← Stay Conversation Toolkit Pipa

Stay Conversation

The best time to have a stay conversation is before you think you need one. Use this when you sense someone is disengaging or being pulled elsewhere — and you want to understand what’s really going on before they walk out the door.

Context
What prompted this conversation
What signals did you notice? Be honest with yourself here — the earlier you act on a signal, the more options you have.
What they love
What’s working for them
Ask before you assume. What do they find most meaningful? What energises them? What would they miss? This tells you what to protect.
What’s frustrating them
The honest friction
Create space for this. Most people won’t say it unless you ask directly and make it safe. "What’s one thing that, if it changed, would make a real difference to how you feel here?" is often better than "what’s frustrating you?"
What would make them stay
What they actually need
Ask directly. "If we could change one or two things, what would make the biggest difference?" Don’t promise what you can’t deliver — but don’t dismiss what you hear either.
Career aspirations
Where they want to go
Not just the next role — the longer view. What kind of work excites them? What are they building toward? Does this company have a path that fits?
Your commitments
What you’re going to do
A stay conversation without follow-through is worse than no stay conversation. Whatever you say you’ll do here, do it. If you can’t commit, don’t imply you can.
Retention confidence
Your honest read after this conversation
Not about how the conversation felt — about how likely you think they are to stay in the next 6 months.
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