How to Ask Useful Questions – Josh Kaufman - Deepstash
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Asking useful questions require practice

Asking useful questions require practice

Inexperienced questions such as "I'm thinking about [action]. What do you think?" are seldom answered because answering would take too much effort.

This is because naive questions lack the necessary context while failing to respect the recipient's time, energy and attention. Instead, it transfers responsibility for the end result from the questioner to the recipient. If you want helpful answers, it is worthwhile to learn to ask better questions.


1K reads

Asking for information

"I would like to know more about A. I found you via B. Are you the best person to ask regarding A?"

  • Be specific about the information you require.
  • Give context. Reference why you're asking them and how you found their contact information.
  • Asking if the recipient is the best person will save time for both of you.


839 reads

Asking for clarification

"From our discussion about A, it seems like B is the case. Is that correct?"

  • Include a summary of the topic for context.
  • "It seems like" helps to find clarification without sounding confrontational.
  • "Is that correct" clarifies your position.


766 reads

Asking for help

"I'm trying A. I've tried B and C, and it resulted in D and E. What should I try next?" 

  • Be exact about what you're trying to do. 
  • Include what you've tried, which makes it clear that you are trying to solve your own problems.
  • "What should I try next?" sets the recipient as the expert.


591 reads

Asking for agreement

"Based on our conversation about X, we decided to do Y. The next step is Z. Agreed? If yes, I'll do it right away."

  • Spell out the decision. 
  • "Agreed?" gives the recipient a chance to voice disagreement.
  • "I'll do it right away" makes it clear that clarification needs to be made right away.


574 reads

Asking for advice

"I'm working on A. My priorities are B and C, but I'm not sure it's the best option. If you have a moment, I'd appreciate your thoughts . If you can't, no worries. Thanks."

  • Be precise about what you're trying to do. 
  • Be clear about your priorities.
  • State that you're asking for advice, nor for the recipient to decide for you.
  • Give the recipient an easy out. "If you can't, no worries. Thanks"


572 reads



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