What I Learned About Leadership the Hard Way

I’ve spent my career designing learning experiences for others—helping people grow, communicate, and collaborate better. But the toughest leadership lessons I ever learned weren’t from the classroom; they were from being a boss.

When I started my own training company, I didn’t see myself as a leader. I saw myself as a facilitator, a creator, maybe even a performer. Leadership, I thought, was for corporate managers with corner offices and org charts.

Then I hired my first assistant. Suddenly, my “projects” became “people,” and every training principle I’d ever taught—about feedback, motivation and accountability—was being tested in real time. It was humbling to realize that running a team required the same empathy, structure, and adaptability I preached in my workshops, but at a higher personal cost.

Here’s what I wish I’d understood earlier—and what I now share with leaders I train.

1. Many of us are “accidental managers.”

In the training world, we talk about intentional design—but leadership careers often happen by accident.

Most people I’ve met didn’t set out to manage teams; they just became really good at what they did. Then one day, someone said, “You should lead this.”

That’s how it happened to me. I was busy delivering programs, juggling clients and building content. I hired help because I needed it, not because I wanted to “manage.” It took me far too long to realize I’d crossed into leadership territory—and that I had no roadmap.

Here’s the truth:

• Most new leaders don’t get training before they lead.
• Even great communicators struggle when authority changes the dynamic.
• The skills that make you successful as a doer aren’t the ones that make you effective as a leader.

As trainers, we see this gap everywhere. The moment someone steps into management, their job shifts from doing the work to creating the conditions for others to do great work. And yet, most organizations treat that as an afterthought.

2. Leadership is about focus, not multitasking.

I used to think being a good boss meant keeping a dozen plates spinning at once. But multitasking is a myth—especially for leaders. The real skill is focus.

Through trial and error, I learned that effective leaders need to balance four key functions:

Project implementation: Helping the team execute and deliver results.

Vision and strategy: Keeping everyone aligned with the long-term purpose.

Team relationships: Building trust, communication and cohesion.

Career development: Supporting individual growth and learning.

Ignore any one of these, and things start to break down. New managers tend to live in the first quadrant—projects and deadlines—because it feels tangible. But in doing so, they neglect people, strategy or growth.

As learning professionals, we can teach leaders to “time-block” their focus:

• Weekly check-ins for projects and execution
• Quarterly discussions for strategy and vision
• Semi-annual one-on-ones for career development
• Daily micro-moments for relationship-building

This rhythm builds the muscle memory of leadership. It also models something critical for any trainer to teach: consistency.

3. Culture is built in micro-moments.

Every training professional knows that culture is learned behavior, not a slide deck. But when you’re leading, you start to see just how fragile it is.

Culture isn’t set by company values—it’s set by what leaders reward, ignore or tolerate.
I once noticed my team was constantly firefighting. People who swooped in to “save the day” were getting praise, while those who quietly prevented problems got overlooked. Without realizing it, I had created a system that rewarded chaos.

What I learned:

• People repeat what you celebrate.
• Process beats heroics.
• A kind word in public often matters more than a bonus in private.

For those of us in learning and development, this lesson is vital. We teach theory, but culture sticks through repetition and reinforcement. Leadership programs that help managers spot and adjust these “micro-behaviors” can transform entire organizations.

4. Fear doesn’t create performance—it kills it.

One of the most damaging myths I see in corporate training is the idea that pressure produces excellence. It doesn’t—it produces burnout.

Fear may create short bursts of compliance, but it destroys creativity, safety and initiative. In our own teams and our clients’ organizations, we should be helping leaders replace fear-based tactics with strength-based accountability.

Here’s what that looks like:

• Replace “Why did you mess this up?” with “What can we learn from this?”
• Trade performance reviews for coaching conversations.
• Swap control for empowerment—ask “How can I help?” instead of “Where are we on this?”

It’s possible to be strong and kind at the same time. In fact, that balance defines the best leaders I’ve met through decades in the training industry. They hold people to high standards but do it with respect and empathy.

5. Consistency is the ultimate leadership currency.

Early in my career, I prided myself on being innovative. But too much innovation can look like chaos. Every week, I’d have a “brilliant” new idea that changed direction. My team started rolling their eyes. I had become what I now call a “disco-ball leader”—always spinning, always changing, always shining light in too many directions.

Employees don’t need constant novelty; they need predictability. They need to know what matters and what won’t change.
Now, I anchor my leadership around a simple mantra: Lighthouse, not disco ball. Steady, visible, and guiding through the fog.

As trainers, we can help leaders create that stability through:

• Clear priorities (no more than three at a time)
• Visible progress tracking
• Regular communication rhythms

Consistency breeds trust. And trust is what turns learning into performance.

Final Reflection

If there’s one takeaway for trainers and leadership coaches, it’s this: teaching others to lead starts with practicing what we teach. Every principle we champion—clarity, empathy, focus, consistency—isn’t just content; it’s conduct.

I’ve made every mistake I warn others about. But every failure taught me the same truth: Great leadership isn’t about knowing more—it’s about noticing more. Noticing when people are struggling. Noticing when culture drifts. Noticing when your own behavior teaches the wrong lesson.

That’s the real work of a leader—and the real opportunity for those of us in the business of helping them grow.