Why Change Feels So Hard—And What Great Leaders Do Differently

What driving on the wrong side of the road taught me about leadership change

A blue car is driving along a highway with trees on the right and an open yellow field with a single green tree on the left.

A few months ago, my wife and I rented a car while vacationing in a country where people drive on the left side of the road. I knew it would take some getting used to. What I didn’t expect was how fiercely my muscle memory would fight back.

Every time I meant to signal a turn, I activated the windshield wipers. At intersections, my brain told me to look left-right-left—but that sequence was all wrong. Despite my best intentions and full focus, I kept slipping into old habits. Even after four days, I was still wiping the windshield instead of indicating a turn.

It was frustrating—but it was also illuminating.

As an executive coach, I’ve found that the same dynamic plays out in leadership. We assume that knowing what to do is enough to start doing it. But change doesn’t work that way. Understanding the right move and making the right move are separated by something much more powerful than knowledge: habit.

The Habit Trap That Holds Back High Performers

One of the most common habits I see in rising leaders is the belief that they’re supposed to have all the answers. For many, this belief has served them well—especially early in their careers. Being the “smartest person in the room” can build confidence, win praise, and drive results.

But that same habit becomes a liability as they take on broader leadership roles. Instead of inviting ideas, they shut them down. Instead of fostering collaboration, they dominate. And often, they don’t even realize they’re doing it—because the habit runs on autopilot.

That’s where the real work begins.

Awareness Is the First Step. But It’s Not Enough.

In my coaching, I teach clients to develop a muscle that most have never trained before: self-observation. I define it as catching yourself in the act of an old pattern—in real-time. It’s the difference between knowing you interrupt people and realizing, mid-sentence, that you’re doing it again.

With enough awareness, you can choose a different response. And when you make that choice over and over again, you begin to rewire your leadership reflexes.

Sounds simple. It’s not.

Most leaders grasp this idea quickly. They nod when I explain it. They even quote it back to me. But few are willing to practice it consistently—at least at first. Why? Because the habits they’re trying to shift are the same ones that made them successful. And it’s hard to walk away from a recipe that’s worked.

Practicing Change Like a Pro

To support this shift, I teach my clients a weekly practice of self-observation. We choose a specific behavior to watch—say, interrupting or rushing to solutions—and they capture moments during the week when it shows up. Then we debrief. What triggered it? What other options were available? What would they do differently next time?

Some resist the exercise. They’re busy. They “get it” already. They’ll do it in their head.

But those who embrace the practice—who really commit to it—experience dramatic transformation. They start seeing themselves with new clarity. They stop defaulting to old responses. They gain what I call “range”—the ability to flex, adapt, and lead with intention rather than impulse.

In short, they begin to look and sound like the sophisticated leaders they aspire to become.

What Sets Great Leaders Apart

The leaders who rise above the pack don’t just know how to lead differently—they actually practice it. And that practice changes everything:

• They pause before reacting.

• They stay curious instead of needing to be right.

• They ask better questions.

• They align their actions with their values, not just their instincts.

• And they understand that leadership isn’t about always having the answer—it’s about creating the space for better answers to emerge.

These are not traits you’re born with. They’re behaviors you practice. Over and over.

So if you’re committed to getting to the next level—not just in title but in impact—ask yourself:

What habit is no longer serving you? And what new response do you need to practice until it becomes second nature?

Change isn’t instant. But it is entirely possible—with awareness, repetition, and the willingness to grow beyond the habits that got you here.

And yes, eventually, you will stop turning on the windshield wipers every time you mean to signal a turn.