Ask a room of business owners why they started, and a surprising number will mention a boss.
Not always as the main reason. But somewhere in the story is a manager who took credit for their work, humiliated them in a meeting, broke a promise about a raise, or called them on a Sunday about something that could have waited. And a quiet resolution: I will never run things like that.
Those experiences are one of the most useful leadership curricula you’ll ever have. Most people just don’t use them deliberately.
Write down what they actually did
General resentment isn’t useful. Specific behaviour is.
Think back to the worst manager you’ve had and write down, concretely, what they did. Not “they were awful” — “they corrected me in front of the client,” “they changed the priority three times in a week and then blamed me for the delay,” “they said the raise was coming and it never did.”
Then, next to each one, write what it cost. What did it do to your work, your trust, your willingness to go the extra mile?
That list is a specification for the kind of leader you don’t want to be, written from the receiving end. It’s worth more than most leadership books, because you know exactly how each of those things felt.
The uncomfortable part
Here’s what nobody warns you about. When you’re tired, under pressure and worried about money, you will be tempted to do exactly the things you swore you never would.
Not because you’re a bad person. Because those behaviours are the easy ones. They’re what stressed people do by default. Your old boss probably wasn’t a villain either — most bad management is ordinary pressure, handled badly.
The patterns owners most often catch themselves repeating:
- Correcting someone in front of others because it’s quicker than finding a private moment.
- Changing direction without explaining why, then being frustrated that people aren’t keeping up.
- Taking credit, often unintentionally — “we won the account” in a way that erases who actually did the work.
- Being unavailable, then irritated that decisions were made without you.
- Promising something — a raise, a promotion, a day off — and letting it slide when things get busy.
- Ignoring people’s lives: the message on a Sunday, the meeting scheduled over the school play.
Read that list honestly. Most owners will recognise at least one from the last month.
The check that catches it
A simple question, asked regularly: would I want to work for me this week?
Not on your best week. This week, with the pressure you’re under and the way you’ve actually behaved. If the answer is “not really,” you’ve caught it early, which is the whole point.
Better still, ask the people who do work for you. Not in a group, and not in a way that invites a polite answer. “Is there anything I do that makes your job harder?” Then listen, and don’t defend yourself. You can’t see these patterns from where you’re standing, and they usually can.
What good bosses did instead
It’s worth doing the opposite exercise too. Think of the best manager you ever had, and write down specifically what they did.
Usually it’s small things. They told you where you stood. They corrected you privately and praised you publicly. They kept their promises, or explained honestly when they couldn’t. They fought for you when it mattered. They noticed when something was wrong at home and didn’t make you explain.
None of that requires talent. It requires attention and consistency — the ordinary, learnable parts of leadership that make the difference.
If you’re working for a bad boss right now
Some readers are still employed while building something on the side. If that’s you, a few practical things.
Write things down. Decisions, instructions, promises, and anything that crosses a line — with dates. Follow up important conversations with a short email summary. A record protects you in ways memory can’t.
Keep your own standards. Your reputation travels with you. Doing good work under a poor manager is an investment in the next job, not a favour to the current one.
Know what isn’t acceptable. A difficult boss is one thing. Harassment, intimidation or discrimination is another, and some things should be reported rather than endured.
And know when to go. If it’s affecting your health or your sense of who you are, that’s usually the signal. Staying to prove you can take it rarely pays off.
The short version
Your worst boss gave you a detailed specification for what not to do. Your best boss gave you one for what to do. Write both down.
Then check yourself against them regularly — especially in the weeks when you’re under the most pressure, because that’s when the old patterns come back.
