I once took a candidate to a bar in Larnaca with my CEO and our head of projects. The conversation was brilliant. Funny, warm, full of war stories from previous roles. We all genuinely liked this person. By the end of the evening I was mentally drafting the offer letter.
And then, somewhere between the second round and the bill, I realised I couldn’t picture them doing the job. Not the socialising, not the anecdotes, not the charm. The actual job. The 8am standups, the weekend deploys, the unglamorous Tuesday afternoon where nothing is on fire but everything needs pushing forward. Startup is a grind, and this person was lovely but they weren’t a grinder.
Saying no after that evening was one of the most awkward things I’ve done as a CTO. And it made me think hard about why I’d put myself, and them, in that position in the first place.
The “pub test” tells you who’s fun to drink with. It tells you almost nothing about who’s going to show up and do the work.
The problem with “culture fit”
“Culture fit” is one of those phrases that sounds reasonable until you try to define it. What does it actually mean? That someone laughs at the same jokes? That they’d fit in at the team offsite? That they remind you of someone already on the team?
In an office, culture fit has a physical dimension. You can read body language in a meeting room. You can see how someone interacts at lunch. You pick up on dozens of micro-signals that help you gauge whether this person will mesh with the existing team.
Remote teams don’t have any of that. Your culture doesn’t live in a break room or a Friday drinks tradition. It lives in your Git repo, your Slack channels, your PR reviews, your documentation. It lives in how people communicate asynchronously, how they handle disagreement in a thread they can’t walk away from, and whether they write things down or expect everyone to just know.
Hiring for “culture fit” in a remote team usually means hiring for “vibes on a video call,” and that’s a terrible proxy for anything useful.
What I actually look for
I’ve shifted my thinking over the years. Instead of culture fit, I try to hire for three things:
Work ethic that matches the stage. A startup needs people who will grind. Not performative busyness, not “always online” theatre, but genuine drive. The kind of person who sees a problem on a Friday afternoon and can’t leave it alone, not because someone’s watching but because it bothers them. This is incredibly hard to assess on a Zoom call, which is partly why I still do it badly sometimes.
Communication style that works async. This is the remote-specific one. Can this person write clearly? Can they explain a technical decision in a Slack message without it turning into a novel? Can they disagree with someone in a PR review without it becoming personal? In a remote team, communication IS the culture. Someone who’s brilliant but can’t write a clear message will create more problems than they solve.
Curiosity over credentials. Some of the best engineers I’ve worked with didn’t have the “right” background. They were curious, relentless, and unafraid of things they didn’t know yet. The worst hires I’ve seen looked perfect on paper and then waited to be told what to do.
The intern who proved me wrong
I want to tell you about someone who, on paper, shouldn’t have worked out.
We picked up an intern through a university connection that a remote colleague had in Asia. I’ll be honest, I had reservations. I normally prefer people in EU timezones because it just makes everything easier when the team is awake at the same time. The overlap hours are simpler, the standups don’t require anyone to be up at midnight, the Slack conversations happen in something approaching real time.
This intern completely smashed it.
They built out a system that, if I’d described the requirements to a senior engineer, I’d have been told it was impossible as a one-person operation. Not “difficult.” Not “ambitious.” Impossible. And they did it with the kind of quiet, relentless energy that you can’t screen for in an interview. They just showed up every day, asked smart questions, wrote clean code, and delivered something extraordinary.
If I’d been hiring for “culture fit” in the traditional sense, if I’d been looking for someone who’d be fun at the pub, who was in the right timezone, who ticked all the obvious boxes, I’d have missed this person entirely. And my team would be worse for it.
The hard conversation nobody prepares you for
Here’s the bit that doesn’t make it into the hiring advice articles: sometimes you get it wrong, and the conversation you have to have afterwards is brutal.
It’s one thing to reject someone after a phone screen. It’s another thing entirely when they’ve left a previous role to join your team, when they’ve relocated or rearranged their life, and you’re sitting there three months in realising it isn’t working. Not because they’re bad at their job, necessarily, but because the way they work doesn’t fit how your team works.
Remote makes this harder, not easier. You don’t have the casual daily signals that something’s off. By the time it’s obvious, it’s usually already a problem. And the conversation, when you finally have it, carries weight that it doesn’t in an office where someone can just walk down the road to the next opportunity.
I don’t have a clean solution for this. What I do have is a process that tries to reduce the chances of getting there.
What my process actually looks like
I do the first-pass CV cull myself. I’m looking for signals of curiosity and initiative, not a checklist of technologies. Have they built something? Have they contributed to something? Is there evidence that they solve problems, or just that they’ve been employed?
Then my team takes over. I deliberately step back because I want them to find someone who fits their working patterns, not mine. They’re the ones who’ll be reviewing this person’s PRs, pairing with them on tricky problems, and relying on them when something breaks at 4pm on a Thursday. The team is mostly chill, massive geeks, proud of it, and they know what works in their day-to-day better than I do.
The thing I’ve learned is that the best predictor of remote success isn’t personality. It’s what someone does when nobody’s watching. And you can’t assess that over drinks.
The cohesion question
The counter-argument I hear most is: “but remote teams need cohesion, and culture fit builds cohesion.” And I don’t entirely disagree. Remote work can be isolating. You do need people who connect with each other, who care about the team, who’ll jump into a Slack thread to help someone even when it’s not their problem.
But cohesion doesn’t come from hiring people who are all the same. It comes from shared standards, clear communication norms, and mutual respect. It comes from the way your team does code review, how they handle disagreement, and whether they document things properly. It comes from culture, but culture as practice, not culture as personality.
The intern from Asia didn’t share a timezone, didn’t share a background, didn’t share a single after-work beer with the team. But they shared a work ethic and a standard of communication that made them one of the most effective people we’ve had. That’s the kind of fit that matters.
What I’d tell a newer CTO
If you’re building a remote team for the first time, here’s what I wish someone had told me:
Stop screening for personality on video calls. You’re not hiring a dinner guest. You’re hiring someone who needs to write clear commit messages, respond thoughtfully to async feedback, and push through the boring parts of the work without someone standing behind them.
Let your team own the culture-fit assessment. They know their own rhythms better than you do. Your job is to set the bar for technical quality and work ethic. Their job is to figure out whether this person will make the daily work better or harder.
And if you find yourself in a bar thinking “this person is great fun but I can’t picture them doing the job,” trust that instinct. It’s kinder to say no before the offer than after the start date.