I'm reporting to a really senior person. Most of their direct reports are higher in the hierarchy than I am.
At the same time, the culture of my organization is sometimes difficult to navigate. To give you just one example: for my work I need a tool A. There's no viable alternative to tool A. Fortunately, the tool is very cheap. So I write to my boss's report who's in charge of taking this decision (but who's from another area and is not able to understand or has ever used tool A). They reply: "I don't think you need tool A, I don't think you should have it". So I start an exchange on that, explaining why I need A urgently. I offer to discuss it. They ignore me. After several days or weeks I still don't have tool A. (Btw, I've worked in several companies before, never have I been denied tool A).
I don't want to waste my boss's time for such small things, but I'm not able to work without tool A. So normally I would write a short email to my boss and his report something like: "It would be great if I could receive tool A. The alternative is my needing 5 times as much to complete task B. What's the decision?"
My boss gets irritated when I turn to him with such topics and I think my doing so twice (within 2-3 months) has impacted our relationship. They think I should "just talk to people and try to solve issues". But I'm not sure what the alternative is. I do talk to people, I try to build a good relationship with them, which works with most but doesn't help with some requests. To get a tool for 5 USD/ month can take months and fail - at the same time the expectations towards me are high.
Do you have any advice?
HR is useless where I work, so please don't advise me to turn to them. Yes, my boss has an assistant, but normally they can only help to a very limited degree.