The Leadership Problems That Training Can't Solve

Leadership training can be enormously valuable.

If someone needs to learn how to conduct a difficult conversation, understand a financial statement, run a better meeting, make a persuasive presentation or use a particular management process, training may be exactly the right investment.

But not every leadership problem is a knowledge or skill problem. And treating it like one can waste a great deal of time and money.

Consider the senior leader who has attended multiple delegation programs but still gets pulled too far into the details.

Or the newly promoted executive who understands perfectly well that their role now requires them to think more strategically, but continues to operate as the functional expert they have always been.

Or the leader who has been taught how to give feedback, yet consistently misreads what is happening with the people around them.

These leaders may not need another tool. They may be facing a different kind of development challenge altogether.

Knowing what to do isn't always the problem

Training works well when there is something useful to learn and practise.

But many of the challenges leaders face, especially as they become more senior, are not caused by a lack of knowledge or expertise.

Sometimes the issue is judgment.

The leader knows several ways to respond but struggles to determine which one fits this particular situation, with these particular people, at this particular moment.

Sometimes it is identity.

The leader has built a successful career by being the expert, the problem solver, or the person with the answers. Their next role requires them to contribute differently, but letting go of the identity that made them successful is much harder than learning a new leadership technique.

Sometimes it is interpretation.

A leader believes an employee's repeated questions demonstrate a lack of capability. Another person looking at the same situation might see an employee who has learned that decisions are routinely second-guessed and has stopped making them.

Sometimes it is scale.

The approaches that worked when a leader was responsible for ten people, one function, or one geography simply don't work when they are responsible for hundreds of people, multiple businesses across numerous functions, or decisions whose consequences will unfold over years.

Sometimes it is courage.

The leader already knows what needs to happen. They know they need to have the difficult conversation. They know they need to delegate the decision. They know they need to stop stepping in and rescuing their team.

But knowing and doing aren't always the same thing.

Leadership often requires us to disappoint people, challenge assumptions, admit uncertainty, tolerate conflict, and let go of familiar ways of operating. No training program can eliminate the discomfort that accompanies those moments.

And sometimes it’s not the leader at all, but the system.

Conflicting incentives, unclear decision rights, dysfunctional reporting relationships, impossible workloads, or an organizational culture that punishes reasonable risk-taking or over-values image versus substance aren't going to be fixed by sending someone on a course.

Different problems require different development

This is where I think organizations can become much more discerning about leadership development. Before deciding what resource to offer, ask a more fundamental question:

What problem are we really trying to solve?

If someone genuinely doesn't know how to do something, teach them.

If they know what to do but struggle to apply it consistently to the complexity of their own role, coaching may help them examine how they think, interpret situations, make choices, and respond.

If the capability can only really be built through exposure to greater complexity, give them the assignment, responsibility, or experience that will stretch them, ideally with appropriate management AND mentoring support around it.

And if the environment itself is producing the problem, fix the environment.

Often, of course, the answer will be some combination of these.

A leader taking on significantly greater scope might benefit from learning some new skills, working with a coach as they navigate the identity shift, and being deliberately exposed to situations that require a broader enterprise perspective.

That's development.

Not because one method is inherently better than another, but because the investment matches the problem.

Start with diagnosis, not delivery

Organizations spend significant amounts of money developing leaders. Understandably, they want those investments to produce meaningful changes in leadership effectiveness.

But the question shouldn't begin with:

What program should we put this person through?

It should begin with:

What does this leader need to be able to see, understand, decide, or do differently? And what's preventing that today?

Sometimes the answer will be training.

Sometimes it will be coaching.

Sometimes it will be experience, feedback, a different mandate, a better manager, a helpful mentor, clearer accountability, or a change to the system around them.

The important thing is knowing which problem you're trying to solve before choosing the solution.

Because you can't train your way out of every leadership challenge.