The CTO’s Reading List: 12 Books to Level Up Your Leadership in 2025

Reading to Lead: Why CTOs Need a Sharper Stack

Tech stacks evolve fast. Leadership stacks need to evolve even faster.

The problems CTOs face in 2025 aren’t just technical — they’re strategic, cultural, and deeply human. Leading great engineering teams now means understanding systems thinking, communication psychology, organizational design, and personal resilience.

And while experience teaches, books accelerate.

Here’s a curated reading list to sharpen your leadership edge this year.

1. "The Manager's Path" — Camille Fournier

Still the definitive guide for transitioning from IC to manager to executive. Practical, brutally honest, and a north star for building healthy engineering management layers.

Why read it: You’ll level up how you mentor, structure teams, and handle growth pains.

2. "Team Topologies" — Matthew Skelton & Manuel Pais

Scaling teams without scaling dysfunction is an art. This book offers a clear blueprint for designing tech teams that align with software architecture.

Why read it: It will change how you think about org charts, platform teams, and cognitive load.

3. "The Five Dysfunctions of a Team" — Patrick Lencioni

Old but gold. Still one of the best frameworks for diagnosing why even brilliant teams sometimes underperform.

Why read it: Trust, conflict, commitment, accountability, results — in that order.

4. "An Elegant Puzzle" — Will Larson

Written by the former engineering leader at Stripe, this is the tactical, systems-thinking guide for managing complex tech orgs.

Why read it: Practical frameworks for scaling engineering management at speed.

5. "Thinking in Systems" — Donella Meadows

The classic primer on systems thinking. Essential for leaders who want to move beyond symptoms and shape root causes.

Why read it: You’ll see your org, product, and tech debt as interconnected systems — and lead smarter interventions.

6. "Range: Why Generalists Triumph in a Specialized World" — David Epstein

In an industry obsessed with deep specialization, this book argues for broad curiosity and cross-domain learning.

Why read it: It will push you to build teams — and careers — that stay resilient in fast-changing markets.

7. "The Art of Possibility" — Rosamund Stone Zander & Benjamin Zander

A leadership classic that focuses not on control, but on unlocking energy, creativity, and commitment across teams.

Why read it: It changes how you frame challenges and communicate vision.

8. "Trillion Dollar Coach" — Eric Schmidt, Jonathan Rosenberg, and Alan Eagle

A behind-the-scenes look at Bill Campbell’s coaching of leaders at Apple, Google, and beyond.

Why read it: Packed with lessons on humility, trust, and people-first leadership in high-performance environments.

9. "Inspired" — Marty Cagan

The product leadership bible. Cagan distills how top companies build products that users love — and what engineering’s real role is inside that process.

Why read it: Aligns engineering closer to outcomes, not just outputs.

10. "Leaders Eat Last" — Simon Sinek

A foundational look at how great leaders build trust, safety, and long-term team loyalty — especially under pressure.

Why read it: It reframes leadership from authority to responsibility.

11. "Radical Candor" — Kim Scott

Clear, honest, empathetic feedback is a superpower in tech leadership. Scott breaks down how to deliver it without turning into a jerk or a pushover.

Why read it: Helps you grow talent faster without crushing morale.

12. "The Hard Thing About Hard Things" — Ben Horowitz

Not a feel-good leadership book. A real-world guide to making brutal, messy, high-stakes decisions as an executive.

Why read it: It prepares you for the gut-wrenching realities of leading when there’s no perfect playbook.

How to Actually Use This List

Don’t read all 12 back-to-back. Pick one that speaks to your current leadership challenge.

Rotate between tactical (like "The Manager’s Path"), strategic (like "Thinking in Systems"), and emotional (like "Leaders Eat Last") reads.

Leadership isn’t a title you get. It’s a skill set you build — one book, one insight, one decision at a time.