Asking useful questions is a skill, and it requires practice.

Inexperienced or naive questions sound like this:

“Hello! [Insert life story.] What should I do?”

Or this:

“I’m thinking about [action]. What do you think?”

Questions like these make a few critical mistakes:

• They don’t include the context necessary for the recipient to answer the question.
• They don’t respect the recipient’s time, energy, attention, or competing demands.
• They implicitly transfer responsibility for the End Result from the questioner to the recipient.

As a result, questions like these go unanswered due to Friction – answering them would take too much effort, so the recipient doesn’t bother.

If you want useful answers, learn to ask better questions. In most cases, you’ll need to tailor the form of the question to the type of information you’re seeking.

Asking for Information

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

Keys to information-seeking questions:

• Be specific about the information you’re looking to obtain.
• Give context by referencing why you’re contacting them and how you found their contact information.
• Make it easy for the recipient to refer you to the best resource as quickly as possible, which will save you both time.

Asking for Clarification

“Based on our conversation about A, it sounds like B is the case. Is that correct?”

Keys to clarification questions:

• Include a short summary of the topic for context.
• “It sounds like…” leaves room for clarification without being confrontational.
• “Is that correct?” (or a close variant) is clear, concise, direct, and polite.

Asking for Help

“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?”

Keys for asking for assistance:

• Be clear and precise about what you’re trying to do.
• Give context by including what you’ve tried so far, which makes it clear that you’re doing your own work and not asking the recipient to solve your problems for you.
• “Any guidance?” or “What should I try next?” sets up the recipient as the expert and doesn’t transfer responsibility for the problem.

Asking for Agreement

“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.”

Keys for asking for agreement:

• Use this question to get important decisions or agreements in writing. (This question is particularly useful in confirming business agreements.)
• Spell out the decision in as much detail as possible.
• “Agreed?” leaves room for recipients to voice disagreement without equivocating in your description of the original decision conversation.
• “I’ll get started right away” adds useful urgency and makes it clear that any clarifications or changes need to be made right away.

Asking for Advice

“I’m working on A. My priorities are B, C, and D. I’m considering E, but I’m not sure it’s the best option. If you have a moment, I’d appreciate your thoughts. If not, no worries. Thanks!”

Keys for asking for advice:

• Be clear and precise about what you’re trying to achieve.
• Be clear about your priorities, and include any known tradeoffs. The recipient can’t read your mind or set your priorities for you.
• Make it clear you’re asking for advice or perspective, not for the recipient to decide for you.
• Give the recipient an easy out – you’re asking for a favor, so be polite.

Are you asking useful questions? What type of question do you currently have the most trouble asking? How can you practice asking in a useful way?