Stay conversations: secret to keeping great people

Opinion

When employees leave, we often scramble to conduct exit interviews, trying to figure out what went wrong. But by the time someone is packing up their desk, it’s too late to change their mind.

What if we took that same curiosity and care and applied it earlier — while they were still with the company and potentially looking to stay?

That’s the heart of a stay conversation. These are proactive, meaningful one-on-one discussions between a manager and an employee focused on what keeps them engaged, what challenges they’re facing and what might tempt them to leave. Think of it as an early intervention tool, relationship check-in and gesture of respect all rolled into one.

Stay conversations aren’t performance reviews or disciplinary meetings. They’re not driven by metrics or formal HR timelines. They’re simply conversations with a purpose: to listen, learn and make sure that good people feel seen, valued and supported before they start considering the door.

Why stay conversations matter

In today’s workplace, retention is more complicated than ever. People want flexibility, purpose, career growth and a culture that aligns with their values. While compensation is important, studies consistently show feeling heard and having opportunities to grow weigh heavily in whether people choose to stay or go.

Managers often assume they know what their team members want, but assumptions are dangerous. One person might crave a promotion; another is simply hoping to stop working weekends. Some employees will speak up when something’s off; others won’t say a word until they’ve accepted another job offer.

Stay conversations offer a low-pressure space to surface these thoughts before they turn into disengagement or turnover. They allow managers to tailor support, catch early signs of dissatisfaction and build trust. When done well, they’re a sign an employer is invested in the employee — not just in what they produce, but in who they are and what they need.

When to have stay conversation

There’s no wrong time, but there are a few key moments when they’re particularly useful.

A good rule of thumb is to have one with every team member at least once a year, ideally more often. They’re especially powerful after a big win, at the anniversary of their hire, after a major project wrap or when change is coming to the team or organization.

However, stay conversations shouldn’t only be initiated by managers. Employees can ask for one, too — and that is not a sign of trouble. Managers can normalize it as a regular part of a healthy workplace. Just like you’d check in on goals or project timelines, check in on how people are feeling about their work.

How to start the conversation

Managers sometimes avoid these conversations because they’re not sure what to say or they’re afraid of opening a can of worms. But like most things in leadership, the hardest part is just starting. You don’t need a script, just an open mindset and a willingness to listen.

Start with something simple like: “I’d really like to take some time to check in with you — not about performance, but about how things are going for you overall. What’s working, what’s not and what we can do to make sure this is still the right place for you.”

It’s important to set the tone clearly: this is about support, not evaluation. Your employee isn’t being summoned, they’re being invited.

From there, ask thoughtful questions and let the conversation flow.

What parts of the work do you enjoy the most? What frustrates you? Is there anything you’d like to learn or try in the next year? Are there things about your job or our culture that make you think about leaving? What would make this a long-term fit for you?

Some employees might be hesitant to open up at first, especially if this kind of conversation is new. That’s okay. Stay patient. The goal isn’t to rush to solutions, but to build connection and trust over time.

What to do with what you learn

Once the conversation is underway, the most important thing you can do is listen. Not defensively. Not with a ready-made answer. Just listen. You’re not required to fix everything on the spot. You are required to take what they say seriously and respond with respect.

If someone shares that they’re feeling bored, underpaid or unsure about their future, resist the urge to get defensive or explain it away. Instead, say thank you. They trusted you enough to be honest and that’s a gift.

After the conversation, take some time to reflect on what you heard.

What small changes can you make to improve things for this person? Are there career development opportunities you can connect them to? Flexibility you can offer? Recognition you’ve been overlooking? And if the issue is something outside your power — like compensation — can you at least advocate on their behalf or be transparent about the limits?

The key is follow-through. Nothing undermines trust faster than a heartfelt conversation followed by radio silence. Even if you can’t act on every suggestion, circling back to say, “I heard you and here’s what I’m doing with that,” goes a long way.

Letting employees know they can ask

While stay conversations are often manager-led, they’re most effective when employees feel empowered to initiate them, too. Make this part of your team’s culture by talking about it openly. At a team meeting, explain you’re committed to having stay conversations regularly and anyone can ask for one at any time.

You can even include it as part of your onboarding process — letting new hires know that, in addition to performance check-ins, you also schedule stay conversations to keep lines of communication open. That sends a clear message: we don’t just care about your output, we care about your experience here.

This kind of cultural shift takes time, but it’s worth it. When people know they can speak up without fear, they’re more likely to bring up issues early, and more likely to stay engaged.

Simple practice with big impact

Stay conversations aren’t flashy. They don’t come with a budget or a fancy tool, but their impact can be enormous.

Employees who feel heard are more loyal, managers who stay curious build stronger teams and organizations that prioritize retention from the inside out reduce costly turnover and boost morale.

At their core, stay conversations are about care. They’re a quiet but powerful way to say: you matter and I want you to stay. Not because you have to — but because this is still a place where you can grow, thrive and be appreciated.

That’s a message worth delivering. And it starts with just asking the question.

Tory McNally, CPHR, BSc., vice-president, professional services, is a human resource consultant, radio personality and problem solver. She can be reached at tory@legacybowes.com