Early in my career, I used to avoid playing devil’s advocate. It always felt a bit negative, like I was slowing things down or questioning momentum when everyone else was ready to move forward. But after a few projects didn’t go the way we expected, I started noticing a pattern that was hard to ignore.
The decisions that failed weren’t the ones we spent too much time debating. If anything, those usually turned out fine. The ones that caused real problems were the ones nobody really challenged. Everyone agreed in the room, the plan sounded reasonable, and we moved ahead with a lot of confidence. It felt smooth in the moment. And then a few months later, the cracks would show up. Usually in places we could have spotted early if we had just asked slightly harder questions.
Since then, I’ve tried to change one small habit. Before committing to anything meaningful, I take a step back and try to stress-test the idea a bit. Nothing formal, just forcing myself (or the team) to answer a few uncomfortable questions.
Things like: if this fails in six months, what probably caused it? What assumption here are we taking for granted? What would someone who strongly disagrees with this say?
It’s not about being pessimistic or slowing things down for the sake of it. It’s more about creating a moment where it’s okay to surface doubts before they become expensive problems later. I ended up building a small internal tool to make this easier to run consistently, but I’m less interested in the tool itself and more curious about how others approach this.
Do you actively try to challenge decisions before committing, or do most of those questions only show up once things start breaking?