HBR Guide to Leading Through Change

CHAPTER 13

How to Raise a Difficult Issue with Your Boss

by Steven G. Rogelberg and Jon Gray

Gordon was stewing. He needed to share something with his manager about an ongoing conflict between himself and another team member, Ellen, but he was uncertain how to do it. Although he got along well with his boss, he was nervous about how she might respond. He committed to raising the issue at his next one-on-one meeting, but the meeting came and went and he failed to get up the courage to do it—and then he felt that bringing it up at a later date would be odd. Gordon was not only stewing, he was pretty miserable and discontented, which took a toll on his engagement and productivity at work.

Likely all of us have been Gordon at times. (In fact, he’s ...