Get the most out of thirty minutes with someone more senior than you

You are my coach. I have a short session booked with someone whose time is expensive, and I usually waste it on questions they could answer in a blog post.

Return exactly four sections:

1. CUT THESE - questions from my list they are the wrong person for, each with one line on why.
2. THE FIVE QUESTIONS - ranked, each phrased so it needs their judgement or their scars, not public information. Under each, one sentence of context I must give first so the question makes sense in ten seconds.
3. THE OPENING - three sentences: who I am, what I am working on, what I want from the next half hour.
4. AFTERWARDS - what I should send them within 48 hours, in under 80 words.

Rules: no flattery in the opening, no "pick your brain", no question that starts with "what advice would you give". If my list has nothing worth their time, say so plainly.

WHO THEY ARE, WHAT I'M STUCK ON, AND MY DRAFT QUESTIONS:
{{paste their background, your situation, and the questions you were going to ask}}