What’s Good About A Bad Boss


The best thing you can do for your burgeoning career is, in my humble opinion, is to have a really, really horrible boss. Sounds weird, I know, but totally true. A good boss teaches you how to follow. A bad one teaches you how not to lead.

I was blessed to have a couple of atrocious superiors over the years. I learned some incredible lessons from them. Would you like to hear a few? You would? Awesome. Have a seat, I’ve got stories. First off…

Don’t overestimate your relationship.

Once upon a time, a company I had been with for a couple of years decided I would be good in sales. Do a couple of years, they said, to develop your skills and get to know the business. I was on board. And, in what I can only imagine was part of toughening me up, they gave me a new boss who was less than loved. That’s an understatement, of course. (I knew a retail owner in the business who was considering selling their store to company. They would have been in the same part of the org structure. A direct quote from a retail owner, who at that point balked, “I will let my store burn down and my children starve before I work for him.” True story.)

Anyway, I was lucky enough to be sent on an out of town trip with this new boss, along with several other people, for a three day project. Halfway through day one, lunchtime rolled around, and he decided to pick up food for everyone. We were only a couple of hours from home, so all of us drove. For whatever reason, he came over to me, put out his hand and said, “Give me your keys. I’m taking your car.”


He assumed, for whatever reason, that our relationship was at the point he could demand access to my recently purchased car (which I loved dearly). It wasn’t. I turned him down.

Did it impact what I thought of him? Yes. In a good way? No. And when your team loses faith in you as a leader, it’s nearly impossible to recover.

Be careful what you say about others.

I worked for an executive who decided I was going to be their confidant. I’m ok with that role. Working in HR, it happens a lot. But this particular leader loved to tall me how little they thought of others. In very clear, very derogatory terms. It was to the point I was uncomfortable being in the room alone. Some of those opinions were about my team or other executives. It was not a great environment.

Of course, what concerned me as much as anything was what would be said when I wasn’t around. I mentioned that concern playfully one day, and was quickly given a response of, “Oh, I wouldn’t talk about YOU that way. Just everyone else.” Yikes.

Even if it is true, don’t go down that path. You may have a confidant with whom you share your real thoughts about everyone. Trust me, they will assume you have another confidant with whom you share your thoughts of them. Doesn’t matter if it is true. Have a mentor or non-work trustee if you need to vent. Bringing that into the office will cost you trust, key players or, in some cases, your job.

You don’t have a monopoly on good ideas. Or taking credit for them.

Leaders surround themselves with smart people. Smarter than them, ideally. That’s the way you grow talent and capability. It makes it tough, though, to get out of the way of all that talent and let them shine. I’ve had leaders who were very good at it, and leaders that weren’t. The worst had an uncanny knack for building their career on the work of others. Specifically when it came to presentations. Part of your role is making your leader look good, just as it is part of their job to make you look good. It’s how the world spins.

In this case, though, the circumstances were a little different. I was being recruited for a role, and was very interesting in getting it locked up. Following a full day of interviews, I built and sent a deck on a major initiative that I was told would be my top priority. I outlined my general approach, the key milestones I would expect to reach, timing and obstacles I would try to anticipate. I felt good about the work, and a few weeks later was a member of the team.

The presentation wasn’t brought up until about six months later. That’s when I found out that the person with whom I shared the deck was impressed. So impressed, in fact, he used it as HIS OWN PRESENTATION for a group as part of a full day retreat. That’s not to say it was unchanged, of course. He took the time to remove my name and change it to the corporate theme. The worst part is he was pretty proud if being resourceful enough to do so.

I’m not saying that has contributed to my style of using very abstract slides, as I think it’s a much better way to build a presentation anyway. But the truth is I think about that a little every time I share a presentation.

Give people credit. Especially if you have nothing to gain by doing so, and they may never find out. You’ll look better and be far more trustworthy in the eyes of others.

Timely support doesn’t beat no support. In some ways, it’s a lot worse.

It can be tough to speak up when you have something important to say. I’ve found myself in that position at times, and have been blessed in many cases with leaders who know enough to listen to dissenting voices. But not always.

I worked on a major project, and could see that we were burning resources to bring in consultants that, frankly, we didn’t really need. And by burning resources, I mean we were likely going to cut headcount to support ROI for the project. Working with a few others, who were internal resources that had experience with exactly the work we were trying to complete, we put together a plan to do the job for less money and in less time. We presented to our leader, who gave us vocal support and a green light.

The next day our project team was on a call with our sponsor. It was the perfect opportunity to present our case and discuss the options. The call opened, though, with the pronouncement that we had made the decision on using the consultants for the project, and that any disucssion on that point was unwelcome and unnecessary.  A pronouncement made by the very same leader that had given us his backing the night before.

Support is great.  But pulling it back at the wrong moment without discussion will destroy your credibility.

It’s not good enough to be self aware.

My final bad boss example is my favorite.  A team I worked with had a leader who lived the Golden Rule.  He treated the team as he wanted to be treated.  Lots of ambiguity and freedom to define your role, very little restriction on how you worked, and when decisions were to be made, they were proceeded by discussions with the team to get the best ideas around.  And it drove some of the team bonkers.

Sure, he’d make a hard decision when needed, but it was tough to know when that would be.  And when it came to discipline, you could be pretty sure he would go easy on everyone.  Too much of a team member, not enough of a team leader.  Not everyone thrives in that environment, and the team sometimes suffered for it.

Treat others as they want to be treated, not as you want.   That’s the lesson I learned from him.  Why is it my favorite?  Because I was that leader.  I also learned that self awareness can go a long way in your development.

Yup, bad bosses are pretty special people.  I hope you’ve had your share.  But no more than that.


  1. I’ve had a couple of truly bad bosses, a couple of really great bosses, and a boatload of mediocre ones. I understand. I’ve also been a pretty mediocre boss myself at times. My worst boss would randomly order me to fire people, just for fun. Fortunately, we were able to get rid of him fairly quickly. Not everyone is able to pick up on the lessons from bad bosses thought. Nice post.

  2. Some great points here. I worked for an absolutely terrible boss who covered all the bases from being un-ethical, rude, mean, stole ideas, etc; I learned a lot though such as how not to be a manager, how not to run an HR department and best of all how to spot a jerk. That happened early enough in my career that it helped me define my career goals, where, I wanted to work and who I wanted to work for, I’ve looked back only to learn from the experience.

  3. Some great tales here thanks Dwane. I had the pleasure of working for a complete bully for about eighteen months. I called him out in the end and to my surprise a number of other folk he’d been dishing out similar treatment to, backed me. I learned a huge amount about how not to treat folk in that time and though I’d be happy never to see the guy again, I did learn a huge amount from all the manipulation and unpleasantness. Oh, and I popped by after seeing your name on Steve’s carnival post today – just so ya know.

    Cheers – Doug


  1. […] Dwane Lay (@DwaneLay) offers compelling and down-to-earth advice with this great post – What’s Good About a Bad Boss […]

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