When you think about the personality types and professional backgrounds that most often lead someone to the CEO role, you don’t think about introverted tech guys like me. Over the past decade, I have worked systematically and diligently to overcome that bias by becoming a leader myself. One of the ways I burnished my skills was by reading widely in strategy, leadership, and managing people.

Here are the books that have been the most influential on my journey to becoming CEO of Upwork:

  1. Anticipate. The Architecture of Small Team Innovation and Product Success by Ronald Brown
  2. The Charisma Myth: How Anyone Can Master the Art and Science of Personal Magnetism by Olivia Fox Cabane
  3. Continuous Delivery: Reliable Software Releases Through Build, Test, and Deployment Automation by Jez Humble and David Farley
  4. CustomerCentric Selling by Michael T. Bosworth and John R. Holland
  5. The Four Steps to the Epiphany: Successful Strategies for Products That Win by Steve Blank
  6. Getting Things Done: The Art of Stress-Free Productivity by David Allen
  7. The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz
  8. Hooked: How to Build Habit-Forming Products by Nir Eyal with Ryan Hoover
  9. How Google Works by Eric Schmidt and Jonathan Rosenberg
  10. Inspired: How to Create Products Customers Love by Marty Cagan
  11. Jack: Straight from the Gut by Jack Welch with John A. Byrne
  12. Lean Enterprise: How High Performance Organizations Innovate at Scale by Jez Humble, Joanne Molesky, and Barry O’Reilly
  13. Made to Stick: Why Some Ideas Survive and Others Die by Chip Heath and Dan Heath
  14. The New Strategic Selling: The Unique Sales System Proven Successful by the World’s Best Companies by Robert B. Miller and Stephen E. Heiman with Tad Tuleja
  15. Predictable Revenue: Turn Your Business into a Sales Machine with the $100 Million Best Practices of Salesforce.com by Aaron Ross and Marylou Tyler
  16. Rework by Jason Fried and David Heinemeier Hansson
  17. Steve Jobs by Walter Isaacson
  18. Super Crunchers: Why Thinking-by-Numbers Is the New Way to Be Smart by Ian Ayres
  19. Thinking Strategically: The Competitive Edge in Business, Politics, and Everyday Life by Avinash K. Dixit and Barry J. Nalebuff
  20. Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel with Blake Masters

What are your favorite strategy, leadership, and management books? Let me know in the comments.