Exclusive: Donald Trump tells Yale’s Jeff Sonnenfeld why he should be President

September 16, 2015, 3:37 PM UTC
Donald Trump (center) with Jeffrey Sonnenfeld (left) and his Yale colleague Jacob Hacker (right) in Trump's office
Donald Trump (center) with Jeffrey Sonnenfeld (left) and his Yale colleague Jacob Hacker (right) in Trump's office
Photograph by Jonathan Weisberg—Yale School of Management

Donald Trump has said that he’s willing to buy advertising in his bid for the White House, but there seems to be no reason for him to do so. He’s both outpolling all his Republican rivals and generating far more free media coverage than all of the other presidential hopefuls combined.

Many argue that his entertainment value is all that bring out the crowds and the media coverage, but Trump wants to be appreciated for more than just his celebrity, bravado, and headline-grabbing put-downs of his rivals. He wants to be known for his qualifications—especially his skills as a business leader.

Candidate Trump gets a chance to showcase those skills in the upcoming Republican Presidential debate on Wednesday night. But before he appears in front of millions of viewers on CNN, I had a chance to visit him last week, along with my colleague colleague, Jacob Hacker, at his office in his namesake tower on Manhattan’s Fifth Avenue to find out what he’s bringing to the table. What followed was an engaging, blunt, and sometimes surprising interview with the Republican frontrunner:

“Donald Trump and Jeff Sonnenfeld Interview”
Listen to it here.

So what does one take away from our chat? As a business leader, what makes Trump stand out? Among the qualifications and strengths he laid out for me were:

  1. Problem framing and communication.
  2. Negotiation expertise—taking tough, informed positions and winning with them.
  3. Strategic clarity and focus in one’s mission.
  4. Metrics of accomplishment, money, participation, growth.
  5. Accountability and transparence.
  6. Plainspoken direct talk with vivid imagery.
  7. Spotting and developing talent for staffing and leadership development.
  8. Resilience and overcoming adversity.

Up close, Trump has a disarming personality with a surprisingly accessible style. This may sound like a paradox, but despite all his bravado and grandiosity, there is an authenticity about him I saw when I spoke with him in person. He clearly wants to make an impression on everybody, but he cares to know if it works. A truly arrogant person is not that attentive to the audience and does not have the requisite self-doubt to learn, listen, or grow. In private conversations, Trump is surprisingly open to criticism over positions—if always sensitive to personal slights or what he feels are malicious, cynical attempts to diminish his accomplishments and puncture his image.

Going to his office, you can feel his authenticity. Sure his name and photos are everywhere, but the energy and identification are palpable in Trump Tower. You can feel it in the building and see in the people that work with him that they’re all proud to be there. His staff carry themselves with a sense of mission, and Trump makes them all feel important.

It’s quite different than his persona when he hosted NBC’s The Apprentice, where he would sit frowning, lower lip protruding, with his trademark show-me attitude. That couldn’t be more different than how he comes across one-on-one. And now he’s struggling to shift his campaign message to transcend reality show antics and the vanity of a self-told saga.

Donald Trump clearly had many qualities of a politician even before declaring himself as a candidate. Despite his controversial and offensive insinuations about the character of illegal Mexican immigrants and various women, as well as his inelegant criticism of a genuine U.S. war hero such as John McCain, he is aware of the raw, natural, performance side of his discourse. This shocking and disarming candor as a candidate conveys an authenticity showing that you get to see how he thinks and not the way a staffer believes we should think about him. He is obviously not over-managed by platoons of public relations pros.

While many of his political positions are critiqued for not being solidly grounded in hard evidence, Trump is about to reveal his larger positions beyond global trade and immigration, and during a time of highly polarized political parties, his positions do not fit neatly into the narrow boxes of partisan clichés.

He is passionate about the damage being done to a disappearing middle class, with the U.S. tax structure a big part of the problem. “The middle class built this country, and we are destroying the middle class,” Trump says.

His plan to put H&R Block out of business is simply a figure of speech to show that tax filing should not be so complicated. He has indicated a startling progressive position on taxation of the ultrarich—cutting away from the conventional thinking of the Republican party regarding the carried interest classification as capital gains rather than ordinary income. At the same time, he calls inheritance taxes unfair death taxes. “I have seen families ruined because of the “death tax,” Trump says. He also believe the corporate income tax should be lowered to less than 20%—perhaps 15% or lower for stronger global positioning to halt tax inversions leading to the flight of U.S. corporate chartered firms abroad, as well as to stimulate the retention of the intellectual property base of our tech sectors.

Calling Karl Rove a “moron,” Trump despises the impact and influence of the Super Pacs. He thinks they’re ridiculous, and he’s right. It’s a myth or naivety, he says, to believe that deep-pocketed donors are not coordinating their public mission campaigns in the Super Pacs with candidates’ campaigns. Willing to consider ways to limit Congressional district gerrymandering and providing campaign finance vouchers, as recommended by Harvard law professor Larry Lessing, Trump has demanded transparency of all donors as essential to repairing the system of U.S. campaign finances.

As demonstrated by Michael Bloomberg, there are many advantages to entering public life as successful business leader which are beyond specific skills and the treasure chest of resources. There is also the image with which people seek to identify themselves of the wealthy and successful American tycoon. It’s a thread that Thorstein Veblen pointed out a century ago in The Theory of the Leisure Class that you can take up right through Robin Leach’s Lifestyles of the Rich and Famous.

There’s always been a fascination with those who succeed in this system. We don’t like people who cheat to get ahead, but if it’s a success story that combines honest hard work and a little innovation, the American public tends to admire it and wants to emulate it.

Another part of the reason why people are drawn to Trump is that he presents an image, not of a distant god-like business titan, but of someone who’s recovered from setbacks and who’s shown the sort of resilience and plucky spirit that American so deeply treasure in our own collective self-image.

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