Horrible Bosses: 8 Lessons I Learned from Some of the Worst Bosses

I have worked for some exceptional people in my life, including my boss when I taught at a college years ago. I often joke that “he made me what I am today.” His wife has corrected me on more than one occasion, reminding me that it was God who made me what I am today.

Since I was 15 years old, I have worked for at least 10 or more different people. And some of them would not make it on the list of world’s best bosses. But God does not waste those experiences. Even from the worst of them, I learned what never to do and what to do more of. Here are 8 lessons I learned not only from some of my horrible bosses but also from other bosses I have met.

1. Hyper control produces the opposite of what you think.

I bet all of you have worked for a hyper-controlling boss at some point in life. I did! He wanted to control the people around him as well as all organizational programming. Such leaders sometimes do produce amazing results, at least for a while. But eventually, the heavy control that worked at first starts to produce unintended consequences, including holding back the very organization they are trying to grow.

2. Insecurity will hinder innovation.

If you have some drive, innovation, and a bit of confidence, some leaders will love it. But the worst leaders can be easily threatened by it. I worked for a boss once who was not a bad guy. But he was older than me and I think a bit threatened by me and the ideas I was introducing to the organization. He could have thought some of the ideas were dumb (and that is a possibility!), but I think he was fearful that my ideas made him look weak since he was not known for innovation.

3. Failure to show appreciation will not making raving fans.

How many times have you felt under-appreciated? Just what I thought – a lot. I have worked for a few bosses over the years who would not pass the test of showing appreciation. When bosses fail to acknowledge the work of others or give credit to them, they will eventually alienate their best people and even drain their motivation.

4. When your need to be liked is excessive, others will eventually not like you.

There are times when a horrible boss is not actually horrible in the typical sense of the word. They are warm, caring, charming, and… weak. Due to their aversion to conflict and extreme need to be liked by others, they say “yes” to those who want to hear “yes” and “no” to those who want to hear “no.” But they sometimes are giving opposite responses to different people on the same topic! And eventually, this metaphorical house of cards caves in upon them resulting in losing what they most desperately want – people to like them.

5. Looking out for yourself more than others will erode respect.

I once had a boss who was good at caring for his needs but was not good at looking out for the rest of us. Needless to say, his name is not on my “highly respect” list. Colin Powell, the four-star general who held a number of leadership positions in the government, said that one of the lessons he learned as a very young officer was – officers eat last. This is similar to 1 Corinthians 10:24 where the Apostle Paul says we should not seek our own good but rather the good of others.

6. Failing to listen to others will seldom end well.

I once worked for a “leader” who always knew better than others. His arrogance and unwillingness to listen would eventually alienate those around him. Over time, he lost more and more team members and followers until eventually a crisis hit that resulted in him being fired. And even when that was unfolding, he could have avoided the public humiliation if he had only LISTENED.

7. Being socially aloof will alienate you from others and damage loyalty.

On a number of occasions, I have heard about bosses who distance themselves from the people they work with. I once was told by someone that he invited his boss to a special family event, and not only did she not attend, but she also didn’t even RSVP! Such aloofness sends a clear message that others are not important or worthy of time, and this will usually result in damaging trust since loyalty is built by connection.

8. Lying and manipulation are accelerants to destroying trust.

Some of the worst bosses are master manipulators and liars. Psychologist Robert Feldman’s research on lying found that we lie an average of three times during a ten-minute conversation, and sometimes it can go as high as 12. Yikes! Bad bosses shade and varnish the truth so often that it is hard to discern what is true when in a conversation with them. Some bosses have mastered it so well that you almost need a lie detector to keep your sanity! But in the end, such behavior is assured to deliver one guaranteed result – broken trust. 

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Jay Desko is the CEO of The Center Consulting Group and brings experience in the areas of organizational assessment, leadership coaching, decision-making, and strategic questioning. Jay’s degrees include an M.Ed. in Instructional Systems Design from Pennsylvania State University and a Ph.D. in Organizational Behavior and Leadership from The Union Institute.