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Trouble with boss, need help on how to handle

TLDR: I have been having problems with my boss wasting my time with meaningless assignments that don't have all the details necessary to complete. I also have problems with my boss telling me (every time I try to suggest proper planning) that "This is just the way things are". I have already gone to my boss's boss and we may have a meeting later today to discuss my boss and I's interactions, however, I'm not 100% sure about this.

Question: How can I get through to my boss instead of having them shoot down everything I say? How should I approach this meeting coming up?

The most extreme example:

I worked on 4 different assignments for 2 months. 2 of them ended up being completely ignored, one was given to me so late that I had to work overtime for a whole week.

When I realize that I haven't turned in anything for two whole months I tell my boss. I tell them that we could have avoided this waste if we had planned properly.

Boss's response: That's the way things are done around here.

Most recent example:

I've been working on an assignment for a month and its almost done. I go on vacation for a week and decisions are made while I'm gone. When I get back, everything I've done is trashed and I have to almost completely start over. I tell my boss that this could have been avoided with planning and asking the right questions. (Literally this whole waste of my time could have been avoided by asking a single person a yes-or-no-question). I tell them this.

I get the same response.

My boss goes on vacation for a week and a half while I work on this assignment. Before my boss leaves, I tell them this assignment is literally pointless (for those of you who know techy stuff, it is a web service that can be reduced to a couple SQL queries). Today, the first day my boss is back from vacation, we get into a disagreement about this latest assignment. Here is the conversation:

(TLDR of conversation: I tell my boss that this latest assignment can be scrapped and provide multiple pros to doing so. I ask for any counterpoints. Get told to just do the assignment)

BOSS 10:44 AM: hi

ME 10:51 AM: hello

BOSS 10:51 AM: what is the status on the webservices for the patch string?

ME 10:52 AM: Its never going to be as quick as it could be if it were a query especially for a product I am in the process of creating another entry point for the service to get just the patch string because it seems like thats all [other team] needs I still believe that this web service is unnecessary and everything should just be a query by the way

BOSS 10:54 AM: did the DB update complete? (this question ignores my previous statement)

ME 10:54 AM: what do you mean

BOSS 10:55 AM: [other person] was planning to update the DB with the latest changes?

ME 10:56 AM: He hasn't said anything to me about it I'm pretty sure he was out of office last week I seriously think that we need to just forget about this web service and let people read our tables

BOSS 10:58 AM: no

ME 10:58 AM: why not Having this web service means we need to maintain it which means more work whenever a dB change happens we could just get rid of that need for maintenance and just let other teams query directly If a dB change happens when we don't have this service then the other teams can decide if they even care about the dB change. They might not even care Not having this web service means less work for everyone It also provides faster query times for everyone who would need the data I don't see any drawbacks Also, there is no security concern with allowing people to read our data We will not give them write permission And I'm pretty sure we can also control which tables they can view Also, let's say we make a change to this web service some time down the road, everyone who consumes the service will be required to make a change to their program that consumes our web service whether or not they even want/need the change. It is also worth pointing out that the queries that could be used to replace this web service are not complicated. I could easily write a query or two that other teams could use. It's not like there are a bunch of tables involved in the data, there are 3 maybe 4 if they want other information then a couple more its not complicated at all Another thing to consider is that when we were in the meeting many months ago with quentin and hanu and another guy, I forget his name. The question was asked "Why can't this just be a sql query?" [10 minutes pass] I would appreciate for you to at least acknowledge that you have read these messages. I would also appreciate (even more) any counterpoints you have.

BOSS 11:22 AM: I have already indicated that there will be webservices

ME 11:22 AM: That doesn't mean that we need to provide one

BOSS 11:22 AM: you keep repeating the same thing let us focus on the webservice and complete it that is all

ME 11:23 AM: no You haven't provided a valid counterpoint to anything I just said

BOSS 11:23 AM: I have explained it already webservices it is

ME 11:23 AM: You have explained what already?

BOSS 11:24 AM: before I left for vacation

BOSS 11:24 AM: there is no need to go back and forth on this

BOSS 11:24 AM: please complete the webervice

ME 11:25 AM: This is not how to properly handle a disagreement. Just because you are my boss doesn't mean your opinions are better than mine And what you said before you left was that we need to not expose our tables because that's what we've always done in the past That is your only counterpoint I can remember

BOSS 11:26 AM: what else do you expect?

ME 11:26 AM: I expect rationality

BOSS 11:26 AM: if you are having issues with implementing this let me know

BOSS 11:26 AM: I need to talk to [boss's boss] about it

ME 11:27 AM: I do not appreciate you repeatedly implying that I don't have the ability to complete tasks when I don't agree with you about them I have told you my view on this web service and all you have said to me is "No, just do it"

BOSS 11:28 AM: sorry that is the process

ME 11:28 AM: Just because something is the way it is doesn't mean that it is correct

BOSS 11:28 AM: it has to be completed soon

ME 11:28 AM: I would like to point out that the web service works and was working before you left for vacation You are on the email thread where this was pointed out The only problem is that its not instantaneous Which, like I said, it won't be

BOSS 11:29 AM: it need not be

ME 11:29 AM: yes, it does That's what [stakeholder] needs

BOSS 11:29 AM: that is the point of the webservice

BOSS 11:29 AM: it is a parallel operation when the build is compiled and patchstring generated

BOSS 11:30 AM: [other] team has given bogus arguments like this before too

ME 11:30 AM: I'm done talking with you about this

BOSS 11:30 AM: good

ME 11:30 AM: We need to have a meeting with the stake holders or [boss's boss]

This is a single example of our interactions. I have a lot more conversation histories.