The Management Mind: Lessons Distilled From our Glorious Leaders

Andrew Jaye
12 min readApr 1, 2020

Over the last few years while listening to our nation’s chief executive and clenching the business end of a Sharpie pen, I’ve often felt the crazed logic, shameless lying, ‘everything is going better than expected’ (and then I have to fire you) had a familiar ring to it.

Where have I heard this cluelessness mixed in with pomposity along with a healthy dose of self-interest before?

Let me think …

Oh, I know! I’ve experienced many Trump-like personalities during my long tour of duty in the business world. These life forms are clustered in the management classes and in other fauna roaming around the executive suite. I’ve even added my own contribution to the management wild-life literature in another Medium piece, which is a micro-memoir of my time in the tech world.

I was very pleased to see that at least one wise-beyond-her years younger employee of tech-dystopia completely gets it as well. A big thank you to Anna Wiener and Uncanny Valley, a memoir of her two years working for start-ups in San Francisco and observing the childish grandiosity of Silicon Valley executives. And for teaching the next generation about the ways of our paymasters.

Trump (and his family and pals) are all too familiar to me. Satan bless him, but he’s an exaggerated version of the many project managers, department heads, vice-presidents, directors, and CEOs, I’ve had the misfortune of having struggled under at various leading companies and dare-to-be-great startups.

To see it all concentrated in a single person fills one with profound dread. Or to paraphrase from Robert Oppenheimer (himself quoting from the Bhagavad Gita) after witnessing the first atomic bomb explosion, “I have become management, destroyer of employees.”

However, I am on occasion an optimist, and I think documenting how Trump reflects the rampaging id of the business mind may be helpful to some.

Appearances Matter

Trump is really focused on physical appearance, which is, sadly, important in the biz world. It’s just that he says the quiet part out loud. Well, it’s not as if we didn’t know this was true.

It’s no accident that managers all seem to look a certain way — a generic popular kid appearance along with matching persona. It’s a job requirement, but which is smartened up with biz-speak — a “hiring by design” policy or so-and-so fits our “corporate culture”.

It’s more than just physical appearance. You also have to convey a kind of B-movie level “command presence” — with a strong emphasis on acting the part. It is very much a performance and biz meetings are the stage where the soap opera is played out.

Hmmm, women at the Trump Organization seem to have a ‘je ne sais quois’. (Source: NY Times)

As we move up the the hierarchy, senior managers and directors look and sound more like airline pilots or army captains from one of those 1950s war movies. And in Silicon Valley and the start-up world, where it’s all upside down, they have to be teenile but with the temper and craziness of a young Caligula or Steve Jobs.

I’ve seen less women in management roles, but they’ve learned their parts as well. With Annete Benning’s performance in Grifters as the template from which they’re molded.

Managers want to be the center of attention and so surround themselves with those who are designed to attract attention as well. It’s the high-school lunchroom all over again with everyone segregated into their tribes at their respective tables — nerds, jocks, rich kids, creatives, the A/V team, bad kids, etc.

Generally I would classify managers as a combination of jocks, boasting rich kids, with a little bit of school gangsta’ mixed in.

So Trump likes to be around biz-looking types: Mnuchin with those sharpy heavy-framed glasses, Tillerson as Rock Hudson, Flynn as Robert Stack, John Bolton as Wilfred Brimley, Ivanka as a generic blond actress playing the part of a mysterious insider, etc.

Some of the people who Trump-olini ultimately fired had real experience and business chops. But they ran straight into the “fake it till you make it” prime directive of the Trump-verse, and in other parts of the corporate netherworlds.

It’s instructive at this point to watch this interview or read this one with casino executive Jack O’Donnell, who tried to run Trump’s Taj Mahal in Atlantic City. It resonated with me and echoes countless bizarre exchanges I’ve had with the business elite. Anna Wiener’s experiences in San Francisco also tell a similar story of empty suits and C-suite nihilism. It instantly sent chills and nauseas through me.

It directly follows that if you’re mid-level manager or working-stiff employee with even modest integrity who even barely suggests the boss is running with diminished CPU cycles then you’re pretty much toast.

As someone once told me, your job as a staffer is to make your manager look good. I learned that lesson a little late in my career, but that’s probably the best job advice I’ve ever received.

For the working stiffs who want to keep their jobs, they’ll have to struggle with the reality distortion field of these managers. And that’s a polite way of saying they lie. A lot. I mean they really, really lie.

They Lie About Even Small Things

Managers and other snake-oil consultants in hoodies are the great pretenders. In dealing with the underlings and other lesser life forms, thought, they are forced to face differing opinions and pesky facts that contradict what their narrow belief system tell them.

They respond in the only way their species knows how: which is lie, deny, make up stories to validate their lie, lie about the stories they made up.

It’s interesting from purely a research perspective into psychopathology to watch Trump say things like “Many people tell me that I’m right …”. He always has a fake alibi for the actions he takes involving his imaginary friends. Or he’s able to coerce people into saying what he wants to hear. And then if it doesn’t work out, he’ll find a real person to blame and fire!

I’ve watched managers lie about even small things that can be easily checked. Usually, it’s something like, “I asked you to do it this way, and you didn’t so I’m disappointed”. You know it was just the opposite of what he or she said, and it’s right there in the email or everyone heard her say it in a meeting in front of the entire group. It doesn’t matter: they’ll claim you misunderstood or deny it happened or just ignore and then shun you if you persist.

Michael Cohen: “We were going to lie for him on something.” (Source: NY Times)

In tech-istan, managers are more prone to lying using software gadgetry: silly and wrong-headed PowerPoint presentations and spreadsheets, or they boldly display their innumeracy in various other frightening ways, but always involving the latest app. It’s basically the nerds’ computer- can’t-be-wrong philosophy, which they believe older non-technical generation just doesn’t get.

Great combo example of C-level innumeracy and the boss is always right!

Thankfully, the VennPage website has some great examples of charts that validate what I’ve seen in the wild— graphs that say nothing or are incredibly misleading.

I’ve been in way too many meetings where a chart is used to sugar coat outrageous lies. Unfortunately, Excel has made it easier than ever to spew out mirror opposites of reality with cherry picked data. Managers who pride themselves on their presentation skills use charts and graphs as a magicians hat, trying to distract and put one over on the rubes.

High-tech lying, done with charts. (Source: VennPage)

These lies are just what upper management wants to hear and which ultimately makes its way to CEOs, who can then sprinkle it on gullible investors. It’s one giant Ponzi scheme based on lies dressed in scatter plots, regressions, and other “graphical” pornography.

Lying is the exoskeleton secreted to protect against the world as we know it — facts which they reject when it contradicts their money making schemes and job security. It’s a distortion field that you don’t want to be surrounded by for any extended period of time — it is soul destroying.

Might as well say it, but there are some eery parallels between Trump and Steve Jobs. Of course, Jobs ended up delivering the goods, even though he was an epic liar and rage-aholic, whereas Trump was all that as well but his real skill was getting in and out of bankruptcy and inspecting beauty contestants.

Doesn’t take much insight to see there’s a black hole of insecurities at the center of these mole people that has to be fed a continuing stream of even more outrageous factoids and wilder stories. No surprise there’s also alcohol and drug abuse right below the surface or sometimes pretty much out in the open — paging Larry Kudlow. I’ve witnessed barely concealed substance abuse problems in the management classes in various companies I’ve been associated with.

Trump and his cronies are not an anomaly! They very much reflect our poisoned work environment where it’s all about getting away with it and taking the money. Listen closely to the interview with Jack O’Donnell: his observations are pretty much what the average worker has to deal with on a daily basis and which is the stuff of job and career advice columns and books.

This is your leader. He knows the truth! (From an episode of a 1950s TV show “Trackdown” about a Trump-like con man, named Trump, who swindles a town.)

These are insecure cult leaders who are more interested in keeping loyal employers as followers and in maintaining their bloated salaries. In fact, former members of Trumps inner circle, such as bag man Lev Parnas, even refer to the Trump gang using the c-world.

Anna Wiener in her book also has a revealing story about her boyfriend getting fired for asking for more money and title change at the “analytics company” they both worked. During a company meeting where the decision was “explained” by the nutso CEO, it seemed as if her boyfriend had been ex-communicated. The CEO also, in cult-fashion, asked his lieutenants whether they disagreed, and to no one’s surprise, they all uniformly approved of his wisdom.

Wiener also began to question the incredibly young CEO’s overall smarts and started seeing through his fake-it-till-you-make-it smokescreen. I might add there’s more than a pinch of Dunning-Kruger in the recipe with this CEO (and lots of other managers I’ve listened to), who in between their lies are man-splaining in overdrive, convinced of their superior knowledge.

Their Loyalty vs. Our Jobs

Not to beat a dead horse, but the management classes are made up of self-serving low-rent con artists who are convinced they can get away with it.

To pull it off, though, they need to have at least some people who know what they’re doing. Even in the Trump crime family, I mean, organization, there are above-board accountants, attorneys, and executives who keep things running somewhat.

But they’re working alongside Michael Cohen, Lev Parnas, Don Jr, and Ivanka. And obviously that group is up to no good.

So what the Trump family does is test people to see how far they’d bend their ethics.This is phrased differently in the Trump-verse. You’re not bending ethics, instead you’re being “loyal”. If you read the accounts of Michael Cohen and other former Trump ‘goodfellas’, they all describe a similar corporate culture: loyalty was prized above all else. You accept the cult and do whatever the cult leader asks and you’ll be rewarded.

It’s revealing to read how one does business with the Trump organization. This NY Times piece on a Malaysian developer trying to get the Trump brand name on a hotel he was planning explains the process.

You first meet with the kids and then Mr. Trump, but details of the deal are then worked out by non-family professionals. These folks who have not proven their complete loyalty are never going to make obscene amounts of moolah for doing as little real work as say a loyalist lawyer like Michael Cohen, who was, cough, earning between $400-$500K for being Trump’s goon. On the other hand, they won’t have to worry about going to jail.

Example of staff from the 1950s doing all the real work Good job, Baxter.

The untrustworthy employees do the work, get shouted at over minor things, and end up leaving when they’ve had enough or stay on to pay the mortgage and put their kids through college.

This flawed piece about Trump that appeared in The Guardian — for the record, Roger Stone is not a reliable source — encapsulates many of the in-over-their-head managers I’ve battled. Trump is described as a “big picture” guy, which is a euphemism for he doesn’t know WTF he’s doing. I’ve worked for a lot of “big picture” managers.

But Trump also counter-intuitively micromanages — which is another way of saying he’s on the offensive to humiliate employees who have quickly realized this guy is pathetic. Trump, like many managers, has to keep ’em down.

I completely related to the Trump executive in the Guardian article who received a late night call from the boss regarding a used Coke bottle that was spotted in front of one of the hotels. I’ve also watched clueless managers panic over what they’ve gotten themselves into and then had to look managerial by tormenting their underlings.

That explains strange Twilight-zone worthy weekend or off-hour emails and calls about trivial, besides the point things that managers have suddenly found to be critical— “We need to add a bullet point to the first slide in the deck”, “Not what I had in mind — please redo based on my [off the wall] comments” and most alarming, “ I need to learn more about …” because the manager was asked a question they know bupkes about, and they’re going to copy my answer and take credit!

It’s not anything you’ve done wrong when you’ve performed exceptionally in the last year, only to be passed up for a promotion or raise by a team mate who consistently and robotically heaps Pence-like praise on whatever hare-brained ideas your boss announced during the last soul-nullifying 3-hour team meeting — that usually starts at 9:00 AM sharp on Mondays. Since you’re not loyal — willing to accept and repeat lies — in the dysfunctional organization you work at, they’ll be an impenetrable ceiling in salary, title, and perks that you’ll never get beyond.

And the Glorious Leader Always Knows More

You may have noticed that Trump and your manager occasionally seem to know a few things. It’s hard to accept — long agonizing sigh — but every so often they have minor insights into whatever.

Having always played the part of the informed but cantankerous staff member who’s a go-to person for all kinds of non-obvious facts, I’ve learned the hard way how this strange management phenomena of being occasionally right arises.

I’ve had many long, banging-head-against-the-wall talks with management about some problem of the day. I thought I wasn’t getting through or that, more sinister, my ideas were being openly minimized. Well, I wasn’t getting through, but they’re weasels and they were able to process just a teeny amount of truth from me. And I was being minimized. Intentionally minimized.

He’d make a great CEO for an American company.

This would repeat again and again, as I was making the same savvy points. Over time, the managers were able to incorporate an idea or sentence or two of mine into their rusty circuits.

And then, out of nowhere, at a meeting, I would hear something I said weeks or months ago. Word for word!

What genius! What brilliant insights. Everyone at the meeting loved it. You may even get a small indirect mention from Glorious Leader.

As a staffer who has to deal with Trumpy managers, you’ll have to accept that your ideas, projects, and initiatives will have to come out of their mouths. Then it becomes a real thing. Before that— even though it’s true and wonderful — it doesn’t exist.

Sure, you’re minimized. But managers are just smart enough to keep capable staffers around to blame but never to acknowledge they’re right. Dr. Fauci, Trump’s health expert, is finding this out as his warnings about CV ultimately get parroted by Trump, who now truly believes he’s a medical pioneer

What do we the workers of the world get out of this relationship?

We get to keep our jobs with the uplifting knowledge we’re working for a combination of Jesus, JP Morgan, and Jonas Salk.

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Andrew Jaye

Former privacy and data security blogger. Part-time workplace sociologist. Opinions are for better or worse his own. More about me at metaphorly.com.