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Difference between dealing with asshole boss and higher-up

I don't know if I am not mixing up definitions but I see boss as someone directly above you and I use higher up in this meaning as someone above you but not directly.

So for example boss is my team lead and higher-up in this context is team lead of another team.
How power protecting and cautious should I be to him compared to my boss?

For example you need to be very calibrated and power protecting when boss is being an asshole or does not respect your boundaries.
But if the higher-up that is not directly responsible for your future an asshole, he likes to disempower people and hates when you compete and win with him ( even for the smallest things, like tennis ). How much should you care about that?
Are the rules the same as with your boss or as with your colleague? Or is it in between. Should you be less afraid of setting your boundaries, or because he is at the same level as your boss you should be as cautious.
When thinking about future, boss and the CEO matter the most in promoting, but other leaders may have a word or two on how they see this and this person because the company is small.

Contact with him is very limited so it may be even possible to just be disempowered a little and avoid him mostly.
Or is the better situation to show that you are an equal who will not be disrespected easily, as his opinion is not worth the disempowerment?

What would be your way to deal with people like that?

Because context is important, I am a mid level employee that has opinion of getting shit done without complaining, also I am the only full time programmer on one specific project that is semi-important for my lead and a tool everyone uses in another team. I have some contact with everyone in the company yet there is nothing in my work that is truly irreplaceable and my disappearance would at most likely a month or two of delay.

Lucio Buffalmano has reacted to this post.
Lucio Buffalmano

To me, higher-up and bosses in your definition are higher in the hierarchy. I think that what matters the most.

That means that they have the right to task you so they both have power over you.

They also have an influence on your reputation and career.

So I would take care of both. Especially of the person just above you. If he feels you're trying to short-circuit him to get the guy above's favours he's going to resent you. Very important, your boss hired this guy so he trusts him at least at some point. And he has your boss's ears. So what he think of you if your boss asks him he's going to tell him. Hell, he does not even have to ask he can just tell him. I'm now a "middle manager": if I want to destroy someone's reputation I can do it. I just have to notice everything negative a subordinate does, every little error and sprinkle it over time. I can go with the old: "You should know that by now" which people did to me. It's nasty and low but I can do it. Of course I don't. However when we have difficult employees (not your situation), we talk about them together in the middle management and we report it to our bosses above. So what he thinks of you is very important.

So I think the challenge you're facing is actually the good ol': "how to deal with an asshole boss". My recommendation would be to take specific situations with your direct supervisor and write them here for analysis. That will help you to see patterns and come up with strategies. Right now you chose avoidance. Imagine what your direct supervisor would think of you if he feels you're avoiding him. Yeah, right.

My personal goal: I want this kind of person to like me. The strategy depends on the environment, personality, power and social dynamics, etc.

Roberto and Gguwad have reacted to this post.
RobertoGguwad

Interesting question.

It's difficult for me to make a general rule at this point because a lot depends on the environment and situation -you shared some helpful info, but give strong opinions without a specific situation-.

But, generally speaking, if the company is small enough for you to know the CEO, you're right that "random higher-ups matter less than direct boss and CEO".

But John is generally right: they do matter.

In some cases though the only power a random higher-up has over you it's "just" that he may be friends with your boss, or have more influence over him because of the same rank.
That can be a lot though.

But in some cases, if they have a poor reputation in the company and with the CEO and you have a good one, then you're good.

This reminded me of a story my father shared of when he was in the military (and that also told me he did was generally high power).

He was asking his direct boss for some days of leave, and instead of his boss, another officer who was present and known to be a bit of a meddling dick replied:

Random Officer: for me, carte blanche (= "for me, you can")

He had no authority to grant anything.
And my father replied something like:

Yeah, thanks, you're not my officer though (and then looked at his officer for the reply)

Later on his direct boss basically told him he was "right", but still exhorted him to be more easy going in voicing it.

Albeit technically a mistake, also because the other boss "approving" was great for him, it's still a funny story and the way my father shared it, it seemed like he actually gained respect from his direct superior.

Edit:
I asked my father out of curiosity, the meddling guy wasn't an officer at the same level of his boss, he was "just" one level above my father and with longer experience, and my father was reaching that same rank shortly. So in that sense it was even more befitting.

The way you speak, it seems like you're in a semi-solid position actually.
"Only a month or two" of delay can be quite a lot.

Plus, considering that learning this stuff is very valuable, my "based on little" opinion would be to lean more on "risking it" and re-empowering yourself if something happens.

 

John Freeman and Gguwad have reacted to this post.
John FreemanGguwad
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Thank you for insightful feedback!
Quote from Lucio Buffalmano on July 29, 2023, 4:42 pm

Albeit technically a mistake, also because the other boss "approving" was great for him, it's still a funny story and the way my father shared it, it seemed like he actually gained respect from his direct superior.

The way you speak, it seems like you're in a semi-solid position actually.
"Only a month or two" of delay can be quite a lot.

Plus, considering that learning this stuff is very valuable, my "based on little" opinion would be to lean more on "risking it" and re-empowering yourself if something happens.

Good to know that when higher up has bad reputation among people higher than you or your supervisor, it's a lot safer to protect your boundaries.

He may be disempowering later so I will be sure to defend with power protection.
Thankfully I managed to make it work with him, going tennis with him 1 on 1, get closer and work him, so much so that he told my peers later how well I am doing.

So it's always good to remember "make friends, not enemies" that is so often repeated in the course, I jumped quick on confrontational frame of mind but will make sure to remember this when dealing with a value taking higher up.

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Lucio BuffalmanoJohn Freeman
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