Three Lessons Learned from the Worst Bosses I've Ever Had

Let’s face it, we’ve all had shitty bosses. If you’ve had one, I’m sure you can visualize him/her with ease and recall why they were terrible. If you haven’t had one, I’m sure you will at some point in your professional career.

For the sake of this blog entry, I’d like to focus on those of us who’ve had a shitty boss. It’s easy to trash the worst boss you’ve ever had. Whether they treated you like a 2-year-old, micro-managed you to death, stole credit for your work, didn’t trust you or down right harassed you, the list can go on and on. The last thing you want to do is remember that person. Yet, I think it’s important to do just that – remember them. Specifically, remember what they did wrong.

Too often I think people reflect on the best bosses they have had and the qualities they held. There is nothing wrong with this, but I find tremendous value in learning just as much from the worst bosses you’ve had as the best bosses you’ve had. With that said, here are three lessons I learned from the worst bosses I’ve ever had…

Lesson 1: Understand the Team Morale

I had one boss who simply could not understand team morale. Specifically, the team I was on was under a lot of stress, both professionally as well as personally, had a lot of pent up frustrations on work-related matters and was seeking clarity on a number of issues within the company.

Rather than address those issues, try to ease concerns and attempt to alleviate those frustrations, this boss decided to focus on their own work. As team morale took a nose dive, I couldn’t believe my boss was that naïve to not see what was going on. It was as if, their priorities were greater than the teams and that didn’t sit well with me.

I realize not everyone is able to empathize or pick up on visual cues from team members, but I believe if you’re in a supervisory role, it is your job to do so – or at least try. Thus, from this experience, I firmly believe in taking the time to understand your team dynamics and morale. Not only from a skill-set standpoint but also from an empathy standpoint.

How can you do that? Have 1-on-1 conversations with each team member, have weekly team meetings, have informal conversations not pertaining to work. Show your team members that you care about them and their concerns. Admit your weaknesses and ask for help. Send reaffirming emails. Go to happy hours. Reiterate the notion of work/life balance consistently. I realize some of these will work for you and some may not, but the important message is that you try. Be there for your team because at the end of the day, you need them more than they need you.

Lesson 2: Micro-thinking leads to micro-managing = Bad Managing

One boss I had simply could not get out of micro-thinking. Whether it was pertaining to client work or from a company standpoint, they could not seem to think about the bigger picture. They were so focused on minuscule matters and their own agenda, that it led to micro-managing and overall bad management.

It hurt our efforts with the client because rather than being pro-active and looking at the bigger picture of the client’s goals, we focused way too long on tactical details and matters that weren’t important.

Additionally, the micro-thinking led to micro-management which built a lack of trust within the team. As an example, the mentality became, you didn’t have to worry about doing your very best work because you knew the boss would just change it to what they wanted. Rather than the boss helping the team understand the direction they wanted, they just did the work. This led to resentment and lack of effort.

So, how can you fix that? If you’re the boss, be sure to lay out clear objectives and goals with any task that is assigned. Ensure the team clearly understands the bigger picture and let them go to work. You hired your team for a reason – they are talented and smart, so let them do the work. If changes need to be made, make sure you explain your thought process, so they can learn from their mistakes and do better on the next task. Yes, there will be times when a deadline is tight but at the end of the day, the more you help your employees become better at their craft, the more likely they are to help you in the long run.

Lesson 3: Don’t Be an Asshole

This one should be obvious but apparently, it needs to be restated. I had one boss who fired two employees on separate occasions on a Monday. A MONDAY! That means instead of letting these employees know on Friday and give them the weekend to process their next steps, they made them make the commute into work, believe they were starting a new week fresh and THEN, decide to flip their world upside down. I couldn’t believe it.

In another example, I had a boss that thought they were hot shit about everything. It was their world and we were just part of it. If there was a picture next to the definition of arrogance, this boss’s face would have been there. Were they talented? Yes. However, they refused to engage in healthy debate, often belittled employees and were just, well, an asshole. I’m sure they are still an asshole today.

So, what did I learn? In management roles, I’ve tried to remember to be grateful, patient and communicate effectively. Assholes aren’t grateful. Assholes surely aren’t patient and they often suck at communicating. I think a lot of that stems from insecurities the asshole bosses have. Put them in a position of power and there is no telling how much they will abuse that power. Thus, if you are the boss, try to be understanding. Try to uplift instead of tear down. Try to listen vs. always be the one to talk. Try to delegate vs dictate. Most of all, try to be positive vs. an asshole.

In closing, you can learn a lot from the worst bosses you’ve had in the past. I know I have. Rather than talk trash about them, identify what you can learn from what they did poorly. It will make you a better boss down the road.