> Having awkward conversations, about missing a deadline, a particular behaviour, or some other thing, has created a psychological burden in me. In some cases it actually keeps me awake at night, thinking about some displeasing situation, which of course has ramifications in my overall performance later.

The best solution I've found for this is to start reading books related to managing teams, having difficult discussions, etc.

Once I did this, I found these kinds of discussions to be more of an intellectual exercise, opportunity for experimentation, etc. I.e., it gave me a level of personal detachment that made the discussions much easier, and hopefully more productive.