How You Can Subvert a Trump-Like Boss

Big mean boss yelling at a worker

Surely everyone has worked for a jerk before, but I feel my travels through that universal experience contain an extra value. See, an executive that I worked for years ago (we’ll call her Jessica, not her real name) was extremely similar to current USA President and Wannabe Dictator Donald Trump. 

Their behaviors, their attitudes, their quirks, etc. were so similar that not only am I experiencing Trump’s current awfulness, I’m also enjoying some PTSD. Every time the latest Trump sleaze BS hits the news waves, I think, “I’m not surprised. He’s just like Jessica.” 

It’s not all pain, though. I remember how much I learned about stealthy resistance. I am certain that at this very moment, some in the federal government under Trump’s reign of babbling idiocy are exploiting the same flaws I and others exploited while working for Jessica, in order to do good work, and make the workplace something other than a living hell. 

I feel by sharing the tactics I and my allies used, we can not only provide the universal skill of dodging clown managers but also provide specific ideas for anyone in the federal government who isn’t yet resisting with ideas and tactics that they might be able to use. Let’s begin.

Awful Boss Stat Comparison

Like Trump, Jessica was from the New York area and embodied many of its worst stereotypes. She carried arrogance with a lack of skill to back it up. Her main tool was shocking rudeness and meanness. She felt her high-level position meant her commands were not to be questioned. She wanted respect without earning it. 

But don’t take my word for it. Here’s a brilliant script written by a pal (you know who you are!) who wanted to illustrate what it was like working for Jessica (and surely describes what it’s like working for Trump). 

JESSICA: (Points at a yellow object.) This is red.
WORKER: Okay, it’s red.
JESSICA: No, it’s blue.
WORKER: Okay, it’s blue.
JESSICA: No, it’s green.
WORKER: Okay, it’s green.
JESSICA: No, it’s red.
Repeat.

Also matching Trump, Jessica had no desire to learn or listen. She had no vision beyond expanding her own tiny empire. Leadership qualities like helping others thrive were non-existent.

When we underlings enforced company policies, requiring someone to change a work order. If that person was a friend of Jessica’s they would call her. She would override us and make an exception, effectively wasting our time and making us look like we didn’t know what we were doing.

Let’s just bullet point the other similarities…. 

  • We were often given tasks with no clear purpose
  • We were often busy to create the illusion of productivity
  • We were managed with erratic behavior, no clear objective, no forethought, no follow up
  • We were told to never apologize, no matter how small, obvious, and public the error

A strain of hallucinatory paranoia ran through her every decision. She seemed to truly believe others were spending all their time trying to make her look bad. Really, she was doing that just fine on her own.

Okay. I’ve made the case. She was very Trump-ish. Now on to the resistance tactics. 

Managing Your Manager

My immediate manager, thankfully a shield between myself and Jessica, taught me a concept: “Managing your manager.” I don’t know if it was her original idea or someone else’s. But it’s damn good career advice, even if your manager is decent. Know your manager. Know their tendencies and work with them.

Or around them. 

With Jessica, like Trump, because there was no reflection, no vision, no guiding principles, and no real ability, managing her – and even better, manipulating her – was easy. 

Small minds only think about things that affect them, what they see in front of them, and whatever fantasies they imagine. You can’t do much about that last one, but usually if they don’t see something, and no one reminds them, chances are good they will forget about it. They won’t touch it, address it, or try to bring it under their influence. Which means it will be safe to flourish instead of wither under the rot of their touch. 

Yes, a terrible manager has lots of bad ideas, but often you can just ignore them and they will never follow up. They never say, “How are we progressing with that pointless errand I told you to do yesterday?”  Always remember that. Be quiet, don’t bring up something and it likely won’t be brought up. 

Find Allies Who Will Provide “Air Cover”

You are not alone. There are others around you who agree that what is going on is unacceptable. Do your best to find them by noting eye movements (involuntarily eye rolls) and body language. While I was working for Jessica, it was easy to feel alone with thoughts of, “Is anyone else seeing this stupidity and/or corruption?”

Then a supervisor between us on the org chart implemented a program where we could work from home one day a week. He demanded it be kept secret and said frankly to his assembled team, “She (Jessica) cannot find out about this. If she does, the whole thing will go away.” He was leaving unsaid that he would get in a lot of trouble, too. He stuck his neck out in a smart calculated risk, improving morale despite Jessica’s best attempts to destroy it. The program lasted until my last day. I can only conclude she never found out.

Forcing Things on Record

Jessica was very hesitant to use email. Though I can’t know for sure, this was either because she would not admit she didn’t know how or she refused to learn anything new. Likely both. It’s also possible she knew she contradicted herself, but self-reflection was missing in her skillset. 

Only after repeated requests could anything be put to any sort of record. We often pushed for it so we could go back and say, “But you said this.” Obviously, this led to awkward moments where she couldn’t deny regularly going against what she had previously said.

We would be professionally persistent in demanding a record of assignments before such assignments began. We would express an interest in efficiency and preventing duplicate work and use other corporate buzzwords that even entry-level employees know are smart goals. We would write it up and ask, do we have this right? She would confirm and then she’d be locked in. Ha! Got ya! 

The Fall of Mediocrity 

Just to conclude this tale with its real-life happy ending. Eventually there were rumors that layoffs might be coming. My desk was close to the office of Jessica’s boss. She was summoned and left the door open. I could hear tense whispering. I couldn’t make out the words but I could tell Jessica was mad! That always made me smile.

The meeting was brief. Jessica bolted from the office and yelled back over our heads, something like, “I guess I’ll just take a vacation!” As far as I could tell, I was the only one who understood the reason for the outburst.

Because that’s when I was sure the layoffs were coming. It was just a question of when. The next day they hit gen-pop. There was a lot of crying and hugs and all that good stuff. I ended up being rehired at the same company with a better job and a far better manager. Jessica never returned.

How it All Ends

Despite all my dislike here, I would be lying if I didn’t say that toward the end, Jessica did seem to sort of maybe kind of perhaps get the idea that she was a jerk. There were some small but noticeable changes in her many bad behaviors. But it was far too little, far too late. 

In the end, true power had spoken. The invisible decision makers with their hands on the levers of cash flow had issued their rulings. 

I suspect that’s how the Trump era will end as well. The true power (the super-duper-wealthy invisible decision-makers behind even the visible billionaires) are going to say, “Okay, this little project is over. We’ve squeezed all the juice from this rotten, wrinkled orange we can get. The people are ready to riot. Let’s put all the blame on him before the people blame our system.” 

But who knows? 

In the meantime, manage your manager. Say yes, but do no.

Image with this article generated by Chat GPT AI with this prompt: a cartoon drawing. an overbearing manager stands over a worker at a computer terminal, screaming at the worker. the worker cowers in his seat


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