← All Toolkits Pipa

Prepare for a stay conversation.

The best time to have a stay conversation is before you think you need one. Answer five questions and you'll know how to walk in.

Question 1 of 5

Who is this conversation with — and what's made you decide to have it now?

Name the signal, however small. Acting early is the whole point.

Question 2 of 5

What do you already know about what matters most to them here?

From previous conversations, how they engage, what they've expressed. Don't go in blank — but hold it loosely. People change, and this conversation might update what you think you know.

Question 3 of 5

What's actually in your power to change or offer — if they raise it?

Know this before you open the conversation. You can't promise what isn't yours to give. But knowing the edges of what you can genuinely do changes how you listen.

Question 4 of 5

What's the thing you're most worried they'll say?

The thing you're hoping won't come up. Name it — if you can't address it honestly, that's important to know before you're in the room.

Question 5 of 5

What do you want them to feel when they leave this conversation?

Not what you want to say — what you want them to take away. Heard. Valued. Clearer. Surprised you asked. Name it.

Stay Conversation Prep Sheet

Conversation with —

The Person
Who you're going into this with — and why now
What You Know
What matters to them — going in
What's In Your Hands
The honest range of what you can offer
Opening
How to start — without it feeling like an ambush
Your Worry, Named
What you're hoping won't come up — and why it might be okay if it does
What You're Aiming For
How you want them to leave
Before you go in

Record this conversation →
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

How to open it, what to ask, and what to do when it's harder than you hoped.

The opening sets the whole tone. Get it wrong and the person goes into self-protection mode. The goal is to be genuinely curious — not performing concern, not fishing for a confession.

What works
Direct, warm, no agenda visible
The best openings are short and honest. Name that you wanted to check in — not on projects, on them. Then ask and wait. Don't fill the silence. The pause after a genuine question is where the real answer usually starts.
"I wanted to carve out some time to check in properly — not about work, but about you. How are you actually finding things right now?"
What to avoid
The signals that shut people down
Avoid anything that sounds like an HR script ("I just wanted to touch base on your engagement"), opens with the company's needs ("we really need you on this team"), or implies you already know something ("I've noticed you seem a bit checked out lately"). All of these make people feel managed, not heard.
If it feels awkward
Name it
If the conversation feels a bit unusual — you don't usually have this kind of check-in — you can say so. "I realize we don't always make time for this kind of conversation, and I want to change that." Naming the awkwardness takes the pressure out of it.

The point of these questions is to understand, not to retain at all costs. Ask with genuine curiosity. The answers belong to them — don't argue with them, minimise them, or immediately pivot to solutions.

  • What's been giving you energy lately — at work or outside it?
  • What's one thing, if it changed, that would make a real difference to how you feel here?
  • Is there anything you're not getting here that you feel like you need?
  • What kind of work do you most want to be doing in the next year or two?
  • Do you feel like there's a path for you here — and does it feel realistic?
  • Is there anything I do — or don't do — as a manager that makes things harder for you?
  • What would need to be true for this to feel like the right place for you, long term?

You won't ask all of these. Pick one or two that feel right for where things are. Let the conversation go where it needs to go — these are starting points, not a script.

Sometimes you open the conversation and realize it's further along than the signals suggested. They're actively looking. They have an offer. They've made a decision they haven't said out loud yet. Here's how to handle each.

If they're actively looking
Don't panic — get curious
Ask what's driving the search before you respond. Is it money, growth, culture, a specific opportunity? Understanding the real reason is more useful than counter-arguing. Then be honest about what you can and can't offer. "I'd rather know this and try to do something about it than not know."
"I'm glad you told me. Can I ask what's driving it? I want to understand what's actually pulling you before I respond — I might be able to do something about it, or I might not, but I want to try."
If they have an offer
Take it seriously without panicking
Resist the urge to match immediately or dismiss the offer. Ask what's appealing about it — often it's not only the money. Then be honest about what's possible here, without over-promising. A counter-offer that buys three months and then they leave anyway helps no one.
"What is it about the opportunity that's attracting you? Is it the role itself, the money, a change of scene — or something else? I want to give you a real response, not just try to keep you."
If the decision feels already made
Let them go well
If someone has mentally moved on, trying to retain them often makes things worse — for them and for the team. The most useful thing you can do is acknowledge what they've contributed, wish them well genuinely, and make the transition as clean as possible. People leave companies. They remember how they were treated on the way out.
"If you've made a decision, I respect that — and I want to support it. Can we talk about how to make the transition work well for everyone, including you?"

The pressure to promise things in a stay conversation is real. Resist it. Over-promising damages trust more than a clear "I don't know yet" or "that's not in my hands."

Things you can commit to
Within your control to follow through on
You can commit to: taking what they've said seriously; following up on specific things by a named date; advocating for them internally; having a dedicated career conversation; removing something that's in your gift to remove; checking in again in a defined timeframe.
"What I can commit to right now is this: I'll look into [X] and come back to you by [date]. And I want us to have a proper career conversation before end of month — not a passing chat, an actual conversation."
Things you can't commit to
Say so clearly — vague hope is worse than a clear no
You can't commit to: guaranteed promotions or timelines, matching an external offer without going through the right process, changing things that are above your level, or outcomes that depend on factors neither of you controls. Say you don't know rather than implying you can when you can't.
"I can't promise that — it's not mine to promise. What I can do is make the case and tell you honestly what I hear back."

A stay conversation that doesn't lead to action is worse than no stay conversation. It signals that you asked but didn't care enough to follow through — and people notice.

The same day
Write it down while it's fresh
Use the Stay Conversation record to capture what came up, what you committed to, and your honest read on where they are. Do this the same day — detail fades fast and the record is what makes your follow-through credible.
Within the week
Show the first small action
Even something small — a message, a calendar invite, a piece of information — signals that you meant what you said. The gap between the conversation and the first visible action is where trust is either built or lost.
Ongoing
This isn't a one-off
Stay conversations work best as a pattern, not an intervention. If you're only having them when you're worried, you're already behind. Build them into your rhythm — every quarter for people who matter, whenever the signals shift.