How to facilitate interesting interviews / conversations

  • If I were an interviewer.
  • 1: I think it’s important to get all the preliminary questions out of the way ASAP. Most dialogues- (especially all the ministerial ones, etc) spend a lot of time going through introductory details.
  • Have you watched any Elon Musk interviews? They all follow the same pattern asking about everything from his early life about the stories of Zip2, PayPal, Tesla, SpaceX. They can talk about that stuff for 1-2 hrs but it’s also the same thing every time. Strikes me as very wasteful. You ideally want start where the last set of interviews left off instead of asking what other ppl have asked before. That’s what I’d like to see.
  • Suppose you asked me to interview, say, a startup founder. I would start with- “Before we can get to the fun questions, give us the quickest summary you can of your entire experience from start until now?” They’ve probably already had to tell this story over and over again, so it should be quite short and snappy.
  • Actually, no. I’d summarise the startup journey for them and ask them what they thought of the summary. And ask them what the most interesting, challenging, exciting bit is. What were they excited about? What surprised them? Fundamental emotions. Fear. Anger. Lust. Excitement.
  • “What do you like thinking about these days?”
  • From there i’d ask things like- “What have you been wrong about? What have you been forced to change your mind about? What are the hardest decisions you’ve had to make? What were the mistakes you’ve made? What would you do differently? What would you do if you had more time/energy than you do now, if you could clone yourself? What do you think everyone else (or most people) are missing or doing wrong? Etc.
  • I think you want to look for surprises, because anything surprising is newsworthy. You want to try and ask a question they haven’t been asked before. If you enter that territory, you’re helping them think and see things in a light that they might not have seen before. Then they’ll love you! They’ll say new and interesting things. What do you think the scene is lacking? What could/should be added? Who should do what? How can we grow and learn faster? How do you handle your management, hiring, firing? Etc. If a Q&A went through that sort of thing, I would pay close attention.
  • Actually, if you have the time, you should prepare yourself as an interviewer by asking budding founders what they want to know that they don’t already. The thing is… they probably don’t know what they don’t know.
  • If you can find the space between what successful people know and what unsuccessful people don’t know, and bring that out, you’ll create a lot of value for people. Ultimately it’s about sharing expertise & knowledge in a way that benefits everyone.
  • So after you assemble these questions right you wanna see if the person you’re going to interview has already answered them somewhere. Let’s say you want to ask about how to fire people, and she says “Oh, I just fire people based on my intuition,” (in some interview somewhere else) then you can ask- in X interview, you said you anyhow hamtam fire… do you ever regret any of your fires?etc
  • What’s the hardest part of your job? Why so hard? If you get a response saying “Hmm, I’ve never thought of that,” win liao lor.
  • Conversation from there is very interesting and real, rather than rehearsed answers another way of thinking about it is… people usually know stuff that they don’t even know that they know The interviewer’s job is to pull that out. But… that requires a bit of homework and a kind of hungry curiosity I guess (actually if you’re very inquisitive, you’ll probably do your homework just because you’re inquisitive.)
  • Fun fact: I wouldn’t have written this post if Vanessa from TIA hadn’t asked me about my thoughts about interviews.
  • On hindsight, it occurs to me that the interview game is quite a funny one. A lot of “human interest” questions actually have remarkably low (or even misleading) utility. Optimizing for an interview that makes the audience happy isn’t necessarily what is most useful to them. I suppose it’s the same case with the media optimizing for “what’s interesting to the public” rather than “what’s in the public interest”.
  • But I also suppose that the idea behind an interview at a conference is to make people feel like they’re a part of a broader movement or culture that they like, identify with and want to be a part of. People need their heroes and narratives. (See: Fuzzies vs. Utilons).

Leave a Reply