The Question You’re Afraid to Ask Is the One That Keeps Them

Issue #30

By Debbie Lawrence

Read time: 8 minutes

It was October, about 30 years ago, and Lorinda and I were walking through Bannerman Park.

I was in a senior leadership role at the time, and Lorinda was my office manager. We worked side by side every day and she was very, very good at what she did.

Six months earlier, we’d sat down for her annual performance review. She told me she loved her job and wanted to keep working there. Then, near the end, she said something that stayed with me:

“If there are some new challenges I can take on, I just want you to know I’m open to that. Don’t hesitate to ask me. And if I don’t know how to do it, I’m open to learning.”

It sat in the back of my mind. And then the months went by, the way they do.

But I kept getting a feeling about her. There wasn’t anything specific I could point to because Lorinda was still doing excellent work. She just seemed a little restless, like someone who’d already figured out every aspect of her job and the delight in being challenged had dimmed.

Around that time I’d learned about something called a stay interview, and I thought of her right away.

So I arranged coverage for the office and asked her to step out with me. Lorinda was an active person who loved being outdoors, so we went to the park, and we walked and talked.

I’ll be honest about what was going through my head on the way there.

What if this conversation helps her realize she wants to leave?

I don’t remember every question I asked that day. I know I started with the easy ones, about what she liked in her work and what made for a good day. And the longer we walked, the more Lorinda opened up about what she was really hungry for.

She wanted a new challenge. She’d told me so six months earlier, and now I was hearing it with a level of clarity I hadn’t previously had.

We’d been doing some planning at work around new roles, and as she talked, something clicked for me.

“Do you think working in Student Services might be something you’d be interested in?” I asked.

“Absolutely,” she said.

“Well, can you give me some time?”

It took a couple of months but by the winter semester, Lorinda had moved into a support role in Student Services. She had more autonomy and was using her skills in a whole new way. It was a promotion, and she kept her career inside our organization.

What I didn’t know before that walk was that the question I was afraid to ask was the one that kept her.

The review tells you how she’s doing

An annual performance review is about the work. Is she meeting the standard? Where can she grow? What’s coming up next year?

A stay interview asks something else entirely: does she still want to be here, doing this, with you?

Lorinda had given me the answer in her review. I’m open to new challenges. I’d originally filed it away as something to think about. Looking back, it was the first sign of an itch, and if I hadn’t gone looking, I think she’d eventually have scratched it somewhere else.

The pattern I see everywhere

When I talk about stay interviews with the leaders I coach, I typically see one of these flinches:

“I don’t want to open a can of worms.” If you ask what someone would change, it’s highly likely she’ll tell you. Then you have to do something about it, or at least have a reason why you won’t.

“I don’t want to plant a seed of doubt where there isn’t any.” This one sounds considerate. Why stir things up? When I ask a follow-up question or two, the leader usually admits she already suspects the doubt is there and would just rather not confirm it.

“What if she says she wants to leave?” Underneath this one is a bigger fear: What if I don’t have anything to offer her? So the leader says nothing, and hopes the status quo will remain.

“Isn’t that what the annual review is for?” A lot of good leaders have simply never heard of a stay interview. They assume the review covers it, so the question never gets asked.

All four feel reasonable. And all four lead to the same place, where you find out how she was feeling in her resignation letter.

Richard Finnegan, who has spent much of his career helping organizations use stay interviews, put it plainly at a SHRM conference in 2011. Talking about exit interviews, he said: “After they’re gone, you can’t do anything about it.”

When the stay interview is for you

These days I use the same approach in my coaching practice, and sometimes the person sitting across from me is the one thinking about leaving.

Caleigh was in a leadership role with the provincial government. She came to one of our sessions unsure whether she wanted to stay. She’d learned how to run stay interviews with me, so I said, “Well, let’s do a stay interview. Let me ask you the questions.”

So I asked her the same questions she’d ask her own team. What makes for a great day at work? What keeps you here? What would make this role more satisfying?

As we worked through them, Caleigh realized something. Things weren’t perfect, but she really did like what she was doing, and she still felt challenged.

“I’m not ready to go yet,” she told me. “But there are a couple of tweaks I’d like.”

What she needed was to ask for more of what she wanted, be willing to hear no, and then decide what to do with the answer.

So she went to her director and opened the conversation herself. She explained she’d been working with her coach, shared what she’d realized, and named the tweaks. Her director was more than happy to accommodate her.

Caleigh had been carrying around a story that her organization would never say yes and hadn’t checked to see if there was any truth to support her story until that conversation. I see this so often where people decide what the answer will be and take action based on that without ever asking for real.

The part that takes courage

Sometimes you’ll sit down for a stay interview and discover you can’t give her what she’s hungry for. There’s no new role, no new challenge, or a position to move her into.

I believe that’s still a good outcome.

If I couldn’t have challenged Lorinda any further, I was prepared to say, “You have my absolute blessing to look for something else. And if I hear of something, I’ll help you get it.”

Good leaders celebrate when someone outgrows the experience they created for her. You built a place where she could get to her best, and her best wants more room. That’s success in my books.

And I’ve always believed that, as amazing as Lorinda was, I found her once, which meant I could find another Lorinda. Nobody is indispensable. Her replacement was wonderful too, and because Lorinda stayed in the organization, she mentored the new person through the transition. It worked out well for everyone.

What I did after Lorinda

After Lorinda, I held a stay interview with every direct report at least once a year. I tried to keep it about six months from the annual review, so the two conversations didn’t blur together. (That’s what the stay interview guides I’ve read recommend, and it’s exactly the timing I stumbled into with Lorinda.)

I gave it about an hour. The first time with each team member usually ran longer, especially if we hadn’t talked like this before.

I also preferred to take it out of the office when I could, somewhere private but neutral. It might be a park, a quiet coffee shop corner, even a hotel lobby where you can tuck yourselves away.

When I invited someone, I explained what a stay interview was and shared a couple of the questions ahead of time. It was new territory, and people worried a little about what to expect. My job was to put them at ease.

I started easy. What do you look forward to at work? Then, as we both settled in, I got to the harder ones. What are you seeing that I’m not seeing? How could we support you better? One of my favourite questions is: “Are we using all of your skills, and are we using them fully?” You’ll get answers you probably won’t expect.

And I followed up. If someone tells you what they need and nothing changes, you become the flavour of the week, and the next time you ask, they’ll give you the polite answer.

There was a second half to this that I did on my own, and some people call it the reoffer. Around the same time, I looked at each person on my team and asked myself one question: If she were sitting across from me today, would I offer her this position again, as it is right now?

The stay interview told me how she felt about the job. The reoffer told me how I felt about her work and her fit with the company. When you do both every year, you stay ahead of what’s coming, and nobody’s caught off guard.

Your turn

Think about the person on your team you’ve been wondering about. The one who seems a little restless, or the one who said something in her last review that you haven’t followed up on.

This week, invite her to a stay interview. Tell her what it is, share two of the questions you plan to ask, and put a date on the calendar.

Then comment below and tell me which question you’ll open with. If you’d like my Stay Interview Planner to help you prepare, just say so in your comment and I’ll send it to you.

I read and reply to every response.

P.S. You can also listen to this issue on The Compassionate Leader School podcast episode, which drops the same day on Apple Podcasts, Spotify, and all major platforms. Click here to explore all the episodes.