If you lead people long enough, you’ll run into that moment.
Someone on your team isn’t hitting the mark. You’ve been noticing missed deadlines, lower quality work, maybe some frustrated peers. And you keep thinking, “I should say something.”
But you don’t. Not yet. You want to give them space. See if they can reverse course on their own. You don’t want to come off too harsh. Maybe they’re just having a rough week.
Until the moment you can’t ignore it anymore.
You pull them into a 1:1, take a deep breath, and say the line we’ve all said—or had said to us:
“You’re not meeting expectations.”
And suddenly, what felt like a reasonable, even overdue conversation turns into a complete derail. They didn’t see it coming. They’re frustrated and feeling attacked. You’re frustrated they didn’t pick up on it. The vibe shifts. Now it’s a performance conversation you’re both walking away from feeling worse.
I’ve coached hundreds of engineering leaders, and this comes up constantly:
We wait too long to have a hard conversation, and then we fumble it because we’re reacting instead of preparing.
That’s why I’m spending the next 5 weeks breaking down the toughest conversations in management—and how to approach each one with clarity, empathy, and structure.
Over the next 5 weeks, we’re going to cover:
The Underperformance Conversation
The Difficult Feedback Conversation
The “No” Conversation
The Career Expectations Conversation
The Boundary-Setting Conversation
Let’s start with the one most managers struggle with the longest: underperformance.
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