Boosting Retention: Insights and Questions from Stay Interview Experts
Stay interviews are a powerful tool for enhancing employee retention, but how can organizations make the most of them? This article presents valuable insights from experts in the field, offering practical strategies to transform these conversations into meaningful opportunities for growth and engagement. Discover how to uncover employee motivations, create an environment for open dialogue, and identify the conditions that lead to peak performance and job satisfaction.
- Reframe Stay Interviews as Growth Conversations
- Uncover Motivations and Friction Points
- Proactive Listening Reveals Employee Priorities
- Balance Enjoyment with Potential Improvements
- Create Space for Meaningful Dialogue
- Identify Conditions for Peak Performance
- Explore Energy Sources and Drains Regularly
Reframe Stay Interviews as Growth Conversations
Start by reframing your thinking. A “Stay” interview is at least somewhat tethered to the mindset that the goal is to “keep employees from leaving.” This is not the goal — the goal is to help them grow as professionals and achieve more. In that conversation, there is an exploration of their wants and needs, and the company’s. Have that conversation; it works better.
So to go directly to your question, I’d ask the employee: “What are the top three roles, goals, or experiences that would help you grow your career?”
Nathan Deily
Chief People Officer, nth Venture
Uncover Motivations and Friction Points
I hold stay interviews as casual, low-stress conversations with the intent to find out what retains employees and what would drive them to leave. I don’t utilize scripted frameworks but attempt to encourage open dialogue by framing questions around their everyday experiences.
One question that has received very insightful responses is, “What gets you in the door every day, and what makes you think twice?” This question reveals both the source of intrinsic motivation and points of friction that can be solved to improve retention.
George Fironov
Co-Founder & CEO, Talmatic
Proactive Listening Reveals Employee Priorities
I’ve learned that the best way to retain great people isn’t with perks or policies — it’s through real conversations. That’s why stay interviews have become a key part of how we build culture and trust.
Unlike exit interviews, which are often too late, stay interviews give us a chance to ask: “What’s keeping you here, and what might push you away?” It’s not about checking a box. It’s about making space for open, honest feedback before someone starts looking elsewhere. I treat these conversations less like interviews and more like listening sessions — no agenda, no judgment, just curiosity.
One question that’s consistently yielded valuable insight is: “What part of your job do you wish you could spend more time on — and what’s getting in the way?” It’s deceptively simple, but it opens up so much. I’ve had designers tell me they feel buried in reactive tasks and miss the space to think creatively. I’ve had engineers say they’d love to mentor more junior teammates but don’t know if it’s encouraged. And I’ve had people share that they feel energized when collaborating cross-functionally, yet rarely get the chance.
What makes this question powerful is that it reveals both what people want more of and the obstacles we may not be seeing from the top. It gives us actionable direction — whether it’s adjusting workload, rethinking team structure, or simply giving permission for someone to step into more of what lights them up.
We don’t wait for an engagement survey to tell us if something’s off. Stay interviews help us stay in tune with what matters most to our team — before they feel the need to go elsewhere to find it. And in a competitive talent landscape, that kind of proactive listening isn’t just smart leadership — it’s essential.
Balance Enjoyment with Potential Improvements
When conducting stay interviews, I focus on creating a comfortable and open environment where employees feel they can speak honestly. I approach these conversations with curiosity and active listening to truly understand their experiences and perspectives. One question that has consistently provided valuable insights is, “What do you enjoy most about your role here, and what’s one thing you would change if you could?” This question highlights what motivates them and helps uncover opportunities for improvement, making employees feel heard and valued.
Robbert Bink
Founder, Crypto Recovery Services
Create Space for Meaningful Dialogue
The most effective way to approach an interview is to turn it into a conversation to understand the psychology behind it and make it meaningful. It’s not always about typical HR check-ins. Instead, it’s about creating a space where employees don’t feel constantly judged or evaluated, but genuinely heard and valued. These are neither performance reviews nor exit interviews. Rather, they are meant to set a tone, making it a conversation about what makes employees stay or leave. Additionally, it’s about exploring what can be done to enhance their day-to-day experience.
Asking questions like, “What part of your job makes you feel most fulfilled, and how often do you get to do that?” helps in building a culture that will always be encouraged and uncovers much more than surface-level job satisfaction.
Ansh Arora
CEO, Inspiringlads
Identify Conditions for Peak Performance
I find that most stay interviews focus too much on the risk of leaving. They often ask what’s wrong or what might push someone out the door. My approach is different. I treat it like a continuous improvement conversation, focusing on what enables high performance. The most insightful question I use is: “Think about a day in the last month when you left work feeling truly energized and successful. What were you working on, and what conditions made that feeling possible?”
This question reframes the entire discussion. Instead of a list of complaints, you get a blueprint for the specific, tangible conditions that create engagement. It might be uninterrupted focus time, a clear goal, or a specific type of collaboration. These are the factors that truly drive retention. You’re not just trying to prevent people from leaving. You’re actively building an environment where they can do their best work and want to stay.
Maria Matarelli
CEO, Formula Ink
Explore Energy Sources and Drains Regularly
I treat stay interviews as ongoing conversations — not one-off events. We recommend quarterly check-ins instead of annual ones to help leaders catch concerns early and track shifts over time. Tools like Pulse Surveys or our Positive Culture Index (PCI) are great for spotting emerging trends and shaping these interviews as conversations rather than evaluations. Managers are trained to listen actively — without jumping in to defend or explain—so employees feel heard.
One question that consistently yields powerful insights is: “What part of your work feels most energizing — and what part feels like a drain?” It opens the door to honest reflections about role fit, team dynamics, and the emotional climate of the workplace.
Paul Fayad
Co-Founder and Managing Partner, Positive Leader