Managing Developers vs. Leading Technical Strategy: If You’re Going to Double Up on Hats, Make Sure One Is Strategy—But Don’t Stop There

Not All Hat Combos Are Created Equal

Here’s what I see all the time:

• You have a sharp developer who’s also managing the team—because, well, someone has to.

• Suddenly, they’re running standups, handling project plans, putting out fires, and still writing code.

• But here’s the problem: no one is steering the ship strategically.

Managing and coding? That’s a common combo. But managing and leading technical strategy? That’s where the real leverage is.

A Real Example: When the Wrong Hat Combo Hurts

I saw this play out at a startup in the service industry. Their dev team was junior-heavy, and their “manager” was really just the most experienced developer—good at keeping the team moving and handling the day-to-day. But strategic thinking? Not on the radar. The team focused only on the loudest operational need of the week, always reacting, never planning ahead.

When the economy shifted and they had to downsize, the cracks started to show. With no technical strategy or long-term vision, the team was in survival mode—treading water, constantly putting out fires, and never building a solid foundation. The juniors eventually recommended a massive, expensive platform rewrite as a fix. It was a classic band-aid solution that didn’t address the real issues.

And here’s the kicker: they didn’t even have the skills or experience to pull off the rewrite. The project got abandoned halfway through, after months of wasted effort and resources. In the end, they were no better off than if they’d never started—and all that lost time just left them further behind. The business was stuck with one developer, barely keeping things afloat, and no real progress on the features that would actually move the business forward.

A Word of Caution: Not All CTOs Are Created Equal

Now, here’s another layer. Sometimes, companies try to solve this by hiring a “CTO” who’s also the manager. But titles can be deceiving. I’ve seen teams bring in someone with a CTO label, but whose only real experience was running small teams or short-term projects. They were great at keeping things organized, but when it came to painting a multi-year vision, making tough architectural calls, or knowing when to hold off on a big rewrite, they just didn’t have the experience. The result? The team still suffered—stuck in management mode, not strategic mode.

So, if you’re looking for that CTO/manager unicorn, make sure they’ve actually worn the strategy hat before. Ask them how they’ve handled big, complex shifts. Get them to talk through how they’d set a technical vision that lines up with your business goals—not just for the next quarter, but for the next few years.

The Lesson: Double Up on Strategy, Not Just Implementation (and Vet for Real Strategic Chops)

If you have to combine roles (and most startups do), it’s way more valuable to have someone who can manage and set technical direction, rather than just manage and code. But don’t just look for the title—look for the track record. Implementation can be hired, contracted, or delegated. But strategy—the ability to say “no” to distractions and “yes” to what matters for the long haul—that’s what keeps your company on course.

Why a Fractional CTO Makes Sense

That’s where a fractional CTO comes in. You get senior-level strategy and management in one person, without the full-time CTO price tag. Someone who’s been through the scaling journey, can mentor your team, and—crucially—can chart a technical path that actually supports your business goals.

Bottom Line

If you’re going to ask someone to wear two hats, make sure one of them is strategy—and make sure they actually know how to wear it. Otherwise, you risk moving fast… but in the wrong direction—and losing precious time and momentum you might not get back.

Curious what this could look like for your team? I’m always up for a candid chat—no pressure, just real talk about what’s working and what’s not.