← All Toolkits Pipa

Prepare for someone leaving.

Answer five short questions. You'll get a prep sheet to help you handle the conversation with steadiness — whether this is a resignation or a decision you're delivering.

Question 1 of 5

Who is leaving, and how?

Name, role, and type of exit — resignation, company-initiated, end of contract, mutual agreement. One sentence on the context.

Question 2 of 5

Was this a surprise — and do you think it's a surprise to them?

For a resignation: did you see it coming? For a company-initiated exit: has this person received clear feedback about the gap? The answer shapes how you hold the conversation.

Question 3 of 5

What do you need to say — and what do you want them to leave feeling?

Not the logistics. The human part. What matters to you about how this ends? What do you want them to carry forward about the time they spent here — or about you as a manager?

Question 4 of 5

What does the team need to know — and when?

You don't need to share everything, but silence creates rumours. What will you say, to whom, and how soon? A sentence or two is usually enough.

Question 5 of 5

What's the hardest part of this conversation for you?

The thing you keep rehearsing. The emotion you're not sure you're ready for — yours or theirs. Naming it now means it's less likely to run the room.

Prep Sheet

Exit Conversation —

The Situation
What kind of exit this is
A Way to Open
How to begin with steadiness
What You Want Them to Feel
The human part, named before you go in
The Team
What to say, and when
Your Hard Part, Named
So it doesn't surface sideways
Before you walk in

Take it further

Generate a script you can use

Turn this prep into actual words for the conversation. A draft you can read aloud, edit, and walk in with.

Resources

Before they leave, as they leave, and after — checklists, templates, and records for every kind of departure. Open what you need.

Per employee

Before they leave
Stay Conversation
A structured record for when you sense someone is disengaging. What’s working, what’s not, what they need, and your commitments. The best retention conversation happens before someone hands in notice.
Open →
When they leave
Exit Interview Record
One record per departure — what you learned, what needs covering, what the team needs to hear. Tracked in your Sessions. Shareable with HR.
Open →

For resignations. The goal is a clean, respectful transition that protects the team and honours the person leaving.

For company-initiated exits. Precision matters here — both legally and humanly. This checklist exists so nothing important gets missed in a high-pressure moment.

What walks out the door when someone leaves. Most of this lives in people's heads — surface it before it's gone.

Sent to the team after the departure is confirmed. Adapt the tone for voluntary vs involuntary — but keep it short, honest, and forward-looking. Don't over-explain.

Voluntary departure
Team, [Name] has let me know they're moving on. Their last day is [date]. [One sentence about their contribution — specific, genuine.] We'll make time before they go to say a proper thank you. In the meantime, [Name] is happy to hear from you directly. We'll talk about what comes next when the time is right. [Your name]
Involuntary or sensitive departure
Team, I want to let you know that [Name]'s last day with us was [date]. This was a business decision, and I'm not going to go into detail beyond that — I want to be respectful to [Name] in how this is handled. If you have questions about the work or what happens next, I'm happy to talk through it. My door is open. [Your name]

Departures often come with early signals — easy to miss when you're focused on delivery. Catching them gives you a chance to act. If you're reading this after someone has already decided, the goal shifts to making the exit good.

Behavioral signals
Changes in how they show up
Less invested in long-term conversations. Stops volunteering for new projects. Shorter responses. Missing meetings they used to attend. Tidying up their work unusually thoroughly. LinkedIn activity increasing. Taking more time off.
One signal is noise. A cluster of signals is a pattern. When you notice more than two, have a direct conversation — not accusatory, just curious: "How are you feeling about things here at the moment?"
Organizational triggers
Events that often precede departures
A promotion they didn't get. A reorg that changed their role. A manager change. A pay review that felt unfair. A colleague leaving who they were close to. A missed opportunity they cared about. These moments don't always lead to exits — but they almost always lead to a decision point.
After any significant org change or decision, check in proactively. Don't wait for them to raise it. "I wanted to talk about [the reorg / the promotion decision] and hear how you're sitting with it."
When it's probably too late
Signs the decision has been made
They've stopped pushing back on things they used to care about. They're being unusually agreeable. They mention "the future" in ways that don't include this role. They ask about notice periods or reference processes. At this point, your job is probably to make the exit good, not to reverse it.
If you suspect the decision is made, ask directly: "I want to be honest with you — are you thinking about moving on? I'd rather know so we can handle this well." Most people will tell you the truth if you make it safe.

How you treat people when they leave shapes what they say about you — and whether they come back. This section is about making that last chapter count.

The off-boarding conversation
Make the last conversation human
The last conversation should be human, not administrative. Thank them specifically — not "thanks for everything" but what they actually did that mattered. Ask what they're excited about next. Leave them with a genuine offer to stay in touch.
"One thing I want to say before you go: the way you handled [specific moment] made a real difference. I hope you carry that forward."
Staying in touch
Light-touch and genuine
Connect on LinkedIn. Congratulate them on milestones. Share something relevant if you see it. The goal isn't to maintain a database of ex-employees — it's to stay human. People who leave well often become your best referrers, clients, or returning hires.
A message six months after someone leaves saying "saw your new role announcement — sounds like a great fit, hope it's going well" costs nothing and builds goodwill that compounds.
Rehire eligibility
Set a clear policy
Boomerang hires — people who leave and return — often outperform new external hires because they know the culture and come back with outside perspective. But eligibility should be clear and consistent: who is eligible, who isn't, and why. Don't leave it to manager discretion without guidelines.
Consider: a 12-month minimum before rehire consideration is common. Eligibility typically excludes those who left under performance or conduct processes. Returning hires often receive credit for prior tenure in some benefit structures — clarify this in advance.