There’s hardly a worse feeling than firing someone you like.

I’ve had to do it several times in my career and it is a dreadful thing to have to do. When I worked as night shift supervisor over 10 years ago now, there was someone who was just a pleasant person, kind, punctual and enthusiastic, and someone who obviously really needed the job, too.

I worked with her for weeks and weeks, even staying late to help her out. She was just too slow, though, and too inflexible to really do the work. I couldn’t cover for her any more, and I had to let her go. One of the worst days of my working life, I think; what made it worse rather than better is that she hugged me in thanks as I walked her out the door. I appreciated being thanked for helping her, don’t get me wrong, but I felt like a devil walking back to my desk.

I have no problem firing terrible people, though. I kind of enjoy it. Canning someone who was harassing women at work was pure fun.

Strangely enough at the same job I nearly got fired myself for refusing to let someone go who while also slow was the most accurate person at any job I’ve ever met. I’d give her the most complicated, insanely unorganized tasks imaginable (as that’s the way they came in) and she’d do them with no issues and no questions — and unlike anyone else who did them (including me), they were 100% correct at the end.

Unfortunately, literally the day I left as team leader, she was let go and the department’s quality never recovered after that.