A manager's guide to getting it wrong


Think you're the fun boss? Think again!

I've worked with people at many stages of their management careers, from first-timers to the highly experienced executives that I coach. It never ceases to amaze me how the problems that leaders face are so similar at every stage: how to align the right work to the right people, how to uphold accountabilities, how to build teams that collaborate, how to have hard conversations, how to listen.

Here are seven things I wish I’d known about management before taking my first manager job. Most of what I assumed about these things was wrong. What's more, I had to relearn most of them every single time I got promoted.

A good mentor isn’t automatically a good manager.

A good mentor is fantastic; their only goal is to help you succeed. But a mentor is not actually responsible for your success. A good manager is responsible for delivery and managing to expectations, not just for dispensing wisdom and hoping for the best.

If it’s important, you have to say it and show it every single time.

Values and priorities aren’t one-and-done. You can’t say them once and assume they’re real. You have to say them and use them every single occasion you have an opportunity to do so. Otherwise you shouldn’t even bother.

Don’t ask for feedback unless you intend to use it.

Nothing makes people feel worse than being asked for feedback and then ignored. You don’t have to agree with their feedback, but you do have to consider it and tell people how you think about what they've shared. If you aren't going to consider it, don't ask for it.

No one can tell you what decisions to make.

Your employees don't have all the context or tradeoffs to tell you what decisions to make. But people are the absolute authority on the experience they are having as a result of your decisions. Ask them about what they're experiencing, not about what decisions you should make.

It’s more important to be clear and structured than it is to be charismatic and fun.

Look, it’s great to have fun at work! But people already have friends and they’re not looking for their boss to be their friend. They’re looking for clear, reasonable expectations, well communicated. Sorry!

You don’t have to choose between being honest and being kind.

It’s not honest to avoid giving feedback. It’s not kind to give feedback like a jerk; it’s also not kind to give it sideways, abstractly, or not at all. Just give feedback clearly and without drama.

Most of all: Just say what you value.

Tell people explicitly what gets them promoted on your team. Don’t worry that it might be unpopular. Who cares? It’s the truth. Pretending that you have different values than you do just sets you and your team up for disappointment.

If you value working around the clock, say that. If you value taking risks or frugality or people who dance by the light of the moon, say that. Be honest about what you value and trust that people are adults and will opt in or out. The right people for you will opt in. The people who opt out aren’t your people.

There are about a hundred things I wish I’d known so much sooner in my professional journey. But above all else, I wish I’d known these seven.

What do you think? What do you wish you'd known before stepping into management?

Thanks for reading!

Kieran

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Every week, I write a deep dive into some aspect of AI, startups, and teams. Tech exec data storyteller, former CEO @Textio.

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