What I learned from my worst boss ever

“I brought you in. I can take you out.”

This is an actual phrase uttered to me by my actual boss when I finally worked up the courage to tell said boss that I was feeling mistreated and unappreciated. By “take you out”, the boss in question, let’s call him/her Pat, wasn’t suggesting a fateful meeting with shady characters down at the docks. Simply that, as my boss, Pat had the power to terminate my employment.

Horrifying? I guess so and a similar comment today might warrant a trip to Human Resources and a permanent blemish in Pat’s file. But by the end of our relationship, I had a great deal of empathy and admiration for Pat. That doesn’t mean I didn’t hate Pat at the time. When I worked for Pat, I started smoking and drinking more. I complained incessantly to my friends and coworkers and sometimes cried myself to sleep. During one of my frequent rants, a new-age friend of mine calmly suggested that the qualities we hate most in others are the things we most need to work on in ourselves. I reacted viscerally. Who wants to imagine that they are anything like their enemies? Not me.

But the idea lingered with me and if I was totally honest with myself, I had to admit that Pat’s criticisms of me weren’t totally off-base and I was somewhat out of my league in a take-no-prisoners work environment. Pat believed that I wasn’t tough enough, assertive enough or detailed enough to succeed and Pat was right. I was woefully unequipped in all of those areas. I could have crumbled, quit or complained but I hate to fail so I decided to stay and learn. For a year, I studied how Pat methodically approached a problem. When Pat was presenting to a client, I listened instead of offering my own opinion. When Pat threw back a sloppy memo or noted my failure to adequately follow up on a task, I agreed instead of fighting back. When Pat screamed at junior staffers I cringed but I noticed that they never screwed up again on Pat’s watch.

Most of all, Pat taught me that the “devil is in the details” and even if you’re sure you’ve dotted all the “i’s” and crossed all the “t’s”, you need to have one more look because there could still be a lurking typo, a transposed number or some other error that, however tiny, could alter the outcome significantly. It was a lesson I needed to learn and it wouldn’t have stuck if it was delivered to me in soft, coddled tones designed to boost my self esteem and encourage me.

I’ve had 15 bosses since I started my career three decades ago taking orders at the A&W Drive Thru in my home town. A couple were amazing, three were horrible and the others tried hard with various degrees of success. Many of them weren’t management material but to be fair, they were plopped into management roles as a reward for great work as an employee, usually with no training. One day they were having drinks with their peers and the next they were writing their performance reviews.  I’ve also been the boss a few times and I’m the first to say that striking a balance between the desire to motivate employees and the need to reprimand them is one of the toughest things any of us can face. Some people are natural leaders and they just nail it but most of us struggle and flail through uncharted territory.

What about you? What have you learned from your worst boss?


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