I’ve had a lot of uncomfortable discussions with bosses. A few things I’ve told them that come to mind…
“You deliberately humiliated another employee on a group call, and that level of immaturity and pettiness is professionally unacceptable.”
“Your administrative assistant, whom you love like a son, says casually and openly racist things whenever you’re not in the room.”
“You need to pay me $20,000 more dollars.”
To be fair, I said that last one nicer. And I had some great PowerPoint slides to go along with it!
Unlike a lot of people, I am actually very comfortable with conflict. I would even say I thrive on it. (There’s no way to say that and not sound like an asshole, but I am what God made me: an ENTJ.) Of all people, I probably go into a confrontational situation with the least possible amount of anxiety.
Nevertheless, I need extra deodorant on those days. My hands shake. My voice trembles. Which I really, truly hate. It makes people think I’m nervous, when it’s more of an under-exercized-border-collie-looking-at-a-fat-city-pigeon-and-trembling-with-overwhelming-herding-instinct situation.
Having a difficult conversation with your boss is really hard. They’re often terribly high-stakes. Depending on the nature of the conversation, you may feel like you’re ambushing your boss with new and unpleasant information. Your life and livelihood may feel like they hang in the balance. It is not easy to stay chill.
That’s why I have a secret weapon for going into such conversations.