If you speak to your boss's boss, does your boss ask you why?

[CrapBag]

I've noticed this has become a thing and it's starting to annoy me. I have a boss who I generally deal with day to day. Then there is a boss higher up, who is around and I am free to speak to. Last week I asked my boss if higher boss was in as I needed to ask her something and she wanted to know what about (I always ask her stuff so it's not like she thinks I wouldn't speak to her). I answered as I didn't feel that I couldn't but it annoyed me and made me think. It was only a question that higher boss could answer. It's happened before.

A while ago I had a request for certain personal information from another team that does relate to my position, I spoke to my boss about it and was told not to bother as it didn't affect my role. This made me uncomfortable tbh. I mentioned it again on another occasion and again was told not to bother. So I've discussed this with bigger boss as I felt it is something that needs doing and I have been told I am to get this information and my boss cannot overrule this other team and will be spoken to about it. Now I'm glad my instincts were correct but I know this won't go down well and it will be seen as me going behind backs (I purposely discussed with bigger boss when we were in a conversation about something else as I know my boss will ask why I discussed it with bigger boss).

A similar thing has happened before, I was told something I have to do later on by bigger boss, mentioned it on another occasion to my boss who immediately started questioning me and asking when this was said and I needed to ask bigger boss again (because she didn't agree with it basically), so I asked on a day my boss wasn't in and of course as I knew, bigger boss said the same thing she said the first time. When I said I'd checked this and it was what I am to do, my boss was immediately on the defensive and wanted to know when I had asked this.

I'm getting a bit fed up of this and it feels like I have to run every little thing past my boss, down to minor conversations that don't actually affect her. Is this right? Is this how it should be done and I'm just being silly?

The problem is, I don't know what my boss thinks. She's a closed book really and I am not good at reading people at all and often get things wrong in my perceptions (I have ASD). Initially I was frustrated at having to clarify to her exactly what I needed to ask big boss, because it really was a simple question that didn't need anything from my boss. I do go to my boss a lot for things, clarification and I always go to her first, but there have been a couple of things where I knew she wasn't telling me the right information and it made me uncomfortable. As I do go to her first, I was suprised at why she felt the need to question what I needed to speak to big boss for, it's not like it's a common thing that I do.

But I get that as my boss, she is the one I go to, which I do, and I need to be aware of keeping her in the loop, if there is anything. I do need to tell her that I am going ahead with the request from the other team, as told to me by the big boss but I'm dreading it because I think she will question me and get the hump. I'm not good at dealing with this sort of thing.

The problem is, I don't know what my boss thinks.

Hence me saying “go and talk to you boss”.

This really isn’t an unsolvable problem. Just say that you realise she needs to be in the loop but you don’t want to bother her with every little thing. How would she prefer to be kept up to date other what you are doing for big boss.

It’s really not that complicated.

For you it's not that complicated, for me it's different. I have a habit of saying things in thw wrong way when I don't mean to, hence I'm always wary and never know what I should say and what I shouldn't.

Anyway I mentioned 1 thing today so I could keep her in the loop and in future I will be mindful that she will want to know why I need to speak to the bigger boss.

But please don't assume it's easy to deal with this stuff. It really isn't for me.