First, let's stipulate that, ideally, none of us should work for a jerk. Don't wittingly do it — full stop.
Nice idea. Sometimes, this is where we find ourselves: a jerk gets brought in by higher-ups, or we get reorganized, and despite our best efforts, a jerk now occupies that box above us, rules over our daily tasking, and spews mistrust, disrespect, or other venom into group culture and interactions. Let's also stipulate that, while a coup d'etat might be fully justified, it requires goodwill and solidarity with skip-level managers and beyond that might not be there. Overall, this jerk situation demands resourcefulness and quick action to avert misery. So, how can we prepare?
The martial art that I studied is one in which breaking some number of one-inch-thick pine boards is a part of testing for each new belt. They take it easy on you at first, starting with a front snap kick, where you put the ball of your foot through a board as it is being held by a black belt. At the next test, the black belt again holds a board as you break it with your knuckles, by throwing a punch. A logical and unthreatening progression so far. Everyone has to break the same one-inch boards, regardless of age or size. Two tests further along (for green belt), you hold your own board in your non-dominant hand, and they have you throw a knife-hand strike, where you put the pinky-finger edge of your dominant hand through the board. Everyone is terrified of this break, fearing both injury and failure.
When I first joined my martial art school, it was impossible not to notice a slight, spindly, 10-year old kid named Jay, who was in the higher-belt class (several belt levels ahead of me). Jay was always fiercely determined and focused during his workouts. His dad, Rob, often came to watch. One night, I was watching Jay's class when Rob sat down next to me, smiling, and said, "The doctors can't believe his progress. His lung capacity has increased by 75%." I asked what he meant. "Oh, Jay has cystic fibrosis." Jaw on floor.
As Jay took his green belt test, I and every attendee winced in sympathetic agony as he beat his scrawny little knife hand into that pine board, over and over again. He never broke the board (that day), and ended up with a bone bruise.
Outside of work, I was an instrumental musician, and it happened that the knife edge of my hand was quite bony, so I was afraid for its integrity. Between these personal circumstances, and Jay's experience, I was totally psyched out about this break. After my instructor told me I could test for green belt, over a period of weeks as the test day approached, I thought my way through the fear. It came down to requiring myself to make two decisions: that I could break that board, and that I wanted to, in that order. If I didn't decide first that I could break the board, there was no way that I would overcome my fear enough to want to do it. So, I committed to those two things repeatedly, daily, during those weeks. Nevertheless, I did not practice the break. (I wasn't that crazy.)
The day of my test, the moment came. I positioned the board on the fingertips of my left hand, lined up my strike along the woodgrain, visualized my hand going past the board, and wailed on it. I blinked just at the moment of impact, opening my eyes in time to see the two halves of the board tumbling to the floor. It felt like butter. The pain was so minimal — my fear so unwarranted — that I burst out in gales of laughter. (Seven black-belt judges simultaneously gave me stink eye; they were unamused by my amusement.)
If I think in terms of merely surviving jerk interactions, I will suffer, and most likely fail to improve the relationship. I think this can+want pair of decisions is equally applicable as a foundation for working for a jerk. With those decisions, I obtain a crucial mindset shift. What is the nature of it? I relinquish judgment as a primary thought process, and engage with what can be. We all know intuitively that judgment seeps out of us in subtle ways: the curl of a lip, the tone of a word or phrase. I err if I think that I can harbor a critical attitude toward anyone and have them not sense it. The longer I allow such an attitude in myself toward my boss, the more likely I am to make a mistake that cements an adversarial relationship. (I have made this mistake; I've seen it made by other talented individuals. It is all but impossible to come back from. If you screw yourself this way, I recommend you apologize immediately, and deliver a good idea along with your contrition. I waited too long.)
Having made this pair of decisions, and relinquished judgment, where am I propelled? Right next to the jerk, as a trusted advisor. I tell her things she cannot otherwise know; I ask him questions that no other person can ask. I ask more questions that point to conflicts within group dynamics — or poorly defined tasking — whatever is going to bite us in the collective ass. Asking a question lets him think he has found the answer. He begins to associate me with his success, and starts soliciting suggestions. This is a path toward success for me that can benefit everyone.
This mental process of deciding that I can do something, and that I want to, turns out to be very similar to a Stoic concept called amor fati, or "love fate." When you face a difficult situation, you can embrace it, and use it. You ask yourself not only "Can I endure this?," but "Who better than me to experience and learn from this?" This way, every adversity becomes a growth opportunity. This, to me, is one of the most powerful ideas of Stoicism: it makes every situation better, and is at the root of my being able to face my brother's illness. (See Entry #2.)
Now, let's say that making myself into my jerk's trusted advisor is not possible: I can't bring myself to do it, or don't have access to the jerk. I can pursue other adaptations.
Let's say I'm managing a project, and some director (or other higher-up jerk) requires a presentation of the final report. Knowing this person will be a jerk, I get everyone on my team together, and say, "Yes, Stan will be a jerk. That's his job, to some extent. We know he is rude; he will interrupt before we've finished our points. What questions or issues will he raise?" We think through every imaginable objection or uncertainty, come up with responses, and make final enhancements to our deliverables. I use this process to put everyone into a confident frame of mind; we know we are as prepared as can be. Even high-strung people are able to sleep the night before the presentation, and the presentation tends to go very well.
Blair Singer describes this same basic approach in his book, Sales Dogs. His teams use it to prepare for customer calls, but in the sales context, they are far more brutal. The whole team gets together and lambasts the presenter for hours with horrible personal insults and objections to their material, and the presenter must stand there and take it, until they can rise above it, and respond constructively.
These mental preparations are versions of another key practice that the Stoics refer to as premeditatio malorum: loosely, "imagine trouble." Nearly two-thousand years ago, beset by war, plague, and dire misfortune, these intellectual badasses figured out the coping methods:
When you wake up in the morning, tell yourself: The people I deal with today will be meddling, ungrateful, arrogant, dishonest, jealous, and surly.
— Marcus Aurelius
What is quite unlooked for is more crushing in its effect, and unexpectedness adds to the weight of a disaster. This is a reason for ensuring that nothing ever takes us by surprise. We should project our thoughts ahead of us at every turn and have in mind every possible eventuality instead of only the usual course of events...
Rehearse them in your mind: exile, torture, war, shipwreck. All the terms of our human lot should be before our eyes.
— Seneca
If they could persevere through plague and exile with these practices, I'm confident that we can withstand a jerk manager, and perhaps even guide her toward higher ground and better outcomes.
There's one more thing worth saying. I find it difficult in the moment not to judge critically someone who is being a jerk, but I try to take a breath, and remind myself that they are broken. Sometimes, that can help me shift my mindset to one of sympathy and open inquiry, to explore what they need, and believe they are not getting.
What approaches have you used to manage your problematic higher-ups?