• Be specific.

You need to show that you've thought seriously about the topic already, rather than simply asking open-ended questions like: ‘What should I do?’ Vagueness will be met with vagueness.

• Give sufficient context.

Questions don't exist in a vacuum. You should give the person you're asking all the information you feel is relevant if you want a comprehensive, actionable answer. That includes how you found them, why you're getting in touch, topic summaries and solutions you've tried so far.

• Take responsibility for the end result.

If you place too much weight on the recipient's response, they'll feel it. Giving you an answer will seem like an effort, so they might not bother. They also don't want to feel responsible for the problem you're asking about. So, while you should stress that you're asking because of the person's expertise, you need to come up with targeted questions to really respect it. Be clear that you're after a perspective, rather than a course of action.

• Communicate your personal priorities.

Just as the recipient doesn't know about all the moving parts behind your question, they also don't instinctively know why you're asking. Particularly if you're asking for advice, summarize the kind of person you are and any trade-offs that you're juggling.

Example questions from Josh.

• ‘I'm interested in more information about A, and I found you via B. Are you the best person to ask about this?’

• ‘Based on our conversation about A, it sounds like B is the case. Is that correct?’

• ‘I'm trying to A, and I'm having trouble. So far, I've tried B with result C, and D with result E. Now I'm stuck. Any guidance?’

• ‘Based on our previous conversation about X, we decided Y is the best solution. The next step is Z. Agreed? If so, I'll get started right away.’

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