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My cellphone rang around 2:00 p.m. on a Sunday as I was driving my youngest daughter to the gym. I hesitated to answer, but I knew that ignoring the call would be worse. I gingerly picked it up, and for the next 10 minutes, I rode an emotional roller coaster as I listened to my new boss trying to get his head around one of our marketing initiatives. 

When the call ended, it was time to drop off my daughter, but before she got out of the car, she asked, "Who was that? He sounds terrible."

I told her it was my boss, and in her seventh grade wisdom she replied, "Why do you work for him?" It was a great question. At the time, I didn't have a good answer.  

Like most people, I've worked for some fantastic leaders who have shaped me as a leader and taught me some game-changing career and life lessons. 

And I've also worked for some fantastically terrible people who made things difficult, to say the least. Yet, with each one there was a silver lining: They taught me just as much as the best ones. 

Here are 10 leadership lessons I've learned from my terrible bosses—and what you can learn from them, too.

1. Conversation is a success portal. Terrible bosses have difficulty with a two-way conversation that values listening to connect versus listening to reply. They generally tell people what to do and rarely co-create and respect that success starts when we speak with each other, not at each other. 

2. “Yes, and" beats "Yes, but." Miserable bosses who lead with a "yes, but" approach and are focused on what's wrong or weaknesses can teach you that  a team elevates faster with a "yes, and" philosophy that builds on people’s strengths and accomplishments.  

3. Thank-you’s are timeless.  Incompetent bosses recognize others and show genuine appreciation as frequently as they admit they are wrong (that is, rarely). Thank-you’s, especially handwritten notes, never go out of style and go a long way toward strengthening trust, reinforcing behavior, and getting the most out of others. 

4. Let your people breathe. Working for a stressed-out boss who believes grinding it out, looking over your shoulder, and staying on the hamster wheel can make anyone want to hand in their resignation letter. A better approach gives team members a chance to breathe and think, and the autonomy to produce quality work on the things that truly matter most.

5. It's not about me. Working for egocentric bosses who lead with a "power over" approach and fail to understand that leadership isn't about them can help you see that you get more juice with a "power with" style and valuing "we over me.” 

6. Ethics matter. Working for a boss who skipped out of his college ethics classes and cuts corners can teach you that a "fish rots from the head down," and enabling unethical behavior can cascade throughout the organization. Just like the thank-you card, integrity never goes out of style. 

7. Everything is figure-out-able. Terrible bosses can test our belief in ourselves and leave us feeling stuck. They can become your best teachers in helping you see the resilience and grit within you and the value of exploring different ways to get stuff done.

8. Community matters. Lousy bosses have an uncanny ability to divide people. Trying to survive in siloed work environments reinforces the importance of the leader bringing people together and of community. 

9. Everything is neutral. When you are under the thumb of a terrible boss, it's natural to believe that everything happening is awful. It’s a trigger that can lead to a bad day. The truth is that everything is neutral until you label it. You always have a choice between getting hijacked by your terrible leader or using it as an opportunity to learn, and not let it take over your day.  

10. Love always beats fear. A thread that links most horrible bosses is that they lead by fear, which can work in the short term, but leads to disengagement over the long haul. They can help you realize the signs when others are worried or anxious, and the importance of leading with compassion to build trust and success. 


Unfortunately, I don’t have a magic formula to avoid terrible bosses; they are part of almost everyone's career. When you do have a horrible boss, try to remember that what they say and do is about them, and you have a choice in how you respond. One of the most productive ways to respond is by trying to discover the leadership lesson they are unintentionally providing to you.

Try to discover the leadership lesson horrible bosses are unintentionally providing to you.”

Michael O'Brien | Chief Shift Officer, Peloton Coaching and Consulting

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