What 700+ Leaders Wish They’d Known Before Starting a Leadership Program

Every leader who enrolls in a serious leadership development program has some idea of what they’re signing up for. Most of them are wrong about at least part of it.

Not in a bad way. They usually expect a training, a set of frameworks, maybe a few useful ideas to bring back to the team. What they get is bigger, harder, and more personal than that, and almost every one of them says the same thing once they’re a few months in: I wish someone had told me what this actually was before I started.

We’ve worked with over 700 leaders across more than 100 organizations through our LEAD 24/7 cohort program. After a decade of watching people go through it, here’s what they consistently say they wish they’d known before day one.

Here’s what we’ll cover:

• It’s a year, not a workshop
• Vulnerability isn’t optional
• The coaching matters as much as the content
• Your team notices before you do
• It’s not just about you
• Why this matters more now, not less

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Key Takeaways

• Real leadership development takes sustained time. A single workshop rarely changes behavior that took years to build.
• The honesty required is uncomfortable at first and is exactly where the growth comes from.
• Roughly 75% of L&D professionals estimate that less than half of what’s taught in a typical program actually gets applied on the job. Coaching and accountability close that gap. Content alone doesn’t.
• Change in a leader shows up in their team’s behavior before the leader fully recognizes it in themselves.
• Leadership development isn’t just personal growth. It’s a direct investment in the people the leader leads, and in who’s ready to lead next.

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1. It’s a Year, Not a Workshop

The leaders who get the most out of LEAD 24/7 say the same thing: they underestimated how much the time commitment mattered, and they’re glad it was there.

A one-day workshop can deliver a good idea. It rarely changes a habit that took a decade to form. Real behavior change needs repetition, real-world application, and a group of people checking back in on whether it stuck. That’s why the program runs twelve full-day sessions across a year, with a two-hour coaching session every month in between. Leaders who come in expecting a quick fix are usually the ones who initially resist the pace. By month six, most of them understand why it’s built that way.

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2. Vulnerability Isn’t Optional

Leaders often expect a program built around frameworks and case studies. What they find is a program built around honesty.

The sessions ask leaders to talk about where they’re actually struggling, not the polished version they present in a board meeting. That’s uncomfortable, especially for leaders used to having the answers. But the growth doesn’t come from the framework. It comes from being honest about a blind spot in front of peers and a coach who can actually help you work through it. Leaders who hold back get a partial return on the investment. Leaders who show up honestly get the transformation the program is actually built to produce.

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3. The Coaching Matters as Much as the Content

Most leaders expect the twelve sessions to be the program. What actually drives change is what happens between them.

Roughly 75% of learning and development professionals estimate that less than half of what gets taught in a typical leadership program is ever applied on the job. Content alone doesn’t stick. That’s precisely why individual coaching is built directly into LEAD 24/7, not as an add-on, but as a core part of the design. A two-hour monthly session gives a leader somewhere to bring what’s actually happening in their work, get direct feedback, and be held accountable to the change they said they wanted. Leaders consistently say the coaching, more than any single session topic, is where the real work happened.

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4. Your Team Notices Before You Do

Leaders going through real development often can’t see their own change clearly. Their teams usually can.

It’s a pattern we hear constantly: a leader reports feeling like progress is slow or invisible, and in the same week, someone on their team mentions that something feels different, meetings run better, feedback lands more clearly, conflict gets addressed instead of avoided. Nearly 70% of the variance in employee engagement traces back to management quality, according to Gallup’s research on the global workplace. When a leader changes, their team feels it long before the leader has fully internalized it themselves.

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5. It’s Not Just About You

Leaders often enroll thinking about their own growth. They leave understanding it was never just about them.

A leader who develops real self-awareness, better communication, and stronger conflict skills changes the experience of everyone who reports to them. It shows up in retention. Nearly 71% of Millennial employees say they’d consider leaving a job within three years without adequate leadership development from the people above them, and 59% of workers report receiving no meaningful workplace training at all. Investing in a leader is an investment in every person that leader will lead for the rest of their career, and in who on that team is quietly being prepared to lead next.

One CEO who put his entire senior team through the program put it this way:

“This program was a great combination of teaching, practice, and walking alongside (coaching) my team to make sure the learning was maximized. I put all nine of my senior leaders through the program. Every single one of them expressed that this was the best training program they had ever been a part of.”

— Nelson Sanchez, CEO, RoMan Manufacturing, Inc.

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Why This Matters More Now, Not Less

AI tools can now generate frameworks, summarize research, and deliver leadership content on demand. What they can’t do is sit across from a leader and call out a blind spot only a coach who knows them would catch, or hold a room of peers accountable to change they committed to months ago.

As the informational side of leadership development becomes easier to get for free, the sustained, human, accountability-driven version becomes the actual differentiator. The leaders who invest in it now aren’t just keeping pace. They’re building the one capability AI can’t replicate.

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Know Before You Go In

Every leader who’s been through LEAD 24/7 wishes they’d known it would take a year, ask for real honesty, and change more than just how they lead. That’s exactly why it works.

For leaders weighing whether now is the time, the ones who’ve done it all say the same thing: the only regret is not starting sooner.

Reserve your spot in an upcoming LEAD 24/7 cohort at leadingbydesign.com →