Perhaps one of President Donald Trump's most endearing qualities to his supporters – a trait he promoted throughout a contentious 2016 election campaign – is that he isn't a lifelong politician.

He's a businessman. A salesman. A brander. He was the patriarch of the Trump Organization real estate empire before trading his iconic Manhattan tower for a seat in the Oval Office. And he sold himself to the American people on the idea that he could better streamline the bloated Washington bureaucracy – draining the swamp and running the country with a business-like efficiency.

But after six months rife with high-level turnover, legislative hiccups and public feuds within Trump's own team, questions have been raised as to how effectively the CEO in chief is guiding the ship.

"In general, the CEO skill set has a lot of applicability to running a large political organization. I think [former New York Mayor Michael] Bloomberg epitomizes how that could go well," says Maurice Schweitzer, a management and operations professor at the University of Pennsylvania's Wharton School of Business. "Running New York is enormously complicated, and you need to think about a large organization chart. There are a lot of things to execute. You need to stay at a high level and not get lost in the weeds."

Schweitzer says those challenges aren't exclusive to New York and hold true for the presidency. But Trump isn't Bloomberg. And he isn't Amazon's Jeff Bezos, Facebook's Mark Zuckerberg or Apple's Tim Cook. Trump successfully presided over a private real estate empire where he called the shots without needing to appease shareholders or a board of directors. Though his bankruptcy filings generated buzz publicly, his company didn't need to disclose financial information to nearly the same degree as publicly traded enterprises.

"What is different about Donald Trump is that a lot of the value that he created has to do with branding. It's a little bit more like the Kardashians, where they've created a brand. People want the Trump Tower or the Trump Casino or the Trump Resort," Schweitzer says. "And I think the Trump brand without that media [presence] would have very little value. So he's unusual as a CEO in that a lot of the value he created was around building a brand."

That branding ability proved to be a huge asset during his presidential campaign, as Schweitzer recalls Trump's ability to get his soundbites out in spite of what was often negative press coverage. 'Little Marco,' 'Lyin' Ted' and 'Crooked Hillary' stuck while attacks from his opponents often failed to stick to Teflon Don.

"As a candidate – ‘We’re going to win, we’re going to get tired of winning’ – this sort of hype was something he was very effective at," Schweitzer says. "He has a knack for criticizing people who he doesn’t like. ... When you have an adversary or a few adversaries, he’s really into that."

But some analysts believe Trump's branding background doesn't necessarily lend itself to deftly steering the executive branch of the U.S. government.

"Trump was more someone who built a brand than someone who ran a business. ... Getting elected is a different skill set than running the White House, and I'm not sure we've seen that transition yet from building a brand to now governing," says Lindred Greer, an associate professor at Stanford Graduate School of Business. "You can look at objective outcome indicators, and that's one way to assess the White House right now – looking at laws passed and the stability of the team. And all of those indicators right now are a little iffy."

Greer first points to the composition of Trump's Cabinet on which he notably installed wealthy and experienced private sector allies for key administrative positions in an attempt to streamline federal governance. Former Goldman Sachs President Gary Cohn directs Trump's National Economic Council. Goldman Sachs and CIT Group alum Steven Mnuchin heads the Treasury Department. Billionaires Wilbur Ross and Betsy DeVos lead the Commerce and Education departments, respectively. During a June speech in Iowa, Trump justified his decision to recruit wealthy folks from the private sector into his Cabinet, saying he "love[s] all people, rich or poor. But in those particular positions, I just don't want a poor person."

Greer notes this kind of homogeneous leadership is often closed off to new and varied perspectives. It's something she says business leaders often try to mitigate to receive a broader range of input.

"When you're choosing the right team, you want diversity. You want different ideas," she says. "It's the richest team we've ever had in the White House. There's not a lot of racial diversity. And those are both real issues in America right now."

Meanwhile, Hal Gregersen, executive director of the MIT Leadership Center, says the White House amounts to "one of the biggest bubbles on earth" regardless of who's in charge. For this reason, he says, "systematic, day-to-day efforts" are necessary to push the administration out of its comfort zone to identify what former Defense Secretary Donald Rumsfeld once coined as "unknown unknowns." It's something he says successful executives wrestle with daily.

"Frankly, I could care less what president it is, at some level. Presidencies are defined by the unexpected. And the only way to be ready for the unexpected is to have a deeply committed set of diverse people who are willing to step up to a problem with candid honesty," Gregersen says, noting that a Cabinet's objective should be less about "propping up a leader" and more about "solving a problem" and "seeking the truth."

Arguments can be made about the degree to which those around Trump are actively seeking truth, but Schweitzer notes stability hasn't been a hallmark of the Trump administration to this point. The abrupt resignations of White House Press Secretary Sean Spicer, Chief of Staff Reince Priebus and Communications Director Anthony Scaramucci in recent weeks simply served as more departures for an administration that already ousted FBI Director James Comey and suffered several other high-profile resignations.

"Everything that's happened in the last few weeks, it's just incredible. But attacking [Attorney General] Jeff Sessions has been one of the most unbelievable pieces to it, because it's such a bad political calculus," Schweitzer says. "Spicer or the Mooch, other people might sort of come and go that also looks bad, but the conflict with Jeff Sessions is really a bad calculation. When you get Democrats lining up to say, 'Don't fire Jeff Sessions,' it's a funny place that we've arrived at."

Indeed, Greer notes "we haven’t seen a lot of backing up of people when they’re trusted to work on their own." She says this sort of behavior can be demoralizing to teams and isn't indicative of healthy delegation practices.

Trump's tweets antagonizing Sessions – and, more broadly, his active presence on social media – also makes White House messaging tricky. Trump utilized social media to great success during the campaign, but Schweitzer says it's atypical for a CEO or a president to be as "public facing" as Trump has been in recent years.

"He’s used to sort of threatening people. And, in the process, he's creating enemies he doesn’t need to create. Attacking his attorney general has been a disaster," Schweitzer says.

Ironically, though, Schweitzer says Trump's habit of bashing others – particularly Democrats – may have helped ingratiate himself with the GOP base in the first place. He's conducted extensive research into trash talking and found that it can be motivational and unifying in some settings.

"Trash talking as a part of a group actually helps build a sense of team identity. As he keeps trashing the Democrats, that helps build a sort of sense of unity among Republicans. I think it’s actually been very helpful for him because he hasn’t been a lifelong Republican or a standard bearer of the Republican party," Schweitzer says. "But by attacking the Democrats, he’s really made himself part of the Republican Party and created a stronger sense of identity around the Republican Party."

He acknowledges, though, that this behavior can be "distracting" for colleagues and isn't always an asset. But Trump is still an atypical executive in that he has for decades been able to call his own shots and live without fear of being ousted by a board of directors. Distracting behavior could be punished in terms of profitability, but Trump's terms of employment as head of his own company weren't exactly in jeopardy under normal circumstances regardless of whether he chose to play nicely with others. It would still take a significant push from lawmakers to threaten Trump's current position, but he now has voters and Congress to answer to and is situated under significantly brighter lights.

Governing in a system with checks and balances, Greer says, is a different animal and has more parallels to leading a public company. She says CEOs of public enterprises have "a greater onus to learn leadership" than those who run their own companies without the need to answer to higher-ups. In the absence of appeasing shareholders and conducting "high-level interactions with board members," she says many private executives "haven't necessarily spent a lot of time learning the skill set of how to navigate with their peers."

"He's not used to developing long-term working relationships with many people, but particularly people he doesn't like at first blush. And that's different in politics," Schweitzer says. "He called McCain 'not a hero' early on during the campaign. And then he doubled-down and refused to apologize about it. And then he called him crusty more recently. And then it's a surprise perhaps only to Donald Trump when he calls McCain and says 'I personally need your vote for health care' and McCain sort of relishes the moment of sinking the vote."

Trump's ability to brand and market is unquestioned, and Schweitzer and Greer both note several skills and attributes CEOs could potentially utilize in the Oval Office.

But his corporate background and managerial style thus far, they said, have left something to be desired as the leader of the free world.