There is a curious contradiction at the heart of the multibillion-dollar leadership development industry.

We want leaders to become more courageous, more reflective, more adaptable and more comfortable with uncertainty.

And then we design their development to be as comfortable, predictable and convenient as possible.

We promise transformation in two-hour masterclasses. We compress complex human challenges into bite-sized learning modules. We offer frameworks, handouts and practical tools, carefully packaged to ensure nobody spends too much time away from their actual work.

The experience is efficient. The feedback is positive. Everyone receives a certificate.

And on Monday morning, remarkably little changes.

Perhaps the greatest problem with leadership development is that we have become too good at delivering it.

This was the uncomfortable proposition at the centre of The Leadership Experiment's October 30 dialogue, led by Sanna Rissanen, founder of My Human Self.

Rissanen began with a deceptively simple question: What learning experience has changed you most?

The answers were revealing. Coaching. Difficult assignments. Formal study. Personal challenges. Even having children.

What these experiences shared was not convenience.

Quite the opposite.

They demanded time, effort, vulnerability and, frequently, considerable discomfort.

One participant recalled an executive coach who challenged him relentlessly while providing enough support to prevent him from becoming overwhelmed. He compared the experience to struggling in deep water with someone standing nearby holding a life ring.

The coach would rescue him if necessary.

But first, he would let him struggle.

It was a powerful metaphor for something modern leadership development may be losing: the productive value of difficulty.

The tyranny of convenience

Drawing on seventeen years in leadership development, Rissanen described an increasingly familiar set of organisational requests.

Could the program require less time? Could everything happen during work? Could the content be delivered through microlearning? Could the theory be removed? Could the entire experience fit into a single day?

None of these approaches is inherently wrong.

But collectively they reveal an uncomfortable possibility.

Organisations may be designing leadership development around what executives will tolerate rather than what genuine development requires.

Richard Kelly captured the absurdity with a memorable question: how do you solve world peace with a two-hour masterclass?

Yet Rissanen revealed an even more interesting contradiction.

When she examined feedback from participants in her programs, many were asking for precisely what organisations were reluctant to provide.

More time.

More discussion.

More reflection.

More opportunities to explore how ideas applied to their lives.

The people commissioning leadership development wanted efficiency. Many of the people experiencing it wanted depth.

Perhaps the customers and the learners were asking for fundamentally different products.

The discomfort paradox

The discussion challenged another comfortable assumption: that a successful learning experience should feel enjoyable.

Of course, psychological safety matters. Nobody learns particularly well when they feel threatened or humiliated.

But safety and comfort are not interchangeable.

A demanding coach can make someone feel deeply uncomfortable while simultaneously helping them feel supported.

A difficult simulation can expose flawed assumptions more effectively than an elegant presentation.

And confronting feedback about one's leadership can be profoundly unsettling.

That may be precisely why it matters.

As participants observed, the most valuable development often involves discovering that something we believed about ourselves is wrong.

Yet organisations frequently reward learning designers for removing friction.

The danger is obvious.

If we remove every obstacle from the learning experience, we may also remove the conditions that make learning transformative.

The measurement trap

A second provocation concerned the obsession with measurable behavioural change.

Every leadership program, it seems, must now demonstrate an immediate return.

Every activity needs an outcome. Every outcome needs a metric.

But what happens to the experiences that cannot be easily measured?

The conversation offered an instructive example.

A facilitator arrived at a workshop armed with an extensive booklet of prescribed content. Instead of proceeding through the material, the facilitator discovered that participants were frustrated and disengaged.

The morning was spent listening to their concerns.

Much of the planned content went untouched.

Yet the facilitator reported receiving exceptionally strong participant evaluations.

Was the workshop a failure because the prescribed material was not delivered?

Or a success because the facilitator recognised what people actually needed?

The dialogue did not dismiss measurement. Participants rightly observed that behavioural feedback can expose the gap between how leaders perceive themselves and how others experience them.

But the distinction matters.

Measurement should illuminate development, not define its boundaries.

Some of the most consequential changes in leadership begin with an uncomfortable conversation, an unexpected insight or a question that refuses to disappear.

These rarely fit neatly into a spreadsheet.

The organisation that won't let leaders learn

There was, however, an important challenge to Rissanen's argument.

What if leaders are not avoiding development because they lack commitment?

What if their organisations simply refuse to give them the space?

Participants described unsustainable workloads, insufficient managerial support and development experiences whose inspiration evaporated almost immediately upon returning to work.

This exposed a deeper contradiction.

Organisations claim leadership is critical, yet frequently treat developing leaders as an interruption to productive activity.

The workshop is encouraged.

The time to practise afterwards is not.

The new behaviour is celebrated.

The old performance expectations remain unchanged.

Under these conditions, leadership development becomes less a process of transformation than an elaborate exercise in organisational theatre.

The courage to make learning harder

Towards the conclusion, Rissanen returned to what actually appears to help leaders develop.

Repetition. Practice. Feedback. Coaching. Self-awareness. Experience.

Not simply acquiring knowledge, but repeatedly testing it against reality.

The discussion also touched on emerging leadership capabilities, including trust, self-leadership and unlearning.

That final capability is particularly provocative.

Because unlearning requires something that conventional leadership programs rarely advertise.

The willingness to discover that yesterday's successful behaviour may be tomorrow's liability.

Perhaps this is the real challenge facing leadership development.

Not how to make learning faster.

But how to make it matter.

Not how to minimise discomfort.

But how to create the conditions in which discomfort becomes growth.

Not how to provide leaders with more answers.

But how to help them become more capable of questioning their own.

The irony is difficult to escape.

We spend enormous amounts of money developing leaders to navigate complexity, ambiguity and uncertainty.

Then we offer them learning experiences designed to eliminate all three.

Perhaps leadership development hasn't become too difficult to fit into organisational life.

Perhaps organisational life has become too unwilling to accommodate genuine development.

And perhaps the most radical innovation in leadership development would be to stop making it so easy.