What Having a Terrible Boss Taught Me to Be a Better Leader

Despite all you may be subjected to, there is real value in working for a bad boss if you want to become a great one.

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Once upon a time, I had a bad boss. A terrible boss. An insecure, mean, vengeful boss. She liked to drop offensive and demeaning comments to cut you, knowing you could not really say anything back to her since you know she will go straight to the CEO to discuss your insubordination.

She played odd political games, like sending her minions around to plant information to see if these fake rumors would spread so she could tell if someone was loyal or not. Or she would ask you questions tied to these rumors to see if you would tell her what you’re hearing or keep the information to yourself and keep her in the dark.

She was not very good at it, so it was easy to tell what was going on, but it was exhausting at best, and incredibly destructive and wasteful at worst.

One particularly hilarious (in a bad way) incident involved her coming to my office while I was on a conference call, holding my latest expense report in her hand, and mouthing the words, “Come see me in my office right now.”

I excused myself from my call, and walked down to her office. I popped in and said, “Hi. You wanted to see me?” To which she quickly said while shaking her head disapprovingly with her eyes closed, “I don’t know what you’re talking about.”

Confused, I said, “Oh, didn’t you just stop by with my expense report?”

She replied, “I did no such thing. I haven’t seen you all week. But speaking of your expense report, what are you doing?”

I had expensed my cell phone bill, as I was supposed to do, for the amount of the bill. The company allowed up to a certain amount to be reimbursed, and I put in for less than that since the bill wasn’t as high as that limit.

Therein was the source of her displeasure with me. She insisted we were supposed to just put in the maximum amount, and since I didn’t, I was forcing her and the entire Finance department to waste their time reading over my bill. So, to be clear, I was ‘bad’ because I did not unnecessarily expense roughly $30 I did not spend on the company’s behalf. Aside from what I’m pretty sure is a violation of tax laws, I would have been stealing from the company. Shame on me for not breaking tax laws or stealing, right?

She had done two things in this example.

First, the whole, “I haven’t seen you even though I was literally just at your door 23 seconds ago,” game was meant to mess with my head and make me question whether I was losing it.

Second, the expense issue, if you can call it that, was meant to show me who was in charge–even on the most mundane of things (and even if she insisted on doing the wrong things!).

But what do I know?

Well, I know a lot from having to deal with her, and I use it every day as a senior executive responsible for a large staff.

See, if your leadership abilities are worth a damn, you make good hiring decisions. If you do that, you have capable people who can at least do the job you hired them for–including making calls about what to expense or not–and likely things beyond that. And if you don’t make good hiring decisions, you can tell from honest interaction and evaluation of how your people perform. You do not need to resort to trickery, mental games or demeaning people to expose their issues.

If they do have performance issues, being mean, dishonest or unfair certainly will not help them do better or grow. It might make them want to leave so you do not have to deal with their performance issues, but that isn’t really being a leader, now is it?

Now, I’m being a bit provocative here. Of course I did not need to work for this person to know that this behavior was wrong. But there is a difference between theory and learning things first hand. I would never have done these types of things to anyone I work with, but I certainly understand at a much deeper level what it would feel like for an employee I did this to. And that is quite a powerful teacher.

I hope you never have to learn this lesson first hand. If you do, at least keep track of the stories–they can be hilarious memories once you are safely working for someone else!

This post is inspired by my best-selling book, “Do a Day: How to Live a Better Life Every Day” available in print, eBook and audio book formats. It originally appeared in my column on August 1st, 2017.

Originally published at

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