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Book Review: Serve to Be Great: Leadership Lessons from a Prison, a Monastery, and a Boardroom

Sunday, February 1, 2015  
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By Matt Tenney 

Reviewed by Lee Hark, Upper School Director, Durham Academy, Durham, NC

I have a confession to make: I don't like business leadership books. All the nodding sententiously about “getting the right people on the bus.” The anecdotes. The dull platitudes. The inevitable unveiling of a new leadership model. It all leaves me cold. 

Matt Tenney loves business leadership books. In Serve to Be Great: Leadership Lessons from a Prison, a Monastery, and a Boardroom, he doesn't resist that worn-out template so much as celebrate it. Instead, this book is about a re-orientation toward service leadership, which, while not especially radical advice for educational leaders, is certainly an important principal to remember. But it’s hard for me to believe that an effective leader would be edified by the bromides expressed in this book. 

The book’s first section recounts Tenney’s ill-advised attempt to defraud the U.S. military of millions of dollars and his eventual capture and incarceration. He doesn't give much of an explanation for this near-disastrous decision, other than his hankering for “achieving financial freedom" (pg. 9), a goal that seems tough for Tenney to relinquish, even after six years in the brig.

At some point during his imprisonment, Tenney literally decides to “C’mon, get happy.” “I decided that it must be possible to be just as happy in the brig as I could be anyplace else" (pg. 10), he says. The tool for this transformation? Mindfulness! "Awareness training sets us free from the pull of our comparative thinking,” he continues. “That insight was accompanied by a very liberating thought: Awareness training could help me be happy under any circumstances, even while I was in the brig" (pg. 11). I suppose that sanguine thinking is a preferable alternative to smuggling in cigarettes to trade for protection (which would’ve been my plan).

Tenney frames his mindset this way: “Imagine that you are in a brig cell sitting on your bed. You are not in any pain, you are not hungry, and the temperature is comfortable. If you’re not comparing that moment to the memories of the past, or the hopes of the future, what’s wrong with that moment? Nothing.”

Nothing indeed, as long as you don't have cause to fear being shivved in the yard or have a family outside the brig dependent on your financial support. For most of his prison term, Tenney had a fairly cushy gig (by prison standards). He writes, “We went to work each day as most people do. In our free time, we had access to books, magazines, music, television, movies, and games" (pg. 13).

This isn’t a comment on Tenney’s practice of mindfulness or its ultimate effectiveness as much as it is a rejection of the fatuous, self-helpy, Tony-Robinsonesque logic that under-girds this section of the book. 

Truth be told, Serve to Be Great isn’t really much about mindfulness anyway, other than Tenney’s assertion that “It worked for me, and it will work for you.” His link to mindfulness in the book is ultimately indirect – it’s more of a general application of the importance of staying centered, present, and focused on others.

Part I of the book, entitled My Journey from Prisoner to Monk to Social Entrepreneur, ought to be re-titled The Semi-Charmed Life of Matt Tenney. Tenney leaves prison after almost six years and moves to Mexico (probably not a bad idea), where he finds work as an English teacher in an orphanage. Miraculously, he lands squarely on his feet. “Despite having a felony on my record, job and business opportunities have seemed to come very easily. It seems that most people I meet offer to help me once it becomes clear to them that my focus in life is helping others" (pg. 21).

We should all be so lucky. I recognize employment standards differ from country to country, but it is still surprising that a convicted felon was able to find a job working with adolescents so easily. He later scores two job offers to teach in American middle schools, offers that are rescinded because of a recently adopted district policy not to hire people with criminal backgrounds (nice to see some hiring standards are still in place). He establishes his own 501(c)(3) and continues to volunteer for various organizations. Ultimately, Tenney parlays that work into a successful career as a consultant and (apparently) meets a lot of successful people.

Part II of the book – which is much stronger than the first -- presents an analysis of a variety of businesses that have leaders with a strong service orientation and the innovative programs they establish for their employees. Some of these case studies, especially that of nextjump, and the lessons imbedded in them are quite interesting and potentially useful for schools. For instance, nextjump has a laser-like focus not only on hiring talented people, but also those who fit into their corporate culture. In this case, the parallel for schools is easy to see.

The lessons aren’t always transferable, though; some of these companies are extremely well-resourced, a fact reflected by their generous and creative employee benefit programs. Tenney wisely places the emphasis on dispositions, mindsets, and values rather than dollars, perks, and benefits, but still it’s sometimes hard to find inspiration in less expensive suggestions like “starting a leadership library.” I want the in-house sushi bar and free laundry service!

Throughout, Tenney is nothing if not a true believer. The stories he tells of corporations and their innovative and compassionate leaders are heartwarming (despite my best attempts to resist them) and run counter to the standard notion of unfeeling bureaucracies that care only about the bottom line. Still, Tenney re-plows already well-tilled soil with his clichéd lineup of corporate success stories --, Google, SAS – and exclaims a standard set of business tropes: Customer service is important! Empower and trust your employees! Be an awesome human being! Read more books like this one! And so forth.

Despite my cynicism, some of Tenney’s message in the book’s second section does resonate. He argues effectively that the “spirit of serving and caring for others is universal in nature. It doesn't end where we encounter the borders defining our team. When we value and nurture this spirit of service, it gradually starts to expand quite naturally to include anyone we encounter who is in need of help …" (pg. 77). It’s hard to debate that. Whether or not you need to read this book to be reminded of it is, I suppose, a personal choice.

Part III details how to shift one’s disposition to becoming a more service-centered leader and is based on the premise that “[All great leaders know] that there’s nothing more important in leadership and in life than doing what we can to make the people around us happy" (pg. 103). This idea is thought-provoking, but it’s hardly the truism that Tenney believes it to be. And it proved hard to resist cynicism (again) when Tenney concludes the book with a section entitled What a Teenager Dying of Cancer Taught Me About Leadership and quotes like, “So this is my question to you: If a butterfly flapping her wings can result in a change in the global weather pattern, what could happen with just one act of extending yourself for the benefit of those around you?”

Ultimately, Serve to Be Great contains some wisdom, but it takes some serious mining to uncover it. Instead, log on to and do your digging there.

  Lee Hark is the Upper School Director at Durham Academy in Durham, NC. He can be reached at or on Twitter @leehark.


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