The Death of a Salesman: Donald Trump and the Persuasion Paradox

Donald Trump’s reputation as a salesman conceals a secret: he's terrible at the art of persuasion.

By John Paul RollertOctober 25, 2018

The Death of a Salesman: Donald Trump and the Persuasion Paradox

THAT DONALD J. TRUMP has proven himself an unpersuasive salesman for his own policy agenda may be the most surprising development of his nearly 20 months in office. The soi-disant dealmaker sold a credulous electorate on the idea that the business acumen that saw him brand his name into the side of every piece property he owned like a 24-karat cowpoke, would translate into the political prowess of a successful commander-in-chief. And yet aside from the tax cuts, last December, President Trump has given no evidence that he is practiced at the art of the legislative deal, or any deal for that matter, a failure that says less about those who voted for him than the peculiar bargaining style he honed over 40 years in business.

“I aim very high,” Trump writes in The Art of the Deal, “and then I just keep pushing and pushing and pushing to get what I’m after.” If such an approach smacks of an implacable sales pitch — and, to Americans exhausted by more than three years of relentless braying, brawling, and braggadocio, the elevator music of an endless descent — it shouldn’t be confused with the banalities of other How to Succeed in Business books whose encouragement often amounts to Quitters never win, and winners never quit. Indeed, when Trump himself says in a later book, “You will not be successful if you listen to nos,” he is describing less a behavioral flaw for the aspiring dealmaker than a high-pressure approach to deal-making.

“I’ll do nearly anything within legal bounds to win,” Trump avers in The Art of the Deal, a declaration borne out by decades of trash-talking rivals (“part of making a deal is denigrating your competition”), sweet-talking city officials (“When a reporter later asked me why I got a forty-year tax abatement, I answered, ‘Because I didn’t ask for fifty’”), and strong-arming contractors (“If you try screwing me on this job, you won’t be getting a second chance”). Indeed, ever since he emerged on the New York real estate scene in the 1970s, Trump’s approach to deal-making has typified Thorstein Veblen’s acid-tongued assessment that the “arts of business are the arts of bargaining, effrontery, salesmanship, make-believe, and are directed to the gain of the business man at the cost of the community, at large and in detail.” The ultimate victims in Trump’s phony deals are not the developers shunted aside, nor the unwitting taxpayers underwriting one man’s ambition, nor even the subcontractors accepting pennies on the dollars promised when a litigation-prone counter-party has deemed their completed work unworthy — no, it is the countless Americans, impressionable and unsuspecting, whose faith in Donald Trump (emboldened, as it so often is, by encouragement from his minions) has afforded them dubious peace of mind for some thoroughly disreputable investments.

Set aside Trump’s potemkin villages, the housing developments he claims to have nothing to do with notwithstanding the fact they’re named for him, or the one public offering he floated (DJT on the ticker) which raised $140 million for Trump Hotels and Casino Resorts in 1995, helping Trump to retire debt he had personally guaranteed and affording him lavish compensation as chairman, all while the company lost money every year until its bankruptcy in 2004. Even beyond these, the best illustration of Veblen’s inventory and the peculiar approach to business that has distinguished Trump’s career is Trump University and the “playbooks that were distributed to sales associates detailing the high-pressure sales tactics they should use to help them close the deal.

“You don’t sell products, benefits or solutions,” reads one of these documents, which were unsealed during the class action lawsuit brought against the for-profit enterprise, “you sell feelings.” To that end, the goal of a Trump University sales associate was to guide customers along the “roller coaster of emotions” until they arrived at the terminus of enrollment. In turn, notwithstanding the fact that tuition packages could run tens of thousands of dollars, agents were instructed not to allow prospective students to ask too many questions. “The person asking the question always has the power,” one playbook warned. While a broker “may begin with some small-talk to establish rapport,” he had to be on guard lest his customers “take control of the conversation.”

Accordingly, the playbooks directed sales associates to waste no time in making their pitches. “You must be very aggressive during these conversations in order to push [customers] out of their comfort zones,” one commended. If they question the price of the packages, “remind them that Trump is the BEST!! This is the last real estate investment they will ever need to make,” a bold declaration that is essentially incoherent, given that the aim of the education is to train one how to invest in real estate.

Once prospective students had arrived at the decisive moment, if they could not put the full cost of tuition on their credit cards, which they were strongly encouraged to do, agents were instructed to counsel them to open a new card, tap into their savings, or find other “seed capital.” And if they hesitated, they should be reminded of the very inadequacies that led them to Trump University in the first place. “You’ve had your entire adult life to accomplish your financial goals,” reads the script supplied by one playbook. “I’m looking at your profile and you’re not even close to where you need to be, much less where you want to be.” Having cataloged their shortcomings, a sales associate should then present customers with a “Three Choices Turnaround.” First, they can “choose to do nothing more” and be “content” in their failure. Second, they can try to turn things around all by themselves and continue making the same mistakes. Or, third, they can enroll in Trump University and learn from the “experts,” a truly remarkable faculty, the trial later revealed, that would include individuals who had absolutely no experience in real estate.

All this, the playbooks advised, in a deal that should be closed in “two minutes or less.”

“You hear lots of people say that a great deal is when both sides win,” Donald Trump writes in a book co-authored with Bill Zanker, the founder of the Real Estate & Wealth Expo, the cross-country roadshow where pricey get-rich-quick packages, including, once upon a time, Trump U, are peddled with similar high-pressure tactics. “That is a bunch of crap. In a great deal, you win — not the other side.”

First released in 2007, the book by Trump and Zanker was originally titled Think BIG and Kick Ass In Business and Life. However, sometime before Trump became president, modesty prevailed upon the publishers and the book was renamed Think Big: Make It Happen in Business and Life. This is a shame, not only because little thinking goes on in the book, but because the moral aptitude and practical posture of kicking ass, and what they say about how one should view customers and counter-parties alike, are central to the book’s approach to deal-making.

While its advice often resembles threadbare tributes to simple persistence, Think BIG and Kick Ass distinguishes itself from the average popular business book by suggesting that persistence is necessary not so much because it is synonymous with hard work, and all the virtues we associate with that commitment, but because the nature of business is inevitably adversarial. Consider the following counsel for being a successful deal-maker: “Do not let somebody’s arbitrary ‘no’ stop you. Find a way to turn the ‘no’ into a ‘yes.’ Don’t let anybody stop you!” Set aside the fact that here, as in so much of the book, it can seem like the author is shouting at you, what stands out is Trump’s peculiar interpretation of what it means to engage in business. Rather than a straightforward exchange of goods or services between two free and independent parties, for Trump, any business deal is a contest of wills where one party will ultimately emerge triumphant, the other ripped off. The person on the other end of any deal is always an enemy, an aggressor, and an impediment to individual success. She cannot be trusted or engaged as an equal. She must be overwhelmed. “You crush the opponent,” Trump says of such engagements, “and come away with something better for yourself.”

If such an approach to business sounds less like the elements of a commercial bargain than the evidence of a Viking raid, that is exactly how Trump conceives it. And this is not only true for business. The crude Darwinian struggle that characterizes deal-making carries over into every type of human interaction. “The world is a horrible place,” Trump maintains at the end of a chapter appropriately titled “Fear Factor”:

Lions kill for food, but people kill for sport. People try to kill you mentally, especially if you are on top. We have all friends that want everything we have. They want our money, our business, house, car, wife, and dog. Those are our friends. Our enemies are even worse! You have to protect yourself in life.

He continues:

The same burning greed that makes people loot, kill, and steal in emergencies like fires and floods, operates daily in normal everyday people. It lurks right beneath the surface, and when you least expect it, it rears its nasty head and bites you. Accept it. The world is a brutal place.

If you accept this diagnosis, one that makes no room for the ameliorative effects of cooperation or common cause, persistence is absolutely essential. Anything you desire, anything you might accomplish, can only be obtained by brute force or fraud, and whether you are taking on the champ or dealing with a chump, the ultimate outcome doesn’t change. There is a victor and there is the vanquished, and the notion that it could be otherwise, that human interaction could ever afford win-win scenarios? Again: “That is a bunch of crap.”


Life as one long Darwinian struggle is the lurid leitmotif of Trump’s worldview, one that not only informs his approach to cutting a business deal but to brokering any type of human exchange. “We may live in houses in the suburbs but our minds and emotions are still only a short step out of the jungle,” Trump muses in Think BIG and Kick Ass. As such, even those interactions that would seemingly involve at least a dash of sweetness and sympathy, such as romantic engagements, are still nothing more than a hollow drama of human dominance.

“In primitive times women clung to the strongest male for protection,” Trump says, playing the poor-man’s anthropologist. “They did not take any chances with a nobody, low-status male who did not have the means to house them, protect them, and feed them and their offspring.” He concludes, “That kind of attitude was and still is associated with the kind of men women find attractive.”

If every human interaction takes the shape of a struggle for dominance, the interplay is less a matter of exchange than acquisition, and the ultimate aim for a given actor complete and total submission. No doubt, this is something of a tall order. Modern life seems hard enough without having to worry about exercising dominance over every person you meet, but to be further burdened with a worldview that instills, at once, a deep sense of insecurity in the face of every unmet challenge and a sustained fear in the face of others for triumphs already claimed (“everyone wants to kill me” is a familiar Trumpian refrain), well, it all sounds a little exhausting. In the face of such constant pressure — that applied by others but, more so, the stress that is self-inflicted — a normal person might be forgiven for having second thoughts about the wisdom and crude requirements of such a worldview and wondering, altogether, whether it’s worth it.

But Donald Trump is not a normal person, neither by his own reckoning nor much anyone else’s, and with respect to second thoughts, the seeds of self-reflection, he prefers to keep his own mind untroubled and barren. “Every time a negative thought comes at you, zap it,” he says. “Replace it with a positive thought. This takes energy, but the result will be stamina — positive stamina, a necessary ingredient for success.”

The lesson, he says, is one he drew from The Power of Positive Thinking, a best-selling book Trump credits with decisively shaping his approach to business dealings and to life in general. The book was released in 1952, when Trump was barely out of diapers, but long before he had a chance to read it, he had ritually imbibed the words of its author, Norman Vincent Peale, the pastor of a Reformed congregation in midtown Manhattan where the Trump family attended services. On the whole, Donald Trump gives credit to others about as much as he takes their counsel, but any doubt that Peale made a formidable impression on him is quickly dispelled by reviewing the take-away lessons that conclude the first chapter of The Power of Positive Thinking, gently titled “Believe in Yourself.” They include:

1. Formulate and stamp indelibly on your mind a mental picture of yourself as succeeding. Hold this picture tenaciously. Never permit it to fade. Your mind will seek to develop this picture. Never think of yourself as failing; never doubt the reality of the mental image. That is most dangerous, for the mind always tries to complete what it pictures. So always picture “success” no matter how badly things seem to be going at the moment.

2. Whenever a negative thought concerning your personal powers comes to mind, deliberately voice a positive thought to cancel it out.

3. Do not build up obstacles in your imagination. Depreciate every so-called obstacle. Minimize them. Difficulties must be studied and efficiently dealt with to be eliminated, but they must be seen for only what they are. They must not be inflated by fear thoughts.

Reviewing the book for The Nation in 1955, when it was midway through its remarkable 186-week run on The New York Times best-seller list, Robert Murphy suggested that the “folksy, monotonously cheerful book” had captured the popular consciousness by offering “guaranteed solutions in easy steps” to “the problems of a frightened and desperate America.” Peale’s prescription was relatively straightforward: practice an irrepressibly positive outlook and you will cultivate the Can Do! attitude that will prepare you to face down all of life’s challenges, paving the way to personal and professional success.

To put it mildly, Murphy was unconvinced. As he pointed out, the challenges we face are often not only stubborn before even the most socially effervescent personality, they are the fruits of internal conflicts that involve weighing incommensurable goods (say, the desire to fully participate in a child’s life or aggressively climb the corporate ladder) or wrestling with the very mysteries that give our lives meaning, scope, and purpose. In other words, it is not so much that such challenges aren’t easily resolved or that struggling with them isn’t a worthy activity that often proves therapeutic and enlightening, rather that the relative power of one’s positivity is largely irrelevant to addressing them.

Which is not to say that coming to grips with such challenges doesn’t affect one’s disposition. It certainly does, but this is only an irremediable problem if sustaining an unblemished, upbeat outlook — and the approach to the broader world consistent with it — is always a foremost concern, an accusation Murphy levels at Peale’s peculiar self-help prescription. “Facts, thoughts, creative strivings, self-contemplation, all these fall under his ready knife if they can be shown to cause mental anguish,” he writes. “Self-knowledge in Mr. Peale’s understanding, is unequivocally bad; self-hypnosis is good.”

Murphy’s criticism is not entirely fair insofar as it largely dismisses the central role of faith in Peale’s philosophy. “Drive your prayers deep into your doubts, fears, and inferiorities,” the reverend tells his readers. “Pray deep, big prayers that have plenty of suction and you will come up with powerful and vital faith.” Such encouragement, however anodyne and dogmatically indefinite, fills the pages of Positive Thinking and even headlines one chapter (“Try Prayer Power”). It gives the book a patina of best intentions, blunting criticisms like that of another reviewer who observed that “[i]n more classic literature, this sort of pretension to mastery has often been thought to indicate an alliance with a Lower rather than a Higher Power.”

Goethe’s Faust is an unlikely candidate for the literary wheelhouse of President Trump, but General Zod seems like a safer bet. The New York Times’s Maggie Haberman noted in a tweet last December that, when he first took office, the “kneel before Zod” approach more or less encapsulated Trump’s understanding of presidential leadership, a vision endorsed by those around him, such as Omarosa Manigault Newman, who famously told Frontline that the moral upshot of the 2016 election was that “[e]very critic, every detractor, will have to bow down to President Trump.” She continued, “It’s everyone who’s ever doubted Donald, who ever disagreed, who ever challenged him. It’s the ultimate revenge to become the most powerful man in the universe.”

Setting aside possible objections from the panjandrums on Alpha Centauri, Omarosa’s vision of executive authority is the logical extension of Peale’s Positive Thinking once it has been shorn of any spiritual self-awareness or higher purpose. Indeed, it becomes little more than the battle cry of a crude will to power, a mantra of sound and fury signifying nothing beyond a single man’s preeminence.

The evidence that this is precisely the way Trump views himself is not only abundant — “I am the only one that matters,” he has maintained as president — it is celebrated by those who would abet his megalomaniacal self-conception. Consider Corey Lewandowski’s memoir of the 2016 campaign, too perfectly titled Let Trump Be Trump. In the book, Lewandowski gleefully recounts an episode from the spring of 2015 when Paul Manafort suggested that Candidate Trump stay off television while he worked to obtain the necessary delegates to secure the Republican nomination. Trump did not exactly appreciate the counsel. “I’ll go on TV anytime I goddamn fucking want,” he screamed over the roar of a helicopter that had apparently been lowered to an altitude that would allow him to make a call to Manafort. “Tone it down? I wanna turn it up!”

According to Lewandowski, one phone call did not sate the candidate’s outrage, so Trump placed a second when he was on the ground again. “He got Paul on the phone and completely decimated him again verbally,” he writes. “Ripped his fucking head off.” Manafort, Lewandowski says, tried to reason with Trump, or at least make the case that, in respect to politics, he knew what he was talking about. Trump, however, would have none of it. “You’re a political pro?” he bellowed. “Let me tell you something. I’m a pro at life.”

As Lewandowski admits, such exchanges were de rigueur when dealing with Trump, who expected not only that his staff would treat him with the crooked-knee of imperial contemplation but would gladly discharge any command he gave them, however demeaning, from fetching Big Macs to the motorcade to steam ironing his slacks when he was already wearing them. And as Manafort apparently discovered, for anyone who fell short of Trump’s regal self-regard, he could soon count on reaping the whirlwind. “Sooner or later, everybody who works for Donald Trump will see a side of him that makes you wonder why you took a job with him in the first place,” Lewandowski says. “The mode that he switches into when things aren’t going his way can feel like an all-out assault; it’d break most hardened men and women into little pieces.”

The brutality of Trump’s leadership style is of a piece with his high-pressure approach to business, a coincidence that should hardly be surprising, for the art of deal-making is ultimately an exercise in getting other people to do exactly what you want in furtherance of your own private ends. And if, in pursuing deals as president, Trump draws inspiration, direction, and sustenance from the way he has conducted his business ventures, his shocking political success seems to have left him convinced that he might improve upon that experience by streamlining his strategy: in brief, you need neither strong arm nor swindle when you can simply command.

Such an approach to the business of politics, when combined with an adulterated version of Peale’s “positive thinking” in which the avatar of one’s imagination becomes the fulcrum and essential force of all human reckoning, is reminiscent of another famous literary figure who lacks General Zod’s interstellar panache, if not his cosmic self-importance.

In his final appearance in the play Shakespeare named for him, Julius Caesar is implored by a pack of senators to reconsider the banishment of Publius Cimber, a distinguished citizen. “I could be well moved if I were as you,” Caesar sneers at the supplicants. “If I could pray to move, prayers would move me.” He continues:

But I am constant as the northern star,
Of whose true-fix’d and resting quality
There is no fellow in the firmament.
The skies are painted with unnumber’d sparks,
They are all fire, and every one doth shine;
But there’s but one in all doth hold his place:
So, in the world; ’Tis furnish’d well with men,
And men are flesh and blood, and apprehensive;
Yet, in the number, I do know but one
That unassailable holds on his rank,
Unshak’d of motion: and, that I am he,
Let me a little show it, even in this;
That I was constant Cimber should be banish’d,
And constant do remain to keep him so.

A nation’s leader as the shining north star around which the heaven of humanity turns — one suspects that Trump himself might embrace this image as emblematic of his own leadership.

Or, again in his own words, “I’m a pro at life.”


For those who haven’t recently spent time with Shakespeare’s play, it seems important to note that the scene above is Caesar’s swansong. Shortly after this paean to immobility, he is assassinated by the same senators who have gathered around his feet in apparent supplication. A well-choreographed performance carefully balances Caesar’s oblivious arrogance against the obvious motives of the senators. For Caesar alone it makes sense that so dignified a man as Brutus would find his way to keeling before him, whereas the audience knows that the blind spot of excessive self-estimation prevents Caesar from clearly seeing that something is wrong, terribly wrong, that rather than being certified in his superiority, he risks epitomizing the adage that pride goes before a fall.

To be so blinkered before others is part and parcel of a leadership style that favors command over counsel, intimidation over influence, imperial mandate over a negotiated community of peers. It is not so much that other people are viewed a pawns on a chessboard — to be moved, and removed, at one’s whim — rather that going through life under such an apprehension inures one to an exceedingly narrow spectrum of social interaction and a single vector of human behavior: demand, demand, demand.

In many respects, such an approach is akin to an older, more primitive vision of authority, albeit one marked by childlike uncomplication. To be in charge, to be a leader, is to be held in awe by others such that, when one gives orders, they are immediately obeyed. Politics, as such, is not really a matter of brokering deals but issuing commands, and for those who receive the directives, they bear no greater consideration than one would give a handsaw, a hammer, or any other tool. Their views — to the degree that one would ever bother to consider them — are advisory, at best. A substantial difference of opinion is considered an insult, dissent intolerable. Indeed, for the authority figure in the thrall of such a vision, the tired proverb never seems truer: a leader leads. Everyone else follows.

One has the impression that this is exactly Donald Trump’s conception of leadership, or at least the one he carried to the White House, where reports suggest that, contrary to an elemental feature of American government, the separation of powers, he initially believed that everyone in the federal government worked for him. The fact that the president has no such authority, especially with respect to elected members of Congress, is where the limits of Trump’s leadership style — and, therein, the deal-making he would do as president — come into view, for if you cannot command, you must persuade, and President Trump has proven himself most unpersuasive with anyone not already enamored of him, a group that includes most Congressional members, the majority of the American people, and nearly every world leader not named Vladimir Putin.

In many respects, this is a curious failure, for Donald Trump came of age at a time when the dominant literature that claimed to foster one’s professional success and prepare him for the responsibilities of leadership was exploring the fault line between the brute exercise of power and the delicate craft of persuasion.

The most famous of these works, and the foundational text of the genre, is Dale Carnegie’s How To Win Friends and Influence People, a book that has sold more than 15 million copies worldwide since it was first published in 1936. The very title of the Carnegie’s book signals its organizing logic: namely, that to be an influential person, you have to first ensure that others actually enjoy your company. To that end, Carnegie offers a litany of anecdotes and allegorical stories that teach you, by turns, how to “Become a Friendlier Person,” “Win People to Your Way of Thinking,” and, finally, “Be a Leader.” The book’s central claim is that only by first establishing the bonds of shared interest and mutual respect can you hope to prevail upon others as to your own point of view, which is essential when you want to lead individuals who are always free to say no and part ways — which is to say, people who are quite literally not enslaved to you.

If such advice seems commonsensical, today, that is only because, culturally speaking, Carnegie’s vision has triumphed in the United States. This is evident not only in the endless emphasis on networking and the cultivation of “soft skills,” but more profoundly in the attention given to empathy and the mollifying effect it has on the individual ego. In contrast to the assumption that the surest route to being liked, admired, and respected is by dominant displays that more or less amount to chest beating (or, for that matter, kicking ass), Carnegie’s advice always sees the energy of an human interaction flowing outward to engage, allay, and inspire another person. Consider three of his takeaway lessons from “Become a Friendlier Person”:

7. Be a good listener. Encourage others to talk about themselves.

8. Talk in terms of the other person’s interest.

9. Make the other person feel important — and do so sincerely.

Rather than elevating one, such counsel, which is consistent with the advice Carnegie gives throughout the book, tends to put other people on an equal footing, a common ground where communication can meaningfully take place. At the same time, by reorienting the energy of personal persuasion — from an inward underscoring of one’s own preeminence to the outward assertion of another’s importance — it has the effect of habituating one to the kind of personal modesty necessary for an honest accounting of another person’s opinions.

The Reverend Peale, who name-checks Dale Carnegie in The Power of Positive Thinking and clearly believed his own work to be a helpful addendum to his teaching, picks up on this point when he describes a young man who carried about him “a notable attitude of superiority.” Superficially speaking, Peale says, he was a handsome individual — “splendidly proportioned and impressive” — but he nonetheless had an abiding problem with “personal relationships.” As the young man summed up his predicament, “People just don’t like me, and what is more, I am aware of it.”

Peale notes that it didn’t take very long to determine the problem. “The young man was decidedly self-centered and egotistical,” he says. “The person he really liked was himself. Every statement, every attitude was unconsciously measured in terms of how it reacted on himself. We had to teach him to love other people and to forget himself, which was of course a complete reversal of his development.”

The idea that forgetting oneself might be essential to becoming a more likable individual and, therein, a more persuasive person works in two ways. On the one hand, every human interaction is an implicit negotiation, and when one cannot forget himself, he has the tendency to push aside the concerns of another to make ample room for his own. In addition to affording an interlocutor nothing in the way of encouragement, such exchanges tend to be exhausting. Indeed, as a communications guru for the Trump campaign once described the matter, “[t]here’s nothing more tedious than a person who takes himself so seriously.”

The remark comes in You Are the Message: Getting What You Want by Being Who You Are, a 1988 book by the defrocked former chairman of Fox News, Roger Ailes, who signed on in summer of 2016 to coach Candidate Trump through debate prep, just as he had done for Ronald Reagan nearly 30 years before. Spotting such self-obsessed people, Ailes contends, is really quite easy, for “they are either brooding or talking a great deal about themselves.” These behavioral tics function like a toxic feedback loop, both consequent to and productive of a kind of professional “intensity” which overweights the relative importance of one’s work. Together they make for the irritating dinner guest who spends an entire evening anatomizing the nothings of an uneventful Tuesday, distancing himself from everyone else at the table for reasons that remain a mystery to him. Such people simply “cannot understand why everybody around them doesn’t take them and their job as seriously as they do,” Ailes says. They are blind before the “reality” that

[N]obody cares as much as you do. Others may pretend they do. They may nod knowingly and look intent and compliment you, but running around behind their eyeballs is the feeling that “this guy is wearing me out. He is so intense about what he is doing. And he thinks it’s so important that if he stops, the world stops.”

(Or, in the celestial pretensions of Shakespeare’s Caesar, the stars fail to circuit.)

No doubt, being a determined bore is socially disadvantageous, but in respect to being a persuasive person, it is not the only or even the most malignant consequence of the inability to forget yourself and focus on others. The greater detriment is a kind of ontological inflexibility. By never bothering to accommodate others, you become a rigid projection of your own gross self-estimation.

Trump actually prescribes such behavior in Think BIG and Kick Ass. “People take their cues from you as to how they should think about you,” he writes. “Develop an attitude that you are worth a lot, and others will value you. Walk briskly and purposefully, eyes looking straight ahead, like someone who knows where he or she is going. Define yourself in a big way.”

Notably, such advice runs directly counter to that given by Ailes. “Many traditional how-to books advise you to stride into a room and forcefully take charge, purposefully invading others’ space and asserting your personality in an attempt to dazzle and impress,” he says near the very beginning of You Are the Message. “They instruct you to greet others by using viselike ‘power hand-shakes.’ They tell you to rivet your eyes on the other person as if you were a hypnotist.” Such advice will not only “drive everyone else crazy,” it will turn the devoted pupil a little batty, too. More importantly, the counsel is entirely counterproductive. The key to being a persuasive person, and the stated aim of Ailes’s book, is to develop a well-honed ability to “analyze or ‘absorb’ the moods, feelings, and hidden agendas” of others, which is to say, to cultivate a heightened capacity for empathy.

Empathy plays two important roles with respect to one’s persuasive power. On the one hand, understanding the internal incentives of others is crucial to cutting deals in business, politics, or any other profession. The reason for this is the simple but so often overlooked fact that the mark of a savvy dealmaker is not the ability to strike a deal, per se, but to do so on advantageous terms. If I offer you $1,000 to seal a bargain when $100 will do, I may achieve my aim, but no one would say that I’ve mastered the art of the deal. Giving away too much is a danger in any negotiation where one of the participants is blinkered by self-obsession. If I only know my own immediate needs, I have no idea what you’re willing to concede for me to realize them, and I’m left to negotiate blindly. And while it is true that the act of empathy doesn’t literally permit one to peer into the minds of others, a knack for it allows one to better divine the sentimental factors that shape another person’s decision-making.

For Trump, such a blind spot has limited his deal-making abilities with members of Congress, especially when combined with his meager understanding of legislative gamesmanship, the larger designs of GOP grandees, or even the broad strokes of most public policy initiatives, even those he nominally champions. On a few occasions, President Trump has pursued the only approach he understands instinctively — “we used to have a bully pulpit,” the presidential historian Jon Meacham has lamented, “now we just have a bully in the pulpit” — but the high-pressure tactics have not only failed to convince recalcitrant lawmakers to sign on to bills, in some cases, they have backfired spectacularly.

Thankfully, for Congressional Republicans, President Trump seems have no strong beliefs one way or another about most major pieces of legislation, leaving him with a role in the policy-making process akin to that of 1930s-era Louisiana Governor Oscar "Okay" Allen, who was installed by Huey Long when he was elected to the United States Senate. The Kingfish intended to retain control of the legislative deal flow in Baton Rouge while he was in Washington, and Allen was the type of guy who “so agreeable,” he said, “when a leaf blew onto his desk one morning, he signed it.” Trump gives every appearance of being pliant, a quality that may allow legislative deals to get done but makes him like the fancy pens they’re signed with: a gilded accessory to the goings-on, essential, perhaps, but also irrelevant.

Still, it is a second way in which empathy plays a central role in one’s persuasive power that makes for the more remarkable defect in Trump’s deal-making skills, his utter lack of versatility. For Ailes, the liabilities of an inflexible personality are a preoccupation of You Are the Message. “Many people, particularly business executives, freeze their faces regardless of the emotional state they are in,” he writes. “They believe a poker face is a strategic advantage. Sometimes it is. But often you only gain complete credibility with an audience when you are completely open and not masking anything from them.”

The persuasive shortcomings of the fixed-face approach are twofold. On a superficial level, as Alec Baldwin’s devastating send-up of Donald Trump has made clear time and again over the last two years, there is nothing inviting about someone whose face gives the appearance that he’s waging a failing battle to keep from passing gas. “Stiffness or woodenness in use of body” — which Ailes counts among the most common problems in communication — suggests neither personal warmth nor inner confidence. Peale makes a similar observation in his own book (“Be homey,” he advises), but he suggests that the failure to be “easy-going and natural” not only makes one a less-attractive individual, it also creates a communications “barrier that others can’t get over.” The barrier is less a matter of unprepossessing conduct than what it indicates about individual’s receptivity to the world around him. While human interaction shouldn’t necessarily aspire to a sustained engagement with a mirror image, any normal exchange between two people has a tidal surge of emotions that ebb and flow from one person to the other. When someone’s behavior never changes, no matter the circumstances, it not only suggests that he isn’t receptive to the changing world around him but that he has no awareness of the sensitivities or concerns of another, especially those who, fairly speaking, should move him.

The observation helps to underscore the immense strain, empathically speaking, a president is under during his time in office. Franklin Delano Roosevelt and Ronald Reagan both remarked on the theatrical requirements of the American presidency, but it would be a mistake to see them as suggesting that a successful president requires no deeper dramatic talents than the ham actor in a spiritual dumb show. Almost every day a president is called upon to participate in a nearly unfathomable range of ceremonies that call upon the widest array of emotions: tackling barbed criticisms from the opposing party, welcoming high school students to a White House ceremony, defending drone strikes a half a world away, taping a breezy interlude for a late-night talk show, interviewing applicants for a judicial vacancy, firing up the faithful at a political fundraiser, sending best wishes for yet another holiday, comforting the grief-stricken survivors of a mass shooting — the list goes on. It is not only absurd, but absurdly long, requiring an emotional versatility, and the behavior to go along with it, that would challenge even the most gifted character actor.

Donald Trump is no doubt a character, but he is certainly not a character actor. Set aside moments when he is gleefully inappropriate, the president seems flummoxed by how to act in any situation unrequited by the papier-mâché machismo of a “kick ass” attitude. Much of the time, he blindly barrels ahead, and whether it is offering a grieving Gold Star parent a $25,000 check or shoving aside the prime minister of Montenegro or threatening to pull Neil Gorsuch’s arm free from its socket, nothing better examples the single gear of Trump’s behavior than when he shoe-horns the drama of an immediate moment into some superlative exchange of strange aggressiveness.

In addition to the tendency of such displays to distance the president from others, including those he might like to persuade, the discomfort often seems to be shared by Trump, himself, whose occasional moments of self-awareness seem less like lucid bouts of Pauline revelation than the flickering of a pilot light. Something is wrong, clearly wrong, but the president has no idea what it is, much less how to deal with it.

The evidence of such discomfort is not lost of those in the press who cover Trump and, thus, spend an inordinate amount of time in his presence. In November, New York Magazine’s Washington correspondent Olivia Nuzzi tweeted out after a White House event that it was the only time in her experience that President Trump “genuinely appeared at ease as president,” tweeting, again, just an hour and a half later: “Cannot stress enough how odd it was to see Trump taking to a presidential ceremony naturally.”

The ceremony in question? The turkey pardon.


For anyone who has trudged through Donald Trump’s literary catalog before he became president, such inflexibility is entirely predictable. Instead of encouraging the accommodating spirit whose worst offense is unctuousness, Trump has made a career out of giving the appearance of being strong, of not giving an inch — “I pride myself on being obstinate, stubborn, and tough” — and yet that commitment has kept him from ever cultivating the essential talent required for friendship, empathy, and politics alike: meeting another halfway. This involves a versatile soul rather than a shallow commitment to immobility.

In many respects, the contemporary approach to power and persuasion — one whose wisdom Shakespeare memorably encapsulated: “Your gentleness shall force / More than your force move us to gentleness” — is the inverse of the precept that “it is better to be feared than loved.” And yet, Machiavelli’s famous dictum has a proviso that is often overlooked: “If one must choose between them.” It is an essential insight of the work of Carnegie, Peale, Ailes, and others that, in the modern world, would-be leaders must aspire to be loved, as credible threats consistent with being feared are socially unacceptable and intimate a spirit of lawlessness.

The choice was otherwise for Machiavelli’s Prince just as it is for authoritarian leaders like Kim Jong-un or Vladimir Putin. Indeed, fear is far better suited to the unanimity a strongman requires than the dexterity that commends a democratically elected leader. We’re lucky that such a choice is not available to President Trump — not yet, at least. He longs to be strong, but for now, he’s merely stiff.


John Paul Rollert teaches classes in leadership, ethics, and politics at Harvard and The University of Chicago. His work has been featured in Harper’sThe Atlantic, the New Republic, theParis Review, and The New York Times. He also writes the “In-House Ethicist,” a featured column for the Chicago Booth Review.

LARB Contributor

John Paul Rollert teaches classes in leadership, ethics, and politics at Harvard and The University of Chicago. His work has been featured in Harper’s, The Atlantic, the New Republic, the Paris Review, and The New York Times. He also writes the “In-House Ethicist,” a featured column for the Chicago Booth Review.


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