Book recommendations.

Folks occasionally ask me to recommend books to help them in their professional career. I can usually think of a couple recommendations in the moment, but always feel like I’m forgetting far more good books than I’m recommending. In the hope of providing a better answer going forward, I’ve written up some of the general purpose, leadership and management books I’ve read.

Not all of these are classically great books, some are even a bit dull to read, but they’ve changed how I think in a meaningful way. They’re roughly sorted from those I found most valuable to least:

1. Thinking in Systems: A Primer by Donella Meadows. For me, systems thinking has been the most effective universal tool for reasoning through complex problems, and this book is a readable, powerful introduction.
2. Don’t Think of An Elephant! Know Your Values and Frame the Debate by George Lakoff. While written from a political perspective that some might find challenging, this book completely changed how I think about presenting ideas. You may be tempted to instead read his more academic writing, but I’d recommend reading this first as it’s much briefer and more readable.
3. Peopleware: Productive Projects and Teams by DeMarco and Lister. The book that has given generations of developers permission to speak on the challenges of space planning and open offices. Particularly powerful in grounding the discussion in data.
4. Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency by Tom DeMarco. Documents a compelling case for middle managers as the critical layer where organizational memory rests and learning occurs. A meditation on the gap between efficiency and effectiveness.
5. The Mythical Man-Month by Frederick Brooks. The first professional book I ever read, opening my eyes to the wealth of software engineering literature waiting out there.
6. Good Strategy Bad Strategy: The Difference and Why it Matters by Richard Rumelt. This book gave me permission to acknowledge that many strategies I’ve seen professionally are not very good, and a structured approach to writing good strategies.
7. The Goal: A Process of Ongoing Improvement by Eliyahu Goldratt. Explores how constraint-theory can be used to optimize process.
8. The Five Dysfunctions of a Team by Patrick Lencioni.
9. The Three Signs of a Miserable Job by Patrick Lencioni. Another Lencioni book, this one explaining a three-point model for what makes jobs rewarding.
10. Finite and Infinite Games by James Carse. Success in most life situations is about letting everyone continue to play, not about zero-sum outcomes. This seems pretty obvious, but for me it helped reset my sense of why I work.
11. INSPIRED: How to Create Tech Products Customers Love by Marty Cagan. A thoughtful approach to product management.
12. The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail by Clayton Christensen. A look at how being hyper-rational in the short-run has led many great companies to failure. These days I think about this constantly when doing strategic planning.
13. The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It by Michael Gerber. The idea that leadership is usually working “on” the business, not “in” the business. Work in the business to learn how it works, but then document the system and hand it off.
14. Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time by Susan Scott. How to say what you need to say, particularly powerful in giving structure to get past conflict aversion.
15. Becoming a Technical Leader: An Organic Problem-Solving Approach by Gerald Weinberg. Permission to be a leader that builds on your strengths, not whatever model that folks think you should fit into.
16. Designing with the Mind in Mind by Jeff Johnson. An introduction to usability and design, grounding both in how the brain works.
17. The Leadership Pipeline: How to Build the Leadership Powered Company by Charan, Drotter and Noel. This book opened my eyes to just how thoughtful many companies are in intentionally growing new leadership.

If you’re looking for even more to read, here are books I took something valuable away from, but only one or two things. Unlike the first list, they’re not sorted in any discernible order!

1. The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change by Camille Fournier.
2. High Output Management by Andy Grove.
3. The First 90 Days by Michael Watkins.
4. The Effective Executive: The Definitive Guide to Getting the Right Things Done by Peter Drucker.
5. Don’t Make Me Think: A Common Sense Approach to Web Usability by Steve Krug.
6. The Deadline: A Novel About Project Management by Tom DeMarco.
7. The Psychology Of Computer Programming by Gerald Weinberg.
8. Adrenaline Junkies and Template Zombies: Understanding Patterns of Project Behavior by DeMarco, Hruschka, Lister, McMenamin, Robertson and Robertson.
9. The Secrets of Consulting: A Guide to Giving and Getting Advice Successfully by Gerald Weinberg.
10. Death by Meeting by Patrick Lencioni.
11. The Advantage: Why Organizational Health Trumps Everything Else in Business by Patrick Lencioni.
12. Rise: 3 Practical Steps for Advancing Your Career, Standing Out as a Leader, and Liking Your Life by Patty Azzarello.
13. The Innovator’s Solution: Creating and Sustaining Successful Growth by Christensen and Raynor.
14. The Phoenix Project by Kim, Behr and Spafford.
15. Accelerate: Building and Scaling High Performing Technology Organizations by Forsgren, Humble and Kim.

I’m sure I’ve missed hundreds of wonderful books. Drop me a note! If you’re looking for even more to read, I’ve also written up my favorite technical papers.