• Home
  • Latest
  • Fortune 500
  • Finance
  • Tech
  • Leadership
  • Lifestyle
  • Rankings
  • Multimedia

Trendingnow

1

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year

2

Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'

3

Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 

1

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year

2

Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'

3

Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 
LeadershipDonald Trump

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

By
Jeffrey Sonnenfeld
Jeffrey Sonnenfeld
Down Arrow Button Icon
By
Jeffrey Sonnenfeld
Jeffrey Sonnenfeld
Down Arrow Button Icon
September 16, 2015, 11:37 AM ET
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 officePhotograph 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:

https://content.fortune.com/wp-content/uploads/2015/09/v2-edited-9-10-2015-donald-trump-and-jeff-sonnenfeld1.wav“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.

About the Author
By Jeffrey Sonnenfeld

Jeffrey Sonnenfeld is the Lester Crown Professor in Management Practice and Senior Associate Dean at Yale School of Management.

See full bioRight Arrow Button Icon

Latest in Leadership

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025

Most Popular

Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Finance
Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam
By Fortune Editors
October 20, 2025
Fortune Secondary Logo
Rankings
  • 100 Best Companies
  • Fortune 500
  • Global 500
  • Fortune 500 Europe
  • Most Powerful Women
  • World's Most Admired Companies
  • See All Rankings
  • Lists Calendar
Sections
  • Finance
  • Fortune Crypto
  • Features
  • Leadership
  • Health
  • Commentary
  • Success
  • Retail
  • Mpw
  • Tech
  • Lifestyle
  • CEO Initiative
  • Asia
  • Politics
  • Conferences
  • Europe
  • Newsletters
  • Personal Finance
  • Environment
  • Magazine
  • Education
Customer Support
  • Frequently Asked Questions
  • Customer Service Portal
  • Privacy Policy
  • Terms Of Use
  • Single Issues For Purchase
  • International Print
Commercial Services
  • Advertising
  • Fortune Brand Studio
  • Fortune Analytics
  • Fortune Conferences
  • Business Development
  • Group Subscriptions
About Us
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • About Us
  • Press Center
  • Work At Fortune
  • Terms And Conditions
  • Site Map
  • Facebook icon
  • Twitter icon
  • LinkedIn icon
  • Instagram icon
  • Pinterest icon

Latest in Leadership

Beyond the diploma: Skills that actually get graduates hired
Future of WorkWorkplace Innovation Summit
Beyond the diploma: Skills that actually get graduates hired
By Ashley LutzMay 22, 2026
5 hours ago
satya nadella
AITech
Microsoft reports are exposing AI’s real cost problem: Using the tech is more expensive than paying human employees
By Jake AngeloMay 22, 2026
5 hours ago
She grew Salesforce’s team by 600% in South Asia. Meet one of India’s most powerful women
NewslettersMPW Daily
She grew Salesforce’s team by 600% in South Asia. Meet one of India’s most powerful women
By Angelica AngMay 22, 2026
7 hours ago
Svenja Gudell, chief economist at Indeed
SuccessWorkplace Innovation Summit
Indeed chief economist says we’re entering an era of ‘great mismatch’ thanks to a generational imbalance of workers
By Emma BurleighMay 22, 2026
7 hours ago
Steve Wozniak
SuccessCareers
Apple’s Steve Wozniak says he cofounded the tech giant after 5 rejections from HP—not to ‘make money.’ For years, his paycheck was just $50
By Preston ForeMay 22, 2026
7 hours ago
A year in the life at HP: What matters to its sustainability lead in May 2026? 
EuropeHP
A year in the life at HP: What matters to its sustainability lead in May 2026? 
By Francesca CassidyMay 22, 2026
11 hours ago

Most Popular

Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year
Success
Jeff Bezos wants the bottom half of earners to pay zero income tax—he says nurses making just $75K should save $12K a year
By Preston ForeMay 21, 2026
1 day ago
Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'
Success
Despite a $500 million net worth, Shaq just finished his fourth degree. He warns graduates: 'Your character will take you further than your resume'
By Preston ForeMay 20, 2026
2 days ago
Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 
Workplace Culture
Bolt CEO says he let go of his entire HR team for creating problems that didn’t exist: ‘Those problems disappeared when I let them go’ 
By Preston ForeMay 19, 2026
3 days ago
Pay transparency is exposing a bigger problem: Most companies can't explain why they pay what they pay
Workplace Culture
Pay transparency is exposing a bigger problem: Most companies can't explain why they pay what they pay
By Sydney LakeMay 20, 2026
2 days ago
McKinsey partner says up to 50% of work hours could be transformed within the next 5 years
AI
McKinsey partner says up to 50% of work hours could be transformed within the next 5 years
By Emma BurleighMay 21, 2026
1 day ago
Current price of oil as of May 21, 2026
Personal Finance
Current price of oil as of May 21, 2026
By Joseph HostetlerMay 21, 2026
1 day ago

© 2026 Fortune Media IP Limited. All Rights Reserved. Use of this site constitutes acceptance of our Terms of Use and Privacy Policy | CA Notice at Collection and Privacy Notice | Do Not Sell/Share My Personal Information
FORTUNE is a trademark of Fortune Media IP Limited, registered in the U.S. and other countries. FORTUNE may receive compensation for some links to products and services on this website. Offers may be subject to change without notice.