Hard Conversations
Nobody teaches you this part. You get promoted, and suddenly you’re responsible for conversations that have real consequences for real people — and there’s no manual.
Here’s what I learned from having a lot of them.
The Main Thing
Most hard conversations feel enormous before they happen and are over in three minutes.
The anticipation is the worst part. The longer you wait, the more the thing grows in your head, and the more damage it does in the meantime — to the crew member, to the team, and to your credibility as someone who handles things.
Have the conversation. Have it sooner than feels comfortable. You’ll get through it.
The Uncomfortable Ones Nobody Talks About
Personal hygiene. New FTOs ask about this constantly. The answer is the same as everything else: private, direct, kind, fast. “Hey, I want to give you a heads up — there’s a hygiene concern that’s come up. I want to address it now before it becomes a bigger issue for you on the job. Can we talk through it?” That’s it. Don’t elaborate beyond what’s necessary. Don’t make it weird by over-softening it. Say it, give them space to respond, and move on.
Performance that’s declining. Don’t wait until it’s a disciplinary issue. The earlier you have the conversation, the more options everyone has. “I’ve noticed X, and I want to check in before it becomes a pattern. What’s going on?” leaves the door open. Waiting until you’re writing someone up closes it.
Interpersonal conflict between crew members. Don’t pick sides. Don’t adjudicate who was right. Talk to each person separately first, understand what they actually experienced, then decide if a joint conversation makes sense. Sometimes people just need to be heard. Sometimes the issue is structural and the conflict is just the symptom.
The Serious Ones
At some point in your career as a supervisor, someone is going to bring you something serious — harassment, misconduct, something that has to go to HR and beyond.
When that happens:
Be the person they came to. They came to you for a reason. Honor that. Listen fully before you do anything else.
Be clear about what you’re required to do. Don’t make promises you can’t keep about confidentiality. If what they’re describing requires you to report, tell them that — before they finish the story if possible, or immediately after. Don’t let them believe the conversation stayed between you when it didn’t.
Act quickly. The moment you know, you’re on the clock. Slow-walking it protects no one and creates liability for everyone including you.
Follow up. Whatever happened to the person who came to you matters. Check in. You don’t always have the ability to share details, but you can say “I want you to know I took this seriously and it’s being handled.”
The measure of a supervisor in these moments isn’t perfection — it’s whether the person who came to you felt heard, protected, and respected.
The Conversation After Something Goes Wrong
Crew makes a mistake. Something bad happens on a call. Now what?
Resist the urge to make it immediately about accountability. Lead with the person first — how are they doing, what are they carrying. Then, when the moment is right, move into the debrief. See The Debrief for the full framework.
The goal is not to assign blame. The goal is to understand what happened, support the crew member through it, and extract whatever learning is available. Those are three different things and they need to happen in that order.
Your Own Hard Conversations
You’re going to have supervisors above you who are wrong, political, inconsistent, or ineffective. You’re going to have to disagree with people who have more authority than you.
Be specific and factual. “I’m concerned about X because Y” is a conversation. “This is unfair” is an argument. Bring the data when you can. Pick your moments — not in front of others, not when the other person is already defensive.
And sometimes you’ll be right, make the case clearly, and still not win. That’s part of the job. Disagree, document if necessary, and continue doing your work well.
Related
- The Debrief — for conversations about specific calls
- Training FTOs — coaching FTOs through their first hard conversations
- Leadership Philosophy — trust as the foundation
Take this further
The companion tool for this chapter is Tool 05: Performance Conversation Record — documents the conversation, sets clear expectations, tracks severity level. Not a disciplinary form. A record of a conversation that already happened. Included in the EMS Supervisor Field Guide, free with your email on Gumroad.