A mentor and a mentee

Two people, one further along than the other, meeting deliberately. Asymmetric but chosen.

50 questions
  1. When did you last teach somebody a shortcut, and did it work?
  2. What advice do you hand out that you have never once taken?
  3. Whose advice do you always ask for and never take?
  4. What did you fail at that you would happily do again tomorrow?
  5. What's a shortcut you worked out yourself that nobody taught you?
  6. What did you get good at because you had no other choice?
  7. What's the most useful thing you learned from someone who never taught anyone else?
  8. When did you last read the manual before pressing the button?
  9. When did you last hand-write a card, and who received it?
  10. When did you last copy a habit from someone without telling them?
  11. When did you last teach someone to do something with their hands?
  12. When did you last stay up late finishing something nobody asked for?
  13. When did you last keep an object from a place you left?
  14. When did you last change your mind because of one sentence?
  15. When did you last build something with your hands that still exists?
  16. When did you last redo something that was already good enough?
  17. When did you last say you did not know, in front of people?
  18. When did you last abandon a book halfway, and at which page?
  19. When did you last stop to watch a stranger do their job well?
  20. When did you last take advice from someone younger than you?
  21. When did you last introduce two people who then became friends?
  22. What advice do you give often and never follow yourself?
  23. What did work teach you that your friends now complain about?
  24. What shortcut do you take that you would never teach a beginner?
  25. What did you teach yourself wrong and still use anyway?
  26. What part of your work do you enjoy that others find boring?
  27. What do you leave until the last minute and still get right?
  28. What did every other child find easy that you found impossible?
  29. What did you fail at and would do again tomorrow?
  30. What do you refuse to automate, and how long does it take?
  31. Whose taste do you trust more than your own, and about what?
  32. What do you do slowly on purpose when everyone wants it fast?
  33. What kind of message do you rewrite five times before sending?
  34. What are you good at that you would rather not be known for?
  35. What small detail do you fix that nobody else ever notices?
  36. What did you learn from a teacher you did not like?
  37. What would you tell whoever replaces you that nobody wrote down?
  38. What could you teach us to do properly in ten minutes?
  39. What do you spot on a walk that nobody with you sees?
  40. What's a skill from an old job you never get to use here?
  41. What's the first thing beginners get wrong at something you do well?
  42. What can you do with your hands that you learned by watching someone?
  43. What do you know about this place that isn't written down anywhere?
  44. What's a trick you use that you've never seen anyone write down?
  45. What advice do you repeat so often that people quote it back?
  46. Guess what I do first when I get home, and why you think so.
  47. Guess my first job, and what makes you say that.
  48. Guess what I wanted to be at ten years old, and why.
  49. Guess how I spend a free evening, and what makes you think that.
  50. What advice do you give that you have never taken yourself?