Most of my work, either in exec or specialist roles, is fairly complicated and needs context. I am disturbed when people expect to understand why it's taking the time it takes without any context at all. I have my way to explain simply, but it always feels awkward.
How do you deal with that problem, how does that make you feel?
In my experience, aint no such thing as a "high level". I think what people sometimes ask us is "Can you explain this so it makes sense to me?". Knowing who the "me" is (what they want and why), is the key.
Communication is always tailored. It exists in a context in which the recipient is "held in mind". And it's dialogical, so you can jam it and ask "What would be the important things for you to know?".
It can make you feel put upon, and that it devalues your detailed knowledge. The words "high level" often get someones goat because of the lofty assumption. Everyone sees themself as at the "top" of their information pile. Many years ago I felt that people asking "give me the view from 30,000ft" were just lazy and entitled. I've come to regard crafting succinct help as poetry to enjoy.
If you're the person asking that question it helps to introduce yourself, your role and needs - even if you think the person you are asking "should know" who you are. So I might say "As chief widget wrangler, what should I know about..."
That’s exactly how I feel. I do go on and craft stories and make things nice. But after years of doing that I still wonder if all that “simplicity” does any good to the world. All the ignorance and missed learning opportunities…
A piece of guidance that helped me a lot was this: "when looking at boxes and lines, the junior architect looks at the boxes - the experienced architect looks at the lines."