One of the hardest things to do as a leader is to talk to people when you have to deliver bad news.  It could start out at the beginning as a quality of work issue that eventually leads to a chronic lack of performance.  Eventually, you begin to ask yourself the real question, Does this person really belong on our team?  This HBR post is very helpful:

I was in denial for about a year and a half before I admitted that I needed to fire Randy.

His work performance had made the conclusion inescapable for years, but he was so darned nice and likeable that I gave him the benefit of the doubt. Not only did I like him, I also knew his income was crucial to his family. Furthermore, over the nine years he worked for me, his income had grown to the point that he would find it difficult to get comparable compensation.

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