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I developed a bad case of perfectionism-procrastination after working for a toxic boss.

It didn't matter how polished our product was, he'd find a way to tear it apart. When he'd have a bad day, he'd start picking apart a random team's product. "Unbelievable!" he'd say in Slack, dropping a screen recording of the app that showed something we were supposed to be embarrassed about. It could be that the app took 3 seconds to load and show fresh data from his hotel WiFi, or it could be as simple as the UI not matching some directive he gave to the UI designers who failed to update the designs or tell us about the change. He would rant about how disappointing we were. At his worst, he fired some people on the spot for a problem that wasn't even their fault.

I quickly learned that the only way to avoid that pain was to not ship anything. The people he liked most were the ones who were operating in hypotheticals: The people who made UI designs in Figma, or the architects who drew nice diagrams about how things would work, or the people who wrote long design documents to hand to other teams. They never shipped anything for him to critique, so he thought they were the geniuses of the company. As long as they could avoid having to actually implement anything, they continued to be favorites.

It took me longer than I like to admit to shake that habit when I finally escaped. I found myself delaying shipment, pivoting from design doc to design doc, and trying to operate in that hypothetical space as long as I could. Fortunately I learned to get over it, but it was scary how much that single job could shape a large part of my personality.



You put into words something I've had a hard time understanding for a long time. Some people really do have a clear preference for people who don't ship.

Out of curiosity, what kind of background did your toxic boss have? Is it technical or business side?

I have a couple hunches for why this happens: 1. These people are dreamers and dislike people who bring them back down to reality, even if they need those people to actually build things.

2. They feel superior to people on the ground doing the building. Like they're above getting their hands dirty.


> 1. These people are dreamers and dislike people who bring them back down to reality, even if they need those people to actually build things.

I worked for a non-toxic-personality friendly boss of this type. Took me a long time to figure out how to manage upward in that case. Everything that had worked with previous "builder"-type bosses seemed to backfire and I wasn't sure why.

Because the personality was good it was especially frustrating. Deliver stuff on time without bugs or surprises, but still fail to change his mind about ambitious-yet-unrealistic goals, or put a dent in his confidence in (and preference for) the "idea people" feeding him similar goals in hypothetical-land. "But really, if you'd just build [vague idea], we'd be golden!"


These are possibilities but I think you missed a much more likely one -- they're just bullies who like to pick on people.


If they were just bullies, then there shouldn't be a preference for hypothetical UI and architecture folks.


Even bullies can be lazy in their metier - it's quicker and easier to find a tangible target for abuse in a finished product, and, perhaps more importantly, it doesn't risk an ego brusing when a critique of an abstract proves to be incorrect.

I've certainly seen my fair share of these types - too busy (ie. lazy) to really get stuck into detail during a project even when invited to do so, but very quick to point out an issue after a few minutes of expressly looking for one when it's too late.

They seem to see it as demonstrating their experience and superiority over others ie. "I only need a few minutes to find an issue". In my experiences, they also tend to insist on saying "everything needs to go through me", but never make time to follow through - out of laziness. This gives a high ROI on effort expended to stress created.

The best times I had with these people (when I was beyond caring) was laying low and doing launches semi covertly, so that there was time for clients to provide positive feedback and praise first. Then play dumb and deliver news about launch and feedback as a package.


Is this true? Are bullies indiscriminate and swing in all directions or do they focus on where the power dynamic benefits them? I feel like I've seen both.


I'd call that the difference between bullies and sociopaths.

At least to me, one of the defining bully characteristics is an inability to moderate their own behavior, even for their own benefit.


A sociopath can bully people though. In terms of words I don't think the distinction you're talking about is widely accepted.


That falls under the "feeling superior" bucket. And like others have said it doesn't explain bias towards certain people.


Yes it could. The boss seems to show strong tendencies of narcissism. Narcissists gather so called “flying monkeys” around them which fuel their sense of superiority and they bind them through various techniques to them (until they are also discarded). In this case the narcissist the PowerPoint-mockup people are these flying monkeys, feeding the narcissist all the grandiose ideas and it gives the narcissist a high for going towards that idea - similar how somebody just announcing they will do a hard task, e.g. stop smoking will make somebody feel good immediately before even reaching that goal.

Then, the people to whom the actual task of implementing it was left can’t deliver the grandiose perfectionist idea, and the narcissistic boss can and actually wants to fiercely abuse their power over them in order to feed on the high of superiority and control over them. It’s the perfect position for this kind of person, they can feel high all the time (eventually the tolerance will kick in and the boss must leave though but this can take some time).

Organization-wise it’s a bad boss really. It’s the job of the creatives to come up with great ideas, then the boss should moderate that working together with the feedback from the implementers. Instead the boss is due to personal weakness too suggestible against the creatives and puts the damage of his own making on to the team with bullying.


Thank you for bringing narcissism to the table and explaining the flying monkeys so well! Especially in this two staged process of designing and implementing it's easy to pick up the utopian ideas and see the realistic implementation and/or timetable on which one can blame the inperfect people not reaching the high (unreachable) goals.


This so accurately describes my own experience a couple years ago, down to the specific anecdotes, that I had to double check the username to make sure it wasn’t something I drunkenly wrote last night.


Not a toxic boss, but reading this is making me realize that I developed exactly this due to the trauma of being disabled by severe chronic fatigue, ADHD, and eventually worsening cognitive decline.

I used to enthusiastically throw myself into projects and other endeavors, but over the years, as it became impossible to think, focus, motivate myself... for nearly a decade, things have only been "possible" until I attempt them, find myself unable to, and end up crying in my bed for the five-thousandth time in my life.

To a point where even when I'm a bit better, I'm perpetually trapped in this "hypothetical space", never trying to do anything for real. Using my energy to dream about a better life and life goals in lieu of as much as lifting a finger to do any of them.


I have recognized at some point that I had something similar, but originating in my childhood. Most of the time I would be told to do something vague (e.g. clean your room), and no matter how much did I do, the feedback was usually negative (e.g. "You call this done?"), following with me getting grounded. Eventually, I've developed a mindset that told me that there's no point in trying, because it's impossible to do things properly. This has spread out into personal interests as well - I would give up quickly, because what's the point?


Aurornis really hit the nail on the head about how a toxic boss can twist your work habits into a loop of perfectionism and procrastination. It's wild how avoiding criticism can lead to playing it safe in the land of hypotheticals, instead of actually getting stuff done. And hats off to the_cat_kittles and neon_electro for recognizing the struggle and the learning curve that comes with such experiences.


Be proud of yourself for surviving that toxic environment and eventually recognizing and overcoming the negative effects it had on your own performance and behavior. You’re a survivor!


The introduction of Tacitus' Agricola is about survivorship, and it is not positive. "Few of us are left, survivors even of ourselves, with so many years of our lives gone missing." (translation from memory)


im still thinking about this because its so fundamental. it applies in almost everything. think about how many times people have called professional athletes stupid or bad. it happens all the time because the mistakes are unambiguous. but the coaches have a much longer grace period before people generally decide they are bad. when a musician messes up a piece everyone cringes and lots of people probably think that person is a failure even though they are playing at a level less than a tenth of one percent of people reach. in any discipline that can be (more or less) directly measured, lots of people perceive the people doing those disciplines to be more incompetent because their mistakes are more easily visible.

when someone who is like your old boss (i think a huge percentage of people are) finds themselves in a situation where their mistakes are unambiguous and obvious they panic and have an identity crisis. most people do not live with the accountability of their mistakes like people who make and do things with unambiguous results. it would be great if more people did, but in a way, thats the whole point of those "ideas" / bullshit jobs, to insulate you from your mistakes.


This is psychological abuse. Let’s start calling it what it is.

Corporations should start screening for personalities like this. They’re sick, and often seek out positions of power.


These stories are almost certainly describing leadership, possibly a Founder or a VP.

(Doesn't sound like a bad middle-manager that snuck in through the cat door. But I could be wrong!)


Your boss displayed the opposite behaviors most all the creativity literature says are barriers to creative expression: close-mindedness, evaluation, etc - that is, creating environments that have no psychological safety where people don’t feel comfortable expressing their ideas. Wild that this boss was involved with product development and crazy how people like this come into positions of power and just ruin shit left and right.


I love places like this because I can thrive quite happily on doing fuck all and getting paid for it.

Edit: I made some logical comment about doing something useful with half that time but deleted it because it would be hypocritical.


I’m sorry you had to go through this, and I’m glad you learned from it.


youve very succinctly explained an incredibly frustrating reality. it really helps to understand it clearly like that


Sounds awful. And I can guess exactly how that boss responded to any feedback or criticism directed in his direction!


Thanks for mentioning this in a work context. It describes one of my parents, with the results you'd expect.

Do you remember any of the thoughts or techniques you used to shake it?


You should write something in-depth about this. This is a really interesting take, and you seem like a great writer.


1. Use a issue tracker to report issues. If a ticket doesn't exist, create it.

2. Stick to the facts: what happened, and what should have happened instead? Remove all the noise such as blame, emotional reactions, etc. Less drama, more clarity.

3. If the root cause is something dumb such as the hotel WiFi, close the ticket as "can't reproduce" and add an explanation.

You can avoid reading the text, then use a LLM prompt such as: "Can you rephrase this removing all emotional reactions and extracting only the parts that relate to reproduction steps".

Do not waste energy on toxic people. You are not a therapist, an emotional support animal, a sandbag or a doormat. You are a software engineer.

Unless you are getting rich you should avoid working there.


Hmm, that is an interesting idea. I bet someone could write an app that rephrased incoming messages through an LLM to match some metric you chose. You'd definitely need the ability to read the original message and there's about a million and a half ways out could go wrong but it's interesting nonetheless. Just evaporate toxicity from all communications before they even reach your brain.


It seems like a good idea at first... but it also would mean everyone could communicate as toxically as they wanted with no consequences. Uh oh.


If you cross certain lines, toxic messages should be blocked and sent to HR for review.

Criticism is fine, when it is constructive and done with tact.


You have described a major problem with tech "leadership". They are incompetent and don't want to hear it.


Almost everyone, given the power to avoid it, would rather not hear they're incompetent.

Hence why telling truth to power, in a productive way that gets things done, is an important skill.


Lol, imagining some bored unhappy middle aged neckbeard go with "unbeliavable...."


Why bring age into something that has to do with a shitty personality? That could be at any age.




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