If someone is surprised by their performance review, you’ve failed as a manager.
I definitely failed at this.
Early in my career I shied away from small uncomfortable conversations. Big discussions? I could handle those. I’d prepare mentally, deliver the harsh truth, push through the discomfort.
Regular feedback? Not so much.
People on my team got blindsided. I can still remember David’s face during his review. The confusion when I mentioned concerns about his work. Then the switch - jaw tightening, eyes narrowing. “Why didn’t you tell me sooner?”
I didn’t have a good answer.
As I learned to embrace the discomfort and started sharing more consistent feedback, I got better. Fewer surprises. More trust.
But I realized something new.
You can minimize surprise, but you can never completely eliminate it. As hard as you try, some things fall through the cracks.
Why?
Management is constantly failing at eight things so that you can crush the two most important priorities.
So you need to learn to fail well.
Three steps:
Acknowledge the mistake
Do the right thing anyway
Learn from it, with compassion
Acknowledge the Mistake
I remember sitting across from Marcus, about to deliver devastating feedback.
For months, I’d been expecting senior-level work. He’d been delivering solid mid-level work. The gap? My fault. I never told him what senior-level actually looked like here.
This wasn’t my first time screwing up calibration. In the past, I’d just delivered the hard news. Plowed through. Hoped they wouldn’t notice I’d failed them first.
It doesn’t work.
This time, I started differently.
“I need to own something first. I should have told you months ago what senior-level looks like here. I didn’t. That’s on me.”
His shoulders dropped slightly. Not relief exactly, but acknowledgment that we were in this together.
Then I delivered the hard feedback anyway.
That’s the first step. Acknowledge that you messed up. Not to soften the blow - it won’t. Do it because it’s true.
Do the Right Thing Anyways
Here’s where many managers fail.
When you deliver hard feedback, the conversation is about them. Your job is to help them grow. To support the team and the project.
It’s not about you.
But when you acknowledge your mistake, you make it about you. And there’s a danger in this.
We all have defensive mechanisms that kick in when we hear things we don’t like. The person getting feedback? Their defenses are in overdrive.
When you say you messed up too, they latch onto it.
After I acknowledged my mistake to Marcus, I watched it happen in real time.
“So... if you’d told me earlier, I could’ve fixed this?”
Yes. True. Also irrelevant to what we needed to discuss.
“Maybe. But we’re here now. Let’s talk about what senior-level looks like going forward.”
Your apology becomes their deflection. It blocks their growth.
I’ve done the opposite too many times.
You acknowledge you should have shared feedback earlier. Their performance now means a lower rating or they need to leave. Because you know you could have done better, you share this news with guilt written all over your face.
Their defenses pick up on it.
So you roll back your feedback. You delay.
Everyone loses.
The project suffers. The team suffers. You suffer. Even the “low performer” suffers.
Here’s what to do instead.
Do the right thing even if it hurts. You screwed up, yes. That doesn’t mean you get to avoid the hard call.
Learn From It; With Compassion
Later, once the dust settles, that’s when you learn.
Marcus’s performance didn’t magically improve after our conversation. But something shifted. We both knew where we stood. No more ambiguity. No more surprises.
Three months later, I sat down to review what went wrong.
I could have set clearer expectations in month one. I could have checked in at month three when I first felt the gap. I could have asked him what success looked like instead of assuming.
I couldn’t change the past. But I could change my next hire’s onboarding. I could change how I checked in with the team.
Six months after that, I almost made the same mistake with someone new. Caught it earlier this time. Still not perfect - I should have caught it even earlier - but better.
That’s the goal. Not perfection. Better.
You’ll mess up again. Different people, different situations, different mistakes. Management is constantly failing at eight things so you can crush the two that matter.
Learn to fail well.
So what mistake are you avoiding right now? What hard conversation have you been pushing off?