How To Have The Hard Conversations You’ve Been Avoiding

There is someone on your team you need to talk to.

They’ve been showing up late. Or dropping the ball. Or bringing an attitude everyone can feel. You know the conversation needs to happen. And you’ve been telling yourself you’ll get to it next week.

Here is what most newly promoted managers miss. Issues don’t age well. They rot.

And when you finally do have the conversation, if it comes out as “because I’m the boss, that’s why,” you just made it worse.

In this episode of The Leader I Needed, host James Rosseau Sr. draws on more than 20 years leading teams in corporate America to walk through why most hard conversations go sideways and how to have them without avoiding them or pulling rank. He shares the working relationship that went off the rails for over a year before he figured out what he was doing wrong, and the story of a head of strategy at Allstate who stopped him cold with a piece of pushback he wasn’t ready to hear.

Most workplace blowups aren’t actually about the issue. They happen because the leader walks in ready to be right instead of ready to be objective.

Before the next hard conversation, run the issue through three questions. Is it recent? Is it relevant to the person’s actual job? Is it recurring? If the answer to any of those is no, it isn’t time to have the conversation yet.

James also walks through the four moves that let a leader be direct without being destructive, the short list of do’s and don’ts that keep any hard conversation from going off the rails, and why “because I said so” is rarely a sentence. It’s a posture. And the antidote, he argues, is the relationship.