Asking the right questions

Are you good at asking the right questions in the right context?

Here are some questions I will ask more of.

When you hear things are impossible, problematic or difficult, try to lift the cognitive load of reality and let the person play with the imagination, and solutions may become more accessible.
  • What would it look like if it were possible? What would it look like if it were easy?
  • Imagine a miracle happened and your problem was solved. How would you know?
Instead of examining something problematic, difficult or bad in isolation, try to get clarity from contrast.
  • "This is so hard / bad / problematic ...", ... compared to what?
Have you met people who are very confident and firmly believe they are right and that they know the answer or solution? Be curious, and ask some questions.
  • How do you know that? How do you know that this is the right thing to do?
  • What leads you to that conclusion or to that assumption?
  • What might happen if it's wrong?
  • What are the uncertainties in your reasoning?

When you are presented with new strategies, directions or processes, don't you sometimes wonder ...

  • Do we have to change in an obvious way in order to execute this strategy?
  • What do we need to do in order to deliver on this? What do we need to stop?
  • How do we know if this new strategy, process or whatever is successful? How do we recognize a successful execution?
Sometimes I feel overwhelmed and stressed over all the problems and opportunities that should be addressed and solved.
  • But what happens if we do nothing? Maybe that's a question we should ask more often.
Have you ended up in a deep rabbit hole where the discussion leads nowhere?
  • What are we trying to accomplish here?
  • What are we up against here?
  • How would you like me to proceed? How can we solve this problem?
Learning is important for me. These fun questions are difficult to answer, but they at least trigger some reflections.
  • What have surprised you the most?
  • What's the most difficult thing you did the last X weeks/months, and what did you learn from it?
I am not good at small talk with new people, so here's at least one opening I use.
  • What are you currently working on that you are most excited about?

What questions do you tend to ask and why?

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