Do you ever ask Claude what information it's missing in order to accomplish a task?

Yes — a common practice is to explicitly ask Claude follow-up questions like "what is my blind spot here?" or "what do you need from me?" before starting a task (e.g., before creating a promo video). One member also described a custom skill for pitch prep: activating a "be mean to me" skill so Claude critiques a presentation and identifies why the pitch might not work, useful before presenting to stakeholders like a VP of tax.