What If Retention Starts Before Someone Ever Works for You?

Better Hiring Conversations

What if retention starts before someone ever works for you?

Every business is in business to stay in business. That sounds almost too obvious to say out loud.

We need customers to stay. We need revenue to continue. We need relationships to last. And somewhere in that equation, we need the right people to stay too. That has me thinking differently about retention. Most conversations about retention seem to begin after someone becomes an employee.

We talk about onboarding, 30-day check-ins, leadership, culture, compensation, career growth, and engagement. All of those things matter. But this week I found myself wondering if we are starting the retention conversation too late.

Maybe retention begins before someone ever accepts the offer.

I’ve spent a lot of years recruiting and interviewing people, and one thing I continue to notice is that the first reason someone gives for wanting a new job is not always the real reason they need a change.

“I want more money.” “I need a better schedule.” “I want more opportunity.”

Those answers matter. But I’ve learned not to stop there.

Why does the money matter? What changed about the schedule? What does opportunity actually look like to you?

Sometimes something happens when the conversation gets a little deeper. The candidate starts thinking differently about their own answer. That moment of self-awareness can be pivotal.

Because changing jobs does not automatically change the problem someone is trying to solve.

Someone can leave one company for more money and discover that money was never really the issue.They can leave for a better schedule and realize they were actually looking for a leader who respected their time. They can leave for growth without ever defining what growth meant to them. And we can make what looks like a great hire only to find ourselves recruiting for the same position again months later.

That makes me wonder how much of retention actually begins with self-awareness.

Not just ours. The candidate’s too.

A deeper hiring conversation should help us understand the person sitting across from us. But maybe it should also help that person understand themselves a little better.

Why am I really considering leaving? What am I hoping will be different? What am I unwilling to repeat? What matters enough that I would stay somewhere when another opportunity eventually comes along?

Those questions are harder than asking about salary expectations or years of experience. They also require something from the recruiter. We have to resist becoming too certain too quickly. That was another thought that stayed with me this week. Experience teaches us patterns. After enough interviews, you recognize certain answers. You notice pauses. You pick up on inconsistencies. You develop instincts. That experience matters. But I’m becoming more careful about what I do with those instincts.

An instinct should lead to another question, not automatically to a conclusion.

Because the moment I decide I already understand someone may also be the moment I stop trying to understand them. Maybe that is where deeper hiring conversations become more than an interviewing technique.

They become part of the system. If retention is the goal, we cannot guarantee someone will stay. People change. Businesses change. Life changes. But we can create a better process for understanding what someone is moving toward before we ask them to join us.

We can help candidates think more deeply about the change they are considering. We can be more honest about what our opportunity can and cannot provide. And we can give both sides enough information to decide whether there is something worth building together.

Hiring someone is a moment. Retention is everything that follows.

But I’m becoming convinced that what follows may be influenced by the conversations we were willing to have before Day One ever arrived. Maybe the question is not simply how we keep good people.

Maybe we should first ask whether we took enough time to understand why they chose us in the first place.

Better hiring starts with better conversations. And maybe better retention does too.

Thank you for reading, for challenging my thinking, and for continuing to be part of these conversations each week.

I appreciate every comment, every message, and every perspective you share. Many of the ideas I write about do not start at a keyboard. They start in real conversations that make me stop and think a little differently.

Better conversations. Better hiring outcomes

Brandon Labonte