"You're not meeting expectations" doesn't mean what you think

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:

1. The Underperformance Conversation
2. The Difficult Feedback Conversation
3. The "No" Conversation
4. The Career Expectations Conversation
5. The Boundary-Setting Conversation

Let's start with the one most managers struggle with the longest: underperformance.

Underperformance isn't always obvious - until it is

You'd think this would be the easiest one. Someone isn't doing what they're supposed to do, so you address it.

But in practice, it's rarely that clean.

Maybe they're new-ish.
Maybe they've done solid work in the past.
Maybe you haven't been as clear as you thought.

So instead of starting the conversation, you justify the delay. You want more data. You're not sure it's bad enough yet. You tell yourself it'll get better soon.

And then, suddenly, it's "bad enough," and you're having the conversation from a place of frustration instead of support.

(If this resonates, know that you're not alone. I've fallen into this trap several times.)

So what should you do?

First: take the emotion out of it. That doesn't mean be cold. It means be clear.

Here's a simple structure I use when I coach managers on this:

The CARE Framework:

• Clarify the specific gap (use data, not feelings)
• Ask what support they need
• Redefine expectations collaboratively
• Establish a follow-up plan

Here's what that sounds like:

Sarah, I've noticed that three of your last four deliverables were submitted 2-3 days after deadline, including yesterday's overdue QA review, which flagged several issues that are unusual for your work.

Help me understand what's been going on from your perspective. What support would help you get back on track?

No judgments. No assumptions. No "you always" or "you never." Just facts, curiosity, and a path forward.

Why it matters

Too often, we treat underperformance as a character flaw instead of a solvable problem.

We make it personal when it's almost always systemic.

That doesn't mean you lower the bar. It means you build a bridge.

And when you do that? You give your team member the dignity of a clear, actionable conversation. You reinforce expectations for the rest of the team. And you stop the slow leak of energy and morale that happens every time you let something slide "just a little longer."

This isn't about micromanagement. It's actually the opposite. It's about leadership.