How to Run Stay Conversations to Understand What Each Person Values
Find out directly what keeps a top performer here and what would make them leave, while there is still time to act on it. Schedule the conversation right, ask and listen, hold steady under pushback, and close the loop between talks.
Developing
Start here. Build the foundation.- 1
Book a private conversation with each top performer at least twice a year on a set cadence, not squeezed into a project check-in. Say in the invite itself that the purpose is their experience and future, so they arrive ready to talk about staying rather than status.
- 2
Open with what parts of the work they enjoy, what drains them, and how they like to be recognized, then stop talking and let them fill the silence. Ask what they would miss if they left rather than 'Are you happy here?'; the goal is to learn, not to fix anything on the spot.
Proficient
Build consistency and rhythm.- 3
When they raise a complaint about pay, workload, management, or direction, acknowledge it first and ask a genuinely curious follow-up. Do not justify, minimize, or change the subject in the same breath; staying open is what earns the next honest answer.
- 4
Draw out where they want to be in a few years and the specific conditions that would make them consider another offer, and name both out loud so you can check you heard right. Assumed goals are how a manager ends up acting on the wrong ones; let the person correct you.
Mastered
Operate at the highest level.- 5
Right after the conversation, record what you heard and any commitments you made, then follow through before the next one. Open the following conversation by referencing what was said last time, so the person sees the record is real. A good talk with no follow-up costs more trust than not asking at all.
Common Pitfalls
Avoid the common failure modes.- Folding it into a performance review. The setting changes what people are willing to say. Keep the stay conversation separate and private.
- Filling every silence. Leading them to the answer you expected teaches you nothing. Ask, then wait.
- Rebutting a complaint on the spot. The person shuts down and stops testing whether honesty is safe. Acknowledge first, ask second.
- Making a commitment and forgetting it. A promise with no follow-up reads as performative and costs more trust than never asking. Record it and close the loop before the next conversation.