Some of the sharpest, most capable leaders I coach are walking around with a warped self-image. They don’t see themselves through a mirror—they’re squinting at an old, blurry Polaroid. A snapshot from years ago, out of date and out of context. But they still let it define who they are.

Sound familiar?

Step One: Reality Check

When I hear someone say, “I’m not good at coaching,” or “I’m too weak on the business side,” my first move is simple: I ask for examples. Concrete, recent, real-world examples. If you say you’re bad at coaching, how exactly has that hurt someone on your team? Show me the evidence. Allowing the conversation to go forward with these generalizations often enables the impostor syndrome to go on.

The funny thing is most of the time, they struggle to come up with anything. Or they realize that the “big issue” happened once, months ago, and they’ve since course-corrected. Or perhaps it’s really something that happens a couple of times a year and doesn’t do any real damage. So what are we even talking about?

Self-doubt is slippery like that. It thrives in vagueness. Once you shine a spotlight on it and ask for tangible examples, it often vanishes or shrinks into something much more manageable.

Step Two: Separate Flaws from Fraud

Here’s the truth: even after this kind of review, you will find gaps. Great. That doesn’t make you a fraud. It makes you… a leader.

Read any good biography. They all have chapters where the protagonists had no idea what they were doing, messed up, and got better. It’s not a bug in leadership—it’s the damn job description.

We have to stop treating imperfections as signs of being unworthy. Not being perfect at everything doesn’t make you an impostor. It makes you human.

Step Three: Tackle It Like a Real Problem

Let’s say your gap is real. Considering the evidence, you still think it merits being prioritized to tackle. Now what?

One senior tech leader I worked with was convinced he wasn’t credible because he hadn’t kept up with the latest in modern software practices. It was eating away at him. However once we mapped the actual knowledge gaps, it turned out that most of what he needed could be learned in a few focused sessions. Suddenly, that “fundamental flaw” became just another item on the calendar.

The inverse happens too. I’ve worked with technical leaders who freeze up the moment the conversation drifts to marketing or finance. They feel like fish out of water during board meetings. They’re intimidated by the language, the frameworks, the vibe.

But let’s be honest: if you’ve survived two decades of tectonic shifts in tech (from pre-smartphone to post-AI), you can wrap your head around CAC and positioning. Business isn’t magic. It just looks that way because you haven’t read the manual yet. Find a couple of good books, and learn how to ask the right questions. You’d be surprised how quickly you can cover material with a couple of good YouTube channels or a stellar subreddit.

Final Word

If you feel like a fraud, stop indulging in it like it’s a personality trait. Diagnose it. Deconstruct it. And then deal with it.

The only true impostor move is staying stuck in that old photograph—while the world, and your actual self, have moved on.