5 Stay Interview Questions to Boost Employee Retention Now

Managers often learn what went wrong only after someone hands in their notice. Stay interviews reverse that dynamic by openly discussing what’s working — and what isn’t.

Held regularly, these conversations give managers clarity on each employee’s priorities and reinforce the idea that retention is a day‑to‑day responsibility, not just an HR program.

A stay interview is a focused one‑on‑one that uncovers:

• Why employees stay engaged
• What might push them to look elsewhere, and
• How managers can act before doubts turn into departures.

When leaders listen and respond in real time, they build the kind of trust that makes people choose to stay.

Why Stay Interviews Matter More Than Ever

Stay interviews are more important than ever because they give managers a way to uncover potential problems early — before an employee starts weighing other options.

These conversations go deeper than survey data and give managers direct insight into what each person needs to stay motivated and engaged. They also give employees a clear signal that their input matters before disengagement sets in.

Here’s why stay interviews are now essential:

• Real-time insight into engagement and risk. Engagement surveys can show trends, but they don’t uncover what may cause a high performer to leave next quarter. Stay interviews provide real-time, individual-level insight into satisfaction, friction points, and potential flight risks — often before red flags show up in performance data.
• Personalization matters more than ever. Stay interviews allow managers to learn and possibly act on what matters to each employee — whether that’s growth opportunities or greater flexibility.
• Managers are now retention owners. HR can set strategy, but managers shape the day-to-day employee experience. Stay interviews equip people leaders with structured conversations that build trust and surface concerns early. Plus, they send a clear message: “We want you to stay, and we’re listening.”
• The cost of reactive retention is too high. Counteroffers, backfills and rushed searches are expensive. Stay interviews give HR time to respond proactively, such as adjusting development plans, reallocating workload or addressing toxic team dynamics before these problems push someone out.
• Employee retention is now tied to culture and brand. When employees feel heard and valued, it reinforces an internal culture of trust and an external employer brand that attracts new talent. Stay interviews can help protect your reputation as a great place to work.

When done right, stay interviews let employees know they are valued.

Why Traditional Retention Strategies Fail

Why is retention so hard to maintain? Because many companies get retention all wrong, according to Richard Finnegan, a stay interview expert and CEO at C-Suite Analytics.

Many take a “one size fits all” approach, where the onus is on HR to improve retention through:

• Engagement surveys
• Exit surveys
• Exit interviews
• Salary surveys
• Benefits surveys, and
• Employee committees.

But retention isn’t an HR-only problem. In fact, employee retention has more to do with day-to-day interactions and processes, meaning that supervisors and leaders can significantly influence whether an employee stays or goes – and it all comes down to trust.

“Leaders drive retention by building one-on-one trust with each employee,” Finnegan says.  

To make a lasting positive impact on retention, it’s essential to move the responsibility from HR to operations, “where it’s always belonged,” according to Finnegan. HR can help shift the responsibility by coaching managers to conduct stay interviews to get more in touch with what employees need.

Stay Interview Best Practices to Improve Retention

A stay interview can uncover what’s working – and what’s not – and provide valuable insight into what employees really need. In addition to bringing forward information that can be used in the here-and-now, they provide an individualized approach to employee retention, as well as help put managers in the solution seat.

However, stay interviews are only effective when they’re done right. Here are three best practices for conducting an effective stay interview:

• Ensure interviews are always done by supervisors, never HR
• Separate stay interviews from performance reviews, and
• Conduct interviews once a year with team members and twice with new hires in their new-hire goal period.

5 Stay Interview Questions to Ask

Here are five proven questions, courtesy of Finnegan, that give managers a structured way to uncover what matters most to each employee.

1. When you come to work each day, what things do you look forward to?

“Our brains are built to be negative,” says Finnegan. Asking employees what they look forward to forces them to shift their mindset from negative to positive and can help bring their thinking into the here and now.

2. What are you learning here?

“Helping people learn is not low-hanging fruit; it’s fruit on the ground,” Finnegan says.

With more employees desiring opportunities for learning and development, focusing on learning and career development can help give managers insight into what an employee already knows and what skills they can improve on.

3. Why do you stay here?

Many employees don’t have an immediate answer because it’s not thought about very often, but having an employee identify why they stay can help shine a light on the positive and give leaders insight into what they enjoy so they can be more engaged at work.

“The goal is to get the employee to discover why they stay and announce it out loud so they hear themselves say why they stay,” says Finnegan.

4. When was the last time you thought about leaving our team, and what prompted it?

This can be a vulnerable question for employees, especially when talking to their supervisor, but it can uncover what’s not working within the company and help leaders identify areas for improvement.

5. What can I do to make your experience at work better for you?

This can help managers identify what they can do for employees to improve retention and engagement.

In stay interviews, employees complain the most about work processes, Finnegan found, showing that many gripes employees have are about day-to-day activities that could be simplified or streamlined.

Final Takeaway

Retention improves when leaders stop guessing and start asking.

Stay interviews offer a simple, structured way to understand what matters to employees before issues turn into exits. They help managers take ownership of employee engagement and identify actions that keep high performers motivated.