Why “Culture Fit” Is a Lazy Question. And What I Prefer To Ask Instead.

I’ve heard this line more times than I can count:

“We’re really focused on culture fit.”

I’ve said it myself.

As a hiring manager, it felt like the right thing to say. As a leader, it sounded responsible. Over time, though, and after a few hires that didn’t work out, I realized something uncomfortable:

Looking back, ‘culture fit’ often covered for conversations we hadn’t taken the time to have.

Not because culture isn’t important. But because “culture fit” is vague, subjective, and not very helpful when we are trying to figure out whether someone will actually succeed.

What matters more is much simpler:

Do we agree on how the work gets done?

Where Culture Fit Breaks Down

When a hire struggled, including a few I was directly responsible for, the issue was rarely values or intent. It was clarity.

Culture fit often meant things like:

• “They seem like someone I’d enjoy working with.”

• “They feel familiar.”

• “They remind me of people who’ve done well here before.”

Those instincts aren’t necessarily wrong. They’re just incomplete.

None of them tell you how someone will show up when things get hard.

I’ve seen strong leaders struggle when expectations and decision-making were not clear. I’ve also seen people succeed, even when they weren’t an obvious fit, simply because the rules were clear.

Comfort, so I have learned, is not the same as capability.

The Questions I Have Learned To Ask Now

Over time, I changed the way I evaluate roles and people. Whether I’m hiring or joining a team, I focus less on fit and more on clarity.

Here are a few questions that have proven far more useful:

1. What does winning actually look like?
Not the aspirational version, but what success really looks like in the first 6, 12, and 24 months.

2. How are priorities set and revisited?
When everything feels important, how do decisions actually get made?

3. What happens when results miss the mark?
Is feedback direct? Is it timely? And who owns fixing the problem?

4. Where do leaders have room to decide, and where don’t they?
Autonomy sounds great until no one knows who owns what.

5. What hasn’t worked here before?
This question usually tells you more than any success story.

Culture Is Built From Day-to-Day Behavior

The healthiest cultures I’ve been part of weren’t created by hiring people who “fit.”

They were shaped by:

• Clear expectations

• Honest conversations

• Follow-through when things got hard

• Respectful disagreement

• Consistent decisions

When those things are present, culture tends to take care of itself.

When they aren’t, culture fit tends to become an explanation after the fact.

What I Have Learned Over Time

I don’t ask whether someone fits the culture anymore. I ask whether we’re clear and aligned on how work gets done, how decisions are made, and how success is measured. Those conversations aren’t always comfortable. But they’re far cheaper than getting it wrong.

Because in the process, culture isn’t something we can really screen for. It’s something we build, one decision at a time.

A Closing Thought

A lot of my work starts after a hire or growth push that looked right on paper but didn’t work in practice. Most of the time, the issue isn’t effort; it’s that the right people, systems, or expectations weren’t in place before the business tried to scale.

I help teams get the basics right first, so growth has something solid to build on.