#069: Two Kinds of Bosses You Don’t Want to Work For!

I consider myself to be truly fortunate in that during my career that has spanned 40+ years (so far) I have only had two bosses that I considered being ‘bad.’ The grand total amount of time I worked for these two was about 4 years, less than 10% of my working career. Yet, both left me confused, discouraged and stressed out.

Bad Boss

The two bad bosses I worked for had some striking outward differences, yet inwardly had some interesting similarities.

Boss #1 came along fairly early in my career. He was a big, burly guy with a personality that resembled a giant teddy bear. Expressive and outgoing, charisma oozed out of his pores. He would be your best friend and the kind of guy you want in your corner rooting for you helping you to succeed.

Boss#2 came along later in my career. He was small in stature but had a huge personality. He was a quiet guy, caring, even pastoral. He was the kind of guy you would pick to sit down with and pour out your heart over a cup of coffee.

Well, that’s what they were like before I said, “no” to them. It turns out some people do not like hearing the word, “no” from a subordinate.

Boss #1 would do anything to succeed. He would dance ever further into the gray areas of company policy, and pushed his employees to do the same if it meant getting his ‘numbers.’ My problems came when I said ‘no’ to a particular request that was immoral, and then a subsequent request that was a clear-cut violation of company policy. This big teddy bear of a man suddenly morphed into a grizzly bear. He threatened to fire me. The next few months were a constant battle between the two of us, until fortunately, some top level executives realized what was going on and ‘encouraged’ him to resign.

Boss #2 was an intellectual with a split personality. Outside of work, he was the most pleasant guy you would ever meet. Inside the workplace, his other personality emerged. He liked to think he was the smartest guy in the room who could do anything better than anyone else. His dogmatic micromanagement style drove the staff to distraction. Our relationship began to sour when I insisted that we bring the organization into compliance with some new state employment and insurance laws. As I continued to push changes that would prepare the organization for success in the future, he became more and more passive-aggressive: nice to my face, then stab me in the back or undercut my authority.


Both of these men had outgoing personalities. They were easy to like and were able to build relationships quickly. On the flip side, both were narcissistic, full of pride with huge egos.


The biggest danger of this type of boss is that they work to advance themselves, and do not care about the collateral damage they leave behind in their wake. They will do whatever they have to do to advance themselves or their cause, and will not hesitate to turn on anyone who resists their path. These bosses also tend to be insecure and vindictive. Their egos can’t take being challenged, and their response is to take out the challenger.

Warning Bells

Bad bosses come in all shapes and sizes. There is no single attribute that sets off the danger warning bell. However, I have learned that one tell-tale sign of a bad boss is to ascertain whether their “talk” matches their “walk:”

  • Watch carefully how they interact with others. How do they treat subordinates? How do they treat peers? How do they treat their bosses?
  • Listen carefully to what they say about others. Do they denigrate the opinions of those who differ from them? Do they speak condescendingly about others?

What Are We to Do?

Practically speaking, if you are already working for a bad boss like one of these two, there is not much you can do except extricate yourself from the situation.

As a Christian, I believe in James’s advice when he writes, “Consider it all joy, my brethren, when you encounter various trials, knowing that the testing of your faith produces endurance” (James 1:2-3).

Working for a bad boss is a painful experience, no doubt about it. But, that pain can lead to valuable life lessons IF we are willing to learn from them. This is important. Painful trials are sure to come our way at some point in our lives, so let’s not waste the pain by not learning something from it. If you don’t learn something, the pain is wasted.

Join the Conversation

As always questions and comments are welcome. Have you worked for a “bad” boss like one of the two I’ve described here? If so, how did it go? What did you do? How was the situation resolved?

Category: Personal Development | Leader Qualifications

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