How Do You Manage an Out-of-Control, Self-Destructive Boss Like Donald Trump?

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As you may have noticed, Donald Trump has recently launched multiple tirades against Gonzalo Curiel, the judge overseeing the lawsuit against Trump’s exceedingly scammy-sounding Trump University. The presumptive GOP presidential nominee has repeatedly invoked Curiel’s Latino heritage as a reason for the judge’s ostensible bias against him, even calling the Indiana-born judge “Mexican” at first — the idea being that since Trump wants to build that giant wall down south, a Latino judge can’t give him a fair shake. (There’s no evidence Curiel has done anything improper or unusual in overseeing the lawsuit.)

These rather racist-sounding attacks, leveled against a highly respected judge who did some courageous, life-threatening work prosecuting cartel members, have not gone over well — just about everyone whose name isn’t “Donald Trump” thinks it was a mistake to go after Curiel the way he has. Remarkably, Bloomberg reported yesterday that in a conference call, Trump ordered his surrogates to double down on the attacks, even after his own campaign — apparently unbeknownst to Trump — sent out an email over the weekend instructing them not to address this issue to the media. “Take that order and throw it the hell out,” he snapped on the call, according to Bloomberg.

This is a big political story, but if you dig a bit deeper it’s also a management cautionary tale. Well, reverse-management, maybe: The key question here is how employees can control an out-of-control boss who consistently acts against his own — and his company’s (or campaign’s) — self-interest. What strategies can they adopt from the rather constrained position of trying to tweak the behavior of someone well above them on the organizational totem pole?

Trump isn’t the first boss to elicit these sorts of questions, of course — such managers are unfortunately common, and that’s why they pop up again and again in popular coverage of workplace and productivity issues. Take a 2014 article in Harvard Business Review called “Managing 3 Types of Bad Bosses,” written by leadership specialist and onetime CEO Vineet Nayar, in which one of the three species of bad boss is “The All-Knowing Leader.”

Nayar describes this species thusly:

Some executives think they know it all. They assume they are the smartest people in the room, feel they are the only ones interested in succeeding, and constantly tell stories about how they pulled off impossible things in the past. They also believe that without them, everything will fall apart. Such leaders aren’t incompetent, but you wish they would trust more, listen more, and be more inclusive.

With the possible exception of the “not incompetent” part, this is a perfect description of Trump: He is so positive that his ideas are the best ideas that he hasn’t really bothered to hire a full-blown campaign staff around him; he is constantly talking about the “great deals” he negotiated in the past and the even greater ones he’ll negotiate after he’s elected (Mexico will pay for that wall!); and he clearly holds his own business expertise in exceedingly high regard, and thinks it is the key that will unlock the doors to the White House for him.

So what do you do about a boss like this when that boss’s own worst tendencies are running the organization into the ground? Let’s examine Nayar’s three suggetions and gauge how realistic each one is for Trump’s embattled staffers.

Nayar writes: Allow your boss to discover your ideas. Omniscient leaders will challenge you and mire your ideas in discussions about the pros and cons if you present them as prescriptions. However, they love spotting great ideas themselves. Try presenting your ideas as if they are half-baked, or as though you’re unsure of their efficacy and need to hone them. That will ensure immediate buy-in by your supervisor, and rapid decisions.”

Hypothetically, there are situations in which this could work on Trump, but the problem is that once he discovers an idea that he likes and which he feels resonates with the crowds at his oftentimes-kinetic rallies, he tends to latch onto it. In an open-ended discussion about a campaign issue that hasn’t yet been decided, maybe it would be possible to plant the seed of an idea in Trump’s head, almost Inception-style, and then help him “discover” it, but there’s no version of this that would work to get him to back down from his most terrible ideas.

And that’s probably one of the primary challenges of reverse-managing Trump at the moment: He often makes key decisions without input from anyone else, digs in quickly and deeply, and then takes any criticism of those ideas quite personally. If you’re a Trump staffer, you can’t really incept your way out of the magical Mexican mega-wall or the Curiel criticisms. In fact, you’d probably feel too scared and cowed to even bring those subjects up at all.

Nayar writes: Channel the boss’s energy. All-knowing executives like to be engaged with something new all the time. Once they have a new idea to play with, employees will get the time and the space to do their job. The trick, though, is to create productive areas of diversion, so the organization benefits from the boss’s energy.”

There’s what feels like an element of Trump-truth here — Trump does have a certain ADD-ish tendency to jump from thing to thing a bit wildly, even during short snippets of a single speech. But overall, this advice is probably a no-go for his staffers. Their boss doesn’t quite fit the mold of the all-knowing executive here, since he doesn’t seem to be particularly interested in keeping himself busy in quite the sense Nayar describes. Heck, Trump’s campaign has even indicated that he sees himself more as a chairman of the board than a CEO or COO, that he intends to outsource the day-to-day job of running the country to his vice-president.

Trump seems more to flit from idiosyncratic obsession to idiosyncratic obsession than to keep himself busy with a steady stream of new ideas and campaign initiatives. If one of his campaign staffers brought him a new idea in the hopes that Trump would latch onto it, in other words, it just doesn’t seem very likely that Trump would take the bait, that he would be interested in that idea at all unless it had to do with, say, Judge Gonzalo Curiel and how corrupt he is.

Nayar writes: Enable the boss to experience reality. Some years ago, I recall, HCL’s country manager in France was convinced that the company should double its investment in that market. He presented his arguments to his boss every which way he could, but they fell on deaf ears, so he finally quit. His successor, who had been briefed on the situation, smartly invited his boss over to France to help him get started.

When the boss landed in Paris, he found that he had a full calendar for three days. As he visited companies and spoke to executives, he experienced the opportunities in France first-hand. The country manager asked him for nothing, but eventually, the boss extended his visit, drew up an investment plan for France that significantly upped investments, and sent me his recommendations before he flew back from Paris. I still remember the subject line in his email: ‘Urgent & Immediate Action Recommended.’”

I’d argue that while this approach isn’t perfect, it’s Trump staffers’ best — if not only — hope. Now, in certain senses, Trump is proudly anti-reality: in addition to regularly saying and repeating stuff that is plainly false, he has stated that he doesn’t really care about, or pay attention, to advanced analytics or many of the other forms of information modern campaigns use to win.

But there’s one form of reality that might resonate with Trump: threats to his own reputation, and to his own quest for power. These threats are the only things he seems to really care about or respond to, in fact. While his responses have usually come in the form of lashing out at those who question him, maybe — maybe — a skilled-enough staffer could take his hand and guide him gently toward the reality that the stuff he says and does on the campaign trail might be hurting his reputation, that he’s at a point where he needs to be liked not only by the core fans who propelled him to his victory in the GOP primary, but by a much larger swath of the country.

It could go something like this: You’re great, Mr. Trump. And a lot of people know you’re great. But some people are still on the fence, and if we want to put you in the White House, we need to convince them of that fact. And at the moment — here the adviser picks up the remote and flips through channel after channel of less-than-glowing coverage of Trump’s antics — I think our campaign is giving a bit too much ammunition to those newsroom hacks who want to keep you down. Potential Trump voters watch CNN, unfortunately — they shouldn’t, but they do. Let’s figure out a way to not make it so easy for people to bash you unfairly. You’re such a great, dynamic speaker that you can control what they say about you if we just tweak things a teensy little bit.

Would it work? Eh, I wouldn’t bet on it. But the Trump campaign seems to be running out of other options.

How to Manage a Self-Destructive, Trump-like Boss