What Actually Develops Leaders Over Time (and What Doesn't)

Let’s get one thing out of the way:

Most leader development programming is designed like a Costco sample.

Tasty and quick…but you’re still hungry afterward, and nothing changes in your actual life.

And I say that as someone who has designed leadership programs, facilitated rooms full of leaders at all levels, coached leaders who were drowning quietly, and helped organizations determine who’s “ready” and who’s not. So, please hear me when I say, I’m not anti‑training. I’m anti‑training as a default setting.

The myth: “If we teach it, they’ll become it.”

The myth is that development works like this:

1. Take a workshop
2. Learn a model
3. Apply model
4. Become better leader
5. Congratulations on your new personality

I remember a leader, years ago, proudly proclaiming that they “spent an ENTIRE DAY training emotional intelligence skills” in their internal leadership program. Good intentions, sure…but let’s be honest, what is likely to change in one’s leadership behavior after sitting in one day of (likely mandatory) training?

I think you see where I’m going with this.

When leader development does work, it’s usually because the environment made it impossible not to change—and someone helped the leader translate experience into real-world application and learning. That combination matters.

What Actually Develops Leaders Over Time:

Challenging work that has consequences (a.k.a. “stretch, but real”)

If you want a leader to grow, don’t just give them more work. Give them different work:

• ambiguous problems to solve
• decisions without perfect information or context
• responsibility that requires influence, not authority
• cross‑functional messiness
• consequences that matter to other humans

This isn’t just “my opinion from the trenches.” Decades of research on how leaders learn points to experience, particularly challenging assignments, as the primary driver of development.

🔥Hot take: Most organizations confuse high performance with high developmental value. Your best operator can crush goals for years and remain stagnant, because they’re running the same play with increasing efficiency.

Strategic development requires novelty, complexity, and real stakes.

Reflection + feedback loops (experience alone is not a teacher)

Just like content doesn’t matter much without the context to understand it, experience doesn’t automatically equal learning. Experience on its own is just…experience.

The difference-maker is whether the leader:

• gets feedback they can actually use
• has space to reflect
• can test new behavior
• gets another rep quickly

We see it all the time in Talent Development research - not all experiences are created equal. Actual learning comes from processing the experience, not merely surviving it.

And this is where most companies fall short. We hand people a “stretch assignment,” then leave them alone with it like, “Good luck, we’ll talk about it in your next performance review.”

Coaching and developmental relationships (not just a cheerleader)

People don’t grow simply because someone “supports” them. They grow because someone helps them see themselves clearly - the strengths AND the blind spots.

There’s increasing evidence that coaching can improve leader effectiveness through mechanisms like increased self‑efficacy and more effective leadership behaviors. This aligns with the long‑standing 70‑20‑10 model, which I’ve referenced often in my former blog and on the Career Dreams podcast. It’s not a sacred ratio, but as a directional truth: challenging experiences + relationships do the heavy lifting; coursework plays a smaller supporting role.

Psychological safety (because no one learns while self‑protecting)

Perhaps this should be at the top of my list…because if people feel punished for mistakes, they will choose safety over growth. Every time.

Psychological safety, the message that communicates, “it’s safe to take interpersonal risks here,” is consistently associated with team learning behavior and performance outcomes in organizational teams.

Translation: if a leader can’t ask questions, admit uncertainty, or say “I missed that,” the organization will get compliance, box-checkery and image management - not learning.

And yes, leaders themselves set the tone for this. (Which is why leader development without culture work is basically a treadmill.)

Repeated reps in the real world (not one-and-done inspiration)

Hearing an inspiring keynote is a wonderful experience; however, leader development is more about skill development than enlightenment.

Research on “deliberate practice” is often discussed in expertise domains like music, chess or sports, but the lesson that transfers is simple: improvement comes from consistent practice over time, not from occasional exposure to ideas.

• Leaders at all levels need to do the reps:
• Engaging in hard conversations
• Making sound decisions under pressure
• Negotiating prioritization tradeoffs
• Influencing peers
• Reflecting and bouncing back after getting it wrong

The consistent, compounding reps are what create “executive readiness.” Not a 3-ring binder. Not the LMS. Not the “Leadership University” logo coffee mug.

What Doesn’t Develop Leaders (At Least Not Reliably):

Workshops without application

Leadership training can be effective, but effectiveness depends heavily on design and implementation factors like feedback, practice, and relevance to the job.

Please believe me when I say, the workshop itself isn’t the villain. I absolutely LOVE a thoughtfully designed workshop. The villain is the event mindset:

• “We sent them.”
• “We covered the content.”
• “Attendance was high.”
• “Leaders developed. Check!”

No. Leaders developed when their behavior changed and stuck.

Competency models as a substitute for decisions

Competency models can be useful. But they also become corporate wallpaper.

If a competency model isn’t shaping:

• Selection decisions
• Who gets stretch assignments
• How feedback is delivered
• What “ready” looks like

…it’s unlikely to achieve its intended purpose.

Promotion as development

Promoting someone with fingers-crossed, hoping they grow into the role is not leadership development.

That’s a risk transfer strategy. Sure, sometimes it works - but often it creates:

• Overwhelmed leaders
• Avoidant behaviors
• Fragile confidence
• Downstream messes for HR to clean up

“High potential” labels without a path

Truth be told, I really dislike the term “high potential,” despite it being pretty common in our profession. Labeling someone a HiPo without providing the education, exposure, and experience to grow is a great way to create entitlement and disappointment (in the same person). Developing your bright-future talent should include:

• the experiences to earn readiness
• relationships to accelerate learning
• feedback that tells the truth

Here's the thing...

If you want leaders to develop over time, you need a system that repeatedly does three things:

1. Give them the right kinds of experiences. Not more work—more developmental work that builds exposure to your business, industry, and behind-the-scenes decision-making.
2. Build a learning loop around those experiences. Feedback. Reflection. Coaching. Rinse and repeat.
3. Create an environment where learning is safe. Because people cannot grow while performing invulnerability.

And if you’re reading this as an aspiring executive people leader, here’s the punchline:

You don’t become executive-ready by consuming leadership content. You become leadership or executive-ready by collecting the right experiences - and extracting the right lessons from them.

Your turn:

This week, pick one leader you’re developing (or yourself) and ask:

• What’s the most developmental thing they’ve done in the last 90 days?
• What did it teach them- specifically?
• What support did they have while it happened?
• What rep are they getting next?
• What would make the learning faster (feedback, coaching, clarity, safety)?

If you can’t answer these, you don’t have a development plan. You have hope.

And hope isn’t a strategy. Sorry-not-sorry.