A few years ago, an organization I worked with made a significant investment in developing its senior leadership team.
The program was strong. Feedback was excellent. Leaders spent months learning together. They came away with useful frameworks, a shared vocabulary and plenty of enthusiasm.
At the end of the year, the CEO posed a simple question: “We invested so much in this. Everyone loved the program. Why are we not seeing a change?”
I have carried that question with me ever since.
Because sometimes, the leadership program did work. Participants learned. They understood the concepts. They could explain what good delegation looked like, how to have a difficult conversation, how to coach rather than direct or how to involve others in a decision.
And still, back at work, their behavior did not change.
When that happens, the instinct is to add more development: another workshop, another framework, another coaching session. But before we prescribe more, there is a question we should ask instead: What is getting in the way of the behavior?
I find it useful to consider the following four scenarios and their corresponding solutions.
1. Does the leader know what to do?
Sometimes the answer is straightforward. A leader may genuinely lack a critical skill: A newly promoted manager may never have been shown how to run a performance conversation, delegate meaningful work or give feedback that lands. In those situations, learning and development has an important job to do.
While good frameworks, models, examples and practice give leaders options they did not have before, we should be careful not to assume that every behavior problem is a knowledge problem.
Consider a senior leader who has attended delegation training: She understands that good delegation means being clear about the outcome, agreeing on decision rights, establishing appropriate checkpoints and then giving others room to work. Ask her in a workshop and she can explain it perfectly.
Then, a critical client project begins to slip. The deadline is approaching. The client is unhappy. The leader’s reputation is attached to the results.
She steps back in, rewrites the work and takes over the client conversation. The problem is not her delegation skills. Something else happened.
2. When the stakes get higher, can the leader access what they know?
This is a distinction leadership development often misses.
Knowing what to do in principle is very different from being able to act on that behavior when pressure, hierarchy, uncertainty, approval or identity enters the room.
A leader may know how to give candid feedback but soften the message when the relationship matters. Another may genuinely believe in empowerment but tighten control when the consequences of a mistake feel significant. A learner may speak confidently in a classroom but become silent when disagreeing with a senior executive carries political risk.
In these moments, the barrier is not necessarily capability. The individual may already know what effective behavior looks like, and is fully capable of demonstrating it. The challenge emerges when competing fears, habits or identities are activated:
- What am I trying to protect?
- What becomes difficult for me when the stakes rise?
- Which leadership habit has served me well enough in the past that I continue to rely on it, even when the situation now requires something different?
- What happens when being an effective leader asks me to give up some control, certainty, approval or expertise?
If we diagnose this as a knowledge gap and teach the skill again, we may add very little. L&D must help the leader work with the moment in which the behavior disappears. The critical question is not: Do I know what to do? It is: What happens when doing it becomes difficult?
3. Has the leader practiced where the behavior will actually be tested?
We use the word “practice” a lot in leadership development. But not all practice is equal.
Discussing a case, role-playing a conversation or working through a simulation is useful. But practice becomes more powerful when it includes some of the real tension that makes the behavior difficult.
If the challenge is speaking candidly upward, practice needs to involve hierarchy. If the challenge is making decisions without complete information, practice needs uncertainty and consequences. If the challenge is letting go of control, the leader needs an opportunity to entrust meaningful work to someone else and notice what happens when that person approaches the work differently.
This changes the question for L&D leaders. Instead of asking: Did we teach the skill? We also need to ask: Did leaders have an opportunity to practice the skill where it is most likely to break down?
Application cannot be something we hope happens after the program. It needs to be part of the development process. A leader tries something in the real work. They see what happened. They receive feedback. They reflect. They try again.
That is how insight begins to turn into behavior.
4. Is the organization asking for one behavior while rewarding another?
The last scenario—where a leader may be trying to change in a system that rewards an old behavior—is often the most uncomfortable one.
Organizations encourage leaders to delegate, but when something goes wrong, the first question is: Why didn’t you have greater control? They ask people to collaborate across functions, while goals and incentives continue to reward individual business-unit performance. Leaders are told to speak up and challenge constructively, while everyone can name someone who paid a price for challenging the wrong person.
The formal message is one thing, the lived message is another. And leaders are good at noticing the difference.
When the leadership program says “empower” but the organization says, “do not let anything go wrong,” the organization usually wins.
This is why behavior change cannot sit entirely with L&D. Managers, decision rights and performance systems matter. Senior leader behavior matters. What happens after someone takes a reasonable risk and gets it wrong matters.
The question is not whether the program created the right learning. It is also whether the environment the leader
