Thoughts on Breaking Bad News to Your Boss

A few weeks ago on DiceTV, Cat Miller discussed why you don’t want to make yourself look smart at the expense of the people you’re interviewing with.

You might have spotted it in a research report, a page from the company’s Web site, or a blog post your interviewer wrote. Do you find a way to mention it – to show how much you’re on the ball? No!

Thoughts on Breaking Bad News to Your BossAfter we posted it, a Dice user wrote to ask: “OK, so I don’t mention my boss’s mistake in an interview, but how do I handle it once I’ve gotten the job?”

Good question.

Faced with a mistake made by your boss, you have a distinct advantage: You know him. Unlike a job seeker who’s trying to navigate an uncomfortable situation in the middle of a bunch of strangers, you’re going to have a certain comfort level about what will, or won’t, fly with the person you’re working for.

Writing this, I keep thinking of Jeremiah Murphy, once a columnist at the Boston Globe and an instructor of mine in college. More than anyone else, he taught me that you can ask anybody any question, as long as you ask it in the right way.  The same is true for awkward workplace conversations: You can make any comment you like, as long as you tailor it to your audience.  A good boss – and you know these when you see them – tend to take bad news at face value, and set their sites on correcting any errors. Others, like the ones who get off on the fact they have office doors they can close, have to be approached more carefully.

With these folks, my favorite strategy is to ask a question or mix in a qualifier. For example, “I’m sure you know this, but I figure I should point it out: Section Four of the documentation doesn’t match up with the actual product. Should I worry about that?” This gets across the information you think is important, without being confrontational. Plus, it gives your boss an out. He can tell you not to worry about it.

The main thing is you’re keeping the situation under control here, and you’re keeping it private. It’s not a good idea to point out your boss’s mistakes by e-mail, with your team cc’d. E-mails leave a record, after all, and I’d think most bosses appreciate a quiet and courteous discussion. I know I would.

Have your own tips on handling touchy bosses? Post them below.

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