I am currently the manager of a team of 15 people. In two weeks' time I will leave this job for a totally different one, in a different sector and a neighbouring city.
At my current job, I have one member of staff (professionally qualified) who has a very challenging personality. Although highly intelligent, she seems to have no awareness of how she comes across to people; and she comes across as dismissive, presumptuous and condescending most of the time. She's a know-it-all in the worst kind of way.
Among her more irritating traits is the tendency to reply to brief announcements or requests, delivered to the whole team via email, with very lengthy (500-1000 words), structured emails, outlining what she sees as every possible objection anyone on the team could have to it and detailing every aspect of the request/announcement she thinks could go wrong. She typically sends these within hours of receiving my email, putting into question her time management skills. (Luckily though, she doesn't usually "Reply All".) Prior to a recent conversation she and I had over a more inflammatory missive, she seems to have been unaware that nobody else was responding in this way, and indeed that few of the objections she anticipated ever came to pass, and never seriously. I think she misinterprets idle chatter, and the usual mild criticisms of one's boss, as expressions of deep dissatisfaction on the part of her colleagues.
I know that she has ambitions to move into management, and I also know that the team would revolt if she managed to do this, given her personality flaws. I am sympathetic to her though, because I know she is professionally frustrated. I believe she continues sending me these emails because she wants to show me she has the chops for management -- unfortunately, it shows me the opposite.
Before I leave, should I take her aside and tell her this? Would this help her, or be a waste of time? She has a history of missing the point, and at this stage (she's about 40) she's unlikely to change. But I also feel she has a right to know what is holding her back.