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🧡 The art of the stay interview
#21. And the exact questions to ask to drive understanding

Hello and Happy Thursday!
Today’s 5 minute read lays out a powerful - and often underused - tool for gleaning insight into your team’s current experience at work. Plus I’ve got exactly the template you need to get started as soon as your next one-on-one.
If you’re a manager who cares about your team, a People person looking to introduce a resource to your leaders, or an employee experience buff looking to up your listening game, today’s for you.
Let’s jump in!
Yours in deeper understanding,
Jill
Reflect On This
When was the last time you had a conversation with your direct reports that wasn’t focused on deliverables, performance, or project work?
What has (or hasn’t) changed about the way your team works over the last year? Do you know how your teammates feel about those changes?
Trust me, these conversations matter
A stay interview is pretty much what it sounds like: an interview conducted to gauge satisfaction and understand opportunities for an improved work and career experience. Rather than waiting for the next pulse survey, performance conversation, or - heaven forbid - exit interview, holding regular stay interviews supports a deeper understanding of what keeps individual teammates engaged, productive, and motivated to stick around.
If that sounds like a kickass opportunity to better understand your team, it’s because it is. Well-dialed stay interviews uncover motivations, logistical or resource needs, and insight into teamwide and individual working dynamics.
As always, with great power comes great responsibility (thanks, Uncle Ben). Successful stay interviews require clear expectations, solid context-setting, and a foundation of psychological safety and trust. Follow our guidelines below to set the right tone and start learning more about your team.
➡︎ Define the purpose
The main purpose of conducting stay interviews is to deepen your understanding and glean important insights that help you impact a more positive work experience. Clarify this with your team, adding that their answers won’t be shared with anyone else. Introducing the concept of a stay interview is also a great time to mention that they won’t always yield immediate results or changes, especially as you and your team adjust to the practice.
An important caveat: If you’re not confident that you can maintain appropriate confidentiality, you might not be ready to conduct stay interviews, and that’s okay! Jump down to “Choose your approach” below for tips on easing in.
➡︎ Encourage honesty
Teammates will only be as honest with you as they feel safe being. Before the conversation, be sure to clarify that stay interviews are separate from performance conversation and that feelings discussed in them aren’t grounds for punitive action.
➡︎ Be open to hearing something wiggly
Stay interviews can reveal an uncomfortable truth: that a teammate has outgrown their role, their team, or their time at the company - especially if promotion or growth opportunities are scarce. Remember, the aim is to better understand how you can better impact their experience. A great manager can lean into this insight, supporting the teammate’s career growth needs even if it means they eventually take a new job.
đź”” Resource alert: Would it help to hear a master class in how to support an employee who shares something vulnerable? Have a listen to the discussion Shira Grife and Sara Rodell had on my podcast (and be ready to have your mind blown).
➡︎ Get ready to listen (and only listen)You are only here to listen and confirm your understanding. This is absolutely crucial.
A stay interview isn’t the time to jump in with ideas, solutions, coaching, or your own perspective. It is the time to listen actively and confirm that you really hear what’s being said. Be ready to limit your follow-up participation to questions like “can you help me understand that better?”
Resist the urge to prod or pry. If you come up against vague, cagey, or one-word answers, use my favorite standby, “and what else?” to encourage folks to keep talking.
You care about your team and you want to help. I know the temptation to jump to solutions will be strong. Instead, come prepared to take great notes, and then make a point to address actionable items, coaching opportunities, or clarifications in upcoming one-on-ones.
➡︎ Choose your approach
Our tool below outlines an interview to conduct with each teammate at their yearly “workaversary.” We think it’s a great way to acknowledge a milestone while demonstrating continued commitment to their experience. Or, you can schedule interviews at roughly the same time, posing the same questions to each individual and gleaning insight from various levels of tenure. This can be a great option if your organization doesn’t have many employee experience feedback or survey mechanisms in place.
Not sure you or your team are ready for stay interviews at all? That’s okay! Our guide below offers great questions that you can start sprinkling into your one-on-ones or team meetings. You’ll start uncovering new glimmers of understanding, while learning more about how you and your team navigate new levels of trust or transparency.
Your Turn
Ready to give it a go? I’m so excited for you! We’ve designed a template and question set you can use to conduct one-year stay interviews on your own teammates.
Not sure if the time is right for you or your team?
Have a peek anyway! I’m certain you’ll find an excellent question or two to sneak into upcoming one-on-ones to drive listening and understanding with your teammates.
Things We're Loving Right Now
Totally sold on stay interviews? There are firms and a handful of consultants that specialize in conducting company-wide stay interviews, synthesizing results, and advising on next steps. We love Hear Me Out, which founder Ben Jackson started to “help leaders get the full story.”
The data on all things distributed: Are you an HR or People profesh working at a distributed company? Carve out 15 minutes to complete Shelby Wolpa’s “Distributed Work: People & Practices Survey” by 2/23. Complete the full survey to receive the full results report.
“Being nice does not equal being anti-racist.” This month, challenge yourself to do what Paul Lapido describes so poignantly as practicing both “[needed] niceness AND a willingness to understand and dissect racism.” His awesome LinkedIn post - featuring a crystal clear infographic by Sheva Guy - is a perfect invitation to challenge our notions of niceness.
Pardon our French: Are you "tired of seeing the same broken elements in the workplace happening over and over again?" So is Anessa Fike. The kindle version of her new book, "The Revolution of Work: Fuck the Patriarchy and the Workplace it Built" is available now for pre-order now!
