Insights from The CTO Field Guide (for the First 90 Days)
I remember vividly the chaos of my first leadership role in tech — a mix of excitement, confusion, and imposter syndrome. You want to prove yourself immediately, yet everything seems like a moving target. That’s why The CTO Field Guide hit home in a powerful way. Written with raw honesty and practical wisdom, this guide is a must-read for anyone stepping into a tech leadership role — especially for the first time, or stepping into a new organization.
I picked this book because it addresses the real, gritty aspects of becoming a technical leader. It’s not just about org charts and fancy titles — it’s about people, expectations, delivery, and learning how to survive and thrive in those crucial first 90 days. If you're a new CTO, VP of Engineering, or even a senior engineer considering a shift toward management, this guide will provide valuable grounding and practical direction.
Summary
Part 1: The Inner Game
Chapter 1: Introduction
The author sets the stage with a candid reflection on how the CTO role varies wildly across companies — sometimes it’s titled CTO, other times VP of Engineering, or even “Head of X.” What remains constant is that it’s about leadership in a tech context. The guide focuses on that pivotal moment: the first 90 days of stepping into a new company or role.
Chapter 2: Engineering vs Management
This chapter highlights the clash between hands-on engineering and management responsibilities. The “Y career model” — promising equal paths for managers and ICs — is dissected as often being a retention tactic, not a real opportunity. The author urges us to see leadership as a discipline that needs learning, not a fallback.
“Long are gone the days of the insufferable genius or the distant technology executive.” (p. 5)
Chapter 3: Know Your Team
You can’t lead a team you don’t understand. This chapter underlines the need to genuinely grasp what your team does day to day. It also discusses how culture is shaped by both what you tolerate and what you celebrate. “Brilliant jerks” and “tech dramas” are addressed bluntly as threats to long-term health.
Chapter 4: Decisions
One of the most difficult — and inevitable — tasks: making and owning decisions. The idea of “disagree and commit” is introduced alongside the dangers of perceived “top-down” leadership. The book urges leaders to embrace transparency and context-sharing over command-and-control.
Part 2: The Field Guide
Chapter 5: TL;DR
This quick recap says it loud and clear: it’s okay to step into management if you’ve even considered it. The transition won’t erase your technical chops — instead, it expands your influence. You’ll still be relevant, just in a different way.
Chapter 6: The Plan
Planning before day one is essential. This chapter shares a practical framework for getting started — even if it’s just scribbled on a napkin. It emphasizes setting up a mental map to measure progress later, offering a slide deck as a starting point.
Chapter 7: Learning and Measuring
How do you measure success when everything feels like chaos? This chapter is gold — it breaks down delivery metrics from Accelerate (like deployment frequency and MTTR) and introduces cost tracking, team health, and incident metrics. If you want to earn trust with data, start here.
Chapter 8: Challenges
Every reorg, team shift, or new exec presents a unique challenge. This section warns about undefined roles, unclear lines of authority, and sudden shifts. It’s also packed with reminders to lead by example and invest in feedback culture early.
Chapter 9: Org Structure
The Spotify Model gets called out here — not because it’s bad, but because it’s often misunderstood. This chapter urges leaders to clarify lines of accountability and resist matrix reporting that muddies ownership. RASCI models and cross-tribe coordination are offered as tools for clarity.
Chapter 10: Delivery
Here, the book dives into continuous delivery, GitOps, and automation. It’s all about making shipping easy, frequent, and reliable. The takeaway? Deployment shouldn’t be a ritual — it should be routine. And boring stacks are good stacks.
Chapter 11: Closing Advices
The final chapter offers rapid-fire, battle-tested advice. Limit span of control. Standardize stacks. Grow leaders intentionally. Communicate clearly and often. This is where the author’s experience as a mentor and leader really shines.
“Don’t panic. You are the person that can’t panic.” (p. 45)
Key Takeaways
Key Takeaway 1: You don’t lose your technical edge by becoming a manager.
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Explanation: Management doesn't mean stepping away from tech — it means learning how to apply your knowledge differently. You become the amplifier, not the soloist.
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Personal Reflection: This reshaped how I think about influence. Instead of writing code, you write context and create clarity.
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Quote: “You can be technically relevant, without competing with your team or letting your ego go.” – The CTO Field Guide
Key Takeaway 2: A structured plan, even a rough one, is better than winging it.
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Explanation: Coming in blind is a recipe for reactive chaos. A simple checklist helps create momentum and shows progress.
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Personal Reflection: I’ve learned the hard way that even an imperfect plan keeps you focused when the noise level is high.
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Quote: “You probably don’t need or will check all items in there but it is a good baseline to learn how you evolved later on.”
Key Takeaway 3: Metrics are your best ally for alignment and influence.
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Explanation: From delivery to cost to incident management — metrics help you tell the story of where things stand and where they need to go.
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Personal Reflection: I realized I was advocating for change without showing the data — now I always lead with numbers and narratives.
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Quote: “They are there, somewhere in your organization.”
Key Takeaway 4: Culture starts and ends with people — jerks ruin everything.
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Explanation: No matter how technically brilliant someone is, if they drain team energy or create psychological fear, they must go.
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Personal Reflection: Firing a “brilliant jerk” is hard — but every time I’ve done it, the team got stronger, faster.
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Quote: “Brilliant jerks… take a lot of time and energy to manage from everyone, especially their peers.”
Key Takeaway 5: Delivery and cost ownership go hand in hand.
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Explanation: Good engineering isn’t just about clean code — it’s about responsible use of infrastructure and understanding cost dynamics.
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Personal Reflection: Once I started tracking cloud spend and cost per product line, I saw how much influence engineering has on the bottom line.
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Quote: “Money doesn’t like to be thrown around.”
Personal Reflections
This book made me rethink how I approach early-stage leadership transitions. It reminded me that technical leadership isn’t about being the smartest person in the room — it’s about being the most aware, the most curious, and the most willing to adapt. The clarity around building teams, setting boundaries, and driving impact with empathy is something I’ll carry into every role moving forward. It’s not just a playbook — it’s a mirror.
Conclusion
The CTO Field Guide is raw, insightful, and deeply practical. It skips the buzzwords and hits on the emotional and operational realities of technical leadership. If you're starting a new role, building a team, or even considering the leap into management — this is the book to read. You’ll walk away with frameworks, tough love, and a deeper sense of purpose.
And if there's one line that will stick with me:
“Don’t panic. You are the person that can’t panic.”
That’s leadership in a nutshell.