How to handle moody bosses

Q: I work in a small division located away from company HQ. Three of us are in the office, not including my boss, and two employees work remotely. I avoid interacting with my boss because he is so moody.

My boss is horrible about approving vacation requests. I’ve had a few vacation requests sitting in his queue for more than a month. I’d like to book flights soon, so I can’t just wait for him to get with the program. He should just look at the calendar and either grant it or say, “Sorry, someone has that day off already.” It’s not that difficult.

I’ve thought about mentioning this to HR, but I am afraid of retaliation. I’ll probably try to discuss this with my boss on a good day, but I so loathe him that a great day is when I have no interaction with him.

A: You know what I’m going to tell you to do, don’t you? Partly because I’m a sadist, but mostly because it’s the obvious untried alternative. Hint: It doesn’t involve HR.

But before you hike up your OshKosh B’gosh and march into his office, make your request as easy as possible for him to grant. Start by asking your co-workers yourself if they foresee a conflict with your plans — as you say, it’s not that difficult. When you present the request to your boss, mention that you have already run the dates by your co-workers. Also, build in a deadline: “I’ll need to buy tickets by (date), so if I don’t hear by (earlier date) that my request is denied, may I assume it’s been approved?” Then follow up weekly so there’s no “gotcha” when you hit your deadline. It may or may not produce the result you want, but it beats passively loathing him from afar.

Not that you asked, but I can’t imagine how a six-person work group functions when a third of the members aren’t interacting. I realize it’s easy for me to suggest, and maybe you’ve tried this — but what if you made a little effort to connect with your boss when he’s not being moody, and not just when you want something from him?

Q: What would you say about a boss who casually says, “You are fired” all the time? For example: “Questions? Complaints? If so, you are fired.”

A: About him: That Don Rickles has fresher shtick.

To him: Depends how sure I am that he’s kidding.

Not sure: “Er, I hope you don’t mean that, because I want to make sure I do this right.”

Sure: “You can’t fire me. I quit,” mimicking his cadence and tone.

Ÿ Karla L. Miller has written for and edited tax publications for 16 years, most recently for the accounting firm KPMG’s Washington National Tax office. You can find her on Twitter, KarlaAtWork.