Being Your Own Worst Boss! By Kevin Eikenberry

Are you your worst boss?

Every boss you have had has had an impact on the leader you are today. Chances are you have had some bosses you didn’t love, and hopefully you have had some that you respected, looked up to, and tried to emulate. Most of us try to forget the worst boss we ever had. Today, I am going to ask you some questions so you can learn from that worst boss and make sure you haven’t become them.

Put on your thinking cap and pick up a pen and paper and answer these questions.

Who would you think of as your worst boss? You may have several names in mind.  If so, consider the following questions for each of them. The key to making these questions helpful is to be specific.

What made them ineffective? Chances are there are two or three things that come to mind immediately. Start there.  Write down what those habits, behaviors, and choices are, and why they are ineffective. After you have identified them, think about what you would do in place of those behaviors.

Were they ineffective with most everyone or specifically with you? It is helpful to think about the behaviors beyond your personal experience. The point here isn’t to downplay your experience, but to see if part of the challenge was a style clash with you. Thinking this through may give you deeper understanding on what they did and why it might not have been most effective.

What were their redeeming qualities? Chances are they didn’t do everything wrong, so don’t just mentally define them as horrible in every way.  Spend some time identifying what they did well and write those things down too.

What can you learn from them? Now you have a list of behaviors and skills – positive and negative.  Now review them and ask yourself what you can learn from these lists.

In what ways do you lead like them? This might be the hardest question – because you might not like the answer. Consider the negative list above, but you might need to look beyond that to find other things that you have emulated from your worst boss.

If you now look in the mirror and see them looking back at you, what are you going to do about it? If you found areas to improve, now is the time to get serious about changing those habits and behaviors.  You still have your pen, so make that plan right now.


We can always learn from the leaders around us – whether they are great, or no-so-much-so.  And while one wants to be a copy of their worst boss, it can happen, usually without us knowing it. The questions above are meant to help you take those lessons, be more self-aware, and become a better leader.

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