version that never comes.


What Happens When Leaders Have It


I have watched senior leaders have conversations they had been avoiding for months, sometimes years. The pattern of what follows is consistent enough that I can describe it with confidence.


Short-Term Relief


In the short term, there is almost always relief. Not just for the leader, but for the person they spoke to. The thing that was not being said was frequently not being said on both sides. The person who needed to hear it was often aware, at some level, that something was wrong and was experiencing the silence as worse than the words.


Medium-Term Changes


In the medium term, something changes in the quality of the relationship. Not always in the direction the leader feared. More often, it shifts towards greater honesty, more directness, and less managed politeness. The relationship becomes more useful, even when it becomes temporarily uncomfortable.


Organisational Culture Shift


At the organisational level, something shifts in the culture. Not because one conversation transforms a culture, but because people notice when their leader is willing to say what needs to be said. That willingness creates permission. Others begin to have the conversations they have been avoiding. The cumulative effect, over months and quarters, is a measurable shift in the quality of information that flows through the organisation and the speed at which real problems surface rather than accumulate unseen.


One Thing Worth Doing This Week


If there is a conversation you have been meaning to have and have not yet had, the most useful question is not how to have it. It is what specifically is stopping you from having it now.


Name the real obstacle. Not the timing, which is almost certainly a proxy. Identify the actual concern underneath it. Is it the fear of the reaction? The fear of being wrong? The fear of what you will be obligated to do next? The belief that you are not yet certain enough to speak?


Whatever the real obstacle is, it is worth knowing clearly. In almost every case, the obstacle is more manageable than the leadership cost of continuing to work around it.


The conversation you are avoiding is almost certainly the most important leadership act available to you right now. Not because confrontation is good for its own sake, but because clarity is. The people around you deserve a leader who is willing to provide it, even when, especially when, it requires some courage to do so.


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

© 2026 QUEST COACHING INTERNATIONAL

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