These are the touchstone books and articles I share with founders and product managers. The more you learn about product design, how people think and make decisions, what feelings are, how to run efficient teams and how groups operate, the more it all blends together. Only a few of these books are subject-matter specific to technology. Many of them are about understanding what it is to be a human being, from the inside out.
I have a high standard for books. The following are books that needed to be books, and would not have sufficed as articles or Medium posts. Remember that books do not have feelings, no matter how many episodes of Tidying Up you’ve watched. They will not be offended if you skip around for the best parts.
In order to complete reading books, I’ve started buying both the Kindle and the audio versions. I’m able to read in environments conducive to reading and listen when I’m walking or driving. I also listen to most audiobooks at 1.5x speed.
Mindset by Carol Dweck
This book is a therapist and hype girl at once — perhaps the perfect antidote to the misguided classism of Lean In. If you were ever lumped into the gifted and talented bucket as a kid, Dr. Dweck will break you out of the prison of other people’s opinions and rebuild your resilience. Success is not about avoiding failure, it is about pushing yourself so that you learn from your inevitable failures. Follow her advice and you will learn to seek failure and constantly improve.
In short, the growth mindset lets people — even those who are targets of negative labels — use and develop their minds fully. Their heads are not filled with limiting thoughts, a fragile sense of belonging, and a belief that other people can define them.
The Undoing Project by Michael Lewis
I commonly recommend this book instead of Daniel Kahneman’s Thinking Fast and Slow; while the latter is fine… it could have been a Medium post. /ducks
Michael Lewis is an unparalleled non-fiction writer. Not only is The Undoing Project a handy and contextual summary of the psychological studies that form the basis of behavioral economics, it’s also a touching story about friendship and collaboration. I finished the book while walking to meet friends for dinner, tears streaming down my face.
The point, once again, wasn’t that people were stupid. This particular rule they used to judge probabilities (the easier it is for me to retrieve from my memory, the more likely it is) often worked well. But if you presented people with situations in which the evidence they needed to judge them accurately was hard for them to retrieve from their memories, and misleading evidence came easily to mind, they made mistakes. “Consequently,” Amos and Danny wrote, “the use of the availability heuristic leads to systematic biases.” Human judgment was distorted by . . . the memorable.
Never Split the Difference by Chris Voss
As any one of the 100+ people I’ve mentored on Twitter can attest, Have you read Never Split the Difference yet? is the first question I ask. Never Split the Difference is the best business book of all time. It’s also the best relationship and parenting book of all time. If you apply the lessons of this book, your midi-chlorian count will increase exponentially and you will become a Jedi Knight. I read this book a few times a year. Yan-David Erlich’s notes and script builder are the perfect companion piece.
Part of what makes this book so great is that Voss tells a story for each of the tactics, which makes the takeaway much more memorable. The underlying lesson is that negotiations are about healthy communication and not adversarial:
These tools, then, are nothing less than emotional best practices that help you cure the pervasive ineptitude that marks our most critical conversations in life. They will help you connect and create more meaningful and warm relationships. That they might help you extract what you want is a bonus; human connection is the first goal.
When you’re ready to really dig in, Voss’ company Black Swan Ltd. also runs negotiation training over video chat. That training is the best way to spend your personal development funds next to Michael Dearing’s General Management class. (I’ve taken both.)
The Art of Game Design by Jesse Schell
Product and software designers have a lot to learn from game design. The games industry pioneered the practice of playtesting, wherein you simply watch people play the most recent build of your game to figure out if it feels right. This is substantially different from how most product teams think of usability testing, which is often oriented around a conversion funnel. If you’re looking just at someone’s mouse during user research, and not at their face or listening to their tone of voice, you are missing out on 80% of the findings.
The Art of Game Design is a seminal game design textbook that illustrates the polymath nature of product design. There are tons of lessons for everyone who makes stuff; one of my favorites is that making a decision beats not making a decision by a country mile.
Some people are quite disconcerted by this combination of snap decisions combined with sudden reversals. But it is the most efficient way to make full use of your decision-making power, and game design is all about making decisions — you need to make the best decisions possible, as fast as possible, and this slightly eccentric behavior is the way to do it. It’s always better to commit to an idea sooner, rather than later — you will get to a good decision much faster than if you bide your time considering potential alternatives. Just don’t fall in love with your decision and be ready to reverse it the moment it isn’t working for you.
Sapiens by Yuval Harari
If you haven’t already been recommended this book 1,000 times, you probably don’t live in the Bay Area. Sapiens is the first book in a series that gives humanity the cosmic scope of a species rather than the narrow scope of a single civilization. Next in the series is the far-future facing Homo Deus, followed by the near-term 21 Lessons for the 21st Century. They are all worth reading, but as far as an examination of humanity goes, nothing beats Sapiens. It’s honest and cutting. For as much time as we spend on the positively transformative while building new technologies, we ignore the destructive selfishness of our species at our own peril.
Moreover, despite the astonishing things that humans are capable of doing, we remain unsure of our goals and we seem to be as discontented as ever. We have advanced from canoes to galleys to steamships to space shuttles — but nobody knows where we’re going. We are more powerful than ever before, but have very little idea what to do with all that power. Worse still, humans seem to be more irresponsible than ever. Self-made gods with only the laws of physics to keep us company, we are accountable to no one. We are consequently wreaking havoc on our fellow animals and on the surrounding ecosystem, seeking little more than our own comfort and amusement, yet never finding satisfaction.
Articles and Posts
Most books should be articles or posts, and these are the best of the genre. I love the article format because they are lessons you should consistently reference while you build products or companies. Articles are quick to read and easy to share.
Ken Norton on prioritized feature lists
Slack CEO & founder Stewart Butterfield used to gently rib me about my apparently too frequent references to this blogpost. I maintain that if the top features on your list is a habitable planet, it doesn’t matter what the other features are. Doing the one thing that matters, in product design, company building, and life, is the one thing that matters.
Rahul Vohra on finding product/market fit
There’s nothing I love more than a real, concrete example. Most people are afraid to share the messy middle of their lives, because we’re all addicted to looking like we know what we’re doing at all time. Rahul’s write-up of the methodical approach his team took to finding product/market fit should be an inspiration and guidepost for every early-stage founder.
Molly Graham on giving away your LEGOs
I cited this article in my post about leaving Slack, and I continue to recommend it to people at hypergrowth companies. It’s very dangerous to hire people who can’t or won’t give away their LEGOs, because that is how toxic politics infest and destroy your culture.
Stewart Butterfield on building products, and more
This post must have been referenced and shared within Slack hundreds of times in the first few years. When I wrote the charter for our Growth team, our mission included this line: “Our job is to understand what people think they want and then translate the value of Slack into their terms.” I still come back to this post for inspiration.
Steven Sinofsky on writing as thinking
I wanted to end with this post, in part because it’s really an annotated Twitter thread and I love Steve Sinofsky for proving the exception to the rule that most books should be articles and most articles should tweetstorms. In this case, the tweetstorm was the MVP and this article is aces. If I could graffiti the following onto every office wall in San Francisco, I would:
All processes, no matter how innovative, positive, or even causal to success, will run their course. In particular as a company matures, processes always have a tendency to cease to function as a tool and become the result themselves. This is always a mess.
There are just two tweetstorms that I think are evergreen enough to share on this list (for now!) and both are about the importance of execution.
The first is from Fareed Mosavat, who runs Lifecycle at Slack and is one of the best growth product people working today. The second is a really touching story from Mekka Okereke about the people who make the visions of visionary founders a reality.
What’s probably evident from this list is that building companies and products is a holistic, messy process that favors autodidactic polymaths over experts and specialists. Go wide with your inputs: there are insights everywhere to blend into your worldview. Go deep with your customers: that is the one subject on which you need to build expertise.