His style is to check every invoice, examine every light fixture. That will have to end, pronto.
He has entrusted his operations to a tight, tiny circle of executives, a handful at most. That circle will expand, greatly.
He has always demanded round-the-clock work and total availability from his staff. That will fit right in.
He has always bristled — and often lashed out — when staffers push back against his decisions. That could damage his presidency.
The people who have worked most closely with Donald Trump say he will bring a distinctly different style of management and leadership to the White House.
He reads little and rules by his gut. He picks people by first impressions, sometimes without even talking to them. He is laser-focused on how he is perceived and what people say about him.
“Donald has to make a huge transition from Trump World to the United States of America,” said Louise Sunshine, the first executive Trump hired when he started out in the real estate business. Sunshine, Trump’s closest sidekick from 1971 to 1987, said her former boss “has to put his own needs aside — his needs for approval and acknowledgment, his inclination to use social media. He has to graduate to a huger universe. It’s going to be challenging, but he will do it.”
To govern a nation of 320 million people, Trump will have to absorb enormous amounts of information about issues he has never confronted and controversies that blow up in moments. His former executives say that’s something he does well.
“He is a quick study,” said Barbara Res, who spent 18 years as Trump’s top construction executive. “You don’t have to give him a long story. He picks it right up.”
But the Washington bureaucracy and Congress will have to get accustomed to a president who can’t stand long meetings and has little patience for complexity, according to Trump’s aides through the years.
“He’ll have someone read the reports for him and give them to him orally, real short,” Res said. “He brags that he’s never read a book all the way through. He doesn’t have the patience to sit in meetings. We always had a hard time keeping his attention during the prep for a deposition or something like that. The flip side is that he can scan something and get it quickly.”
“The guy doesn’t read,” said Jack O’Donnell, who served as president of the Trump Plaza Hotel & Casino in Atlantic City at the height of Trump’s casino empire in the late 1980s. “He reacts to what he sees and hears in the moment; he is a poor listener.”
To correct for those qualities, O’Donnell said, Trump learned to delegate much of his work and give managers broad authority. But those who have worked with him say that Trump’s delegating requires extreme loyalty, and if anything goes amiss, the boss will explode.
“He gets frustrated and impatient,” said Sunshine, who said she thinks Trump will quickly adapt to the vast size and scope of the federal government. “But he is relentless. When Donald puts his eye on a goal, there’s no distracting him.”
By Trump’s own account, he “took my eye off the ball” in the 1990s, when his casino empire in Atlantic City suffered through six corporate bankruptcies. At the time, he blamed his executives for the failures, which led some of his closest aides to lose faith in him.
Trump describes his leadership style as acting as an “army of one” — relying mainly on his own judgment. In his book “Think Like a Billionaire,” he called himself a “screamer” who doesn’t hesitate to berate associates.
That will be nothing new in the Oval Office, where Bill Clinton, for example, was often heard venting at aides who had disappointed him.
But Trump will follow four consecutive presidents who took considerable pride in the depth of their understanding of policy details. President Obama has joked that he knows many areas of policy better than his aides do. President George W. Bush, who had an MBA from Harvard Business School, instituted firm top-down controls and insisted on crisp, clear lines of authority. He ran tight meetings and used his vice president, Richard B. Cheney, as a chief operating officer. President Clinton was so detail-oriented that he often engaged aides in lengthy debates that they said felt more like seminars than decision meetings.
Trump, in contrast, “rarely followed a schedule and never prepared for meetings,” Res said. “When you brought him an issue, you had to tell him how great he was and how his way was right. But if you could get him to think your idea was really his idea, then you could usually get what you wanted.”
Several of Trump’s former executives said staffers knew that the last person to talk to the boss about an issue would usually get what he or she wanted. That trait was so reliable that at least one executive, who asked not to be named because he still advises Trump, said he would camp out in Trump’s office in the final hours ahead of key deadlines, making certain that his would be the last word the boss heard before making his decision.
Trump has never claimed to be interested in deep levels of detail. In “Think Like a Billionaire,” he wrote that when he’s making big decisions, “I try to step back and remember my first shallow reaction. The day I realized it can be smart to be shallow was, for me, a deep experience.” In the same book, he wrote that narcissism “can be a useful quality. . . . A narcissist does not hear the naysayers. At the Trump Organization, I listen to people, but my vision is my own.”
In service of his vision, Trump will outwork even the most industrious young staffer. “He will work longer hours than any president simply because he doesn’t sleep,” O’Donnell said. “The White House staff is going to have a different kind of guy. They will see him wandering around at 3 or 4 in the morning, because that is what he does.”
“There was no down time for them,” Sunshine said. “No down time. It was always go, go, go.”
As Trump’s first executive, when he was first breaking away from his father to develop real estate in Manhattan, Sunshine would spend days bombing around the island with the boss in his black limousine, scouting properties.
“When Donald is on a mission, when his eye is on the ball, when he has a clear-cut goal, he gets there,” she said. “Donald is extremely brilliant, and he doesn’t take any bullsh--. He gives out a lot of it, but he doesn’t take it. He sees right through it, so he does not respect people who are disloyal or who try to get at him publicly. He doesn’t like that at all.”
Trump enforced loyalty by requiring top employees to sign non-disclosure agreements that limited their ability to talk about their work. “Loyalty was prized,” said Randal Pinkett, who won the 2005 season of Trump’s reality TV show, “The Apprentice,” and then oversaw the renovation of Trump’s casino properties in Atlantic City. “People who do well there are people who are willing to follow his lead and remain loyal to him.”
Those who do, tend to stay. Trump’s inner circle has long included people who have worked for him for three or four decades. His chief financial officer, Allen Weisselberg, originally worked for the president-elect’s father, Fred, and has been with the Trump family for almost 40 years. Weisselberg is the man Trump’s closest aides point to as the consummate Trump executive: Good at his work, secretive, press-shy, fiercely loyal, expert at managing the boss.
“I’m sure Donald will keep some of his own people around him,” Sunshine said. “Loyalty matters, and Donald is accustomed to working with just four people around him.”
Although Res and Sunshine disagree on how well Trump will adapt to the White House — Res says it will be a hard pivot; Sunshine thinks her former boss will figure it out on the fly — they agree he is likely to surround himself with a hard-charging staff with mostly women in charge.
“He totally believed that women work harder and are stronger,” Res said. “He called them ‘killers,’ and that’s his highest compliment. And he didn’t feel like he had to compete with them because he was a man and we were women.”
Trump also likes to hire people who have opposed or blocked him. “Donald would hire lawyers who opposed him on certain projects just so they couldn’t oppose him on the next one,” Res said. “He’d say, ‘Keep your enemies close.’ ” Such hires weren’t just put on ice; several became important figures in Trump projects.
Trump sometimes brings aboard people who he thinks just look the part. In 1981, he saw a security guard at the U.S. Open tennis championships who did a nice job of ejecting some hecklers. Trump asked Res to hire the man. “But you’ve never even met him!” she protested. Trump said he liked how the man handled the situation.
That security guard, Matthew Calamari, has worked for Trump for 35 years and is now chief operating officer of Trump Properties. (His son, Matthew Calamari Jr., started with Trump five years ago as a security guard and is now the Trump Organization’s director of surveillance.)
Ultimately, however, Trump’s former executives say he confides only in his adult children, and especially his older daughter. “He doesn’t have friends he can totally trust,” Res said. “He trusts Ivanka.”
In the public imagination, courtesy of Trump’s catchphrase on “The Apprentice,” the new president will summarily fire staffers who displease him. But in reality, although Trump did not hesitate to sack people he considered disloyal or incompetent, he did not do so cavalierly, former aides said. They said he would be sensitive to public reaction to a president who suffered rapid turnover in his senior staff.
Trump has also used the threat of lawsuits as a cudgel against those who block his way or criticize him in public; that’s an avenue he won’t have as president, though he has said he wants to dilute First Amendment protections of free speech.
“He will probably find he can’t do nearly as much in Washington as he thinks,” said Dave Shiflett, co-author of Trump’s book “The America We Deserve,” which was published to set up a possible presidential campaign in 2000. “He wants to drain the swamp, but he is going to find there is a lot of quicksand in the swamp. A lot of people in his party don’t like him, and a lot of Democrats don’t like him. He paid a price for running that kind of campaign.”
The new president will have to decide whether to maintain his fiery, divisive campaign rhetoric or work more quietly to cut deals, said Leon Panetta, President Clinton’s chief of staff and defense secretary. Trump could “create a real crisis” if he tries to build a wall and deport all illegal immigrants, Panetta said, or the 45th president could turn to the more conciliatory approach he described in his victory speech Wednesday morning.
Trump “is not a Republican, and he is not a Democrat,” Panetta said. “He really does have the opportunity to create an interesting coalition if he wants to take the time to do it.”
Michael Kranish and Frances Stead Sellers contributed to this report.