On Leading With Greatness
On Leading With Greatness
How to Be a Lousy Employee Just Like Me
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How to Be a Lousy Employee Just Like Me

Hint — Start with a Lousy Boss

Your loyalty is not to me But to the stars above

Bob Dylan

A tiny man using a large pencil to fight off a giant finger
The lousy employee hard at work

My vast and deep experience working for others and failing miserably at it can stand as inspiration and a model for those who also aspire to be lousy employees. For me, my formula for failure starts with my bad attitude. I have been headstrong, some have even said arrogant, in the cause of doing the objectively right thing. Worse still, in my twisted mind, bosses exist primarily to help their people do their job better, not the other way round. That is why, when I was a boss, I spent much of my effort on smoothing the way for my people to succeed, a source of severe criticism from the bad bosses I then reported to.

No, I have always been a terrible employee. Whenever I have seen that we were doing things wrong, I tended to call it out, which never endeared me to my bosses, at least the crappy ones. I tried calling out missteps in private — bad idea. I tried calling out looming disasters in public — a really bad idea. I tried being vehement about my concerns — always a bad idea. I tried being subtle and understated — still a bad idea. My error? In my obstinate attempt to do the right thing, I overlooked the fact that bad bosses are always right. Always! It’s a paradox, I know, but it is axiomatic: The worse the boss, the more likely they are to be infallible. Who knew?

Of course, I have had a few bosses — one boss in particular — that were receptive to my concerns that selling cigarettes onboard the Hindenburg was perhaps not wise, but these good bosses were decided exceptions. Perversely, when I was a boss, I openly encouraged criticism from my people, which is really hard. Although I can’t say I was perfectly gracious or always welcoming, I made a sincere and ongoing effort to listen to and accept questions and critiques.

As for loyalty to my bosses, I was flat-out incompetent when it came to bosses who persisted in doing wrong. I kept doing foolish things, really, like prioritizing our stated mission, the people we served, our dedicated employees, and — um — success over the pathetic whims of top administrators and such. In short, I was an idiot. I thought doing no harm or even doing good was more important than assuaging my bosses’ fragile egos. I was all turned around on the subject. I blame my upbringing.

When I was a boss, I unaccountably tried to convey to my people that their loyalty was not to me but to our organization, its mission, and our shared success. I should point out how difficult it is to encourage your people to do the right thing and succeed when it goes against your self-interest or your sense of certainty. Boy howdy is it hard!

When I was a middle manager, I struggled all the time with my bad bosses while trying to do things differently with my people. The cost was high. I frequently had to serve as a heat shield to protect my people from my vicious bosses. Some of my people will never know how close they came to getting fired over my bosses misreading a situation, allowing themselves to be misled by malevolent gossips, or being insulted because someone wasn’t licking their boots enough. By the way, being a heat shield in those situations is great fun, which is precisely what one would say if one were being bitterly sarcastic.

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Another thing I always struggled with was trying to get my bad bosses to listen. How do you communicate with someone who is all caught up in themself? I can be pretty persuasive, and I would use outlandish tools like rhetoric and logic to get my point across all the time. Sometimes it even worked, but with the worst bosses, it only served to infuriate. I would present them with the facts, but those facts were sometimes awfully inconvenient for them, which would make them quick to resent the person presenting the facts: me! I once had a college president scream at me, “I hate your words!” Really. This is an adult person. I believe her unhinged reaction was due to what is called “cognitive dissonance.” She suffered that a lot.

Lest you think me pigheaded and unreasonable, I have always been a fan of getting things done through cooperation. I am not afraid of working the politics, but I have a distinct preference for the politics of possibility over the politics of personal destruction. And I maintain that compromise and collaboration are key components to great leadership, which I have always embraced. If you haven’t guessed yet, I am placing the blame squarely on bad bosses and — frankly — on their many enablers who unironically call themselves “colleagues.”

The one thing all these bosses had in common was their utter dysfunction. They were terrible virtually all the time. I am not suggesting that I was perfectly good or even close to it as a boss, but I tried to improve constantly. I avoided self-serving lies such as, “hey, I’m a really good guy, so everything I do must be good.” It’s an easy trap for bosses to fall into.

In contrast, the few decent bosses I had were open to observations, concerns, opinions, suggestions, and even criticism. Imagine. They were also more successful and more content with life. The dysfunctional bosses were always angry and miserable even if they hid it well. Many got canned themselves eventually. Some survived in their positions, but their organizations suffered and may still suffer horribly for it.

In cases like that — middle managers reporting to hopelessly bad bosses — the options are few. You can knuckle under and join the dysfunction as a full-time contributor. You can try to hide, but that lets the bad bosses off the hook. You can keep fighting until you are worn out or worn down. Or you can leave. If you persist in your selfish need to do the right thing, live your values, fulfill the mission, put your ego aside, work for your clients, strive to make your people successful, and all the other many hideously challenging things that true leaders do, you will always be, for your bad bosses, a lousy employee. It’s a noble cause.

The best bosses are the ones that embrace their role as leader. Who work for the benefit of everyone and least of all themselves. Who understand both the limits and potential of human beings and recognize and celebrate our shared humanity.

If you are a boss or wannabe a boss, be like that. Be a leader. I will come clean, though. Being a bad boss will always prove remarkably easy in comparison. Bad bossing is the preference of the indolent and insecure. Being a leader is an ongoing challenge. It takes discipline, self-awareness, and integrity. It takes resilience. It take a commitment to human decency. It’s your choice.


What has been your experience with bad bosses? Did you consider them successes?

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On Leading With Greatness
On Leading With Greatness
Each Thursday I share new ideas for leaders and aspiring leaders on mission clarity, self-awareness, and human skills — a slightly irreverent kit of Tools+Paradigms for leaders and aspiring leaders like you. Visit GuidanceForGreatness.com