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  • Writer's pictureHilary Young

Amazing Lessons Learned From Horrible Bosses

I realized recently that in the ten years I spent working for other people, I never really had a mentor in the workplace. I’ve never, however, had a shortage of people who are just horrible to work for. And I think they’ve actually helped to guide my career in their own way: by taking notes and learning from their mistakes I've been able to become the boss they never were.

Here are five main lessons I learned from horrible bosses over the years:

Don’t get involved in arguments that don’t involve you

I once got into a disagreement with another entry-level employee early on in my career. She was way out of line and I told her so, which she didn’t like. She went running to her boss about the issue, and, instead of her boss being indignant about wasting her time on a petty disagreement between 22-year-olds, she took it upon herself to get involved. It showed poor judgment on her behalf, made her seem petty, and even as a young assistant I couldn’t understand why a 40-something executive had the time to waste on something that didn’t involve her. I lost a lot of respect for the executive that day, and vowed never to get involved in arguments that weren’t mine from that day on.

Check your ego at the door

I’ve worked for a lot of startups and small businesses and the key to getting by successfully is being a team player. I was hired to work for a small business back in 2008 that required everyone to pitch in and take on job responsibilities beyond what they were getting paid for. We had an executive come in from the outside to work on one specific project with us and he was not a team player. He consistently showed up late on days when the rest of us had to be in early, he left earlier than we did on days when we had to stay late, and he had a general air of being better than the tasks the rest of us were doing on a daily basis. Regardless of his year of experience, many of us had trouble working with someone who so clearly felt above it all. A leader who thinks they are superior to everyone else isn’t a very good leader in the long run.

Be open to new ideas

One of the hardest work situations I’ve ever walked into was when I was taking over a running project from someone who was leaving. She had been part of the project since its inception, and the executive team she answered to absolutely adored her. I knew I was in trouble the day she introduced me to them, and they were not very welcoming or receptive to new ideas despite my depth of experience. Everything was a battle with them; they always ended up implementing my suggestions and ideas in the end, but they seemed to love disagreeing with me simply because I was not the girl that came before me. Change isn’t always an easy adjustment, but it can be necessary for growing and moving in a positive direction.

Be idealistic, but also be practical

When I moved from NYC to Philadelphia I worked for a technology startup that had lofty aspirations for the direction of the company. They tried to grow before there was infrastructure in place to sustain it, and the result was catastrophic. They hired me and filled me with high hopes for what I could accomplish for them but couldn’t provide me with the support I needed to actually follow through. Most days, the CEO didn’t bother showing up to the office and when I had questions that needed to be answered, no one was there to provide me with them. The company folded within the year.

Don’t project your insecurities on other people

Shortly after, I landed in a great place doing work that I loved. And at first, I loved my boss, who also seemed to try hard to be my friend. As time went on, however, she started saying bizarre things to me. On several occasions she told me that I was the younger, prettier version of her. It made me remarkably uncomfortable every time she said it and part of me felt like she was just fishing for complements. I started to realize that her behavior towards me was a reflection of the insecurities she was dealing with in her own life. They ended up costing her a job in the end, mainly because her insecurity prevented her from actually doing her job effectively.

While it may seem like the above comes from a collection of bad work experiences, the truth is that I have been incredibly blessed to have had all of these jobs. I’ve learned so much more from the challenges—and challenging people—that I’ve encountered along the way!


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