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I've been fairly lucky with my bosses of late since I've progressed in my programming career. But my absolute worst boss was when I first started working in an office environment doing data entry. My boss at the time was terrible, and she was always against innovation or process improvement. She also always tried to make herself look good and taking credit for the accomplishments of others. If she screwed up it was your fault, and she was "always buried in email" so she could never respond to you for pto requests, or escalation of issues between departments. My whole family pretty much worked in various roles in the department and she fired my brother after my mother left the company for no reason, saying he was "sleeping", but I worked right next to him and he's tall and had to slouch just to comfortable see his computer screen since the same manager refused to approve work station improvements for him.
Our workflow was to receive daily spreadsheets of health care claims that we had to manually process and enter into the system. So being the lazy innovator that I am, and trying to find ways I can efficiently work, I delved into studying visual basic and programmed a few functions and tools in excel to analyze, highlight, and process some of the data since the claims on the spreadsheets always had a specific pattern. This was all before I had any formal education in computer science so the program was very basic and clunky but it tripled my efficiency. When I brought it up to my boss to spread it among the rest of our team so they could use it after a short 20 minute training, she struck it down saying any training or use of it would be a waste of resources since it was too technical and complex to be used and if I were to keep improving it or use it I would be fired. It was literally copy and paste from one spreadsheet to the other en masse and clicking a button to sort and fill in the blanks. Eventually I showed it to the director of the department when working on a large data entry project with her, and I was later offered a job as a technical analyst where I was responsible for the codebase that generated the reports for the department and specifically all the reports my old boss used where I would occasionally mess with her to get back at all the crap she gave me and my brother. Since all the reports were blind carbon copied to everyone, I would send out her reports on a delay while everyone else got them on time. It eventually got her in so much crap she had to step down as a manager. She still works in the same company that I started working at again earlier this year, and like the many careers she's ruined she eventually ruined her own within the company 😂