Tuesday, October 16, 2018

Bosses - One Flew Over The Cuckoo's Nest!

Bosses can be interesting people – I say that tongue in cheek knowing that this is a role I’ve now played for the vast majority of my career. Some bosses teach you what to do, other bosses teach you what not to do. This memory is going to reflect on things I learned not to do after one particularly interesting boss.

In one of my roles I ended up working for a great team. I really mean this, I loved the people and spent a lot of time with them outside of work. Anything from getting together for drinks, to grilling out to playing on rec sports teams. We all enjoyed being around each other. We celebrated life’s successes with each other and we were there for each other in the difficult moments of life. These were great people, they really did care and they weren’t afraid to show it.

Due to nature of our personal relationships, it made work a lot easier. We were all comfortable with each other and it allowed us to not only get a lot of work done together, but to have fun while we were doing it. Practical jokes were played in and out of the office, nothing disruptive, but enough to let the target know that they had been had! I got stung more than once by these friends, and we still laugh about it to this day. I don’t really recall there being a lot of formality in the office, you could approach anyone with an issue and count on them to help you push thru it and find an answer. There are many times I’ve thought about being back with that group of friends/team mates. Everyone, except ‘The boss’.

‘The boss’ wasn’t my official boss, but effectively ran the place. The owner lived out of town and ‘The boss’ had official free reign across the entire organization. ‘The boss’ was also disruptive! Promises were made to customers without ever checking internally to see if it could be done or when it could be done. Decisions were made without any input and without any reason, sometimes reversing the decisions that were made the prior week. ‘The boss’ would play people in the office off against each other. While I was not an official direct report of ‘The boss’, I ended up in many meetings to discuss customer issues, project issues and what was being done to resolve said issues.

These meetings typically devolved into shouting matches, with the end result being who could yell the loudest, the longest and wear the other side down. Or ‘The boss’ would make demeaning statements about your ability to do your job’ To say it was stressful would be an understatement. You would walk out of some of those meetings completely mentally and physically worn out. You never knew when these meetings would occur, your day could be going well and boom – you get called into a meeting with ‘The boss’. There goes the day!

You always knew when ‘The boss’ was back in the office, suddenly office doors closed and the attitudes of everyone changed to sullen and silent. This was no way live and work.

After a couple of years of this insanity, I decided that it was time to move on, working in that environment was not how I wanted to live my life. While I loved the people, ‘The boss’ made it untenable. It was weird, I was on a business trip with a peer taking phone interviews and trying to figure out how to ‘hide it’ so that he wouldn’t know what I was doing. It was toward the end of the trip when we both figured out that each of us were doing the same thing.

While I was glad to get out of that experience, I also look back and realize what I gained out of the experience. I learned a lot of things that I tucked away as examples of how not to treat people:


  1. It is not ok to yell at people in the work place.
  2. It is not ok to promise customers stuff when you haven’t reviewed with your internal teams and have no clue what you are promising.
  3. It is not ok to schedule multi-hour meetings with the express purpose of just using the meeting to wear your opponents down just because you can.
  4. It is not ok to jerk your team around with ping-pong decisions that can’t be explained.
  5. It is not ok to belittle people in front of their peers.


I probably learned a lot more during that experience than I’m remembering at this moment in time. I left because it was the right thing for me to do. I miss the daily interaction with the friends I made, but do not miss the insanity of the situation.

I will forever remember the day I got word that I was selected for one of the jobs I’d been applying and interviewing for, that finally would allow me to get out of the situation – I had been in a meeting that lasted the entire day. ‘The boss’ was in fine form and it was a true death match between development and ‘The boss’. I didn’t say much the entire day as the head of development took the brunt of the heat that washed across the room. That said, the end of the day hit and I was completely spent. I drove home wondering how much more I was going to be able to take.

When I arrived home, my wife asked me what was going on and I started to describe the day – in brutal detail. Part way thru the conversation, the phone rang, I looked at my wife and told her that it was probably ‘The boss’ and to tell her I wasn’t home. My wife answered the phone and told me that I needed to take the call as it was one of the companies I’d been interviewing with. I sat on the phone as the job was offered to me and didn’t hesitate to say yes when asked if I wanted the job. The funny thing, when I handed in my resignation, ‘The boss’ tried to get me to stay. Didn’t happen!

What have you learned from your bosses along the way?

If you'd like more information on my background: LinkedIn Profile

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