Book Review: \"The CTO Playbook\" by Robert Milejko
Most CTO books fall into one of two traps. Either they're so abstract you finish thinking "great, but what do I do on Monday?" or they're so specific to one company that the advice doesn't transfer. Robert Milejko's "The CTO Playbook," published in May 2023, mostly avoids both. It's a phase-by-phase guide that feels written by someone who has lived the job, not just studied it.
I'm always looking for resources to recommend to first-time CTOs transitioning from IC to leadership. There aren't many good ones. This book earns a spot on the short list.
The Five-Phase CTO Journey
The core framework of the book is a five-phase model of how the CTO role evolves as a company grows. This is the most valuable part.
Phase 1: The Builder. You're writing most of the code. You're the architecture. You're the DevOps pipeline. You're the entire engineering team. The key challenge isn't technical — it's recognizing when this phase needs to end.
Phase 2: The Team Lead. You've hired your first engineers. Now you're splitting time between coding and managing. Milejko is honest about how painful this is. You're not great at either because you're doing both. His advice: accept the discomfort, but start delegating the code faster than you think you should.
Phase 3: The Manager of Managers. You're no longer managing individual engineers — you're managing the people who manage them. This is where most first-time CTOs either grow or break. The skills that got you here (technical depth, hands-on problem solving) are no longer the primary ones you need.
Phase 4: The Strategic Leader. Engineering is a function you oversee, not a craft you practice daily. You're in board meetings. You're making build-vs-buy decisions at the organizational level. You're thinking in quarters and years, not sprints.
Phase 5: The Executive. You're part of the C-suite operating as a peer to the CEO, CFO, and CPO. Your job is to translate technology into business outcomes and business strategy into technical direction.
What I appreciate about this framework is that Milejko doesn't present it as linear or inevitable. Not every CTO reaches Phase 5, and not every company needs them to. A 20-person startup needs a Phase 2 CTO. Putting a Phase 5 executive in that seat would be a disaster — and vice versa.
Building Engineering Culture
The middle chapters on engineering culture are where the book shifts from framework to practical advice. Milejko argues — and I agree — that culture isn't something you define in a document and hang on the wall. It's the aggregate of the decisions you make and the behaviors you tolerate.
He covers:
- Hiring for culture contribution, not culture fit. The distinction matters. "Fit" often means "people like us," which leads to homogeneous teams. "Contribution" means asking what perspective or strength this person brings that the team currently lacks.
- Establishing technical standards without micromanaging. Set clear expectations (code review requirements, testing standards, documentation norms) but let teams decide how to meet them.
- Creating psychological safety around failure. If your post-mortem process assigns blame, your team will hide problems. If it focuses on systems and processes, they'll surface problems early.
None of this is revolutionary if you've read widely on engineering management. But Milejko presents it in a way that's actionable for someone who hasn't. He gives you the "here's what to actually do" that many leadership books skip.
Technical Debt as Business Strategy
This was the chapter I highlighted the most. Milejko reframes technical debt not as a failure to be eliminated but as a strategic tool to be managed.
His argument: every business carries financial debt as a deliberate strategy — you borrow to invest, and you manage the interest payments. Technical debt should work the same way. Sometimes you take on debt intentionally because shipping fast matters more than clean architecture right now. The problem isn't the debt itself. The problem is untracked debt — shortcuts nobody documented, assumptions nobody recorded, code nobody understands anymore.
He proposes a simple system: every intentional shortcut gets logged with a description, an estimated cost to fix, and a trigger condition ("fix this before we exceed 10K daily active users"). This turns technical debt from a vague anxiety into a managed portfolio — and gives you a framework to have productive conversations about it with your CEO and board.
How It Compares to Other CTO Resources
The obvious comparison is Will Larson's "An Elegant Puzzle" (2019). Larson goes deeper on systems thinking and organizational design — mental models for sizing teams, managing migrations, running organizational change. Milejko is more personal and more oriented toward the individual journey. It's about YOU growing into the role, not just about how the organization should work.
First-time CTO at a seed-stage startup? Read Milejko's. Engineering VP at a 200-person company? Read Larson's. Ideally, read both.
What's Missing
Distributed teams get minimal treatment. Given that most engineering orgs in 2023 include remote engineers, this felt like an oversight. The challenges of building culture and managing across time zones deserve more than a few paragraphs.
The European startup context is largely absent. Milejko is Polish, but the book reads as fairly US-centric in its assumptions about funding stages and growth trajectories.
Board communication feels surface-level. For Phase 4 and 5 CTOs, learning to communicate with non-technical board members is critical. The book touches on it but doesn't give you enough concrete tools.
Who Should Read It
First-time CTOs recently promoted from lead engineer or co-founding a startup. The phase model alone will help you understand where you are and what's coming next.
Technical founders starting to hire their first engineers and feeling the pull between building and leading.
Engineering managers who aspire to the CTO role and want to understand what the job looks like beyond their current scope.
If you're already an experienced CTO, you'll find the book validates what you've learned rather than teaching you new things. Set expectations accordingly.
The Bottom Line
A solid, practical guide that's one of the most complete end-to-end treatments of the CTO role I've read. The five-phase model is genuinely useful as a self-assessment tool, and the chapters on culture and technical debt stand on their own.
At Conectia, I work with CTOs at different phases of this journey every week. The pattern I see most: the transition from Phase 1 to Phase 2 — builder to leader — is the hardest. The right senior engineers make that transition possible because they carry the technical weight so you can focus on the leadership work Milejko describes.
Transitioning from builder to engineering leader? Talk to a CTO — we help you bring on senior LATAM engineers who can carry the technical execution while you focus on leading.
