While Trump has never before had to pick a political partner, he has had plenty of practice sifting through resumes and hand-picking executives to help run his real estate empire. Four current and past senior managers at the Trump Organization who agreed to speak with CNN -- including the general managers of the Trump golf course in Los Angeles and the Trump International Hotel in New York -- shed light on how Trump deliberates over his corporate hires -- and what kind of qualities Trump likes in a No. 2.
"Many of the same qualities that he would look for for someone to work closely with him within his organization are going to apply to his search for a VP," said Jill Martin, vice president and assistant general counsel for the Trump Organization.
Martin and others describe a boss who demands deep loyalty, both to him and his franchise. He is drawn to conventional markers of prestige, such as Ivy League degrees or past employment at well-known firms. He can be somewhat of a micromanager, at times involved in even the minutiae of decorating decisions throughout his numerous properties. Despite exerting this level of control, he also takes to employees who push back and speak their minds -- as long as they remember he is ultimately the one in charge.
"He wants someone who can really stand up for what they believe in if you have a position or an idea. He wants you to fight for it," said Martin, who has worked for Trump for more than five years.
Selecting a running mate will be one of Trump's most significant decisions as a presidential candidate. It has the potential to help him clinch a swing state in November, quell concerns among establishment Republicans about his unconventional campaign, and, most of all, signal to the country what kind of person Trump believes is capable of serving as its commander-in-chief.
Trump's deliberations over his running mate have already spilled out into the public sphere, as both he and surrogates have hinted at who might be on the shortlist.
He has hired A.B. Culvahouse, a Washington attorney who vetted potential VP candidates for John McCain in 2008, to play the same role for him.
Trump has offered only a few clues as to what kind of person he is looking for. To balance out his lack of experience in public office, he has said he wants to choose someone "political" who can help with "governing."
Two months ahead of the GOP convention in Cleveland, Trump says he is reviewing a shortlist of about half a dozen potential vice presidential nominees.
One of his surrogates and former presidential rival, Ben Carson, appeared to spill the beans recently, telling The Washington Post
that among those on the list are John Kasich, Marco Rubio, and Ted Cruz. Trump later said few, if any, of those were actually being considered, and Carson backed off his remarks.
Trump is accustomed to making high-profile hires out in the open. On the popular NBC TV show, "The Apprentice," young and ambitious contestants competed for Trump's approval and a chance to work at the Trump Organization.
Kendra Todd was the winner of the third season of "The Apprentice." As a member of the "Book Smarts" team that defeated its "Street Smarts" rivals, Todd said she got a feel for the professional and personality traits Trump appears to value most in his top people.
Each episode of "The Apprentice" ended in a darkened boardroom. What viewers didn't see in those final moments on television, Todd said, was that often, Trump would debate for three to four hours before uttering the famous words: "You're fired." Even under the bright TV lights, Trump declined to make any decision related to his company lightly.
"He made sure that he made the right choice on who he fired," Todd said. "Despite what people think from his television persona, he takes the advice very, very seriously of the people who work for him ... He's very thoughtful in his decision-making process."
After winning the show, Todd was put in charge of overseeing the renovation and marketing of a mansion in Palm Beach. Todd, who now works as a real estate broker in Seattle, said she was surprised to learn how intimately involved Trump was in even the smallest details of his company's projects — down to the specific faucet fixtures in bathrooms and kitchens or stones that would be laid down on a patio.
Even as he delegates large projects to his senior executives, Todd said: "He gets the final stamp of approval even on details."
Suzie Mills has spent the bulk of her career in the hospitality industry at the Trump International Hotel. She joined the Trump Organization in 1996 and saw the opening of the Manhattan hotel that overlooks Central Park in early 1997. Promoted to general manager of the property nine years ago, Mills said Trump "doesn't take kindly to people that slack" and will choose a running mate not afraid to "give their honest opinions."
Giving her honest opinion is a regular part of Mills' job. When her hotel upgraded all of its televisions four years ago, Trump suggested to Mills that they install 55-inch TVs.
"I said well, Mr. Trump, 55-inch TV? That seems like a rather big TV," Mills recalled. "He goes: 'Suze. Trust me. Nobody is every going to complain about a large TV.' And of course, what do we get the most compliments of? Our fabulous big TVs. So he won that one."
Mills mused about Trump's VP pick: "He'll definitely want somebody with a strong personality."
If Trump is known for having exacting preferences, his top employees also say there's nothing that annoys Trump more than "yes men."
Lili Amini, general manager of Trump National Golf Club in Los Angeles who has worked for Trump for 11 years, said she has received some of the highest praise from Trump when she pushed back on her boss.
"That's one thing that people don't really know about him. He likes the fact that I'm not a yes man, per se," Amini said. "If somebody does disagree with him, he wants to know why and he may end up changing his mind."
Trump's employees and friends say loyalty will be an overwhelming factor in Trump's VP pick -- in the same way that it is at the Trump Organization.
His top three executives at the company are his children -- Ivanka, Donald Jr., and Eric -- but even they had to first earn Trump's trust.
"He wasn't just going to say, 'OK, congratulations, here's a billion dollar company,' and leave it with us, and hope that those people who have been so loyal to him for so many years are going to be OK," Donald Trump Jr. said at a CNN family town hall last month.
For most of the Republican primary, Trump has kept a small and insular political team around him. Until recently, the day-to-day operations of his campaign were largely run by his campaign manager, Corey Lewandowski, who is known for his fierce loyalty to his boss.
Trump's circle of political advisers and surrogates has gradually expanded and now includes strong personalities like New Jersey Gov. Chris Christie and former vice presidential nominee and Alaska Gov. Sarah Palin, both of whom are rumored to be on Trump's shortlist.
Calling Christie a "good guy," Trump said in November that there could "certainly be a place
" for the governor in his administration.
Chris Ruddy, Trump's longtime friend and editor in chief of Newsmax, said Trump knows better than anyone else just how much is riding on this decision.
"He knows the world will be looking and this as his big presidential decision," Ruddy said. "And he can't pick somebody that doesn't have gravitas and weight."