Years ago, I had a moment that’s stuck with me—not because it was profound at the time, but because (a) it was pretty embarrassing after-the-fact, and (b) because of how perfectly it captures something I see all the time in leadership.
I was trying to reach a friend and dialed his number. Someone else answered. I apologized and hung up. A moment later, I tried again. Same voice. “Strange,” I thought, since I was positive it was his number, and hung up again. I tried a third time. Each time, the same (increasingly irritated) person picked up.
After a few (too many) rounds of this, it dawned on me: my friend had changed numbers, and I was calling someone entirely new. But I was so convinced I couldn’t possibly be wrong that it took repeated, uncomfortable evidence to realize I wasn’t reaching who I thought I was. I was dialing the wrong number—over and over—with absolute confidence.
This is what a blind spot looks like in leadership.
The Problem with Confidence
One of the most valuable traits in a founder or executive is conviction. You’ve likely gotten where you are because you can tune out the noise, trust your instincts, and push through resistance. That’s what makes you effective. It’s also what makes blind spots so dangerous.
Because when something stops working—a product strategy, a team dynamic, a sales process—we’re often the last to realize it. Especially if it’s something that worked well before. Our instinct is to double down. Keep pushing. Keep dialing. The number worked last year—why wouldn’t it now?
But markets change. Teams evolve. What worked to get you here may not be what will get you there.
Why Blind Spots Persist
Blind spots don’t come from ignorance. They come from overconfidence. They’re often the result of:
- Past Success/Confirmation Bias: “This is what got us here.”
- A Bias Towards Action: “We need to get “ISHT* done – we can’t waste time analyzing.”
- Attribution Error: “This plan/approach/product works, but the market is down right now/some clients don’t ‘get it’/the team isn’t executing.”
Like many cognitive biases, these cognitive biases can be occasionally effective (e.g., sometimes taking action is the best move), but they are the reasons blind spots can occur. And they show up in missed goals, team churn, lost time, and that nagging sense that something is no longer clicking.
So What Can You Do?
Start by asking a better question: What am I not seeing?
And more importantly: What am I unwilling to question?
A few practical strategies to uncover blind spots:
- Solicit uncomfortable feedback. Not just a “how are we doing?” but “What’s not working that you don’t think I want to hear?”
- Pay attention to patterns. Repeating the same conversation? Revisiting the same issue? That may be your fourth call to the wrong number.
- Test your assumptions out loud. Especially with someone outside the day-to-day. Someone with no vested interest in preserving the status quo.
- Develop a quick test. Clarify the opposing theory and the current strategy, and develop an A/B test. You don’t (necessarily) need to stop what you’re doing while the test runs, but you are developing a mechanism to assess your current path.
- Create deliberate pauses. Periods of reflection where the goal isn’t to push forward, but to assess whether forward is still the right direction.
The Case for an Outside Lens
Sometimes the best way to uncover blind spots is to involve someone who hasn’t been part of the pattern—someone supportive who can help you build on what’s working while assessing the difference between a strategy hitting bumps that can be overcome and a strategy that has outlived its usefulness and is no more productive than my repeated calls to my friend’s cell number those years ago.