5 lessons in leadership I learned from some of the worst bosses I experienced

I’ve been very fortunate throughout my career in that I’ve worked with and for some wonderful companies, had some fantastic mentors and some first-rate colleagues! They provided me a solid foundation in leadership, business and communication that I use to this day. But if I’m honest, I have learned as much if not more from the horrible bosses in my life as I did from the shining stars. Working for or with some of these people was so painful, if not downright traumatizing, that it burned into my psyche the importance of NEVER doing these things. I encourage you, if you are working for ‘that guy/gal’ to a) Get out! Get out now! And/or b) take heart that even the worst of bosses may be teaching you something valuable.

On the other hand, maybe you ARE that guy/gal. If you see yourself in any of these examples, then that alone means you still stand a good chance of changing. Unless they are a dyed-in-the-wool sociopath, most people behave badly out of either ignorance or fear. Unfortunately, there is also a tendency for people to become addicted to their perceived power and stop seeing the people they lead as human beings. Sadly, the ones these people hurt the most end up being themselves, because you can fool the world but usually your own conscience will convict you. If any of these ring true for you, consider talking to a professional and changing the course of your leadership – which is also your legacy.


1)      The Truth-Challenged

Almost every leader has to struggle with how much information to provide their employees. Those who decide that less transparency is best usually cite competitive vulnerability or lack of employee ability to understand the information as reasons for keeping information close to the vest. As a leader that’s up to you, but there is a line between discretion and outright lying. I remember on business trip my colleague and I were traveling with our boss, who told us employees that we had to stay at one (cheap and shoddy) hotel, which unfortunately was booked so HE would be staying at the 5-star down the street. Little did he know that we were close friends with the company travel agent and quickly made a call to determine whether that was true (it wasn’t). Lying about things may seem to be the simple and expedient path but being caught by your employees in a boldface lie can damage your credibility forever. It’s not worth it!


2)      The Drunk

Most people enjoy a social cocktail every now and then, or maybe even more than one. To each their own, but if you have developed a dependence or an addiction to a mind-altering substance there is no way this won’t affect your career. I had a wonderful and charismatic mentor at one point in my career whose impact on my life was immeasurable. Unfortunately, this person also drank. A lot. Whenever we would meet, they ensured alcohol was involved and they would keep it flowing, turning every event into a party that others might not have wanted to attend. Worse, there were times when we’d have long conversations and they would give me assignments and then clearly not remember them later. They would show up smelling of alcohol and their behavior was erratic and unpredictable. This is heartbreaking because many times alcoholics are high achieving, sensitive and just plain awesome individuals who deal with stress or latent perfectionism by numbing it out. But once it turns into an addiction they become very hard to work for/live with and until they recognize it’s a problem life for everyone involved becomes a tornado of destruction.


3)      The Bully

We’ve all experienced a bully at some point in our lives. This is the person who belittles you, demeans you or is basically just a jerk to everyone in order to get what they want. The bully likes to throw you off guard and try to catch you up. Bullies are usually fearful people who think the only way to stay ahead is by keeping other people down. They will prey on your weakness and leave you feeling exhausted and demoralized. One of the happiest days of my life was when I was finally laid off by my bully (note…the only way to deal with a bully is to stand up to them, but when they own the company it doesn’t mean you will survive the stand-off…and that’s okay). Bullies think it’s okay to swear at you, yell at you and blame you for their own inadequacies. My favorite bully line? “I don’t understand what you’re even doing around here…our culture is terrible and people are all leaving. Why don’t you do your job and fix our culture?”


4)      The Narcissist

The Narcissist and the Bully are related but separate. Whereas the Bully may not have gotten enough hugs growing up, the Narcissist probably got too many. These folks believe to their core that they ARE the smartest, most important people in the room and you exist to serve them. Their ego knows no bounds and you are simply along for the ride. When you encounter a narcissist with a noble vision, it can be exhilarating as the power of their convictions can carry you and the company through a storm and leave you committed to achieving the greatness they know they are destined for. Just know that Narcissists are incapable of giving back, so these relationships usually end up in the painful realization that the only one the Narcissist truly cares about is themselves and you are at best a valuable tool to achieving their goals and if you lose your utility you lose your place in the sun.


5)      The Politico

This may just be the worst of the bad bosses in terms of the emotional disruption. These folks see work and life as something to be ‘spun’. They don’t trade in power or information so much as relationships and they are very, very good at imitating actual leadership qualities in order to build alliances. You can tell a true leader from a Politico by their fruit. Do they sow unity, growth and respect for people or are those just words that precipitate backbiting and coups? Typically these people use flattery and rhetoric to gain allies but eventually their true colors emerge as they begin to reveal hidden agendas masked as ‘strategies’ and lies couched as ‘spin’. If you have a boss who has thrown their boss or other peers under the bus, stay clear. Do. Not. Trust. Them.


Although these were the worst of the worst, here are some other bad boss examples to avoid:

The boss who always wants to promote ‘friendly competition’ between employees in order to drive performance (patronizing at best and downright destructive at worst).

The boss who blatantly IM’s and texts people while in a one-on-one with you, is unprepared for meetings with you or does other things that make it abundantly clear that you or your time are just not that important to her.

So thank you, horrible bosses, not only for the years and years of anecdotes and column-fodder you provided me, but also for showing me the value of honesty, respect, integrity, patience, gentleness, joy, kindness and self-control. 



By Carrie Maldonado

Carrie Maldonado, is an organizational development consultant, author, and speaker. Carrie's eclectic mix of professional interests include writing, speaking, coaching, and consulting on topics ranging from organizational behavior management to spiritual transformation in and out of the workplace. Carrie lives in the beautiful Pacific Northwest with her patient and long-suffering husband and their three children.

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