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  • I think as humans we all have a preoccupation with looking dumb.

  • We are social creatures, hierarchical creatures and we don't want to shame ourselves, humiliate

  • ourselves.

  • But recognizing that by zigging when everyone else is zagging with that particular context

  • you can actually develop a super power.

  • And that is asking dumb questions.

  • And this came up repeatedly when I was interviewing incredible performers, world class of performers,

  • meaning investors, entrepreneurs, writers, you name it for Tools of Titans the new book.

  • And asking dumb questions can take many forms.

  • I'll give you a few examples.

  • Malcolm Gladwell is very good at asking so called dumb questions.

  • And he learned that from his father who was a mathematician had no intellectual insecurities

  • whatsoever, just did not care about looking stupid.

  • And he would constantly ask or he would first say I don't understand.

  • Please explain that.

  • I don't understand.

  • Can you explain that?

  • I don't understand.

  • Can you explain that?

  • And he literally might ask that ten times in a row and Malcolm mentioned that he imagined

  • sometimes what the conversation would it look like between his dad and Bernie Madoff because

  • his dad never would have invested, he just would've said I don't understand that at all.

  • Explain that to me over and over again until Madoff left or his dad got so frustrated he

  • had to leave.

  • But if we look at another sphere, say investing, Chris Sacca, a close friend of mine, billionaire,

  • incredible tech investor, just immaculate track record, is very good at asking dumb

  • questions.

  • And this applies to in the very early days where he did something very clever, which

  • was at Google when he was just an entry level guy really compared certainly to say the Wonder

  • Twins, the founders and others, he would go to as many high level meetings as possible,

  • most of which he was not invited to.

  • And so he would show up at a meeting with say Surgie or whatever and he would walk in

  • and he'd sit down and they'd kind of look at each other and ask him what he was doing

  • there and he go, "Oh I'll just take notes."

  • And they're like oh okay.

  • So he got to sit in on all these high level meetings.

  • And eventually at some point let's say he got through five or ten of those and people

  • started to just expect him to be around, he would then ask these dumb questions.

  • Sort of the pink elephant in the room why is no one asking this what seems like a very

  • obvious question?

  • And he's created some incredible breakthroughs in investing as a result of that.

  • The asking of dumb questions can certainly apply to exploring any topic or interviewing.

  • So Alex Blumberg, who's cofounder of Gimlet Media which has a slew of gigantic podcast

  • hits, just a factory for podcast blockbusters, he was the co-creator of Planet Money, which

  • is a very successful radio and podcast show.

  • For instance, during the subprime economic crisis he asked the question that no one else

  • seemed to be asking but it was just sitting right in front of millions of people who couldn't

  • quite figure out what the hell happened.

  • And it was why would banks lend money to people who stand next to no chance of paying it back?

  • And so very often the dumb question that is sitting right there that no one seems to be

  • asking is the smartest question you could ask.

  • Not only is it the smartest most incisive, but if you want to ask it and you're reasonably

  • smart, I guarantee you there are other people who want to ask they're just embarrassed to

  • do so.

  • And in this case if you can override that embarrassment and be the one who asks dumb

  • questions you can end up having best-selling books, you could end up having a huge blockbuster

  • of a podcast or many, you could end up picking the next Uber.

  • It is a super power in a world that is governed by shame and perhaps political correctness

  • more and more so people are not saying what's on their mind, they're not asking what's on

  • their mind and the questions here are the most powerful.

I think as humans we all have a preoccupation with looking dumb.

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B1 US dumb podcast explain interviewing malcolm smartest

Tim Ferriss: Asking Dumb Questions Is a Smart Move

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    abovelight posted on 2019/03/19
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