The Secretary’s Manual

Giacomo Bagarella
The Envoy
Published in
6 min readOct 21, 2019

Ash Carter’s memoir is a wonk’s guide to the Pentagon, but it lacks in introspection

Deputy Secretary of Defense Ash Carter and General Joe Dunford, ISAF commander, fly in a helicopter over Afghanistan in Sep. 2013 (DoD/Glenn Fawcett/Flickr)

Inside the Five-Sided Box: Lessons from a Lifetime of Leadership in the Pentagon, by Ash Carter, Penguin, $27.00, 480 pages

In an era when the White House was run competently, honestly, and without much fanfare, memoirs by former secretaries of defense caused a stir. The media seized on comments and amplified them to question the approach of the president and his closest aides. Relatively minor events became fodder for critical coverage.

This was the case for Robert Gates and Leon Panetta, who published their memoirs in early and late 2014, respectively. Ashton Carter, by contrast, did not publish his memoir during the quaint, orderly era of the Obama administration, but during the Trump administration’s unending series of crises. (Carter’s direct predecessor, Chuck Hagel, has not written a book about his experience at the Pentagon.)

Released in June 2019, Inside the Five-Sided Box: Lessons from a Lifetime of Leadership in the Pentagon shares extensive details about what it takes to run an organization whose complexity and demanding missions have few rivals in the world. Carter’s story reads like a manual for aspiring Pentagon wonks: Procurement? That’s chapters one and two. Dealing with Congress? Read chapter five. What’s missing from this memoir are thoughtfulness and self-awareness for readers who seek a deeper look at personal elements of leadership in such a prominent and critical position.

Carter’s story in the Pentagon began decades before his appointment to its top job in February 2015. He started, in 1981, by using his physics training to study weapons systems. After serving as an assistant secretary in the Clinton administration, he rose to become the department’s acquisition czar (the number-three role) and chief operating officer (number two) under Barack Obama. Moving in and out of government across a third of a century, Carter accrued valuable experience in a world of evolving technology, geopolitical rivalries, and conflicts. He states, accurately, “So when I was asked to be SecDef, I was pretty well prepared on day one.”

Carter’s insider knowledge of the Pentagon’s arcane offices, processes, and responsibilities give him the ground-up view that “[…] ensuring that our forces are thoroughly prepared for combat, and then making certain that their combat missions are conducted with the greatest possible skill and effectiveness, are the ultimate leadership tests for any Secretary of Defense.”

By his own account, Carter was effective in both preparation and conduction. He chronicles how he helped steer several massive, long-running procurement projects away from failure and accelerated purchasing for equipment that troops urgently needed on the front lines. Carter also changed Pentagon policy to allow women to serve in all combat roles. With regard to military operations, Carter claims credit for planning what had been a successful anti-ISIS campaign in Iraq and Syria. (President Donald Trump’s recent decision to withdraw U.S. forces from Syria is rolling back some of the previous gains.)

Amidst the weeds of what it takes to oversee the Pentagon, the book’s most succinct lesson is the importance of setting the right incentives. Internally, they matter because they determine the success or failure of contracts with vendors and of efforts to develop and retain uniformed and civilian personnel. Externally, incentives influence whether the U.S. can shape geopolitical outcomes in its favor. Incentives are essential to both deterring conflict and to concluding it on beneficial terms, and are thus a core component of strategy.

The cover of Carter’s memoir

In this domain, Carter offers some insightful considerations, as well as some questionable adherence to conventional wisdom. The memoir illuminates the flaws that had existed in planning for a “two-war doctrine” — at a high level, that the military lacked the resources for such a contingency. Carter insisted on developing a new concept that allowed for a more realistic prioritization of threats and responses. His approach has not been tested, but it seems sound, reflective of historical precedent, and considerate of real-world constraints.

On the other hand, the greatest shortcomings in Carter’s strategic analysis concern the Middle East. He describes the U.S. and Saudi Arabia as “two partners that share some values while being deeply conflicted over others.” The two states have interests in common, though it’s hard to see what the shared values would be. Carter contradicts himself as he questions Saudi Arabia’s strategic and tactical importance to the U.S. while implying that the two countries’ partnership should continue.

Carter goes on to call Israel a “reliable partner in international affairs.” Throughout the Obama administration, Israel attempted to undermine the White House’s efforts to reach the nuclear treaty with Iran. Israel’s prime minister, Benjamin Netanyahu, also repeatedly acted to thwart Obama and took partisan positions within U.S. domestic politics. Carter is reluctant to admit that this behavior does not denote reliability.

Most notably, Inside the Five-Sided Box doesn’t offer much in terms of self-reflection and awareness from a leader with a successful career in challenging jobs. The memoir’s tone can be self-referential. The fact that he had made a correct prediction in an old physics paper is “a big reason that my paper is rather famous and is still frequently cited.” Passages like “I was pleased I’d been able to handle a risky moment in the public spotlight so adroitly” and “Thankfully, I was pretty confident I could formulate strategy well” highlight a tendency to be self-congratulatory.

At the same time, Carter is disdainful of others in Obama’s staff. Though he is either appreciative of or vague on senior officials, he uses condescending terms like “yahoo,” “munchkin”, and “zealot” for some of the White House aides he encounters. Such punching down reflects poorly on someone who otherwise portrays himself as a good boss and team player.

The book’s greatest limitation, however, is its neglect of the mistakes and personal toll a high-profile government career entails. There are two admissions of errors, both of which Carter assures readers were minor and swiftly corrected. (They are his decision to create Cyber Command without consulting Obama and using his personal email for non-sensitive communications with his staff.) It’s hard to believe that a three-and-a-half decade career did not entail genuine moments of regret and reflection. Carter glosses over these opportunities to consider the lessons of failure.

Finally, Inside the Five-Sided Box largely ignores the family consequences of an all-consuming job. Carter mentions scheduling meetings on Saturdays to signal his resolve on specific issues, and frequently using weekends to visit wounded soldiers at medical centers. This is laudable commitment to the mission, but what’s less clear is how long workdays and frequent travel affected his ability to spend time with his loved ones or to manage energy and fatigue. Ultimately, Carter displays his vulnerability — and only partially so — in just one episode concerning a back surgery.

Commitment and sacrifices come with the territory of Carter’s senior positions, but to avoid the issue as he does is to convey only a partial view of the experience. While his desire to want to keep his family outside of the spotlight is understandable, the resulting superficiality is a disservice to the difficult trade-offs that the job requires.

Among Carter’s most valuable pieces of advice is that “Perhaps the single greatest key to [communicating a strategic vision] is mastering the art of storytelling — building an instantly understandable narrative to encapsulate a given situation and the logic of the strategy developed in response to it.” Though much more mundane than the public affairs needs he had at the Pentagon, writing this memoir was a similar exercise in narrative and influence.

Carter’s deep experience with the complex world of the Department of Defense provides helpful insights for aspiring planners and strategists. However, as a work of storytelling, Inside the Five-Sided Box is incomplete. It’s hard to empathize with a seemingly infallible and unflappable operator, and Carter does not give readers the opportunity to learn from his mistakes and difficulties. Such lack of perspective detracts from the additional lessons it could have held in a time when moral leadership is ever rarer in today’s cacophony of incompetence.

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Giacomo Bagarella
The Envoy

Passionate about policy, technology, and international affairs. Harvard, LSE, and LKY School of Public Policy grad. All views my own.