Judgment: The Art of Momentous Decision-Making

In the summer of 1993, a day after taking the bar exam, I loaded my belongings into the back of a farm truck I borrowed from my father and headed East. A week later, I walked into an office on Connecticut Avenue in Washington, D.C., wearing a blue suit and silk tie. I was assigned a desk overlooking the steps of the Cathedral of St. Matthew the Apostle, where almost thirty years earlier, John F. Kennedy Jr. saluted his father’s coffin. The cross-country journey was one from student to lawyer, from West Coast to East, from one who could imagine how power, influence, and values shaped momentous decisions to one who worked the knobs and levers to make them.

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. The other founder, Peter D. Robinson, was quieter. He sat with his back to the door in a leather-bound swivel chair, staring out the windows, contemplating the arcs in the political and policy debates the way I imagine a conductor sees music. He felt the highs and lows amid the cacophony and saw shapes and colors emerge from a swirling ether of grays. He was a thinker, feeler, intellectual, and empath. He became my mentor.

To most, political Washington is the pinnacle of chaos and dysfunction, an ever-running theater whose most visible actors are distasteful at best and repugnant at worst. The fundamental institution of Washington, however, was conceived to withstand the worst of human behaviors with a collective resolve to serve higher, more enlightened values–the ones woven into the Constitution. It also endures because of silent stewards who toil not in service to their egos or self-selected tribes, but in service to these higher ideals.

My mentor, Robinson, was one such steward. He had been a parliamentarian in the US House of Representatives, quietly managing the procedures and structures for momentous decisions. After thirteen years, 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. By the time our paths crossed, Robinson possessed two decades of experience in managing the processes by which Congress made decisions. His realm was governed by the mysterious but practiced art of exercising judgment in critical decision-making moments.

The young firm Robinson co-founded had recently been acquired by a global communications company. Within weeks, I went from sleeping in the farm truck to advising CEOs of multinational banks, global financial institutions, credit card companies, insurers, and pharmaceutical companies. 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 shifts in power.

This new realm was a crash course in judgment — the art of knowing when to move, fight, be silent, whom to trust and whom to not, how to overcome dissent, and when to become the dissenter.

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, I’ve studied the alchemy of how people exercise judgment during critical moments. It is a career that has hopped from designing award-winning public affairs campaigns for the likes of the 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 international lawyers at Georgetown; to advising as an adjunct fellow at 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, among others.

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.

Robinson, the parliamentarian and mentor, listened each day for bold and blaring sounds and the single perfect note that would sometimes pierce through. His daily habit was to pore through the news, call insiders, and have meetings. Then he would stare into the ether above the intersection of Connecticut Avenue and M Street Northwest. He saw every chord emerging from the city as a decision arc uniquely unfolding. Robinson surveyed the competing arcs to predict which would result in action versus stagnation. He was sorting the signal from the noise. He would then contemplate the strategies for influencing the arc of his chosen few.

Competitors sought to bend each arc to their favor and, in doing so, were required to exercise their own best judgment. Errors of judgment could cripple an arc, flare it, increase its dysfunction, or kill it. Errors fueled the noise. The media reveled in any failure among the elected and privileged. Interest groups, real or manufactured, fanned the flames to benefit their own aims, and political opponents sensed an opportunity to nick or kill.

I’ve witnessed many leaders who exercised judgment brilliantly in their crucible moments. Many more did not.

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 depends on how leaders perceive, react, and think 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 an opportunity for gifted leaders while proving elusive, career-ending, or even fatal to others. 

In my time with Robinson, I came to learn something ironic — moments in which judgment is brilliantly exercised are often very quiet. This is an injustice, of course. We should celebrate exceptional decision-making. But our society favors storylines of anger, frustration, inequity, and injustice. Stories of decision-making success don’t sell news or send voters to polls.

For those who do come to exercise judgment well, who carefully curates its execution, and who renders a decision that improves the arc of the decision, expect few accolades. You will, however, be welcomed into an elite fraternité — the silent stewards of judgment.

Excerpted from “Judgment: The Art of Momentous Decision-Making” by Chris Mailander (Ironheart). Available now.


Chris Mailander counsels corporate and national government clients through the arduous decision path faced in the pursuit of extraordinary outcomes. His client roster has included MasterCard, Bank of Montreal, the Federal Home Loan Bank System, Unisys, Visa, KPMG Consulting, BearingPoint, the President of Nigeria, the Government of Iraq, and a host of mid-market leaders and Silicon Valley innovators seeking to transform industries. He has negotiated tenders and commercial transactions in more than forty countries across North America, Europe, Asia, the Middle East, and Africa, including in conflict and post-conflict economies. He was previously an adjunct professor at Georgetown University Law School and an adjunct fellow at the Center for Strategic & International Studies. He is author of The Craft (2019). He lives in Asheville, North Carolina.

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