[part of this series]

A few years into my first job, we were doing a product review with a senior executive who was legendary for his temper and for not tolerating dissent. About halfway into the slide deck, the executive looked around and made a suggestion for a new feature. It was instantly obvious that this feature was outlandish and there was no way we could build it. I looked around the room and thought “Why is no one else saying so?”. At the same time, I didn’t want to be the first person to stick my hand up and look stupid - or worse - as someone green behind my ears fresh out of college.

On my right was a good friend of mine who couldn’t have been much older than me. He piped up “Umm…I may be saying what others are thinking..but that would be really challenging given our current resources”.

There was a long pause in the room.

The executive looked at my friend who was easily 6-7 levels below him in the org chart

“Thank goodness someone finally said so, I’m so tired of teams who never push back”. The conversation totally shifted and my friend wound up being relied on by the executive for other key decisions.

I never really forgot that moment. I was both surprised at the courage of my friend and ashamed at not doing it first. Since then, I’ve always found it a useful rule to try and speak up on what you think others and you are feeling but isn’t being said in the room.

This turns out to be quite rewarding in multiple ways.

Early in your career, you’ll quickly learn whether your instincts are correct and align it with your team and organization. It’s much safer than you might expect.. First, you’ll rarely be wrong. Empirically I’ve found humans are very good at sensing what others are thinking. What takes some amount of courage or confidence is saying so.

If you do say so and you are correct, you’ll quickly find you can push your team or organization forward. What many people often need is just one other person to put their foot forward for them to speak up themselves. You’ll win the respect of the people you work with as someone who can be truthful in a group setting.

What if you speak up and you’re wrong? That’s ok too. Well run organizations value honesty and value this kind of input. If you see yourself being punished, you’ve just learned you’re not in a well run organization and you’re better off somewhere else. A choice I’ve had to make one or two times as well.

This gets more important later in your career when you’re the leader in the room and people rely on your input and goodwill. It’s critical to try and get honest opinions, especially those that disagree with yours. By being the first to volunteer what you think others are feeling is the best way to make the space safe for everyone else to jump in. By doing it repeatedly, you’ll not only make your team comfortable with speaking up, you’ll also get on a resonant frequency with them.

On top of everything else, it just makes life at work a lot more fun.