Scott Monty - Strategic Communications & Leadership Advisor

Scott Monty - Strategic Communications & Leadership Advisor


Snow Scene at Argenteuil by Claude Monet, 1875 (public domain - Sailko, Wikipedia)

“Without contraries is no progression. Attraction and repulsion, reason and energy, love and hate, are necessary to human existence.”

— William Blake, 1790

I love my seven year-old daughter. She’s filled with energy and excited to greet each new day (albeit much earlier than the rest of our household).

Yesterday morning, we awoke to a particular silence in the neighborhood. That sense of calm and quiet that accompanies a blanket of snow, only to be pierced by the passing snowplow.

There’s a reverie—ever so brief—as the mind wanders to memories of childhood, when such days would herald an extra early departure of Dad for work as he braved the slippery roads; a sense of anxiety as we listened to the radio, anticipating for our school to be announced as one of the cancellations; and the first of many sojourns outside to frolic in the winter wonderland of our neighborhood.

A snow day as an adult—particularly one well-versed in working from home—doesn't hold the same level of freedom and joy as it once did. Outside in the stillness and cold, the driveway and sidewalks await plowing, but the bed covers act as a temporary talisman against their pull.

And inside, a rambunctious child doesn’t understand the concept of sleeping in.

“I am no longer good through deliberate intent, but by long habit have reached a point where I am not only able to do right, but am unable to do anything but what is right.”

— Seneca, 65

Once we’re downstairs and fed—she, a bowl of Fruit Loops and me, a bowl of steel cut oatmeal—I summon my best Wordsworth and announce that duty awaits.

“Stern Daughter of the Voice of God!

O Duty! if that name thou love

Who art a light to guide, a rod

To check the erring, and reprove”

And then, without hesitation, I hear from her the question I still pray my teenage sons will someday learn:

“Can I help?”

Now, there’s something you need to understand about Grace. While she’s always happy to put in the hard work and eager to help, she’s—how shall I put this?—not quite a skilled laborer. Her shoveling leaves more of a mess than what she attempts to remove.

But I know that if I refuse her sweet offer, there will be tears (hers).

I also know that if I accept her sweet offer, there will be tears (mine).

So I cheerfully encourage her assistance.

And as predicted, try as she might, she had neither the skill nor the equipment to do a diligent job. At that point, my job was to encourage rather than discourage her.

We all find ourselves at that point in a work situation, when presented with facts and a colleague with a hopeful look on their face, we’re expected to give the “yeah, sure” rubber stamp of feedback.

But there are times when we just can’t.

You’ve probably used the term “devil’s advocate” before, meaning that you’re taking up an opposing viewpoint for the sake of playing out a mini-debate with someone.

You don’t necessarily espouse the position you’re staking out, but you’re presenting it for the sake of argument, to ensure your partner in rhetoric is thinking through their position.

Now, let’s be clear: this is different from being an outright antagonist. An antagonist counters every position and makes arguments purely for the sake of doing so, with no intended outcome other than to fluster or simply be negative. He is a contrarian for a contrarian’s sake.

“Quarreling must lead to disorder, and disorder exhaustion.” 

— Xunzi, c. 250 BC

Origins of the Devil’s Advocate

A devil’s advocate has a much more strategic and intentional role. The phrase has its roots in Roman Catholicism, from the process of beatification or canonization of saints.

The Promoter of the Faith was an official position within the Catholic Church. More popularly known as Advocatus Diaboli (“Devil’s Advocate”), he was tasked with critically examining the life of and miracles attributed to individuals proposed for sainthood. As Devil’s Advocate, the canon lawyer attempts to poke holes during presentation of facts to point out everything unfavorable to the candidate.

Pope Sixtus V formally established the office in 1587, although it was on record as having been used under Leo X (1513 – 1521). The office was abolished when Pope John Paul II revised the canonization procedures in 1979.

The phrase survives to the present day, as you know, and it’s a practice that happens in plenty of meetings (“Let me just play devil’s advocate for a moment,” is how it usually plays out.).

It's a healthy exercise for every leader to undertake: to invite peers and subordinates to challenge you. It keeps you on your toes and requires you to justify your decisions and rationale. The best leaders encourage others to challenge them.

From “No way” to “Yes sir”

Let’s flip this on its head. There are leaders out there who refuse to allow dissent. To question their decisions is to question their ability.

Thin-skinned, praise-hungry, and incurably insecure, the weak leader must be propped up, fluffed, and reassured. I was reminded of this in yesterday’s episode of The Daily, on which Donald J. McNeil, Jr. interviewed Dr. Anthony Fauci.

One of the most central figures during the pandemic, Dr. Fauci often had to present evidence that contradicted the president, offering up his professional opinion that was the opposite of anecdotally-driven medicine. He felt it was his duty to speak up, “Otherwise, I would compromise my own integrity and I would also be giving a false message to the rest of the world.”

His ability to force a reality check resulted in an unfortunate nickname: he became known as “the skunk at the picnic.”

“Do we want laurels for ourselves most,
Or most that no one else shall have any?” 

— Amy Lowell, 1922

Some leaders simply don’t tolerate skunks. They have no use for a devil’s advocate, and their vizier takes the form of a sycophant.

For it is the sycophant who blurs all negatives, obliterates opposition, and obfuscates reality. The leader, so desperate for that which soothes his damaged soul, welcomes this fantasy world and ignores the challenges that are evident to everyone around him. And the “yes men” are only too willing to oblige.

This inner circle finds a way to survive and even thrive under such leadership, and tries to work the system for its own benefit. Often such suck-ups will give the boss exactly what he wants to hear, in exchange for favorable treatment for themselves.

President Franklin Roosevelt relied on the advice and counsel of Harry Hopkins, his most trusted advisor. One day, Wendell Wilkie, the Republican nominee for president in the 1940 election, asked FDR why he put his faith in Hopkins.

Roosevelt replied,

“Someday you may well be sitting here where I am now as president of the United States. And when you are, you’ll be looking at that door over there and knowing that practically everybody who walks through it wants something out of you. You’ll learn what a lonely job this is and discover the need for somebody like Harry Hopkins who asks for nothing except to serve you.”

There’s a fine line between an antagonist and a sycophant. One provides a hard “no” and the other an easy “yes,” and each is meant to halt or grease a process.

“It is permitted to learn even from an enemy.” 

— Ovid, c. 8

A devil’s advocate is more independent and meant to ask questions and to make us think for ourselves. Advisors or coaches can act as devil’s advocates, as they’re third parties and can be more detached from the situation.

The best advisors think broadly and help the C-suite see around corners to prioritize issues, frame problems. They may not have all the answers, but they raise important questions. And they're not afraid to offer a contrary point of view.

Every C-suite member should have an advisor who asks the tough questions and raises appropriate objections.

If that person turns out to be a skunk at the picnic, so be it.

But at least you’ll know that it’s time to think about reconsidering your picnic.

Before it snows.

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