Asking Good Questions

If you find yourself asking a question, whether to an expert or your team, use this list as a prefilter before you ask it. The cost of a bad question can be high:

• You won’t get a good answer, or any answer at all.
• You waste the time of the person who is attemping to answer it for you.

The Checklist

When asking an expert:

1. Write the question out fully.
2. Research the answer and include the research in your question.

• It’s embarassing to ask a question that is answered by 2 minutes of googling around.
• “I’ve looked at X and Y but still had trouble understanding Z…”

3. Pretend to be the person you are answering. In turns out in a lot of cases this ends up answering the question for you. Include it in the question: “I figured you might say X, but I was curious about Y”

When asking your team, I use a different checklist heavily inspired from Your Small Imprecise Ask Is a Big Waste of Their Time.

1. Clarifying the expected time investment:
   1. Be specific about the amount of time needed for the task: “Please look into this for me. Do not, DO NOT, spend more than 20 minutes on this. Please come back with whatever you have after 20 minutes.”
   2. Set expectations for time investment: “I expect this to take about 2 weeks and not cause major deprioritization of other efforts. If that timeline doesn’t seem accurate after diving in, or if you end up having to prioritize against other things, reach out to me ASAP.”
2. Prioritizing the task:
   1. Communicate how the task should be prioritized: “Be clear about how it should be prioritized: ‘I expect this to take about 2 weeks and not cause major deprioritization of other efforts. If that timeline doesn’t seem accurate after diving in, or if you end up having to prioritize against other things, reach out to me ASAP.’”
   2. Reach out for help if needed: “If the task requires a higher priority than initially anticipated, inform your manager immediately.”
3. Understanding the scope of the task:
   1. Distinguish between whether you’re looking for prior art or new art: “Tell me if we have anything on this topic already; if we haven’t even thought about it yet, that’s all I need to know.”
   2. Clarify the specific details of the task: “Be clear about what is needed: ‘Please provide a list of potential solutions for X. The list should include at least three options with a detailed explanation of each.’”
4. Understanding how the information will be used:
   1. Tell people exactly what you’re going to use the information for: “Tell people exactly what you’re going to use the information for so that they can calibrate effort levels: ‘I am going to put this into a response to a sales prospect’; ‘I need to know this just in case it comes up during Q&A at our next All Hands’; ‘this is going to be the main topic of our next board meeting.’”
   2. Clarify how the information will be used: “If you’re not sure how the information will be used, ask your manager for clarification: ‘Can you provide more details about how this information will be used?’”
5. Asking for clarification:
   1. Don’t assume that everyone else knows what’s going on: “Do not, DO NOT, assume everyone else knows what’s going on.”
   2. Ask questions if you’re unsure: “If you’re unsure about something, ask your manager for clarification: ‘Can you provide more details about this task?’ or ‘Are you expecting something super thorough, like multiple hours of effort, or a quick write up?’”
   3. Follow up if needed: “If you’re still unclear, follow up with your manager to ensure you understand the task correctly.”