How to Confront Employee Behavior That Makes You Cringe

Some conversations in leadership leave you thinking:

"Why do I even need to say this?"

Or worse... "How the hell is this my problem right now?"

Like having to ask a grown adult to wipe their own fecal matter off the toilet seat.

Or reminding your front desk coordinator that showing up with sopping wet hair—when you’re the first face donors see—isn’t the impression you want to lead with.

You might be thinking... wow, those must be fake examples.

They’re not. They’re real stories and requests for help from my DMs last week.

And the more I sit with them, the clearer it becomes:

Leaders aren’t just managing performance. They’re managing personal quirks that veer into disruptive, unhygienic, or just socially off behavior.

And it’s not just awkward, it’s infantilizing.

Instead of directing strategy or coaching execution, you’re navigating issues that shouldn’t even be on your desk.

And unfortunately, no matter how absurd the behavior is… if you don’t address it, you become the standard people start measuring against.

This is what happens when self-awareness goes unchecked—and no one names it.

The hardest part about all of this isn’t having the conversation with someone.

It’s getting over your own secondhand embarrassment long enough to have it.

Because before you ever say the thing out loud, a voice in your head is already screaming “I can’t believe I’m about to say this to another adult human.”

It feels humiliating, for them and yourself.

And if you don’t metabolize that discomfort first, you’ll either:

• Outsource the issue to HR (and resent that nothing changes)

• Let it slide (and slowly detach from your own standards)

• Or say it sideways, sharp, or too late (and do more damage than good)

This is the double burden of these conversations.

You’re not just navigating a difficult topic.

You’re regulating your nervous system while trying not to shame someone who doesn’t even seem embarrassed.

And that means there are two things you need to lead through:

You already know it’s awkward.

You’ve probably rehearsed the opener in your head three times. You’re still mad this is even your job.

So don’t override it. Sit with it briefly and purposefully.

Here’s what that actually looks like:

1.) Write the pettiest version first. Not the professional one or cleaned-up version you’ll actually say. The unfiltered thought.

“I can’t believe I have to ask you to wipe your fucking ass.” 

Get it out of your system. Let the ridiculousness surface without shame.

2.) Then write the cultural cost. What happens if you don’t say anything?

“If I let this slide, I normalize it. If I stay quiet, I become complicit.”

Anchor in why this matters, beyond your discomfort.

3.) Last, name what kind of leader you want to be. Not perfectly poised or emotionally neutral. Just clear.

“I don’t have to like this conversation. But I do have to own it.”

This will help you work through the mismatch between gravity and absurdity.

Part 2: The Conversation

By the time you sit down to have it, your system’s already been through the full arc: disbelief, embarrassment, irritation, restraint.

Good.

That means you’re not walking in hot. You’re walking in grounded.

Here’s what that sounds like in practice:

Then name it—simply. No sugarcoating.

Or:

Pause. Let it be uncomfortable.

Let them feel the disruption their behavior has caused—without rushing in to make it easier.

And expect this:

They’ll likely say something vague or minimizing.

• “Oh, I didn’t realize.”

• “No one ever said anything before.”

• “That wasn’t my intention.”

Doesn’t matter.

You’re not here to litigate intent. You’re here to name impact and hold the standard.

Once you hold the line. Set the expectation:

And finally, name the consequence. Clearly.

The most important thing to remember in all of this is:

Letting someone sit in the discomfort of their behavior isn’t cruel. It’s sobering.

It communicates: this matters, and I trust you enough not to rescue you from it.

When leaders over-index on being palatable, they end up protecting people from the very tension that would wake them up.

And in doing so, they strip away the friction required to self-correct.

So don’t round off the edge and don’t soften the moment just to make it easier.

Let it land.

And be okay if it stings.