Leadership Development? Start At The Top

I’d bet you’ve seen this scenario in your own organization: There’s been some organizational growth or change in the business environment. Things start falling through the cracks. Senior leadership is stepping into their direct reports’ roles to fill in those cracks. The senior leaders get tired. They start to throw the word “burn out” around. And then someone floats the idea that the real problem is that the direct reports “don’t know how to lead”. They need “leadership development”. They’re probably right.

Leadership development is one of the best investments an organization can make. Better leaders communicate more effectively, make better decisions, handle conflict more productively, and create more engaged teams. Organizations that invest in their people generally outperform those that do not.

After more than twenty-five years working with organizations across virtually every industry, we have noticed a pattern. The biggest opportunity for leadership development is often not sitting where leaders think it is. In fact, many organizations invest in leadership development one level below where it is needed most.

Part of the reason is practical. It is far easier to identify development opportunities in other people than it is to identify them in ourselves. Sending your managers to leadership training feels constructive. Asking whether the executive team itself may be contributing to the very problems it hopes to solve is a much less comfortable conversation.

Unfortunately, comfort and effectiveness are not always the same thing.

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The reason this pattern matters so much comes down to a simple truth about organizational culture: it flows downhill.

Culture is not created by policy, the organizational change manager, or declared at an all-hands meeting. It is created by behaviour — specifically, by the behaviour that leaders at the top of an organization consistently model, reward, and tolerate. When a senior leader says that accountability matters but routinely lets commitments slide without consequence, the organization learns the truth. When an executive team talks about psychological safety but responds to bad news with visible frustration, people stop sharing bad news. When leadership says that collaboration is a priority but operates in silos themselves, silos multiply throughout the organization.

This is not cynicism. It is simply how organizations work. People watch what leaders do far more carefully than they listen to what leaders say, and they calibrate their own behaviour accordingly. The culture at every level of an organization is, to a remarkable degree, a reflection of the culture at its top.

This is why Patrick Lencioni’s foundational work on organizational health focuses so relentlessly on the senior leadership team. In The Five Dysfunctions of a Team and the broader body of work that followed, Lencioni makes the case that an organization cannot be healthier than its leadership team. The behaviours that derail organizations — absence of trust, fear of conflict, lack of commitment, avoidance of accountability, inattention to results — are behaviours that typically originate with senior leaders and cascade downward. You can train middle managers in conflict resolution and accountability all day long, but if the executive team avoids difficult conversations and models something different, the training will not hold.

What Lencioni identifies is not merely a structural problem. It is a modelling problem.

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Daniel Kahneman’s research on human cognition adds a layer that most leadership development conversations miss entirely. In Thinking, Fast and Slow, Kahneman describes how much of human behaviour is driven not by deliberate reasoning but by unconscious pattern recognition — what he calls System 1 thinking and the rest of us call “gut feel”. People absorb social norms, respond to environmental cues, and calibrate their behaviour largely without realizing they are doing it. This is not a flaw in human cognition. It is how we navigate complex social environments efficiently.

In corporate life, this means that employees are constantly reading signals they may not even be conscious of. Who gets promoted? Who gets listened to in meetings? What happens when someone raises a concern? What happens when a deadline is missed? Who is held accountable, and for what? These signals — transmitted primarily through the behaviour of senior leaders — shape the culture of an organization more powerfully than any training program, value statement, or leadership competency framework ever could.

When an organization sends its managers to leadership development, those managers return with new frameworks, better vocabulary, and genuine enthusiasm. They want to apply what they have learned. But if the culture they return to — the one shaped by the behaviour of the people above them — does not reinforce what they learned, the new behaviours fade. This is not a failure of the training. It is a failure of the environment. And the environment is owned by the people at the top.

This is what makes it so important to develop the right leaders first.

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None of this means that leadership development below the executive level is a waste. It is not. Organizations benefit from stronger leadership at every level, and the development of managers, directors, and emerging leaders creates real competitive advantage over time. The argument here is not that development should stop — it is that the sequence matters, and that most organizations get the sequence wrong.

When senior leaders develop themselves first, they do several things simultaneously. They improve their own effectiveness. They model the behaviours they want to see in others. They create an environment where learning and growth are valued rather than merely encouraged. And they establish the conditions under which development at every other level can actually take hold.

When senior leaders skip that step and focus exclusively on developing others, they inadvertently communicate something important: that leadership development is something other people need. That the learning stops at a certain level of seniority. That self-examination is for earlier stages of a career. This is not a message most organizations intend to send, but it is frequently the message that is received.

The organizations that get this right treat senior leadership development as a precondition, not an afterthought. They recognize that the executive team is not just the most senior group in the organization — it is the most influential group in the organization. Developing that group first is not a luxury. It is the highest leverage move available.

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Most organizations recognize the importance of developing leaders. The challenge is that they often begin with the leaders who have less influence instead of those who have more. Developing the next level down feels safer. It avoids difficult conversations. It allows senior leaders to focus on fixing others rather than examining themselves.

But organizations rarely rise above the standards established by their leadership teams.

The executive team sets the tone. They define what accountability looks like. They determine whether conflict is healthy or avoided. They demonstrate whether commitments matter. They establish what behaviours are rewarded, tolerated, or ignored. Whether intentionally or not, they become the model that everyone else follows.

This is why so much of Lencioni’s work focuses on the senior leadership team. It is why culture change efforts so often fail when executive behaviour remains unchanged. It is why organizations struggling with trust, accountability, communication, or execution frequently discover that the root cause is not buried somewhere in the middle of the organization. More often than not, it is sitting around the executive boardroom table.

By all means, invest in leadership development. Develop your managers. Develop your directors. Develop your future leaders. Every organization benefits from stronger leadership at every level.

Just don’t make the mistake of assuming the opportunity exists only below you.

The most effective leadership development programs begin with the people who have the greatest influence over the culture, performance, and behaviour of the organization.

They begin at the top.

And perhaps that is why so few organizations start there.

Because the hardest leadership work is rarely developing someone else.

It’s developing yourself.