5 Leadership Lessons From The Worst Bosses I’ve Ever Had

executive coachingI recently read a fabulous post by Steve Tobak on BNET with tons of great management advice based on his personal experience. It reminded me that after scolding Steve Jobs and other jerk bosses earlier this this week, I actually owe my two worst bosses some props in public. I doubt they’ll read this but you never know so I’m not naming names. You see, my two worst bosses were also my two best bosses. Here’s why.

Both of them were smart as heck and personally driven, and they drove me earlier in my career. Being a Type A (then, not now), I rose to the challenge and learned a ton. I learned how to do things to make them happy – which led me to contribute greatly to the business. They saw potential in me and went out of their way to help me learn more. My experiences working for them were crucial in shaping my professional resume and ethic. I owe them both great debts of gratitude for that. I would not be who I am, or have the opportunity in my career that I do, without both of them.

What not to do


But both of them were insecure human beings on a power trip, and they took much of that out on me (and others, it’s not like I was singled out). Granted, I was young and stupid in some ways and allowed this. One was emotionally abusive, passive aggressive and sometimes I thought a bit bipolar. The other was just egocentric. Working for them was very difficult.

Their greatest gift


But in retrospect, I wouldn’t have it any other way. Not only did I learn a ton, but I began to claim my personal power by deciding I was done with being treated that way. I’ve left lots of jobs in my time, but in these two cases, I was doing it as an act of power - not out of spite but out of respect for myself. Of all the “I quits” I’ve ever delivered, those two meant the most to me. In the years since, I’ve  simply been growing into who I started to become on those two days.

Their other gifts – 5 lessons I’ve internalized


The whole time I worked for them, I watched carefully, trying to understand what made them powerful to me – which was often not at all what they thought made them powerful. I’ve also watched my good bosses (and clients in both categories since becoming a consultant) and watched how my own boss behavior affected my employees. Here’s what I’ve personally internalized from the good, the bad and the downright stupid and which I am sure to pass on to my executive coaching clients. For anyone new in management, I recommend internalizing this early. You’ll get more out of your people by doing so.

  1. Respect your people. “At will” employment is not just a contract term. Your employees are free agents. Treat them with the same respect you would a consultant who has the right to leave on a moment’s notice. I don’t care how bad the job market is, your employees can leave too – and will.
  2. Think ahead. Don’t get lazy about making decisions at the last minute just because you can. If you’re going to make a decision that affects people’s time and work, do your best to make the decision in time for them to adjust smoothly without tons of rework and overtime. Of course you don’t control everything, but if you make an effort to respect their time and energy (see #1), they’ll appreciate it and you’ll actually make better decisions about resource utilization. This is also known as the don’t-burn-out-your-best-because-you’re-lazy-or-on-a-power-trip rule
  3. Get your ego out of your way. Be honest with yourself about your insecurities and deal with them. Otherwise you’re just taking them out on everyone else – your family, your employees and your friends – and pissing everyone off. We all have things we could be better at. The more insecure you are, the more your power and authority is making you insufferable. The day of the authoritarian king is over; the better your character the greater chances of your success. Also, with your own ego out of the way people will trust you more and tell you what’s really going on instead of telling what they think you want to hear.
  4. Be the best jerk you can be. The business requires that you be a jerk sometimes, so do your best to be a good human being when that happens. There is a natural tension between being a good business boss and an empathetic soul – so just accept that this tension is part of the job. Don’t try to be a good human at the expense of the business, but don’t let the business become your excuse for being a colossal a$+@|& either.
  5. Speak your truth to power and let them speak theirs. It's not about who agrees with you or how often you are right, it's about how disagreement and agreement are reached. The business benefits from the tension of good ideas so learn to invite their ideas and mix it up in ways that not only deliver the best business solution but honor and respect both you and your employees. The better YOU are atspeaking your truth to power, the more easily you will be able to hear it when others speak it to you. Be strong, learn to speak and listen.

I have no idea what my two best/worse bosses are like as managers these days. Maybe they’ve learned some of these lessons themselves by now (we were all young). In any case, I’m grateful they helped me learn them and I think I’m a better boss now when I have to be because of them. Thanks, guys.

What is your "worst boss" story? What did that teach you? How have your worst bosses been your best? Best been worst? What's your advice to the jerk-bosses out there? Have you ever had to be a jerk and wished you could have found a better way? Any tips for being the best jerk you can be?

Dana Theus

InPower Leadership Development & Coaching- Helping you live into your purpose through your work. Sign up for my weekly 1-minute coaching newsletter.

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