Interview Questions That Actually Predict Whether Someone Will Stay

We’ve written before about why onboarding is the most important part of recruitment and about how most new hires decide whether they’re staying within the first six weeks, based on how supported they feel rather than what they’re paid.

But here’s the bit that happens before all of that: the interview. And if the interview doesn’t tell you anything real about the person sitting in front of you, no amount of brilliant onboarding is going to save the hire.

Most managers are still asking the same handful of questions every other agency asks…

“Tell me about a time you dealt with a difficult client.”

“Where do you see yourself in five years.”

“What are your strengths and weaknesses.”

These questions are comfortable, familiar, and almost completely useless. Candidates have rehearsed answers for all three over and over again. And honestly, it suggests a lack of effort from the interviewer.

So what should you be asking instead?

Ask what “good” looked like in their last role and then listen for the gap

“What did a really good day look like in your last job? And what did a bad one look like?”

This does two things…

First, it shows you what they actually value… recognition, autonomy, quiet focus time, being part of a team hitting a target together.

Second, if the gap between their “good day” and what your agency can realistically offer is enormous, that’s a red flag worth taking seriously before you hire, not six weeks after.

Ask about ownership, not experience

Instead of “tell me about your experience with lettings,” try: “Tell me about a time something went wrong that wasn’t technically your fault and what did you do about it?”

You’re not looking for a perfect answer. You’re looking for whether they say “I sorted it” or “I told my manager and waited.”

In a small, independent agency, you need people who take ownership without being asked. That single question tells you more than a CV full of experience ever will.

Ask how they’d handle a slow, quiet team

Property is seasonal and unpredictable.

A candidate who’s only ever worked somewhere with a constant stream of leads and structure can genuinely struggle in a smaller, independent environment where things are quieter, less process-driven, and more “figure it out as you go.”

Try: “Describe how you’d spend a Tuesday afternoon with no viewings booked and no calls to make.” The candidates who talk about proactively calling old leads, tidying up the CRM, or checking in with colleagues are showing you resilience and initiative. The ones who go quiet are telling you something too.

Ask what they need from a manager, not what they’re good at

“What’s the one thing a manager could do that would make you want to stay somewhere for years?”

Most candidates aren’t asked this, and most give an honest, unrehearsed answer because of it.

It also opens an important, and often skipped, conversation: are you able to actually offer that?

If someone says they need regular one-to-ones and you know you barely have time to check in monthly, that’s worth knowing now.

The red flag specific to property recruitment

Watch for candidates who talk entirely in numbers: deals done, targets hit, commission earned with nothing about the people side of the job. Property is a relationship business, especially at independent agencies where reputation and repeat business matter more than volume. A candidate who can’t talk about a client relationship, a colleague they helped, or a moment they got it wrong and fixed it, is worth a second look before you commit.

Hiring and onboarding are one decision, not two

The point of all this isn’t to make interviews harder, it’s to stop treating the interview as a box-ticking exercise before the “real work” of onboarding begins. The two are the same decision, made in two stages. Ask better questions at stage one, and stage two gets a whole lot easier.

If you’d like an honest look at where your recruitment process might be leaking good candidates, take our free PROPA Recruitment Health Check. It takes a few minutes and gives you a clear picture of where to focus.