My worst boss was an ENFP.. actually. He was paranoid and viscous he went out of his way to hurt other people. After that, ESTP was nasty but I also had an ESTP good boss.

My worst teacher was an ESTJ. If I had a boss who was anything like she was, I would quit. Unfortunately, a fifth-grader is helpless and vulnerable, and doesn't have the option of fleeing such a threat.

Of the bosses I have had, the ENFJ was the most difficult to deal with, because she would make irrational requests. If I told her what I forsaw going wrong with her plans, she would get upset with me for questioning her judgment, but if I obeyed and did it as she commanded, I would get in trouble for her lack of foresight when I was incapable of achieving the desired results. She yelled a lot. She expected me to be able to read her mind, and to know exactly how she wanted things done without being given any instruction about her preferences. When I was unsure, and tried to ask for more details, she got upset with me for not automatically knowing. I could have guessed, but she was extremely picky about very trivial details that were a matter of her subjective, personal choice, like where to put a decorative item in the shop so it would look best by her standards. I felt like there was no way to avoid her negative judgment, and that no matter how hard I tried to please her, it would always be impossible to earn her respect.