Lessons From Real Performance Management Conversations that Got Tricky

There’s this moment every manager dreads. You see one of your team slipping: missing deadlines, quality is off, or the energy’s just not there. Something’s not right. Maybe you’ve let it slide, hoping it’ll fix itself. But deep down - yeah, you know it won’t.

I’ve had that pit in my stomach more times than I’d like to admit. I still remember my first “real” performance conversation. New to management, feeling nervous, rehearsing what to say. The engineer on the other side of the desk was defensive, confused, and so was I. It wasn’t great. Neither of us walked away feeling like we’d made progress.

Performance management gets messy. You never want to be the “bad guy.” Sometimes, you just want the problem to evaporate. But here’s the truth: the longer you wait, the harder it gets. And the more your whole team pays for your hesitation.

Here’s what leaders get wrong: They tiptoe. They hint and hope. They dance around what needs to be said. Out of “kindness,” they end up creating confusion - and often, a lot more pain in the end.

It’s not just about being direct. It’s about being fiercely clear on expectations. That means telling people exactly where the bar is - and where they stand in relation to it. The best execs I coach do this early and often. In my one-on-one coaching sessions, I ask leaders, when there’s a problem, “Have you told them, in plain language, what needs to change? Not ‘step it up’ - but, ‘You need to do X by Y, and here’s how we’ll both know it’s working.’” Nine times out of ten, the answer is, “Well, not really…”

Real story: I had a client recently wrestling with a senior engineer. Solid skills, shaky reliability. The client tried gentle nudges, performance ratings, even extra support. Nothing stuck. Finally, I challenged him: go have the uncomfortable conversation. Name the issues specifically. Tell them what has to change in 30 days - and what happens if it doesn’t.

It was awkward as hell. The result? The engineer owned it and turned things around. Sometimes, it doesn’t work out that way - but at least everyone sees the truth.

Here’s the other side: Sometimes, after you’ve been honest and direct, the work still doesn’t improve. That’s when “helping someone find a better fit” is not just fair - it’s respectful. The worst thing you can do for a struggling employee (and the rest of your team) is let them wither in uncertainty.

When it’s time to part ways, transparency and dignity matter most. Too many leaders hide behind bureaucracy. Instead, I say: Be up front. Speak clearly. Let them know what’s happening, why, and that they’re valued as a person even if this isn’t the right role. I coached one exec this year who finally had that tough talk with a longtime product manager. It was hard, but she kept it compassionate. The PM left with her head high and the rest of the team breathed easier - no more waiting for the “other shoe” to drop.

So, what’s the punchline? Performance management isn’t about punishment or saving face. It’s about creating clarity. Have honest conversations early. Set expectations in technicolor. Don’t hide from tough feedback - it gets harder the longer you put it off. And if someone needs to move on, do it fast, do it kindly, and never leave them guessing.

You’ll build a team that trusts you and trusts themselves. You’ll sleep better at night. And you’ll grow faster - because nothing slows a team down like a leader who can’t deal with reality.

Think about your team right now: Is there a conversation you’re avoiding? This is your nudge. Do it for them. Do it for you. Honest conversations build momentum. Don’t wait.