How To Ask Good Questions

On podcasting. In order to have an in-depth conversation with a virtual stranger but a public writer, I decided I’d have to read/listen to their works. This caused me to examine their writings more deeply with a view to asking what I then could not understand further or what I thought was particularly insightful. I ended up learning about a wider range of experiences and ideas than was usual and in more depth. Three practical skills emerge:

  • Concise follow up emails

  • Active listening 

  • Asking good questions

Concise emails: At least 3 guests responded to follow-ups once the initial email had faded. The hit rate on well-worded concise (cold) emails is higher than you might think.

Active Listening: To hold good conversations, you need to truly listen to what the person is saying, process that with knowledge you have or you’ve heard earlier and formulate the next point. I think “active listening” covers this point, but it’s about absorbing what the person is saying or trying to say, combining it with other information and formulating something new from this.

Good questions: This leads into being able to ask good questions. For many, the more specific or detailed you can go then the better. I often end up succinctly summarising an idea I think my partner has and then asking them to develop it further and add anything I have left out or misunderstood. This show them how far your understanding has reached and gives them a little time to process what the answer should be. It also gives a general listener a brief baseline for the conversation.

The higher the level of prefaced information, the better the answer as they will not need to go over basics you’ve already expressed.

Avoid bland unanswerable or rote questions.  

Dinner parties or conversation with strangers in real life are somewhat different to podcasts. But another principle I like is to try and get your partner to be the best version of themselves and their argument. Rather than flat out deny or challenge, you want to tease out to the fullest what your partner is expressing even if - and perhaps even more so - if you think you disagree.

(For dinner parties, I like to try and find out the things or areas my partner knows that I know nothing about. Even better if it’s a secret. And if you are up to it, diving into a deeper topic, not simply a shallow one. You can pick upon the internet these type of questions (or books eg Gregory Stock questions, Amazon link ):  Would you rather lose a hand or all access to telecommunication devices? Rather live in the greatest city in the world, or a remote beautiful town? Whose reputation would you destroy? ….)

If a guest, if you can find out about a hobby/cultural interest and ask you often find a revealing answer.

With a stranger on a podcast, try and make your introduction sincere and ask a challenging/insightful question first. Typically, I find after 10 or so minutes, the guest will know by then if you’ve done your research and if you are genuinely interested in what you they have to say. This then makes it fun for everyone.

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