When You’re Done Learning, You’re Done Leading
Every summer since 2018 I’ve shared reading recommendations because leaders are readers (and listeners of books and podcasts). If you’re not a regular reader, summer’s slightly slower schedule provides a great time to re-read a classic or discover a book that might become one. Here are my picks for the Summer of 2026.
Who Says Elephants Can’t Dance?
When Lou Gerstner died two days after Christmas, I decided to re-read his book about the historic turnaround he engineered as IBM’s CEO. In the book’s first five pages the words “open mind” (twice), “open-mindedness,” “think differently,” and “change of heart” appear—reminders for leaders to reconsider initial biases. Gerstner put the odds of saving IBM as no better than one in five, noting it was hard for him to remember why he accepted the job. He suspects “the novel recruitment method” played a part: “You owe it to America to take the job.” Gerstner’s book is a fascinating story of rescuing a legendary company. It’s also a practical guide for any leader whose company needs a jolt. “What IBM needs right now,” said Gerstner four months after arriving, “is a series of very tough-minded, market-driven, highly effective strategies in each of its businesses.”
For people who crave certainty, this book delivers. It’s a collection of 23 short stories “about what never changes in a changing world.” It was recommended by eight-year Vistage member Jeff Jensen, whose goal is to read (or listen to) three books a week. “I am slightly ahead of goal,” Jeff told me last month. Like most successful people, Jeff uses a shortcut that allows him to listen to summaries of books; he then actually reads the books whose summaries interest him. He does it via Blinkist. When a smart person who inhales great books makes a recommendation, I take note. “There are timeless lessons from human behavior that are some of the most important things you can ever learn,” writes Morgan Housel. “What they have in common is that I’m confident each of these topics will be as relevant hundreds of years from now as they were hundreds of years ago.” Housel advises us to pay attention and “you’ll be able to make better sense of your own life, understand why the world is the way it is, and become more at ease with what the future has in store.”
It’s been said that life is tough, and it’s much tougher if you’re stupid. This book was published in 2018 and remains a bestseller. The ideas are compelling, the writing is accessible and urgent, and each of the 48 short chapters distills lessons Keith Cunningham learned leading and selling businesses over a 25-year period. He shares topics and questions to help “spark your thinking, grow your business, make more money, and ultimately avoid doing something stupid.”
Every summer I recommend one book most business leaders would not list as one of their must-read books—but should. Seneca the Younger is one of the three best-known Stoic philosophers. The other two are Epictetus, who was born into slavery and later earned his freedom, and Marcus Aurelius, the Roman emperor whose personal journals were collected into the book known as Meditations.
Back to Seneca. The book I’m recommending is a collection of three essays by Seneca. The first of these essays is De Brevitate Vitae (“On the Shortness of Life”), which was written by Seneca to his father-in-law Paulinus around the year 49 AD. It’s 43 pages. The other two essays in this collection are De Vita Beata (“On the Happy Life”) and De Tranquillitate Animi (“On Peace of Mind”). Seneca’s belief about time is this: “Life is long enough to carry out the most important projects: we have ample time, if we arrange it properly.” In 1908, Arnold Bennett expanded on Seneca’s idea in his book How to Live on 24 Hours a Day. “We never shall have any more time,” writes Bennett. “We have, and we have always had, all the time there is.” The writing is dated in spots (e.g., the use of “man” versus “person”) but the fundamental concepts hold up, there are good ideas for how to organize your time, and at just 84 pages, Bennett’s book is a quick read.
In The Effective Executive, Peter Drucker devotes a chapter to time management. Drucker wrote 39 books, and this one qualifies as a must-read for leaders. “Effective executives,” Drucker wrote in 1967, “do not start with their tasks. They start with their time. And they do not start out with planning. They start by finding out where their time actually goes.” He recommends a time audit that reviews how time is spent then reorganizes time according to a) activities that are the highest and best use of your time, b) activities that can be done by someone else, and c) activities that should not be done at all. “Time,” taught Drucker, “is the scarcest resource and unless it is managed nothing else can be managed.” Or as Seneca wrote, “We do not receive a short life, but we make it a short one, and we are not poor in days, but wasteful of them.”
Two years ago Australian Vistage Chair Jon Lindsay invited me to lead a session with him on goal setting at ChairWorld, the conference attended by about 1,000 Vistage Chairs from around the world. It was an honor to work with Jon and to learn from him. Among the many things I learned from Jon were these: First, every December Jon and his CEO members go offsite for at least one night in order to develop their personal goals for the coming year. The idea is that the extended time, a change of scenery and a relaxed agenda encourage members to engage with one another at a deeper level, which invites them to challenge one another’s assumptions. Jon found these overnight sessions help to “remove some of the myopia” that occurs when we think about ourselves. This process leads to developing broader, more meaningful goals. I stole the idea of a year-end offsite from Jon and can affirm that this process has led to a tighter bond among group members, which in turn has led to the development of more meaningful goals. Second, I learned from Jon that the book How to Begin by Michael Bungay Stanier is a treasure trove of compelling goal-setting ideas, the central one being to “Set a worthy goal” in order to “start doing something that matters.” If you believe Seneca, Bennett, and Drucker, we each have plenty of time to accomplish big things. The trick is figuring out what those things are and then to get going. This book can help.
I’ll close with my own. Accountability is one of the most important factors in determining the success of an individual, a team, and an entire organization. It’s also one of the most universally misunderstood and misapplied concepts in business, making it one of the biggest challenges leaders face. If you aren’t accountable, don’t expect others to be. The book introduces The Seven Pillars of Accountability and is based on data gathered from more than 12,000 executives worldwide, interviews with senior leaders at Fortune magazine’s Most Admired Companies, and conversations with leaders running small- and mid-sized businesses that consistently outperform themselves. The discoveries might surprise you. They might even get you thinking in new ways about how to get things done. Named a “Best Business Book” by Soundview.
Enjoy!