How to deal with jerks
Instead of fleeing or punishing them, you can usually change them.
Some people are frustrating to work with; for the sake of this article, let’s call them jerks. But you’ll never find a role without jerks, so it’s probably worth figuring out how to work with them! Fortunately, figuring out how to work with them will also make them less jerky.
The Jerk Zoo
I doubt you need my help identifying jerks, but for the sake of example here are some of the stories I hear a lot:
The teammate who criticizes every little thing you do
The teammate who lashes out whenever you give a suggestion1
The manager who gives unactionable feedback, or worse, zero feedback
The PM who pushes you to add a new feature without giving you more time
The cross-team collaborator who’s spending all their time on some other project
This list could go on for pages, but I don’t think anyone would read that article2. Sometimes these folks frustrate you with their words, and sometimes with their silence or inaction. What they have in common is that, if you found a new job and discovered that they would be your teammate, you would be less likely to take that job.3
A hidden path
Let me make a few wild guesses about your typical plan when confronted with a new jerk. You try to figure out how to get around them. You dream of getting them fired, but as a realist, you resign yourself to avoiding them. You pick projects that don’t involve them, or change teams, or change companies.
There’s a chance that these are your best options, and I’ll talk about them more under The fallback plan below. But I have good news: there’s another path, hidden in the underbrush, that works a majority of the time. It doesn’t require you to abandon your favorite project, or your teammates, or go through the hassle of another job search.
Instead, you can usually transmute your jerk, alchemy-like, into a non-jerk. Here’s how.
Step 1: Safety
Some bad news first: you will need to have an awkward, uncomfortable conversation with your jerk4 in order to transmute them.
It’s tempting to assume that this conversation will necessarily devolve into a shouting match. So let me assure you that this will only happen if you let it. There’s a kind way to say absolutely anything, even the sharpest critique.
They, too, will go into this conversation expecting the worst: that you’re trying to change their mind or get them fired5. So you need to unambiguously and repeatedly state your intentions to the contrary.
Good: I’m trying to understand your point of view.
Bad: I’m trying to make you less of a jerk, because Simon apparently thinks that’s possible6.
Good: I want to figure out how we can work together more smoothly, and move this project forward in a way we both support.
Bad: I want to beat you in a debate!
Try to anticipate some of the things they might suspect of you, and promise not to do those things.
I’m not trying to trick you into a contradiction.
I’m not trying to change your mind.
I’m not trying to get you fired.
Finally, given all these disclaimers, ask their permission to ask a bunch of questions. They will probably say yes, begrudgingly and/or reluctantly.
Step 2: Curiosity
People always have a reason for doing the things they do. You probably have a few assumptions about this person’s reasoning, but those assumptions are mostly wrong. So the next step is to understand where they’re coming from, and why they do the things they do and think the things they think.
What are their incentives? Who determines whether they get a raise or promotion, and how does that choice get made? Is there some obscure metric by which the entirety of their performance is assessed? Have they staked their credibility on one particular feature they promised to vendors?
What are their limitations and bottlenecks? Budget? Headcount? Personal time?
What is their history? Have they been burned by people like you in other companies? Do they associate your design philosophy with some failed project in their past?
Is the feeling mutual? Do they think you are the real jerk, or are they totally oblivious to the tension between you? How would they characterize your relationship?
Try to make it feel like a casual conversation and not an interrogation. Repeat the disclaimers from Step 1 as needed. Hedge your questions:
“I was wondering why…”
“I’m curious whether…”
“I’m beginning to wonder if…”
“I have the vague impression that…”
Whenever they say anything that feels true or relatable to you, tell them that emphatically, since this will encourage them to say more. But at this early stage, resist the temptation to attack the things they say; most of your sentences should end with a question mark. Rhetorical questions (“Do you really think that’s true?”) don’t count as questions!
Next, invite your jerk to be curious about you, in turn. Look at those questions above, and answer them about yourself. Be forthright in your answers; don’t hold back just because you think it will give them the wrong impression of you. When you think you’re likely to be misinterpreted, just admit that and clarify. It’s fine, I promise, and it gives them space to do the same. Invite them to dig deeper and ask follow-up questions; it’s normal for this to take a significant amount of back and forth until you’re on the same page.
What you’re doing here is filling up a Pool of Shared Meaning7: the set of pre-existing “opinions, feelings, theories, and experiences about the topic at hand.” You don’t need to agree with their weird opinions and biases, but you do need to know what they are, and they need to know what yours are.
You know you’re ready for the next step when you can both authentically say “I see where you’re coming from, but the two things we each want are incompatible.” This second clause is the biggest incorrect assumption of all! If you can get on the same page as another person, you can almost surely find a solution that gives both of you (most of) what you want8. It’s time to find that hidden third option.
Step 3: Consensus
People are complex, and their actions emerge from a wide, deeply-nested tree of root causes. So it’s statistically unlikely that there’s some fundamental or foundational difference between the two of you, because the space of all such trees is so vast. Once you understand one another, and trust that you are acting in good faith, you can frequently find an outcome that both of you will be OK with.
What that solution looks like depends on the nature of conflict between the two of you. If you disagree about how to implement some shared project, maybe you can figure out the part of the project that each of you care the most about, and favor the preferences of that person in that corner of the project. If it’s just a matter of rubbing each other the wrong way in meetings, find some tiny behavior modifications that are easy to make, but have a huge impact on how much the other person is bothered.
The fallback plan
The above strategies will usually work. In fact, you’re not allowed to read the rest of this section until you’ve tried them! I’m serious, scroll up, I’ll know if you don’t.
But sometimes, folks will prove intransigent despite your best efforts. Maybe they refuse to even engage with you. Maybe your backgrounds are too different to find common ground. Maybe they refuse to believe any third option exists. In this case, your only remaining options are escalate or avoid.
Escalate
There’s a chance a lot of people are struggling to work with this person, but if none of them have reported it to company leadership, there’s not much to be done. Talk to your manager, and/or their manager, so that they can spot a pattern if one exists.
If the person you’d escalate to is part of the problem, you should go up a level. Most managers-of-managers are quite interested in hearing feedback about their reports. But if you go through a couple levels of this, that implies that a significant part of the company is incompatible with your working style. At some point, it is reasonable to give up and fall back to avoidance of the whole gosh-darn company! Speaking of which…
Avoid
This was probably your default choice anyways, so I almost hesitate to mention it. But it is a valid choice, in many situations. Be mindful of the cost, which tends to scale depending on how close you are to the person:
If you can get expenses approved by your friend in Finance, it’ll probably be pretty easy to avoid some other person in Finance.
If they’re a cross-team collaborator, you can try to avoid projects that touch that team’s domain. This is likely to slow your career progress, but career progress is worth less than happiness.
If they’re on your team, you’d probably need to transfer to another team, which requires time and high performance (or a fervent ally elsewhere in the org).
If they’re your manager, avoiding them probably means leaving the company, since they would likely need to approve any transfer.
It was a trap
You’d know this if you’d read the footnotes: I was lying when I said you could transmute someone. However, you can transmute yourself into a person who can be productive and happy alongside most jerks, and also maybe stop thinking of them as jerks, just like we did halfway through this article. And, to be sure, your bitter and frustrated feelings towards them are absolutely valid! But you can only control your own actions; thankfully, that is enough.
More than coding, more than writing, more than testing; this one weird trick will drastically unlock the number of engineering roles that you can be happy with. Since you’ll have to learn it sooner or later, you might as well learn it today.9
Sometimes this second one appears in response to the first one!
Maybe they would read it, but they’d also be miserable at the end of it. Just like Reddit!
You can get drips and drabs of this information from the people around the jerk, and that’s a good idea if you have the time and social capital. But by far the best resource is the jerk themselves.
I suppose this is assuming that they are already aware of the tension between you. If you know they don’t, lucky you! You get to skip to Step 2.
OK so technically you’re not quite transforming them into a non-jerk, it’s really more like you’re both changing in subtle ways that affect your shared… look, just go back and read the rest of the article, I promise it will make sense.
Actually this whole book, Crucial Conversations, is a solid resource on this whole topic. Don’t look at the cover or read about the authors; it’s a gaggle of rich white businessmen. But I promise the book is very good!
I’m sure you have a counter-example. Yell at me in the comments, please; I’m a glutton for disagreement.
I swear I really tried to find a good Taylor Swift quote for this article, but she said all of her enemies started out as friends so I’m not sure how well she’d relate to this one.
One of the things I try to remind folks is that interactions are dyadic; a jerk to you may not be a jerk for someone else. So I generally refer out to jerks (while being clear with the new person that my interaction wasn't awesome, so that they can opt-out if they choose).
Generally, people are coming to me for advice. So if, after a meeting, I feel like there is a personality clash, I tend to refer them on to others (with the caveat). The entire framework suggests: stop talking to Idiot/Assholes, refer out Genius/Assholes, give Idiot/Awesome homework.