Every tech leader knows the recommendations that actually matter don’t come from Slack threads or polished thought pieces. They come from other leaders who’ve been through the trade-offs, made the hard calls, and kept their teams moving through it all.
That’s the idea behind Leadership Lessons. We ask engineering and tech leaders one deliberately simple question: Which books actually shaped how you lead?
Not the ones that sounded impressive on a shelf. The ones that changed how they think, decide, and show up when the system is under pressure: people, code, incentives, deadlines, and trade-offs.
Below, you’ll find 20 tech leadership book recommendations from leaders at companies like Reddit, Booking.com, and Zapier. If a book didn’t alter how someone leads in practice, it didn’t make the list.
Best tech leadership books to level up as a tech leader
If you’re a tech leader looking to level up your people skills, decision-making, and impact in software environments, these are the best tech leadership books to read in 2026.
20.Drive
Author: Daniel H. Pink
Publisher's description: Forget everything you thought you knew about motivation, it’s wrong. This book reveals that true high performance and satisfaction come from our deeply human need for autonomy, mastery, and purpose: the drive to direct our own lives, learn and create, and make a positive impact.
Recommended by Riaan Nel, Fractional CTO
19. 7 Rules for Positive, Productive Change
Author: Esther Derby
Publisher's description: Even if you don’t have change management in your job description, your job involves change. Esther Derby offers seven guidelines for change by attraction, an approach that draws people into the process so that instead of resisting change, they embrace it.
Recommended by Lena Reinhard, Engineering Leader
18. INSPIRED
Author: Marty Gagan
Publisher's description: In INSPIRED, technology product management thought leader Marty Cagan provides readers with a master class in how to structure and staff a vibrant and successful product organisation, and how to discover and deliver technology products that your customers will love--and that will work for your business.
Recommended by Gregor Ojstersek, CTO & Founder of the Engineering Leadership Newsletter
17. The First 90 Days
Author: Michael Watkins
Publisher’s description: The First 90 Days offers proven strategies for conquering the challenges of transitions, no matter where you are in your career. Watkins, a noted expert on leadership transitions and adviser to senior leaders in all types of organisations, also addresses today's increasingly demanding professional landscape.
Recommended by Kelly Vaughn, Senior Engineering Manager at Zapier
16. Scaling Teams
Author: Alexander Grosse
Publisher’s description: Startups with a hot product often double or triple in size quickly, a recipe for chaos if company leaders aren't prepared for the pitfalls of hyper-growth. If you're leading a startup or a new team between 10 and 150 people, this tech leadership book provides a practical approach to managing your way through these challenges.
Recommended by Mark Copeland, Delivery Principal at Thoughtworks
15. Peopleware
Author: Tom DeMarco and Timothy Lister
Publisher’s description: Few books in computing have had as profound an influence on software management as Peopleware. The unique insight of this longtime best seller is that the major issues of software development are human, not technical. They’re not easy issues; but solve them, and you’ll maximise your chances of success.
Recommended by Riaan Nel, Fractional CTO
14. Training from the Back of the Room
Author: Sharon Bowman
Publisher’s description: Grounded in how the brain actually learns, this approach replaces lectures and slide decks with 65 practical strategies that make learners or team members active participants. Instead of being talked at, people discuss, practice, teach one another, and apply ideas in real time.
Recommended by Lena Reinhard, Engineering Leader
13. Leadership Strategy and Tactics
Author: Jocki Willink
Publisher’s description: There are principles that can be applied and tenets that can be followed. There are skills that can be learned and manoeuvres that can be practised and executed. There are leadership strategies and tactics that have been tested and proven on the battlefield, in business and in life.
Recommended by James Samuel, Software Engineering Leader at Reddit.
12. Thinking Fast and Slow
Author: Daniel Kahneman
Publisher’s description: Two systems shape how humans think and decide: one fast, intuitive, and emotional; the other slow, deliberate, and logical. Kahneman shows how effective leadership depends on knowing when to trust instinct and when to slow down and think.
Recommended by Ronen Agranat, Senior Engineering Manager at Bookings
11. Scaling Up
Author: Verne Harnish
Publisher’s description: This book is written so everyone from frontline employees to senior executives can get aligned in contributing to the growth of a firm. The book focuses on the four major decision areas every company must get right: People, Strategy, Execution, and Cash.
Recommended by Adriën Erasmus, Co-Founder and Director of Warp Development
10. Facilitating Software Architecture
Author: Andrew Harmel-Law
Publisher’s description: A must-read for tech leaders, this book shows how architects and dev teams can collaborate effectively on system design, align around shared goals, and build better systems through a collaborative, decentralised mindset.
Recommended by Mark Copeland, Delivery Principal at Thoughtworks
9. The Culture Map
Author: Erin Meyer
Publisher’s description: A practical guide to working across cultures, this book explains how deeply ingrained differences in communication, feedback, hierarchy, and leadership can derail global teams. Using real-world examples and a clear framework, The Culture Map helps leaders decode cultural differences and collaborate more effectively in a global workplace.
Recommended by Kelly Vaughn, Senior Engineering Manager at Zapier
8. EMPOWERED
Author: Marty Cagan
Publisher’s description: A practical guide to building empowered teams, this book shows how ordinary people can achieve extraordinary results when given the right context, trust, and support. Aimed at leaders across tech-driven organisations, it focuses on how to unlock the best work from product, design, and engineering teams, teaching not just why empowerment matters, but how to make it real.
Recommended by Gregor Ojstersek, CTO & Founder of the Engineering Leadership Newsletter
7. The Mythical Man-Month
Author: Frederick P. Brooks
Publisher’s description: A revised edition of a software management classic, this book explores why large projects are uniquely hard, why conceptual integrity matters, and why there’s still no “silver bullet” for software complexity, offering timeless insights for managing complex systems.
Recommended by Riaan Nel, Fractional CTO
6. The Making of a Manager
Author: Julie Zhuo
Publisher’s description: A practical, reassuring guide for first-time managers, this book shares honest lessons from the transition into leadership and offers clear, actionable advice on hiring, feedback, difficult conversations, and earning trust.
Recommended by James Samuel, Software Engineering Leader at Reddit.
5. How to Win Friends and Influence People
Author: Dale Carnegie
Publishers description: Offering practical advice and techniques, this book helps you to learn how to get out of a mental rut and make life more rewarding. It supports you to turn your relationships around and improve your interactions with everyone in your life. It’s the most famous confidence-boosting book ever published.
Recommended by Ronen Agranat, Senior Engineering Manager at Bookings
4. The Five Dysfunctions of a Team
Author: Patrick Lencioni
Publisher’s description: Interwoven with the fictional story of a woman who becomes CEO of a struggling, high-profile company with a dysfunctional executive team is an analysis of the five corruptions, diagnostic questions to help readers assess their organisations, and a teamwork model of the action steps to overcome the corruptions.
Recommended by Gregor Ojstersek, CTO & Founder of the Engineering Leadership Newsletter
3. Turn the Ship Around
Author: L. David Marquet
Publisher’s description: No matter your business or position, this book shows you how to apply the author's approach to create a workplace where everyone takes responsibility for their actions, people are healthier and happier and everyone is a leader.
Recommended by Riaan Nel, Fractional CTO
2. The Manager’s Path
Author: Camille Fournier
Publisher's description: Managing people is difficult wherever you work. But in the tech industry, where management is also a technical discipline, the learning curve can be brutal-especially when there are few tools, texts, and frameworks to help you. In this practical guide, Camille Fournier takes you through each stage in the journey from engineer to technical manager.
Recommended by James Samuel, Software Engineering Leader at Reddit.
1. Radical Candor
Author: Kim Scott
Publisher's description: Be a great leader, but don't be a jerk. This book tells you how. Scott earned her stripes as a highly successful manager at Google before moving to Apple where she developed a class on optimal management. Radical Candor draws directly on her experiences at these cutting edge companies to reveal a new approach to effective management that delivers huge success by inspiring teams to work better together by embracing fierce conversations.
Recommended by Riaan Nel, Fractional CTO
Why should you read tech leadership books?
You can take a course. You can follow the right people. You can skim threads and save posts. And some of that helps. But much of what today’s experts and thought leaders teach has already been worked through carefully in books written years, sometimes decades, earlier.
Tech leadership is no different.
You can learn from a lot of places. But reading does something those formats can’t.
Here’s why books still matter:
- Most “new” ideas aren’t new Many leadership lessons shared today were already explored more deeply and carefully in books written years (sometimes decades) ago.
- Reading forces active thinkingYou can half-listen to a podcast while walking, scrolling, or replying to Slack. You can’t do that with a book. Reading demands focus and focused effort sticks.
- Effort improves retentionWhen your brain works harder, it remembers more. Ideas don’t just pass through: you sit with them, wrestle with them, and absorb them.
- Books shape how you think, not just what you knowInstead of collecting tips, you develop mental models that influence decisions long after you’ve closed the book.
- Books are slower and that’s a strengthA blog post can be written in an afternoon. A book takes months or years: written, rewritten, challenged, and refined.
- You’re learning from hard-won experienceA good tech leadership book isn’t “content.” It’s the most complete version of what someone has learned through real trade-offs, mistakes, and responsibility.
Compile your book list
Whether these books get added to your wish or shopping lists, they give tech leaders a new idea, a fresh perspective, or a unique way to tackle technology, people leadership, and modern work at scale.