Your Coworker’s a Mess. Should You Say Something?
How to balance honesty with empathy when a teammate’s behavior crosses the line.
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What do you do when a coworker’s behavior makes your whole team look bad — and your boss blames you for speaking up?
We came across this real workplace dilemma online. It’s messy, uncomfortable, and surprisingly common. And no one really teaches you how to handle it.
The situation:
Let’s call the person Alex. And the difficult coworker, Ryan.
Alex and Ryan work together handling customer finances. But Ryan keeps fooling around — cracking jokes, dancing in the office, making careless mistakes.
It frustrates the team and confuses the customers.
One day, a customer quietly told Alex:
"This is the second time I thought Ryan might be drunk at work."
Alex knew Ryan wasn’t drinking. But the fact that a customer thought so showed how unprofessional Ryan's behavior looked.
Later, when Ryan was joking around again, Alex lost patience and blurted out:
"A customer thought you were drinking the other day. Maybe try acting a bit more professional."
Ryan immediately shut down. He stayed quiet and withdrawn for the rest of the day.
But here’s the twist:
Instead of addressing Ryan’s behavior, the boss scolded Alex for speaking up.
Now Alex is left wondering — was I wrong to say something?
So... was Alex wrong?
No. But the approach could’ve been better.
Let’s unpack some better ways this could’ve played out:
Scenario 1: A Direct but Kind Conversation
Alex could’ve pulled Ryan aside privately:
"Hey, I know you’re having fun, but it’s confusing the customers. One of them even asked if you were drinking. Maybe tone it down during work hours."
✅ Honest but respectful
✅ Gives Ryan a chance to correct himself without shame
✅ Avoids public embarrassment
Scenario 2: Escalate to the Boss First
Alex could’ve raised it quietly with the boss:
"A customer mentioned this about Ryan. I think we need to address it as a team concern."
✅ Keeps emotions out of it
✅ Makes it a leadership responsibility
✅ Reduces personal conflict
Scenario 3: Address It as a Team Norm
If this was happening often, Alex could’ve brought it up in a team huddle:
"Hey everyone, let’s keep things professional when customers are around. Lately, there’s been some confusion about our behavior."
✅ Talks about the culture, not the person
✅ Avoids singling Ryan out
✅ Sets shared expectations
Scenario 4: What Actually Happened
Alex, frustrated, blurted out something sharp in front of others:
"Customers think you’re drunk. Be more professional."
⚠️ The message was true, but harsh
⚠️ It embarrassed Ryan instead of helping him
⚠️ It created more tension, not better understanding
The takeaway:
Speaking up is right. Staying silent helps no one.
But in work life, it’s not enough to be right — you have to be wise about how you speak up.
Alex had the right concern, but the wrong delivery.
If your goal is to fix the problem (not just vent your frustration), ask yourself:
→ Should this be a private conversation?
→ Should the boss handle it?
→ Can I say this in a way that helps, not hurts?
It’s easy to call people out.
It’s harder — but more useful — to call them up.
This post is part of Remote Jobs and You — a daily Substack newsletter sharing remote jobs and thoughtful ideas to inspire how you work and live.