My Core Book Stack

What?

A core book stack is one that literally or figuratively sits on your desk. It contains the core books that make up your belief system. The following is my core book stack on leadership.

Why?

When I first became a CTO, I had an “Oh Shit” moment. You know, that moment when you realize you are being asked to do things you have never done before. That moment when an entire organization is looking to you and nobody else. You want to talk about intimidation!

I believe I was offered the opportunity to become the CTO because I had great relationships with the people I worked with and a proven track record of delivering high-performing systems. But “What Got You Here Won't Get You There” (that one was recently recommended and is on the reading list).

With nowhere else to turn, I immersed myself in books. What I discovered was a world of experienced leaders eager to share their journeys. They offered insights on how to inspire, how to operate effectively, and how to embrace experimentation and learning. They emphasized the importance of focus and prioritization, advocating for a lean approach that starts small—identifying the smallest market and segment where you can build a stronghold, and then scaling distribution and operations from there. These leaders conveyed the rewards of leadership but were candid about the challenges, both physical and emotional, that come with scaling a company. Some days, it can feel like engaging in a full-contact sport.

I owe a lot of my success to the following books and the authors who shared their thoughts and experiences. I hope that by sharing this, at least one of these books can help you too! These have had the most significant influence on me as a leader of people and technology.

Each category starts with the book that had the most impact on me.

Side Note

I am an engineer at heart. In my humble opinion, every single technology leader, whether you are a people leader or an engineer, should read these two books. They are also listed below.

• "Accelerate: The Science of Lean Software and DevOps: Building and Scaling High-Performing Technology Organizations" by Nicole Forsgren, Jez Humble, and Gene Kim
• "Empowered: Ordinary People, Extraordinary Products" by Marty Cagan

Be A Great Leader

I always want to start from a framework. If I have a framework, I can do just about anything. Becoming a great leader is no different. My favorite framework comes from John Maxwell’s?"5 Levels of Leadership." Below, I have listed the books that most influenced me for each level of leadership.

A thought on Bill Campbell. While reading these, I found Bill Campbell's name mentioned in a handful of these books. Now that is a level 5 leader!

Level 5 Pinnacle: People follow you because of who you are, and what you stand for

• "Trillion Dollar Coach: The Leadership Playbook of Silicon Valley's Bill Campbell" by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle

Level 4 People Development: People follow you because of what you have done for them

• "The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever" by Michael Bungay Stanier
• "Start With Why: How Great Leaders Inspire Everyone to Take Action" by Simon Sinek

Level 3 Production: People follow you because of what you have done for the company

Engineering Specific - Engineering Operations, Operations of Product & Engineering Working Together, & Organization alignment.

• "Accelerate: The Science of Lean Software and DevOps: Building and Scaling High-Performing Technology Organizations" by Nicole Forsgren, Jez Humble, and Gene Kim
• "Empowered: Ordinary People, Extraordinary Products" by Marty Cagan
• "Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs" by John Doerr

Leadership Specific

• “Transformed: Moving to the Product Operating Model” by Marty Cagan
• "The Advantage: Why Organizational Health Trumps Everything Else In Business" by Patrick Lencioni
• "Good to Great: Why Some Companies Make the Leap and Others Don't" by Jim Collins
• "The Five Dysfunctions of a Team: A Leadership Fable" by Patrick Lencioni

Product Management Specific

• "Inspired: How to Create Products Customers Love" by Marty Cagan

Level 2 Permission: People follow you because they want to

• Manager Tools Basics - These podcasts were instrumental in my becoming CTO because they gave me a framework for building lasting relationships in the workplace.
• "The Ideal Team Player: How to Recognize and Cultivate The Three Essential Virtues" by Patrick Lencioni

Building Or Scaling A Startup

If you are involved in building or scaling a company, I highly recommend these books in this order. They will help your company succeed, but more importantly, they will help you compartmentalize and survive!

• "The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers" by Ben Horowitz
• "Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets" by Al Ramadan, Dave Peterson, Christopher Lochhead, and Kevin Maney
• "Good to Great: Why Some Companies Make the Leap and Others Don't" by Jim Collins
• "Zero to One: Notes on Startups, or How to Build the Future" by Peter Thiel and Blake Masters
• "Exponential Organizations: Why new organizations are ten times better, faster, and cheaper than yours" by Salim Ismail
• "The Lean Startup: How Today's Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses" by Eric Ries
• "High Growth Handbook: Scaling Startups from 10 to 10,000 People" by Elad Gil