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Critical questions to help you gain useful information, clarify the context, figure out the pain points, and overcome biases.

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what-to-ask-when

When dealing with complex situations, having a list of critical questions will help you gain useful information, clarify the context, figure out the pain points, and overcome biases.

Life

Assessing a story / event

  • (reverse lens) What would the other person in this conflict say and in what ways might that be true? [2]
  • (long lens) How will I most likely view this situation in six months? [2]
  • (wide lens) Regardless of the outcome of this issue, how can I grow and learn from it? [2]

Behavior

  • What do you want to be remembered for? [2]

Career

Changing jobs / teams / projects

  • Are you running away from something or running towards something?

Job (Tech) Interviews

1-1 with your Manager

"To understand her perspective on how the project needs to come together" [1]

  • What do you pay attention to? [1]
  • Where do you get your information? [1]
  • What do you think the 'pulse' of the team is - and what makes you say so? [1]
  • What are you concerned about? [1]
  • What's the lay of the land, as you see it? [1]
  • How is this all going to fit together? [1]

References

  1. https://github.com/yangshun/tech-interview-handbook/blob/master/contents/questions-to-ask.md
  2. What Shape are You? - Brian
  3. Manage Your Energy, Not Your Time - Harvard Business Review

Contribution Guide

Any topics (not just career or technical ones) are welcome!
When adding new questions, please add their source to the References section. For example:

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