When I was a kid and teenager, I was very unhappy. I was stuck in a small town with an anti-intellectual bent, extraordinarily frustrated at school, and it made me mean. I had no patience for people. Because I appreciated straightforward, honest criticism so that I could become better & smarter, I never understood that other people are far more sensitive. So, I'd eviscerate other students when we had to do peer editing, etc. When people tried to make bullshit small talk with me, I'd actually say things like, "Look, we both know that we're not really interested in talking about the weather, so how about we just not?" A lot of this was that I was super introverted and extra-sensitive, and I was suffering from undiagnosed migraines with tons of sensory symptoms, and it often felt physically painful to hear people talking. The other part is that I was having a really hard time at home, and I just needed some peace, which I never got. But that wasn't anyone else's fault, and I was just a bitch.

Because I didn't like how mean I was to people, I spent years in college and post-college making a concentrated effort to be nicer. This affected me negatively professionally because I didn't assert myself where I should have. Now, I'm trying to find the right balance of assertive. I think I'm failing in one respect.

I have a colleague who often fails to grasp the ideas we're discussing, so his analysis is often wildly off-base. I will ask him for his thoughts on a specific issue, and he derails the discussion with irrelevant history of the case. Or, we'll be in meetings with a partner, the partner asks a question, and he starts answering a different, unasked question. It drives me crazy and I find myself cutting him off in front of the partner. I say, "That's not what we're trying to get at, though. We're trying to determine X..." Oftentimes, because he is inarticulate, his diversion leads to more diversions because the partner gets so confused and we have to go back to square -10 to explain ourselves back up to square 1. It takes forever. So I've taken to cutting him off.

I feel like this can read as rude, and I can see it on his face that I sometimes hurt his feelings. But it hurts my day to sit and have a discussion that is irrelevant, because it sometimes leads to 30, 45 minutes more of discussion than was actually needed, and that's 45 minutes that I get home later. That's me missing the yoga class I wanted to go to.

Is there a delicate way to do this that I am missing? Is the way I handle it fine? Should I sit there and let the discussion go on and on? I don't want to be as unpleasant as I was as a teenager. HELP ME not be a bitch to my coworker!