Beyond the Binary: Asking Better Questions in Hiring

"Would you hire them again?"

I took a call on Tuesday, and it turned out to be an unexpected reference call for someone who used to work for me, applying for a keyworker role in a respected organisation. The question landed like a stone in my stomach. A seemingly standard prompt, said with professional ease. But it stayed with me longer than it should have. And the longer I sat with it, the more I realised how much it misunderstands people, work, and the messy, nonlinear business of growth.

It’s not that the question is cruel. It’s shallow, simplistic, and stripped of curiosity. A question that flattens complexity for the sake of convenience. And truthfully, it reveals more about our assumptions around employment, that people are static, success is linear, and context doesn’t matter , than it does about the human being at the centre of the question.

A single word with too much weight

Think about it. That one question collapses a whole working relationship into a yes or no. Years of collaboration, power dynamics, shifting expectations, emotional labour, and quiet fortitude, all of it reduced to a tick-box.

Say yes, and what does it really mean?

That we parted on decent terms?

That they were competent?

That they didn’t disrupt the status quo?

Say no, and it could mean anything. Maybe the role was badly scoped. Maybe the culture rewarded exhaustion over honesty. Maybe they spoke up in rooms where silence earned favour. Maybe they were brilliant , and infuriatingly uncompromising, in other words, principled. Hard to manage, perhaps, but exactly the kind of person who challenges complacency. That doesn't make them wrong. It makes them human. And often, those are the very people we learn from most.

Here’s the bit that troubles me most: the person being asked about rarely gets to explain. A silent verdict, passed in shorthand. Filed away in the fog of recruitment systems.

If we’re serious about fairness, transparency, and building workplaces where people can belong, not just perform, we need to ask better questions.

What if we asked them instead?

So if "Would you hire them again?" misses the mark, what question brings us closer to the truth? Here’s one I’d love to hear in every interview:

“Would you work for that company again?”

Not because it’s a trick. But because it opens a door.

This question invites reflection. It flips the power dynamic. It assumes the candidate has wisdom worth hearing - not just experience to be judged.

Maybe they’d say yes. Maybe they’d say no. But the why? That’s where the truth lives.

What made it work? What didn’t? What did they carry forward? What would they do differently now?

It’s in those stories that you see what drives someone. Where they’re growing. What matters to them.

We say we hire for values and culture. So why aren’t we asking questions that reveal them?

A moment with the mirror

After that call, I looked back at my own CV. Not the bullet points, the jobs.

Would I work for those places again?

There’s only one I’d never return to. Not because of the work, but because of who I became in order to survive it. The rest? I’d consider it. And in one case, I actually did go back.

Different chapter. Different version of me. Different version of them. It worked.

We evolve. So do organisations. Sometimes the ground shifts, and what didn’t work before makes sense later. And sometimes, walking away was the best thing you ever did, even if it didn’t look like success at the time.

What the yes-or-no erases

When we rely on questions like "Would you hire them again?", we double down on a dangerous myth: that good careers are tidy. That good employees are always easy. That goodness can be reduced to a rehire checkbox.

But real careers are unruly. They are full of missteps, sparks, recoveries. They involve speaking truth when it costs you. Learning the hard way. Outgrowing a role. Staying too long. Leaving too soon.

To flatten all that into a binary is not just simplistic. It’s lazy. And it says more about our fear of risk than our belief in potential.

Worse, we end up building teams that look right on paper but lack the richness of tension, divergence, and hard-won wisdom that makes organisations thrive.

For hiring managers and HR folk: from reflection to action

So what do we do with all this?

If that old question flattens people into answers, what might lift them up instead?

What if we stopped treating reference checks as liability screenings, and started using interviews as spaces for relational insight?

Try asking:

• Would you work for that company again?

• What would need to change for you to say yes?

• What did you learn about how you work best?

These are not traps. They are invitations. And in a world that claims to care about people, we need more of those.

You’ll learn more from the why behind someone’s story than from the neatness of their path.

The future of hiring depends on this

Because the future of work isn’t tidy. It’s adaptive. Messy. Human. It asks for curiosity over control, openness over certainty.

We need systems that recognise stretch and struggle. That see the space between roles not as gaps, but as chapters. That view change not as failure, but as capacity.

We need hiring that listens for values, not just filters for keywords.

So next time you’re in a hiring conversation, pause before you ask the usual.

Try asking something human instead.

You might just be surprised by what you hear.

And if you’re the one being asked?

Answer truthfully. Reflect without shame. Speak from where you are now.

Because your story is more than a box to tick. And your voice deserves more than silence.

One good question might not change the system.

But it might just change your next step.

#AskBetterQuestions #WorkplaceCulture #ProgressiveHiring