Mastery: The Keys to Success and Long-term Fulfillment
By George Leonard
Plume, 1992

Yes, the title sounds like a tacky self-help book. And this is, in fact, a self-help book — but it’s not tacky. On the contrary: even though it’s short, it’s also profound. The author, who died in 2010, held a fifth-degree black belt in Aikido. (The book is suffused with lessons from martial arts and Zen.) He was also President Emeritus of the Esalen Institute, editor of Look Magazine, and a U.S. Army Air Corps pilot. In other words, an experienced leader.

Mastery matters. You can be intelligent, educated, proactive, responsible, etc. — but you still won’t realize your true potential if you don’t set yourself on a (lifelong) mastery journey. What is mastery? As Mr. Leonard points out, the term resists definition, but you can recognize it in the actions of athletes, artists, entrepreneurs, etc., who are committed to excellence. (The late Rush drummer Neil Peart comes to mind.)

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High Output Management
By Andrew S. Grove, with a new foreword by Ben Horowitz
Vintage Books, 2015

Management is a crucial business skill. Regardless of your line of work or seniority, at some point in your career, you’ll likely find your work being managed or having to manage the work of others. It behooves you — and your team-mates – to do it right. I know of no better introduction to the practice than High Output Management, written by Intel CEO Andy Grove almost four decades ago.

The book is divided into four parts. The first part covers the basics of how organizations produce value. It does this by introducing a hypothetical example that recurs throughout the book: scaling a small restaurant into a “breakfast factory.” Mr. Grove analyzes this business as an engineer, breaking it down into its constituent elements and how they combine to produce particular outcomes. He then discusses the role of management in making the factory operate successfully.

Part two covers a central function of management: making decisions, which includes planning for the future. Such decision-making requires information, which is mostly conveyed through meetings. Mr. Grove spent a lot of his time meeting with other team members. “Information-gathering is the basis of all other managerial work,” he says, “which is why I choose to spend so much of my day doing it.”

The purpose of such information-gathering is to increase the leverage of managers. That is, “the output of a manager is a result achieved by a group either under her supervision or under her influence.” Managers must focus on those activities that give their work the most leverage. This part of the book provides practical advice on what they might be. Intriguingly, this advice also applies to individual contributors: members of the organization who don’t directly manage others, but whose work influences the work of others.

Part three of the book is about growing beyond simple operations to large enterprises; it covers more complex management structures, including hybrid and matrix organizations. Part four is about working with individuals: teamwork, hiring, giving performance appraisals, establishing compensation, etc. Both parts provide useful pointers to managers facing tough decisions. Mr. Grove backs up his advice with examples from his tenure as a manager at Intel, which is widely seen as excellent.

The best books help you understand complex subjects in ways that change your actions towards better outcomes. High Output Management changed how I understand the work I do with other people. (That is, all of my work.) I include this book in my list of essential reading for anyone doing any productive work at scale.

Buy it on Amazon.com

The Jobs To Be Done Playbook: Align Your Markets, Organization, and Strategy Around Customer Needs
By Jim Kalbach, with a foreword by Michael Schrage
Two Waves Books, 2020

A couple of disclaimers before I tell you about The Jobs To Be Done Playbook: first, the author is a friend. Second, the book is published by Two Waves, which is also my publisher. As a result, I got this book for free. Did these facts alter my perception of the book? Perhaps. I may be more predisposed to like books in which I can hear the author’s voice in my mind.

Still, I think The Jobs To Be Done Playbook is worth your attention. I was about to write, “is worth your attention if you’re responsible for designing digital experiences,” but that’s not necessarily true. This book is useful for anyone responsible for user experiences, whether they are designers or not. (I suspect product managers will also find it particularly valuable.)

In case you’re not familiar with the phrase jobs to be done (JTBD from now on), it refers to a concept popularized in the business world by the late Clay Christensen. The core idea is that customers don’t buy your offerings because they want your offerings per se, but because of what “jobs” those offerings perform in their lives. An example that comes up frequently: the customer doesn’t want a drill bit, s/he wants a hole in the wall. Identifying the jobs your offerings perform allows you to better serve your customer’s needs and stay ahead of the competition.

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The Optimist’s Telescope: Thinking Ahead in a Reckless Age
By Bina Venkatamaran
Riverhead Books, 2019

I first heard about this book from Ms. Venkatamaran’s presentation at the Long Now Foundation’s fabulous series of seminars about long-term thinking. Of all the Long Now seminars I’ve heard in the last few years, this was one of the most directly related to long-term thinking. The subject of this book is described as “how we can plan better for the future: our own, our families’ — and our society’s.”

As suggested by this description, the book is organized into three parts, focused on the individual and the family, businesses and organizations, and communities and society. Each includes examples of initiatives that have helped people overcome the pressures of the “here and now” towards decisions that serve them better in the long-term. (Ms. Venkatamaran discusses several of these examples in the seminar linked above, which serves as an excellent primer to the book.)

The final chapter synthesizes these insights into a list of more concrete strategies for acting with the long-term in mind:

1. Look beyond near-term targets
2. Stoke the imagination
3. Create immediate rewards for future goals
4. Direct attention away from immediate urges
5. Demand and design better institutions

It’s up to the reader to map these to his or her situation. (It’s just as well — expanding on each would’ve made the book too long.)

One of the ironies of our time is that we’re facing existential threats that require long-term action (e.g., climate change), all the while suffering from ever-shortening attention spans. With its many examples and stories, this book is an engaging antidote to the malaise. (If you’re not up for reading it, but interested in the subject anyway, do listen to Ms. Venkatamaran’s Long Now seminar.)

Buy it on Amazon.com

Shoe Dog: A Memoir by the Creator of Nike
By Phil Knight
Simon and Schuster, 2016

In the early pages of Shoe Dog, Phil Knight notes:

Front runners always work the hardest, and risk the most.

This pithy observation summarizes the story to follow. It’s the story of Mr. Knight’s life, and it’s the story of Nike — the two are inseparable. It’s a story of hard work and risk.

Among the things risked: reputations, relationships, money (mostly other people’s), and careers. They’re all on the line, offerings to turn an insight into a material fact. The insight is precipitated by Mr. Knight’s passions (as a college track and field runner) and his astute observations of changing conditions in global markets. He starts a company to distribute athletic shoes from his parent’s house in Oregon. His aim: victory. Competitive sports is a metaphor — and often more than that.

Almost inadvertently, he assembles an idiosyncratic team of managers, each a colorful character in their own right. The story follows this crew as they try to grow their small company. They face many obstacles: unreliable suppliers, nervous bankers, unscrupulous competitors. They also face their doubts. What have we done? Are we too far over our heads this time? Are we good enough? Mr. Knight and his collaborators have flaws and insecurities, but they’re all are committed to the cause.

Still, there’s no master plan. They’re making it up as they go along, one decision — one crisis — at a time. It’s an organic process, perhaps the result of Mr. Knight’s management style, which is summarized by a quote from General George S. Patton that appears several times in the book:

Don’t tell people how to do things, tell them what to do and let them surprise you with their results.

The book is organized chronologically, one chapter for every year from 1962-1980. This structure could be boring if not for the fact that Nike faced existential crises almost every one of those years. Although the company is still thriving today, 1980 seems like a good stopping point: it’s when Nike went public. Ostensibly, this turned it into a different company than the one described in Shoe Dog. A coda (“Night”) brings the story up to the present. It includes revelations that cast the rest of the book in a different light.

Shoe Dog is the best book I’ve read on the experience of being an entrepreneur. The book is enlightening, inspirational, and heartbreaking. Mr. Knight is an excellent writer; Nike’s story reads like a well-crafted novel. If you work with entrepreneurs, or aspire to be one, you owe it to yourself to read it.

Buy it in Amazon.com

Many people take time during the holidays to look back on the past year. Reading is a big part of my life, so around this time I usually re-visit the books I’ve read during the year and highlight the ones that stood out. I share these lists in case you’re looking for book recommendations for the holidays. (Note these aren’t necessarily books that were published during the past year — this just happens to be when I got around to them.)

Without further preamble, here are five books I enjoyed and learned from in 2019:

Design Unbound: Designing for Emergence in a White Water World by Ann Pendleton-Jullian and John Seely Brown. A map for pragmatic design-doing — not for making products and services better (or even better products and services), but for operating at a higher, more systemic level: that of social, economic, ecologic transformation. Buy it on Amazon.com (volume 1/volume 2) or see my book notes.

Design by Concept: A New Way to Think About Software by Daniel Jackson. A compelling argument for the importance of conceptual modeling in software design. It includes clear examples and an actionable framework for defining such models. (The book is billed as a “prepublication draft”; I’d love to read the “final” version.) Buy it on Amazon.com.

The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of The Walt Disney Company by Robert Iger. A memoir/leadership manual from one of the great business leaders of our time. Mr. Iger took the job of Disney CEO at a troubled time for the company; he revived its fortunes by skillfully implementing a clear, compelling strategic vision. Buy it on Amazon.com or see my book notes.

Churchill: Walking With Destiny by Andrew Roberts. Makes the case that Churchill — flaws and all — was the right person at the right time to (literally) save the world. What’s more interesting is that he knew this, even from an early age. (At 16 he predicted he’d save England from an invasion.) He was also hilarious. Buy it on Amazon.com.

Seeing Like a State: How Certain Schemes to Improve the Human Condition Have Failed, by James C. Scott. A treatise on the relationship between top-down and bottom-up organization frameworks. Argues that states seek to simplify social structures to make them more “legible.” (I.e., easier to measure and manage.) This impulse has led, in the most extreme cases, to disastrous top-down “high modernist” schemes. The book is engaging, disturbing, and mind-changing. Buy it on Amazon.com.

The Everything Store: Jeff Bezos and the Age of Amazon
By Brad Stone
Hachette Publishing, 2013

In a 2013 interview, Charlie Rose asked Amazon’s founder, Jeff Bezos, to define his company. “I would define Amazon,” he replied, “by our big ideas, which are customer centricity, putting the customer at the center of everything we do, and invention.” The Everything Store traces the story of how those ideas — which have been at the core of Mr. Bezos’s vision for Amazon — created one of the great entrepreneurial success stories of our time and transformed the way we shop.

But customer-centricity isn’t the only value that has led to Amazon’s success. Ruthless execution — another central value, and one that the book doesn’t shirk from describing — has allowed Amazon to move faster, smarter, and more aggressively than its competitors. The company’s ability to move quickly has allowed it to exploit strategic advantages it gained due to thinking long-term, another central value.

Alas, Amazon’s relentless pursuit of customer satisfaction has often come at the expense of other actors in the ecosystem, especially employees and vendors. The company’s negotiators don’t aim for win-win, and work-life balance is anathema. The book describes a demanding environment that selects for a particular type of employee, one that’s fully committed to — and willing to make personal sacrifices for — the company:
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