Your Culture Happened By Accident. Now You Have to Fix It On Purpose.

Nobody designs their culture. It just happens.

The first five people you hire bring their habits, their communication styles, their definitions of "good work." Then you survive a few crises together, and those survival patterns become gospel. Before long, you have a culture. You just didn't build it on purpose.

That's fine when you're small. The problem is what happens when you try to grow.

I joined a Series B company right after they closed a significant round. They were ready to scale. They went on an aggressive hiring spree, nearly doubling their headcount in about three months. They brought in experienced people from established companies, people who had built teams and shipped products and operated at scale.

I was one of those people. My job, in part, was to bridge the gap between how things had always been done and how they'd need to be done going forward.

It didn't work.

Within weeks, there was a clear divide. The people who'd been there from the early days started calling themselves "OGs." It was said with pride, like a badge of honor. But what it really did was draw a line. You were either in or you weren't.

The OGs had survived the scrappy years. They'd shipped in chaos, figured things out on the fly, built something from nothing. They were proud of that, and they should have been. But they'd also internalized a way of working that couldn't scale. No real processes. No documentation. Engineers treated like a free pool you could poach from whenever your feature felt urgent. Every successful launch felt a little like luck.

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When the new hires tried to bring structure, they got resistance. When they suggested processes, they got eye rolls. When they pushed back on how things were done, they got reminded—sometimes subtly, sometimes not—that they weren't OGs.

The inside jokes piled up. The power dynamics became clear. And slowly, the new people started to realize they weren't really meant to change anything. They were just meant to do more work the old way.

I had a top IC on my team. Brilliant guy. We started within a week of each other. He was one of the best people I've ever worked with. And he left.

When he told me, he made a point of saying it had nothing to do with me. He said I was his favorite boss he'd ever worked with. But he couldn't stay. The CTO—one of the original founders, an OG on a pedestal—just wouldn't work with people. He never shipped anything on time, and there were no consequences. The culture protected him because he'd been there from the beginning.

My guy looked at that and decided he didn't want to fight it anymore. So he walked.

That's what a broken culture costs you. Not the people who were never going to work out. The people who were crushing it but couldn't stomach the dysfunction.

What made it worse was the hypocrisy underneath it all.

The company wanted to scale. The investors definitely wanted them to scale. Everyone was talking about exit strategies and growth trajectories. But the OGs didn't actually want to change how they worked. They wanted the payoff of being a bigger company while staying the small, scrappy team that did things their way.

They hired people specifically to bring fresh perspectives. Then they ignored those perspectives. They brought in operators to implement process. Then they dismissed the process as unnecessary. They talked about becoming a different kind of company. Then they protected the people who made sure it stayed the same.

When the layoffs started, the pattern became undeniable. New people got cut. OGs got spared. Round after round. The company kept saying they were restructuring for the future, but every round looked more like a return to the past.

I wasn't part of the first layoff. I stuck around longer than a lot of the new hires. But eventually my round came too.

That was two years ago. They've had layoffs every six months since. And if you go look at their About Us page today, it's a bunch of OGs.

They ended up right back where they started. Just smaller, and more bruised.

If your company grew the same way—a few early people, some shared chaos, an unspoken set of rules—you have an accidental culture. That's not a criticism. It's just the reality of how small companies work.

But if you're planning to scale, you need to look at that culture honestly. Some of what emerged is probably great. The work ethic, the scrappiness, the willingness to figure things out. Keep that.

Some of it is probably toxic. The in-group dynamics, the resistance to new ideas, the assumption that how things were done is how things should be done. That has to go.

Here's what to watch for.

OGs bypassing the chain of command to other OGs. I had a director who would skip me entirely and go straight to my boss—a fellow OG—whenever she didn't like a decision. When I asked my boss to simply check whether I was in the loop before engaging, he wouldn't commit to it. If your early employees can route around the people you hired to lead them, you don't have a management structure. You have a shadow org chart based on tenure.

Parity promotions. I had a director on my team who was crushing it. Feedback across the board was exceptional. When I proposed promoting him to senior director, I was told we'd also have to promote an OG at the same level because she'd be upset otherwise. Her promotion had nothing to do with performance. It was about protecting feelings and preserving the pecking order. If you're promoting people to avoid OG resentment rather than to reward results, you're building a culture that punishes your best performers.

Process exemptions for the originals. The same OG director refused to follow any repeatable product process. Her direct reports felt like underlings doing grunt work with no development and no praise. When new hires had to follow the process but OGs could ignore it, the message was clear: the rules are for the newcomers.

Decisions happening in side conversations. The actual forums—the team meetings, the planning sessions, the structures you put in place—become theater. The real decisions happen in Slack DMs and hallway chats between the people who've been there longest. New hires show up to meetings where everything's already been decided.

Performance issues that would get anyone else managed out. The CTO at this company missed deliverables by months, not days. It affected revenue. Even other OGs would come to me and say they didn't know what to do, that he wouldn't respond to anything. Of course he wouldn't. He'd been rewarded repeatedly and never held accountable. Once someone learns they're untouchable, they stay untouchable until leadership decides otherwise.

And that's the hardest part.

You can hire great people. You can build processes. You can try to bridge the gap between how things were and how they need to be. But if leadership won't back the change, none of it matters.

The new hires will figure out quickly that they're not really meant to change anything. They're just meant to do more work the old way. The good ones will leave. The rest will either adapt to the dysfunction or burn out.

If you're going to hire people to bring fresh perspectives, you have to actually let them bring fresh perspectives. If you're going to bring in operators to build process, you have to let them build process—and you have to hold everyone to it, including the people who were there before the process existed.

The culture you have is the culture you built by accident. The culture you need is the one you'll have to build on purpose. And at some point, you'll have to choose between protecting the people who got you here and becoming the company you say you want to be.