I thought getting things right was the goal. Turns out, being right too often is one of the most dangerous things that can happen to anyone making decisions.
I used to think being right was the point of leadership. I was wrong about that too, which is probably the most valuable thing I've ever been wrong about.
For years, I had a pretty good track record. My predictions about market shifts turned out accurate. My product decisions drove growth. My hiring instincts brought in people who delivered. I started to believe my own press. Worse, so did everyone around me.
That's when the real problems began.
The most dangerous moment in my career wasn't when I was failing. It was when I'd been right so many times in a row that I stopped questioning my own judgment. When people stopped pushing back on my ideas because "Ali usually knows what he's talking about."
I remember the exact moment I realized how bad it had gotten. We were in a strategy meeting, and I floated an idea that, looking back, was obviously flawed. Not catastrophically wrong, just... not our best option. But instead of the usual debate and refinement that made our decisions stronger, everyone just nodded. A few people even started building on it immediately.
That should have felt good. Instead, it terrified me.
I realized that somewhere along the way, I'd created an environment where being wrong had become so uncomfortable for everyone (including me) that we'd unconsciously optimized it away. We weren't making better decisions. We were just making safer ones that confirmed what I already believed.
Here's what nobody tells you about success. Every time you're right, you get a little more confident in your judgment. Every time people agree with you, you trust your instincts a little more. This sounds healthy. It's not.
What actually happens is much more subtle and much more dangerous. You start surrounding yourself with information that confirms what you already think. Not because you're trying to create an echo chamber, but because confirming information feels more relevant and valuable than challenging information.
Your team learns to present ideas in ways that align with your established viewpoints. Again, not because they're trying to manipulate you, but because alignment feels more productive than conflict. They start filtering their feedback to match what they think you want to hear.
You begin to mistake the absence of disagreement for the presence of consensus. You interpret the lack of pushback as validation rather than what it often actually is: people who've learned that disagreeing with you is more trouble than it's worth.
Before you know it, you're making decisions based on incomplete information, getting feedback from people who've learned not to challenge you, and operating with a confidence level that's completely disconnected from the actual quality of your judgment.
The best decisions I've made came from being wrong first. Not because being wrong is good, but because being wrong forces you to really understand the problem you're trying to solve.
When I'm wrong about something important, I can't just move on. I have to figure out why. What did I miss? What assumptions was I making that weren't true? What information was I ignoring or not seeking out? That process of understanding my failures has taught me more about decision-making than any success ever has.
More importantly, being wrong in front of my team created something I didn't expect: psychological safety. When people see you make mistakes and then learn from them openly, they start doing the same thing. The quality of our conversations changed completely. People started bringing me problems earlier, when they were easier to solve. They started disagreeing with me again, which improved our decisions.
The teams that perform best aren't the ones that avoid mistakes. They're the ones that make mistakes faster and learn from them more systematically than their competitors.
Now I try to actively create opportunities to be wrong. Not because I enjoy it, but because I've learned that being wrong early is much cheaper than being wrong late.
I ask different people for their opinions on the same problem, especially people who I know see the world differently than I do. I try to argue against my own ideas before I present them to others. I deliberately seek out information that contradicts what I want to believe.
Most importantly, I've learned to reward people who disagree with me, especially when they turn out to be right. The moment someone successfully challenges one of my ideas, that's when I know I can really trust their judgment going forward.
The goal isn't to be wrong more often. It's to be wrong faster, learn from it more quickly, and create an environment where the best ideas win regardless of where they come from.
Companies that consistently outperform their competitors aren't the ones with leaders who are right most often. They're the ones with leaders who learn fastest from being wrong. They're the ones where good ideas can come from anywhere and bad ideas get killed quickly, regardless of who proposed them.
That requires a kind of intellectual humility that success tends to erode. It means being more interested in finding the right answer than in being the person who had it. It means creating space for disagreement and uncertainty, even when (especially when) you're pretty sure you know what should happen next.
The dangerous comfort of being right isn't just about individual decision-making. It's about organizational learning. The moment your team stops challenging your assumptions is the moment you stop growing as a company.
So if you find yourself being right too often, that's not a sign of good judgment. That's a warning sign. The most valuable thing you can do is figure out how to be wrong more safely, more quickly, and more publicly. Your future self will thank you for it.