How to ask better questions on Clubhouse (or at conferences)

Founder Collective
3 min readFeb 10, 2021

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By Joseph Flaherty

Clubhouse, and conferences generally, are a great leveling tool where an entry-level engineer can ask unfiltered questions of a captain of industry.

This is an opportunity that should not be wasted — or hoarded!

Here are a few simple tips that will raise your question asking game:

❓ Start questions with an “H” or “W,” not “I”
🚫 No two-part questions
📏 Know your limits
📌 Formulate crisp queries
🕳️ Avoid “talking point” traps
🙃 Be Provocative

Let me expand:

Start questions with an “H” or “W,” not “I”

Ask questions that other people will benefit from.

Questions that start with who, what, when, where, why or how will likely be more interesting to the audience than “I” statements followed by 90 seconds of catharsis.

The speaker is unlikely to be able to solve your idiosyncratic business conundrum.

Your sales pitch, clumsily disguised as a question, is unlikely to lead to a closed deal.

Spending 5% of a session on a personal preamble is rarely a good use of anyone’s time.

If you ever feel the urge to utter – “This is more of a comment than a question…” – don’t.

🚫 No unrelated two-part questions

First, it’s rude. Lots of folks have questions and precious little time is reserved for audience Q&A! Ask one question and queue up again if you’ve got a second.

Second, think back to all the events you’ve been to where a complex, multi-tranche question is asked and both parts are clearly answered — It rarely works. Instead, the speaker, struggling to interpret a complex question, decides to answer the second part and ignores the first.

📏 Know your limits

If you mumble, make an effort to enunciate.

If you get stage fright, ask simple questions.

If you have trouble remembering stats and details, keep to higher-level questions.

If you tend to ramble, write the question down before you ask it.

📌 Formulate crisp queries

Questions should be one sentence long. Two at the most.

Avoid long-winded hypotheticals.

Cut references to obscure books/people the subject is unlikely to know.

The goal is to elicit a smart response, not to showcase your esoteric intelligence.

🕳️ Avoid talking point traps

Most famous people have developed a series of talking points that they’ll reflexively use when asked questions.

Try to avoid questions that will allow the responder to filibuster with facts that would be surfaced with five minutes of googling.

When I was interviewing people for Wired I found questions with words like “surprising” or “counterintuitive” or “unexpected” would force the speaker to think past their handy talking points.

Asking about specific moments in time or people also tends to get good quotes.

🙃 Be Provocative (But Polite)

Moderators often have a relationship with speakers and are unlikely to ask uncomfortable questions.

Don’t be rude, air salacious/unfounded rumors, or workshop your insult comedy, but the audience can add value by asking hard questions.

However, If you’re going to do this, refine your question so that it seems like a legit *question* and *NOT* an adversarial statement. The more honest the question seems, the harder it will be for the subject of the question to dodge it.

When you decide to ask a question you’ve decided to become a performer — embrace your strengths, try to hide your weaknesses, and respect the audience.

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