How do you engage leaders in development programmes? And why is the format the problem!

Every time I sit with an HR manager to design a leadership programme for leaders, it is common for the following objection to arise:

"Will, I believe in the programme. My problem is getting the leader to join."

And then comes the list: the leader who reschedules three times; the one who enters the immersion with several tabs and apps open, answering e-mails; the one who reaches HR and says "I don't have four hours for this, I have targets to hit".

I have heard this from companies of all sizes. And I would say that, in most cases, HR is diagnosing the problem incorrectly. The leader is not disengaged with his own development. But since he is measured and judged by productive time or does not see applicability in the content shared in training, he chooses not to engage.

The arithmetic that does not add up: overload and unpreparedness

Gartner listened to 805 HR leaders and arrived at two numbers that explain practically the entire impasse: 75% say their managers are overloaded by the expansion of their own responsibilities, and 69% agree that these leaders are not prepared to drive change.

Look at the size of the trap. The same person who needs to develop urgently is the one with the least space in the schedule for it. And the same survey shows that 75% of organisations made significant updates to their leadership programmes, more than half increased budgets — and still are not seeing results.

Bringing together these data points, you understand the resistance. The leader has already lived through this. He spent two days away from operations, came back with a notebook full of notes, found the first opportunity to put the learning into practice, but hit doubts or unforeseen circumstances in implementation. And, at that moment, he had no one to turn to.

This leader did not give up on development. He gave up on a training format that does not apply to his reality or that does not provide support for implementing the tools and knowledge.

When the leader says "I do not have time", he is saying: I am not going to trade eight hours of operations for content that might not solve my day-to-day leadership problems.

That is a rational decision. I am an engineer, I respect a good cost-benefit analysis. What we need to change is not his willingness. It is the value proposition. Especially, the "how to develop".

The traditional model: when format was the asset

The most emblematic case that exists is Crotonville, from GE. The world's first corporate university, created in 1956, a 60-acre campus on the banks of the Hudson. The first course lasted 13 weeks. At its peak, GE spent more than 1 billion dollars a year on training and development.

And it worked. Crotonville produced a generation of CEOs who later took over some of the largest American companies.

But GE sold Crotonville. And the reason was not lack of belief in leadership — it was the exhaustion of a model in which the leader needs to leave operations, go to a physical location, receive standardised content and return to apply in the routine, without support. In a world that changes strategy every quarter, the content from twelve weeks ago is no longer today's challenge.

This is the point I want to make clear: immersions, workshops and group courses are not bad. I myself run workshops, and they are excellent for levelling a common gap, creating shared language, generating a moment of collective turnaround and integration. The mistake is using them as the backbone of leadership development. They are events. And behaviour does not change in an event.

The individual model: when format enters the leader's agenda

On the other hand, there are companies that inverted the logic — instead of bringing the leader to development, they brought development to his agenda. See the analysis of two cases by Josh Bersin Company.

Chevron. A global culture transformation that started in 2019 and scaled 1:1 mentoring and coaching to more than 1,000 managers worldwide, with short sessions scheduled by themselves and development circles in groups. The result I find most revealing is not a performance index: 94% of managers rated it as high value, and practically all said it was a good use of their time. Hold onto that phrase — good use of time. It is precisely the objection from the beginning of this article, answered.

Twilio. Took the 1:1 model to over 8,000 employees and, two years later, crossed the data of who received individual development with who did not. Those who participated had 32% more chance of receiving high performance ratings and 5 times less chance of leaving the company.

It is not magic. It is mechanics:

Sessions of 30 to 60 minutes fit the calendar. Leaving a full day away from operations to 45 minutes on a Thursday afternoon completely changes the calculation the leader makes. He no longer needs to choose between developing and delivering.

The content is the real problem. In mentoring, the agenda does not come from a schedule — it comes from what is most critical in the team, that week. The leader does not hear about delegation in theory; he solves the case of the specific person he is leading and cannot seem to delegate to.

He chooses the day and time. Schedule autonomy is not comfort, it is engagement. Those who schedule their own session show up for their own session.

He leaves with a mission, not notes. The session ends with a tool to apply in the routine. And then development becomes part of the work, not a pause in the work.

Notice that, in this design, HR stops pushing. Adoption stops being a persuasion problem and becomes a consequence of the format.

Where Upskill goes beyond that

The 1:1 model solves engagement. But it brings three new problems, and that is where our Mentoring-as-a-Service solution comes in.

First problem: 1:1 mentoring without assessment is just a good conversation. At Upskill, every leader starts with an assessment that identifies their current leadership profile and skill gaps within that profile. Our algorithm — built on over 20 years of mentoring leaders, with proprietary methodology — assesses their performance level on the most critical competencies to leverage the team. Only after that is the journey mapped, with development OKRs aligned to the business.

Second problem: the wrong match kills the programme in the first session. Our Mentor Match has two phases: the algorithm selects the most suitable mentor among over 200 certified mentors, and a senior specialist does the final curation, validating or adjusting. Automation for scale, experienced people for the judgment.

Third problem — and the most serious: between one session and the next, the leader is alone. It is precisely the interval where forgetting happens. That is why we created the mentorIA: a virtualised mentor, trained weekly with the content of our methodology and with the experience of our mentors team, available 24 hours a day, 7 days a week. mentorIA has access to the topics agreed in sessions with the human mentor — so, when the leader gets stuck at 10 p.m. before a difficult conversation the next morning, he has someone to turn to. The human transforms. The AI sustains and amplifies.

And there is a fourth thing, which is what HR needs most and almost never has: proof. The programme manager tracks, in a dashboard, how many sessions each leader has had, engagement level, each session's evaluation, the most recurring topics among leaders and individual and group progress. That is: data to calculate ROI and defend the investment in front of the board.

In our programmes, to date, 90% of sessions were rated as fundamental to progress towards objectives. And in a client from agribusiness — leaders who needed to gain resilience and self-confidence in a shrinking market — we measured 15% performance increase.

What I would say to HR with difficulty engaging leaders

Stop trying to convince the leader that he needs to develop. He knows. He leads people every day and feels in his own skin what is not working.

What he does not accept — and I agree with him — is giving up hours of operations to receive generic content that will not solve the problem on his desk today.

When you change the format, the objection disappears on its own. Not because the leader became more engaged. Because the math finally added up in his favour.

Do you want to understand if Upskill's programmes apply to your reality today? Comment here or send me a message.

Do you want to see how this can replicate in practice, with your context?

Schedule a demonstration.

Sources: Gartner, HR Priorities Survey 2025 (805 HR leaders) · Center for Creative Leadership, study on knowledge retention in corporate training. https://www.gartner.com/en/newsroom/press-releases/2024-10-15-gartner-survey-finds-leader-and-manager-development-tops-hrleaders-list)