Judgment: The Art of Momentous Decision-Making

Preface

In the summer of 1993, a day or two after taking the bar exam, I loaded my meager belongings into the back of a farm truck I had borrowed from my father. My own car had been stolen several nights before the most important and difficult exam up to that point in my life while I studied in a downtown law library. It surfaced several days later, resting on cinder blocks just outside the gates of a Chula Vista chop shop. It had been stripped of its Chevy 305 engine and wheels. No one had apparently seen anything. The police yawned.

It was the end of my first stint in California; I was headed east. I felt a bit ashamed to admit it, but I had grown bored by San Diego’s idyllic weather and vacuous conversations. I was desperate for drama and a feeling of purpose. On the long journey to the other coast, I would treat myself to a poor man’s vacation. In the coming days, I would absorb the divine lands and skies of the West, infusing their grandeur and subtlety into my being. At night, I’d dream of the adventures of a life ahead.

I was down to my last $800 of borrowed money to pay for school. I pushed the old farm truck hard up the I-5 to Sacramento, then bore east on I-80 through Donner Pass, across the top of Nevada and Utah until the expanse of the Great Salt Lake opened before me, then pushed even farther until crossing into western Wyoming. It took a full day and nearly a full night. The push was necessary. It was both a physical and an emotional journey. I had to pass from one realm to the next.

The next morning, I found myself in the early light somewhere in the great expanse of Wyoming, parked along a lonely road, sleeping across the bench seat of the farm truck mounted with a wooden livestock rack and filled with my only possessions. A single coyote poked up from a ditch and sauntered briskly across the road, moving with calm and purpose. A third of my journey to the East was complete. After clearing the blur from my eyes, I set out again, making my way slowly toward the beauty of western Nebraska’s rolling sand hills.

A week later, after a stop to see family living among the cornfields of Iowa, now wearing a blue suit and silk tie, I walked into an office on Connecticut Avenue in Washington, DC. They assigned me a desk on the fourth floor overlooking the steps of the Cathedral of St. Matthew the Apostle, where just three months short of thirty years earlier, little John F. Kennedy Jr. had saluted the coffin of his father, the assassinated president.

I had worked for this firm the previous summer, and they had offered me a job to return to when I finished law school. Last week’s journey was now but the intermission between the realms, from student to lawyer, from West Coast to East, from one who could only imagine how power, influence, and values shaped momentous decisions to one who worked the knobs and levers to make them so. I had seemingly passed through a portal.

The firm was new, still finding its way. One of its founders had a knack for saying just the right thing at just the right moment. In a town where doors are unlocked by subtle shifts in narratives and perceptions, it was his gift. The other founder, Peter D. Robinson, was a quieter man. He could be found with his back to the door in a leather-bound swivel chair, staring out the windows into nothingness. He contemplated the arcs in the political and policy debates around town the way I imagined a conductor sees music. He felt the highs and lows amid the cacophony, saw the shapes of colors emerge from a swirling ether of grays, divined when to move forward in the debates, when to hold, and when to hide. He was a thinker and a feeler, an intellectual, and an empath. He became my mentor.

To most, political Washington is the pinnacle of chaos and dysfunction. It is messy and loud, and many of the most visible actors in two and a half centuries of ever-running theater are flawed human beings we find distasteful at best and repugnant at worst. The fundamental institution of Washington, however, endures. It has survived the stuttering steps of a young nation emerging from revolution. It has withstood civil war. It found power by emerging victorious from two world wars and then searched the depth of its soul in the wars that followed, challenging the assumptions in the country’s own narrative surrounding its identity, power, and purpose. It has struggled with a recurring cycle of violent torment, torn from within, socially and culturally. It has overcome economic cataclysm, again and again. Through it all, it endures.

Something deeper, something with roots in its very DNA, grounds the country with its admirable ethos. Political Washington was conceived to withstand the worst of human behaviors with collective resolve to serve higher, more enlightened values, they being woven into the fabric of the Constitution. The system is designed to survive the messiness of change, radicalized voices, charismatic ideologues, and charlatans. It is designed to evolve and grow, all in service to ideals rooted in certain truths self-evident. It endures also because of those silent stewards who toil not in service to their own egos or their self-selected tribes among the many, but in service to these higher ideals.

Robinson was one such steward of the ideals. He had been a parliamentarian in the US House of Representatives, quietly managing the processes, procedures, and structures for those momentous decisions that must be made under seemingly the worst of conditions. After thirteen years in the well of the House, handing instructions to and whispering into the ear of the chair presiding over each proceeding on the floor, making sure the debates were fair and in service to the elected majority, whichever party that may be during any two-year cycle, Robinson moved to the Democratic Steering and Policy Committee. There, he spent five years advising the House leadership on how and when to introduce major pieces of legislation.

Robinson’s job, in short, was to identify where wins could be achieved and how to achieve them while avoiding the bloody battles and skirmishes that waste the power that must be mustered when the nation faces crisis or opportunity. By the time my path crossed Robinson’s, he possessed nearly two decades of experience in managing the processes by which Congress made decisions on the most important issues affecting Americans; their political, economic, and social institutions; and their place in the world. His realm was governed by the mysterious but practiced art of exercising judgment in critical moments of decision-making.

The young firm Robinson cofounded, and that I was now working for, had recently been acquired by a global communications company. The marriage immediately bestowed the firm with a marquee roster of clients. Within weeks, I went from sleeping in the cab of an old farm truck with only a few dollars in my pocket to advising CEOs of multinational banks, global financial institutions, credit card companies, insurers, and pharmaceutical companies. It was a gift.

Our purpose was to sort the signal from the noise of Washington’s cacophony, sensing the more subtle clues that affect narratives, perceptions, timing, and the shifts in power in political Washington. It was a period during which the North American Free Trade Agreement was passed and President Bill Clinton’s health care reform failed.

In this new realm, I discovered my education had only just begun. It was a crash course in judgment—the art of knowing when to move, when to fight, when to be silent, whom to trust and whom to not, how to overcome dissent, and when to become the dissenter. Our purpose was to find pathways through murky and treacherous portals to achieve something better on the other side. Robinson taught me to look for the subtle clues that would write history’s next story and how to shape it.

One lesson rose above all others:

How we exercise judgment is the most powerful variable

in determining whether a momentous decision

leads to success or failure.

Over three decades of working with politicians, international leaders, and corporate executives, sparked by a unique launch point to a career, I’ve studied the alchemy of how people exercise judgment during a myriad of critical moments. It is a career that has hopped from designing award-winning public affairs campaigns for a global communications firm for the likes of Bank of Montreal, the Federal Home Loan Bank System, and Visa; to lobbying senators and members of Congress for Mastercard, Unisys, and a Blue Cross insurance company; to teaching young international lawyers at Georgetown Law School how to navigate the challenges before them; to advising on shifting landscapes in global finance and banking as an adjunct fellow at one of the preeminent foreign-policy think tanks in the world, the Center for Strategic & International Studies; to launching new technology businesses for the global systems integration arm of KPMG, subsequently spun out as part of a $3 billion initial public offering; to developing the antifraud program for the president of Nigeria and the country’s massive oil sector; to managing the first-ever sale of spectrum for the Government of Iraq; to negotiating acquisitions in over forty countries in the United States, Europe, Asia, the Middle East, and Africa during both conflict and post-conflict economies; to leading a Silicon Valley tech company through its spin-out, capitalization, and growth; to advising young CEOs on unlocking the exponential value harbored within their private equity-backed companies and achieve their greatest potential. In each of these wildly diverse experiences, the essence of the challenge has been the same:

Manage a decision arc through an arduous path;

Cut through the noise and distractions to find clarity;

Shape the direction of the arc;

Shift the rules of the game;

Avoid the pitfalls;

Gain opportunity and advantage; and

Create something bold.

In the course of this journey, I’ve witnessed many leaders who exercised judgment brilliantly in their crucible moment. Many more did not. Judgment is an exploration of those deeper codes and common patterns that explain why.

Before undertaking this exploration of the underlying codes and patterns that help define where success lies, there are several precursors to understand:

Judgment itself is the product of how we have arrived at this moment, what we do in this moment, and whether we possess the discipline and insights to get the critical decision right when it matters most.

Judgment is dependent on how leaders perceive, react, and think in these moments when the noise, pressure, and stakes are at their highest.

Judgment is a construct that feels familiar and readily known to all of us. As we deconstruct it to discover its more fundamental tenets, however, it becomes more mysterious. The properties of judgment have an alchemical quality to them, able to transform adversity into opportunity for gifted leaders while proving elusive, career-ending, or even fatal to others.

The unfortunate reality is that we measure judgment best only when it has failed. It is in this moment, looking backward, when we are privy to the costs of judgment poorly exercised. The more significant opportunity, however—and the place where the beholder can create advantage—is to learn those codes, methods, and techniques that enable the careful curation of judgment.

Foreword

We had to decide how to depart. It was night. The weather was not optimal. Tracer rounds pierced through the dark with gunshot reports all around us. Our airfield was situated in the lowest part of the valley. The enemy lurked somewhere above us, watching. Aircraft coming in and going out were suffering damage from small arms fire. Ground control was not helpful to the next decision. It would be a judgment call, and ours alone. We decided to depart dirty, with flaps down, accelerating into the night at maximum power, and with no lights on the aircraft. We would leave as soon as there was a lull in the gunfire. It was a priority mission. There could be no delay. There could be no failure.

My co-pilot and I were trained for moments like this. Our training took over. Power to climb, rotate early, gear, flaps, radios. We would ascend into the night, desperate to soar through 10,000 feet, where we would finally be out of range for their guns and anti-aircraft weapons. There was a method to it. Landing at the reposture location would be another story. The air controller had nominal English. We would be on our own again, this time landing with only our instruments as the guide. Moments like this became our routine rather than the exception.

I later was stationed at the Pentagon. Decision-making here was different. It was bigger, more complex, and with more layers. I became the briefer to the senior-most leaders of the US Army before and during the invasion of Iraq, and would continue in this role during the follow-on occupation. I along with a team of nearly forty Army officers prepared the daily decision machinery by arming the command with as much operational information as possible. It was essential to their exercise of judgment in wartime.

There was a method to this as well, albeit very different. We would build tomorrow’s brief the night before. I would compile, read, re-read, and absorb everything I could prior to presenting the current fact pattern to the command at an oh-dark-thirty meeting every morning. These morning briefings were dense. They covered everything from the movement and actions of the smallest Special Operations unit; to materiel transit times; to health concerns of a disease-borne pesky local sand fly (leishmaniasis); to, unfortunately, the names, hometowns and next of kin of those US service members killed in action the day before. The leaders wanted to know everything they could. It required the ability to process an absolutely herculean amount of information. What we included or did not include in the briefing, and how we shaped and presented the fact pattern, could have immeasurable impact on our success at the highest levels of military decision-making.

From the Pentagon, I became a lawyer. In my tenure within the office of the Attorney General, decision-making was again quite different. It involved different rules, different processes and a different kind of judgment than required of two pilots sitting on a darkened airfield under fire or within the immense enterprise that is the Pentagon. Here, the decision focused on the likelihood of recidivism by convicted offenders. Our job was to prepare a recommendation, based upon our judgment, for how likely it was that an offender might repeat their criminal actions. The statutory guidelines were tough. The punishments could be harsh. Sometimes rehabilitation worked. Sometimes it did not. Our job was to provide an assessment of what was most likely to happen next. It was all judgment. It was personal. It affected lives.

Yet as different as each of these situations have been, there is a common thread that pulls through each. Whether I was forcing our aircraft to climb out of hostile territory, preparing to arm senior leaders sending Americans into battle, or as a lawyer likely shaping the fate of an offender, the decision in each case turned on how we exercised judgment in a critical moment. The exercise of judgment is always, unfortunately, imperfect. The pressure is always intense. There is never enough time. The stakes are inevitably high. The risks—to oneself and for others—are very real. It is our obligation as leaders, however, to strive for the highest levels of performance.

There are ways in which our own judgment can be heightened so that the decisions we make change the arc, capture the opportunity, avoid the tragedies, and even save lives. With Judgment: The Art of Momentous Decision-Making, Chris Mailander has set forth the structures and methods for doing just this. He plots each point along an unfolding decision arc, highlighting what to look for and what to avoid, identifying the common errors and missteps made by leaders in crucible moments, and setting forth the lessons, rules, and tools we all can use along the way.

There is something deeper going on in Mailander’s study of judgment. There are what he describes as the deeper codes and common patterns that underpin judgment in crucible moments. They are the sort of essential lessons leaders should not only understand, but operationalize within their own decision-making, whether they be young pilots on the battlefield or seasoned executives in the boardroom. What Mailander has delivered is a treatise for how to get it right when it matters most.

Colonel William P. Schwab, Esq., US Army, Retired

Current, Deputy for Combined and Joint Military Exercises

USINDO-Pacific Command

Honolulu, Hawaii

March 2023

The Experiment

Judgment: The Art of Momentous Decision-Making is based upon an experiment. In this work, we will examine three case studies. They are:

Nuclear Brinkmanship in the Cold War, 1986

In the waters somewhere off the coast of Vladivostok, Russia, we study the command of the USS Guardfish, one of the US Navy’s top weapons in the hunt for Soviet secrets. It is 1986, and the Soviet Union and the United States are locked in an escalating battle defined by political and military brinkmanship. Each of their respective gambits runs the risk of triggering nuclear annihilation. The moment-by-moment decisions made by the captain of the USS Guardfish and its crew deep below the darkened seas tell us much about preparing for crucible moments.

The Precipice of Global Economic Collapse, 2008

In 2008, the global economy teeters on the precipice of cataclysmic disaster. The core of the global financial system is melting down. Leading financial institutions are falling. One institution, however, is too big to let fail. If it implodes, it will take the entirety of the financial system and possibly the whole economy with it. Over the course of several days, the fate of the global financial system is determined by several dozen men in tense negotiations in quiet conference rooms across several blocks of Wall Street. The quickly shifting balance of power among them, affecting their leverage over one another and their susceptibility to events outside of their control, informs our own responses to those events we can and cannot control.

Crescendo in the Global War on Terror, 2015

Just before the world’s leaders convene in Paris, seeking to attain the most significant multilateral commitments ever on global climate change, terrorists launch coordinated attacks across the city. Over the course of four hours, as friends and lovers dine in tiny bistros and fans cheer on their national soccer team taking on the world champion German opponent, France witnesses the greatest atrocity on its soil since World War II. We study the decisions made moment by moment in France, as well as from inside the White House Situation Room, the epicenter from which the United States’ own national security apparatus stands up to defend against its newest threat. The events reveal lessons in responding to quickly changing conditions and formulating rational responses to fear-inducing circumstances.

Commonalities

In some ways, these case studies are