Hiring has a funny way of humbling you. The hiring process looks clean on paper, but retention is where the truth shows up, and that’s something I’ve been thinking about a lot lately. Probably because I’ve watched the same pattern repeat itself more times than I care to admit. A strong hire. A confident start. And then, slowly, something shifts.
You feel it before you see it. Replies get shorter. Energy drops. Curiosity fades. And eventually, you’re sitting in an exit conversation wondering how something that looked so right unraveled so quietly.
The thing is, it usually didn’t unravel at all. It was decided much earlier.
We think we’re hiring for skill, but we’re really hiring for friction
Most hiring decisions make sense in the moment. Experience lines up. Interviews feel good. Everyone agrees this person checks the boxes.
But here’s the part we don’t say out loud. Retention isn’t driven by skill gaps nearly as much as it’s driven by friction. How much resistance someone feels once the novelty wears off. How heavy the role feels when it’s no longer new.
I’ve watched people who were more than capable struggle not because the work was too hard, but because the role demanded things no one really explained. Pace. Pressure. Decision making without clarity. A level of autonomy they weren’t prepared for, or oversight they didn’t expect.
That realization stung.
Because technically, no one did anything wrong.
Still, people left.
And it forced me to admit something uncomfortable. We weren’t hiring bad people. We were hiring people into realities we didn’t fully articulate.
The decision that affects retention happens before the offer, not after day one
Companies love to talk about onboarding when retention comes up. And onboarding matters. But it’s not where retention starts.
Retention starts in the interview. In the side comments. In the moments where someone asks a direct question and we soften the answer because we want to keep momentum.
I still remember a candidate asking me, “How structured is this role, really?”
And I gave a careful answer. Not dishonest. Just incomplete. I wanted her excited. I wanted her to accept.
She lasted a month.
I replayed that conversation more times than I’d like to admit. Because if I’m being honest, she didn’t quit the role. She quit the surprise. And that one was on me.
Most early exits aren’t about disappointment. They’re about misalignment that was baked in before the start date. When someone leaves quickly, it’s rarely sudden to them. It’s just sudden to us.
Clarity keeps people longer than motivation ever will
This took me years to fully understand.
We reward confidence in interviews. Energy. Charisma. People who sell themselves well. And sure, that matters. But it can distract us from what actually keeps someone around.
Clarity.
People don’t leave because the job is demanding. They leave because expectations are fuzzy. Because success isn’t clearly defined. Because feedback shows up late. Because priorities shift quietly.
I once watched a solid hire unravel simply because no one could answer, clearly, what success looked like after 90 days. Everyone assumed someone else had covered it.
No one had.
They didn’t need encouragement. They needed a map.
That moment changed how I think about hiring. Not just can this person do the work, but how much ambiguity can they tolerate. How much structure do they expect. And are we actually prepared to give it.
Those mismatches don’t show up on resumes. But they show up in turnover.
Culture fit isn’t about values, it’s about pace
This might rub some people the wrong way, but I’ve stopped asking most traditional culture fit questions.
Values matter. Of course they do. But pace matters more.
How fast decisions are made. How often things change. How much independence is expected. How visible leadership is. How feedback is delivered. Loud teams. Quiet teams. Constant motion versus steady rhythm.
I’ve seen people who shared every stated value still burn out because the pace exhausted them. And others thrive in environments that would overwhelm someone else entirely.
Funny enough, the people who leave usually feel it early. Within the first few weeks. They sense something is off. But they tell themselves it’s just new job nerves. So they push through. Until they can’t.
Retention improves when we stop selling culture like a highlight reel and start explaining it like a real day in the life. The boring parts. The frustrating parts. The parts that don’t look great on a careers page.
The right people don’t need perfection. They need honesty.
The hiring decision is really a self awareness test
Here’s the part most teams avoid.
Every hiring decision reflects how well we understand ourselves. Our managers. Our systems. Our blind spots.
When retention struggles, it’s easy to blame candidates. Or the market. Or timing. I’ve done all of that at one point or another.
But usually, the answer is closer to home.
Are we clear on what this role actually demands day to day? Are we aligned internally on expectations? Are we hiring someone for who they are today, or who we hope they’ll become once they join?
I still remember saying, “They’ll grow into it.”
Sometimes that’s true. Sometimes it’s optimism covering uncertainty.
The hiring decision that quietly impacts retention the most is the one where we choose honesty over hope. Where we stop trying to make the role sound better and start making it sound accurate.
That decision can slow things down. It can cost you a candidate you liked. It can feel uncomfortable in the moment.
But it saves you from a quiet resignation later.
Conclusion
If I’ve learned anything, it’s that retention isn’t fixed with perks or policies after the fact. It’s shaped early, in the small decisions we make when no one is tracking tenure yet. The questions we ask. The clarity we offer. The truths we’re willing to share, even when they’re not polished. If people are leaving sooner than you’d like, don’t just look at who they were. Look at what they were walking into. That’s usually where the real answer lives.
