My Reading List for Startup Leaders
During my leadership journey at two startups that were acquired, through leading teams of up to 150 people at Airbnb, to now coaching startup founders and tech executives of companies funded by the top venture capital firms in the world, these are the books I’ve found to be most helpful to me and the highly successful founders, CEOs, CTOs, and VPs of Engineering/Product that I coach. I hope they'll be helpful to you as well.
Crucial Conversations: Tools for Talking When Stakes Are High
By Kerry Patterson, Joseph Grenny, Ron McMillan, Al Switzler (Amazon)
This is the most important book I’ve ever read on conversations and is the number one book I recommend to the leaders I coach. It will teach you how to have more effective conversations in both low stakes and high stakes conversations inside and outside of work. One of its most important lessons is to create a mutual purpose for every conversation so you and the others involved have something to work toward together. It includes frameworks and practical examples.
The Meaning Revolution: The Power of Transcendent Leadership
By Fred Kofman (Amazon)
Kofman covers how to solve some of the hardest leadership problems of disengagement, disorganization, disinformation, and dissolution by using people-centered solutions involving motivation, culture, response-ability, and collaboration. The final part of his book is on how to become a transcendental leader. Read the whole thing or pick the chapters that are most relevant to you.
The Advantage: Why Organizational Health Trumps Everything Else In Business
By Patrick Lencioni (Amazon)
From the author of The Five Dysfunctions of a Team, The Advantage is a playbook for creating a healthy organization that consistently performs. Lencioni covers how to build a cohesive leadership team, create clarity within an organization, and have a system of highly effective meetings.
The Leadership Pipeline: How to Build the Leadership Powered Company
By Ram Charan, Stephen Drotter and Jim Noel (Amazon)
This book is a very practical look at the differences between every level of management at a company, what it takes to succeed at each one, and what common pitfalls tend to occur when someone moves up a level. The levels include first-line manager, manager-of-managers, leader of a function (e.g. engineering, sales), and CEO. It’s a great way to both understand how to be successful at your level plus how to find the right people to be managers on your team and how to help them be successful.
When reading, keep in mind that at startups the roles don’t always cleanly map to one level. For example, a CTO at a growing company may already be the functional leader yet is still making the transition from manager to manager-of-managers. With this book in particular, feel free to just read the chapters relevant to you and your team.
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
By Ben Horowitz (Amazon)
A true classic in Silicon Valley. Horowitz doesn’t present a formula on how to run a company. Instead, he focuses on some of the hardest things that come up when running a company — often ones that aren’t addressed much elsewhere. It has a very personal feel to it since it's primarily drawn from his own experience. In addition to being very informative, it’s also a fun read.
The Effective Executive: The Definitive Guide to Getting the Right Things Done
By Peter Drucker (Amazon)
A somewhat short read from management guru Peter Drucker originally published in 1967 with lessons that still hold their own today. Drucker covers how to use time efficiently, run a highly effective decision making process, and make people’s strengths productive. Somehow in less than 200 pages, it manages to be both theoretical and practical at the same time.
Secrets of Sand Hill Road: Venture Capital and How to Get It
By Scott Kupor (Amazon)
Written in 2019 by Scott Kupor, a partner at one of the world’s premier venture capital firms, Andreessen Horowitz. This book serves as a much needed view into how venture capital works behind the scenes, including the motivations of VCs and how they assess who to invest in. A really helpful book to any founder raising money, especially if it’s their first time.