Lessons in Lousy Leadership

"Both the military and the private sector should be seeking out, encouraging, and growing team-of-team leaders."

Retired Army General Stanley McChrystal has penned a revealing book—but its revelations are not intentional. The combat veteran of Iraq and Afghanistan and his team of co-authors intended to author a guide on how to use small teams to infuse organizations with dynamic and adaptive leadership. Instead they deliver an accidental expose of what is wrong with the modern major general.

McChrystal's book, “Team of Teams: New Rules of Engagement for a Complex World” (2015) has, not unexpectedly, grabbed a fair amount of attention. McChrystal was a distinguished combat commander with a reputation for being tough, courageous, smart, brave, innovative and successful. Since retiring, he has been teaching leadership at Yale University, serving on corporate boards and running a consulting group. He also authored an account of his military career in “My Share of the Task” (2013). A resume like that is bound to create interest in a tome on leadership.

And, let's be honest, McChrystal's highly publicized run-in with President Obama only adds to the anticipation. That clash came after Rolling Stone magazine published an unflattering profile of the general and quoted him criticizing the administration. It ended, promptly, with McChrystal’s resignation. People are still fascinated with the story of how that dynamic worked out.

On this matter, the book disappoints. It offers scant new insights on the McChrystal-Obama matchup. Indeed, the president rates but one, inconsequential entry in the index. This is the first warning sign that, as a leadership story, “Team of Teams” is one big opportunity lost.

Few leadership challenges are more important than understanding the meltdown in trust and confidence between a chief executive officer (such as Obama) and his chief operating officer (McChrystal) during an absolutely critical moment in operations (like the Afghanistan surge). We know, of course, that Obama had every right to fire McChrystal. On the other hand, this incident is only one of many signs that, at the highest levels of this administration, civil-military relations have been unusually tense. Building a team of teams among senior leaders is an important task. Lessons learned from this high-profile experience would have fit nicely in the book.

While the Rolling Stone dust-up doesn't make it into the pages of this leadership guide, plenty of McChrystal's combat experiences do. The general’s war tribulations and his appreciation of military history are the touchstones that frame the book's approach to leading in the modern world.

McChrystal chronicles the difficulty of adapting the thinking and activities employed in conventional military operations to the chaotic challenges facing civilian organizations. Traditional organizations, he concludes, are ill-suited to solve today’s wicked problems.

“Team of Teams” is essentially a journey of self-discovery. McChrystal finds he must learn to distinguish between "linear" problems (that are decipherable and predictable) and "non-linear" challenges (complex systems where the causes and effects that drive behaviors and outcomes are far more difficult to understand). Hierarchical organizations can be structured to tame and manage linear problems. But non-linear problems require a different kind of leadership: decentralized, empowered, situationally aware, and adaptive. McChrystal’s solution: leader teams that can ride the uncertainty and ambiguity like surfers skimming the crest of a wave.

Liner solutions rule problems with process and programs. Non-linear solutions figure out how to operate in the environment better than their competitors. The less linear the problem, the more the solution hinges on the people leading at the front lines, rather than on the folks developing processes and programs far away from the problem.

What “Team of Teams” champions, then, is a talent solution—and that solution is unquestionably worthy. But, as a leadership text, the ideas offered by the book are hardly novel and have been better told elsewhere. Eric Schmidt and Jonathan Rosenberg's “How Google Works” (2014), for example, deftly shows how cutting-edge tech companies like Google have used this approach to ride the wave of consumer technological chaos and innovation.

What is interesting about “Team of Teams” is not that McChrystal and other Army leaders figured out the difference between mastering linear and nonlinear environments— but that it too them so damn long to do it. Rather than inform, the book prompts the question: What is wrong with the modern major general?

In framing the challenge, McChrystal reflects on the fundamental and original contributions of Frederick Winslow Taylor, the well-acknowledged father of "scientific management" and framer of how to build linear systems to solve linear problems.

McChrystal is also right that militaries adopted many of Taylor's principles to fight Industrial Age warfare. Hierarchical, structured, disciplined organizations became a hallmark of Western military structures throughout the 20th century.

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