Four Great Books on Leadership

Tom Drapeau
Codifying
Published in
4 min readOct 2, 2019

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Books!

One fourth score and seven months ago, I was given a large challenge. There was a need for someone to lead the client engineering teams at iHeartRadio. Until that time (hope my Gettysburg Address math is correct) my experience resided in leading backend teams (REST-based service tier, content ingestion and at that time, the beginnings of a data team). I accepted at once, and as a result, the size of my team tripled and I began the journey towards ensuring all of my new teams had proper leadership, understanding of the mission and good standards/accountability.

In addition, I needed to double the size of my (already large) team in order to meet business needs related to converting the iHeartRadio apps from free to freemium, as well as handling international expansion throughout North America (CA, MX) and Australia/New Zealand. I quickly realized I needed to codify my thoughts to help in guiding my teams to success, and decided to hit the books to learn from the experts.

I ended up reading about 20 books on management and/or leadership. I can wholeheartedly recommend four:

This is a book called Turn the Ship Around, it is a leadership book.
Book: Turn the Ship Around!

Turn the Ship Around!: A True Story of Turning Followers into Leaders, by L. David Marquet. This is the story of a newly appointed nuclear submarine captain and his story of converting his charge (the crew of the USS Santa Fe) from the U.S. Navy’s traditional leader-follower approach to a leader-leader approach. I really like the storytelling and the step-by-step nature of the narrative. I’m generally attracted to books told from an operational point of view, so my enjoyment of this book was heightened even more.

This is a book called High Output Management.
Book: High Output Management

High Output Management, by Andy Grove. This classic read from Intel’s former chairman and CEO is the best step-by-step book on building a company and then running it. The text is easily approachable, its not overly long, and the scenarios explained are both relatable and real.

This is a book called Trillion Dollar Coach. It is a book on leadership.
Book: Trillion Dollar Coach

Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell, by Eric Schmidt, Jonathan Rosenberg, Alan Eagle. This is the best book I’ve ever read with regard to becoming more motivational. It also has the best description on how to handle 1 on 1’s in a very real, productive and scalable way. This is a guy who did not mince words and who advised some of the most revered names in the Valley tech scene (Steve Jobs, Larry/Sergey/Eric, etc).

This is a book called The Manager’s Path. it is a book on technical leadership.
Book: The Manager’s Path

The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change, by Camille Fournier (CTO, Rent The Runway). This is the best book I have read on navigating up the engineering career ladder, and explaining not just what you need to achieve to move up to the next rung, but what you should expect to do / be responsible for once you have moved up to that rung. At the time of reading the book, my role was SVP Engineering. Not only did the book have a great description of how an SVP has the right type and amount of technical impact on the platform(s) s/he leads as a manager of managers, it also had tips for moving up from SVP to CTO. Great stuff here all around!

Honorable mentions: Managing Humans by Michael Lopp, and Coders at Work by Peter Seibel. Both are great reads — Managing Humans has wonderful, very specific and detailed stories to illuminate the day-to-day of a software engineering manager. Coders at Work are a great collection of interviews with many of the luminaries of engineering (think Steve Woz), and is a great read to inspire (or re-inspire) interest in engineering as a pursuit, if not a career.

I hope you find these books as helpful as I did. They were vital in setting a vision for a large team, staffing/ensuring the correct hiring profile, establishing growth paths for engineers, and ensuring the work gets done, while technical debt in our codebases decreases and project successes are celebrated.

Do you know a great book that I missed in my list? Let me know in the comments.

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