"The Startup Ways of Working Don't Always Scale"

What Got You Here Might Need to Evolve

One of the fascinating things about scaling a technology company is that some of the things that helped make it successful can become harder to maintain as it grows. The close-knit team gets bigger, communication becomes more complex, processes appear where conversations used to do the job, and people who once had enormous autonomy can suddenly find themselves spending a surprising amount of their week in meetings.

None of this means you've lost your culture or got scaling wrong. Sometimes the organisation has simply grown faster than the structures around its people.

When Great Engineers Become People Managers

One of the growing pains I see in technology companies is what happens when brilliant engineers move into people management. Suddenly they're navigating performance, feedback, development, difficult conversations and team dynamics - an entirely different skill set from the one that helped them become brilliant engineers in the first place.

It doesn't mean they aren't capable of becoming great leaders. It means we shouldn't assume technical excellence automatically comes with people leadership experience. Being brilliant at solving technical problems doesn't necessarily prepare you for two humans disagreeing on a Tuesday afternoon. 😄

As companies scale, this is where leadership development and career progression start to matter. Not every brilliant engineer wants to manage people, and progression shouldn't automatically require them to. For those who do want to lead, the transition deserves the same intentional development we'd give any other significant shift in someone's role.

The Warning Signs Don't Always Look Connected

The tricky part is that growing pains don't always show up in one obvious place. On their own, none of these necessarily mean there's a bigger problem, but you might start noticing:

Great engineers moving into people management without enough preparation or support.
Early employees feeling less connected to the company as it grows.
Technical people unsure how they can progress without becoming managers.
Hiring becoming harder while retaining great people is becoming just as important.
Teams spending more time in meetings, processes or firefighting and less time doing the work they're actually there to do.
Onboarding that worked for 20 people becoming increasingly clunky at 70.

The natural response is often to tackle each one separately. Manager struggling? Leadership training. Engineer leaving? Retention conversation. Hiring getting harder? Recruitment process.

And any of those responses might be exactly right.

But before jumping to the solution, sometimes it's worth applying a more holistic lens. What else could be contributing to what we're seeing? Are there gaps between functions? Are leadership expectations clear? Have the structures around our people evolved at the same pace as the business?

Sometimes what looks like several separate People, Talent, Leadership or Technology challenges is actually a useful signal that it's time to zoom out and look at how the organisation is growing as a whole.

Don't Wait for Attrition to Give You the Answer

After more than 20 years across technology recruitment, talent, leadership coaching and organisational growth, one pattern I've seen repeatedly is that we often address the symptom long after we could have explored the cause.

By the time great people are leaving, managers are exhausted or teams are disengaging, there may have been clues along the way. The opportunity is noticing them earlier, while you still have more options available to you.

That might mean developing people managers more intentionally, creating technical career pathways so progression doesn't automatically mean management, protecting deep work, improving onboarding or simply getting clearer about how different functions work together as the organisation grows.

There isn't one universal scale-up playbook. What works brilliantly at 30 people might need adapting at 70, and what works at 70 may need another rethink at 150.

That's not failure.

That's scale.

And the earlier you see the pattern, the more choices you have about what happens next.