The Strategy CTO
Background: Consulting, MBA, product management
Great at decks, roadmaps, and architecture diagrams. Knows all the "best practices." But somehow, nothing ships. The engineering team respects them politically, but not technically.
The Pattern
The Strategy CTO often comes from consulting, product management, or got an MBA along the way. They're articulate, polished, and great in board meetings. They can explain microservices, event-driven architecture, and the build-vs-buy tradeoff with confidence.
The problem? They've never actually built and shipped at startup pace. Their experience is in advising, not executing. They know what "good" looks like in theory, but struggle to get there in practice.
Engineers see through this quickly. They'll nod along in meetings, then quietly ignore the CTO's technical opinions. The result is a leadership vacuum where no one is actually driving technical decisions with conviction.
Warning Signs
- Lots of planning, little shipping. Sprints keep getting "refined." Roadmaps are beautiful but deadlines slip.
- Elaborate documentation. Architecture docs that no one reads. Process for process's sake.
- Engineers are quietly frustrated. They don't push back openly, but they don't follow either.
- "We're building it the right way." Meanwhile, competitors with scrappier teams are shipping.
- Technical decisions by committee. No one has the credibility to make a call and stick with it.
- The CTO avoids code. They "trust the team" but can't evaluate technical tradeoffs firsthand.
Why This Happens
Founders often hire Strategy CTOs because they seem "safe." They interview well. They have impressive credentials. They speak the language of investors and boards.
But startups don't need a CTO who can explain best practices. They need one who can ship despite imperfect conditions. Strategy CTOs optimize for looking right rather than moving fast.
The deeper issue: founders who hire Strategy CTOs often can't evaluate technical ability themselves. They're buying confidence, not competence.
How to Fix It
- Get an outside technical assessment. You need someone who can honestly evaluate whether your CTO has the hands-on skills to lead execution.
- Add a strong technical lead under them. Sometimes the Strategy CTO can work as a "face" while a battle-tested tech lead drives execution.
- Set concrete shipping goals. Not "improve architecture" but "ship feature X by date Y." Make execution visible.
- Watch what engineers actually do. Do they bring hard problems to the CTO? Or do they route around them?
- Have the hard conversation. Sometimes the fit is wrong. Better to address it than burn 6 more months of runway.
How I Can Help
I've worked with several startups dealing with this pattern. The first step is an honest assessment: is this a coaching problem (the CTO can grow) or a fit problem (they can't)?
I can help you evaluate your CTO's actual technical depth, identify where the gaps are, and figure out the right path forward: coaching, restructuring, or transition.
Recognize this pattern?
30-minute diagnostic call.
Tell me what's happening. I'll tell you the one thing to fix first.