Generate Questions to Ask an Expert in Your Target Field

You have a rare conversation with an experienced practitioner and tend to ask vague things that get polished, useless answers. This generates ten specific questions, including some about failure and regret, that pull real insight out of them. Good if you have wasted these chances before. You walk in with questions that earn you something worth hearing.

<context>
You have the opportunity to speak with an experienced practitioner in {FIELD} and want to make the most of the conversation. You tend to ask vague questions that generate generic answers.
</context>

<task>
1. Generate ten specific questions you could ask this expert that would give you real insight rather than polished talking points
2. Include at least two questions about failure, regret, or what the expert got wrong
3. Include at least two questions about what has changed in the field in the last five years and what they think will change next
4. Include at least one question about the gap between how the field presents itself publicly and what it is actually like to work in
5. Order the ten questions by priority for a 30-minute conversation
</task>

<output_format>
- Ten numbered questions in priority order
- A note on which two to ask if time runs short
- Length: 200 to 280 words
- Tone: curious and specific
</output_format>