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I read this book on how to ask questions properly and I love-love-hated it. What I mean is that it had good sensitivity: it discussed topics that I'm generally very interested in, but very low specificity: I feel it didn't go in depth enough on how to become a good question-answerer, but rather turned into a general psychology-self-help book, and god knows I'm quite sick of those.

But it still taught me a lot of valuable lessons! I just wish I could've been 10 times less long than what it was, and more focused on just question asking rather than life.

Actionable takeaways:

  1. The main thing about a company you should consider when deciding to join it is: Can the little people become leaders? Can you have impact there? How have the lower ranks been allocated extra responsibilities there?

  2. If you’re not sure if you want to do something or you’re just agreeing to it out of discomfort, ask yourself how you would feel if it was cancelled? Elated or heartbroken?

  3. We should follow the path that will lead to a better story, we are unlikely to regret that.

  4. Don't wait to find your passion: Find something you find interesting, become good at it and passion will likely follow.

  5. A good measure of the future success of a relationship is how partners respond to each other’s bids for attention. If they’re ignored, it won’t last.

  6. Even the most successful creative people are horrible at predicting what will be their best work, they just are better at overcoming the barrier of not knowing and putting work out anyways.

  7. In order to get creative ideas from what you’re seeing you should shift your view from objects in the foreground to those in the background. It’s not what you see, it’s how long you look at it.

  8. Good questions are those that start from curiosity (not "where are you from?" but "what’s the weirdest thing about where you’re from?").

  9. To be a better speaker, it’s good to try and paraphrase what someone has just said as a question “so did you just say…?”

  10. In business you should reward people for asking questions, not always make them solve the issues they raise or require that they always come to you with solutions for their questions. We should also recognise them when the problem gets solved by others. There should be a culture where there are question days: any question can be asked to the manager and leader.

Fave Quotes:

Passion is not something that you follow, it’s something that follows you as you put in the hard work to become valuable to the world.
The problem finder goes out looking for trouble, creates it even, to solve it.
All of us are smarter than any of us
Absolute failure in every field is almost impossible. Once you realise that, you can move forward with more confidence

My favourite questions from the book:

  1. What would I like to be true?

  2. What did I believe that wasn’t true?

  3. If none of the options were available, what would I do?

  4. What would you do if you knew you could never fail?

  5. What are the most likely things that would cause me to fail?

  6. What makes me forget to eat? (Passion)

  7. What if I knew from the outset that there was no money or fame in this? Would I still do it?

  8. What’s the most in love you’ve ever felt?

  9. What was the most difficult thing you faced today? How would you have handled that differently?

  10. If you were an inventor, what would you invent?

  11. And what else? (The awe question, the most valuable question in coaching)

  12. When you heard that good news, how did it make you feel?

  13. What are you doing today? How can I help you?

  14. Steve jobs: What are the next 10 things we should do? We can only do 3, which?

  15. What is the highest, best use of my time?

  16. If an oracle could tell you something about the future, what would you ask?

  17. Who do we want our customers to become?

(Bonus) Adam Grant's Stages of Creation:

  1. Energised and optimistic

  2. Realistic

  3. This is crap

  4. I’m crap

  5. You know, this might be ok

  6. This is awesome

(Bonus) How to helps someone figure things out for themselves:

  1. What is the challenge you’re facing

  2. What have you tried already

  3. If you had endless resources to try this, what would you try

  4. And what else

  5. Which of these options interests you the most

  6. What may stand in the way of this idea

  7. What might we do about that

  8. What is one step you can take right now in that direction

(Bonus) Questions to ask your manager:

  • what does the ideal person in my role look like?

  • What would this job done perfectly look like?

  • What is your main task for the day? How can I help with it?

PS. If you'd like to see me talk through my (very unfiltered and rambly) thoughts, lessons and summaries of books, I host a raw-book-club video series on Nebula. The cheapest deal to get it is through Curiosity Stream, and you can get yearly access to both for under $15 a year with this link:



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