Questioning my best instincts → more learning

“I can think of ten reasons why this won’t work,” I said during a 1:1 with my manager a few years ago as we discussed a risky idea our team had pitched that day.

“Ami, you always think of ten reasons why something won’t work. Can you think of ten reasons it will work this time?” my manager replied.

“But I’m right!” I wanted to protest. My intuition, honed over years of identifying risks, made it seem so obvious that this project would fail — which means I didn’t even give it a chance to succeed.

That conversation was a wake-up call. My skill at spotting risks had accidentally become a reflex. It was a self-reinforcing cycle: I’d call out a risk, things would go well, so I’d call out even more. I stopped experimenting. And without new experiments, I had no data to see if my instincts were still right.

Even as I try to be proud of the intuition I’ve built up over the years, this realization reminded me to constantly pause and keep experimenting, even when it goes against my instinct. For instance:

1. I have a bias toward saying no. So when I see a moonshot proposal from a hungry team, I need to ask, “What would happen if it *did* work?”

2. I’m impatient. So when a product takes longer than I think it should, I should ask myself, “Is the quality we’re getting worth the tradeoff?”

3. I’m (often) diplomatic. So when I see an idea I absolutely disagree with, I wonder, “Should I go beyond asking leading questions and veto this?”

I even share this with my team. “You know my bias is to keep things simple. Can you help me call out where I’m oversimplifying?” Acknowledging the shadow side of my strengths and specifically questioning those has helped me become a more balanced leader.

I think it also helps me be more constructive with my team, and sometimes even a useful contrarian. The longer a team works together, the more likely we are to share the same experiences. We’ve seen the same experiments run, so we form similar intuitions about culture or products. This makes it harder to even notice that there are other ways to operate without looking for them.

Intuition is a hard-won strength. I don’t want to ignore it! But I know that being proud of a skill can naturally make me over-rely on it, even when it’s not the right answer. Questioning my skills every so often (and the reflexes they lead to) helps me keep learning.