Asking better work questions by Shaan Puri

• Don’t ask: When will this be done?
  People may say it will take a long time and then try to deliver it faster. Or they may be overly optimistic and not deliver it in predicted time window.
• Ask:
  • When would you be surprised if we did not have this done?
    (People do not see it as an estimate.)
  • When would you be surprised by not being finished?
    (Setts the bottom bar.)
  • So best case scenario, what are you thinking?
    (You get more accurate time frames.)

• After somebody explaining a long and complex plan ask:
  • Man, all that sounds really hard. What would be easy?
    (People usually do not think what would be the easiest option.)
  • Imagine we all had half the IQ. What would be the dumb and simple plan?
    (This gets people to think outside of the box.)

• When leading / managing someone ask:
  • You do not have to tell me this answer, but it is a good question to ask yourself. What is a conversation you have been avoiding?
    (Everybody is avoiding some conversation. Having it may lift a huge weight off our chest.)

• When you wake up in the morning ask yourself:
  • Who needs my help?
    (It is best to address struggles when they are little sparks.)

• When to-do list is too long:
  • If I could only work two hours today, but still wanted this day to be a huge success, what would I do in those two hours?
    (Cuts through all bullshit.)

• Think of person with a lot of common sense and ask yourself:
  • What would that person do?
  • Sounds like you are stuck and do not know what to do. You have always given me great advice. What would you advise yourself in this situation?
    (It shakes their pattern and gets them to think differently.)

Source:
https://podcasts.apple.com/si/podcast/my-first-million/id1469759170?i=1000622633330