Kyle YeomanSubscribe
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Does your team feel comfortable challenging you?

·3 min read

If your team is having side conversations after the meeting, they didn't feel like they could say it in the room.

Any room where the most senior person has a strong opinion and everyone else goes quiet, it tells you something about how the org is running. The meeting ends, nothing gets challenged, and the real conversation happens in Slack or the hallway.

Everyone defers to you whether you ask them to or not

When you're running the thing, you have opinions on everything and people tend to defer to you whether you ask them to or not. That's just how it goes.

The problem is that without real feedback, you don't actually know if the decision was right. You just know nobody disagreed. I've been on both sides of this. I've pushed ideas through too fast and I've killed ideas too quickly, and in both cases nobody said anything. Not because they agreed, but because the way I handled it made pushing back not worth the effort.

Over time that adds up. People stop bringing things up. They stop being honest in the room. And that's a really hard thing to rebuild.

Forecasting is a good example

New product forecasting tends to surface this dynamic because everyone walks in wanting a different number. Product is proud of what they built and thinks demand is going to be huge. Sales needs the number to fill a gap in their forecast. Finance is worried about cash conversion cycles. Ops is wondering if they can actually make and ship whatever gets decided.

Everyone is pushing in their own direction, and whoever feels the strongest about it or has the most pressure on them tends to shape the outcome. That's how you end up with a forecast that nobody actually believes but everyone agreed to.

For what it's worth, under-ordering is almost always better than over-ordering. Sitting on product that isn't moving for months is worse than selling out for a few weeks. Keeping new launches separate from the base forecast helps too, because when someone's pay is tied to the number, the number stops being honest.

Honesty can't be forced

Telling people to be honest doesn't work. Saying you want pushback in a meeting sounds good but it can come off as combative, and it doesn't actually change how people feel about speaking up.

What I've found works better is just changing how you show up over time. Instead of reacting to something you disagree with, asking how someone got to their number or what they're seeing that supports it. Not as a test, but because you actually need to understand what someone is working from before forming an opinion.

One good meeting doesn't fix this. The team is watching whether it happens again next week and the week after that. It takes a long time to build that kind of trust in a room.

When it goes wrong, own it

When something misses, the people making the product blame the people selling it and the people selling it blame the people making it. Nobody wants to own it because nobody felt like they had a real say to begin with.

The most productive thing the senior person can do is take accountability in front of the team. Don't pick a side, don't single anyone out, just own the outcome and move toward what's next. When that happens, people stop being defensive. Others start owning their mistakes faster once they see it's safe to do that.

Real problems with one person get handled privately. In front of the team, accountability has to come from the top.

We're all going to keep getting things wrong. The question is whether the people around you feel safe enough to say something before it happens, or whether you find out after.

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