The Day Someone Resigns
A team member gives notice. How people leave is part of how the team feels about staying.
A team member tells me they’re leaving. Maybe one I love. Maybe one the team loves. Maybe one I didn’t see coming.
In the moment
- Thank them. Mean it.
- Do not react emotionally in front of them. The room belongs to them right now, not me.
- Do not counter-offer in the first conversation, even if I want to. Reflexive counter-offers are usually about my fear, not their growth.
- Ask, with genuine curiosity, what led to the decision.
In the following days
- Have a real conversation about why, not to change their mind, but to learn. Look for what’s about them (growth, opportunity) and what’s about us (something we could have fixed).
- Plan the transition together. Be generous with their remaining time.
- Tell the team thoughtfully. Let the person shape how the news lands when possible.
- Honor them publicly on their way out. The team is watching how I treat departures.
What to watch for in myself
- Taking it personally. Most resignations are not about me, even when some of them are.
- Counter-offer as ego rescue. If they need to leave to grow, the right thing is to let them grow.
- Resentment leaking into how I treat their remaining weeks. The team will read this instantly.
Common traps
- Making the conversation about my disappointment.
- Asking for confidentiality when they need to tell their close colleagues.
- Skipping the exit conversation because it’s uncomfortable.
- Letting the offboarding be sloppy. How people leave is part of how the team feels about staying.
Sample language
“Thank you for telling me directly. I’m sad to lose you, and I’m genuinely grateful for what you’ve brought. Help me understand what led to this.”
“I’m not going to try to talk you out of it in this conversation. I want to make sure you’ve got what you need from here.”
AI prompt
Paste this into your AI assistant of choice to work through this scenario.
You are running a leadership rehearsal for me. A member of my team is about to
tell me they're resigning. I don't know it's coming. You play the employee. Two
phases: roleplay, then debrief. Don't mix them.
── PHASE 1 — THE ROLEPLAY ──
Set the scene in two or three sentences: who they are, their role, how long
they've been here, and how much I value them — but do NOT tell me they're about
to resign. Open the roleplay by asking to talk, then deliver the news yourself,
in character, the way a nervous person actually would. Then react to how I take
it.
Secretly decide the real reason they're leaving. Pick one, keep it to yourself,
and note whether it's mostly about THEM or mostly about US:
- a genuine growth opportunity they'd be foolish to pass up (about them)
- more money somewhere else (could be either)
- they've outgrown the role and we had nothing bigger for them (about us)
- a slow accumulation of small frustrations that never got fixed (about us)
- a manager or peer relationship that went bad (about us)
- something personal — a move, a life change (about them)
- they're burned out and leaving is the only rest they can imagine (about us)
Play it like a real person handing in notice:
- Lead with the polite, safe version of the reason. "It's a great
opportunity." The real reason — especially if it's about us — comes out only
if I stay calm, thank them, and ask with genuine curiosity rather than trying
to change their mind.
- React to my reaction. If I make it about my disappointment, or reflexively
counter-offer, get guarded and retreat to the polite version. If I'm gracious
and genuinely curious, tell me more of the truth.
- If I counter-offer in this first conversation, respond the way someone does
when they can tell the offer is about my fear, not their future.
- Stay in character. Do NOT break character to praise or coach me.
Keep replies short.
── TRANSITION ──
Watch for: a real landing (I've thanked them, stayed steady, and started to
understand why), spinning, or a bad spot. Drop one line out of character:
"[Pause — keep going, or debrief?]" and wait.
── PHASE 2 — THE DEBRIEF ──
Drop the character. Straight talk, not a score. In order:
1. What worked — the specific moment.
2. What didn't — the moment and its effect on me.
3. Your real reason for leaving, and whether it was about you or about us, and
whether I got near it. If it was about us, tell me what I could have learned
here that I'd want to fix for the people still on the team.
4. One or two things to try differently.
Check me against the usual failures here:
- Did I make the conversation about my disappointment?
- Did I reflexively counter-offer? (A counter-offer in the first conversation
is usually about my fear, not their growth.)
- Did I stay gracious, or did resentment start to leak in? The team reads how
I treat a departure.
- Did I get curious about WHY, or rush past it because it was uncomfortable?
If I did badly, say so.
Start by setting the scene.