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Questions for the Crazy Curious

After my last post, Are You Crazy Curious?, several Red Cape Revolutionaries (and aspiring cape-wearers) asked me a variation on this question: “I’m already crazy curious about something that I think could move my work/career/success forward, but I’m not sure how to find the answers I need. Help!”

Well, I say the answers are in the questions. In Big Questions. Good questions.

As folks who’ve worked directly with me know, I’m a fan of the Big Question, the powerful question, the question that stops the conversation and makes you think twice. (Insider’s secret: when one of my clients says to me, “Hmm. . . that’s a good question,” I secretly do the Happy Snoopy dance in my head, Vince Guaraldi score and everything,  because I know I’m doing my job.)

Questions–Big Questions–are the tool of the crazy curious. And they’re a tool you can use right now, with no training, practice, or investment. What a deal!

Here are some of my favorite Big Questions to ask about anything or anyone you’re curious about–including yourself! I’ve seen clients use these to find out more about their boss’ honest view of their career potential, to quickly surface concerns on a project that looks good on the surface but is starting to “smell funny,” and to test the waters with colleagues and connections before making a professional change.

Here are some good, big questions to try:

  • If you had a magic wand, what would you create [in our company, department, on this project, in my career] that would make the biggest difference right now?
  • If there were no consequences, what would you do to [create whatever the desired result is]?
  • On a scale of 1-10, with 1 being (one end of the spectrum) and 10 being (other extreme), where are you right now on [whatever the issue or concern may be]?
  • What does your gut say?
  • What’s not being said out loud?
  • Why do you care?
  • What’s the question behind that question?
  • When you look back on your career (or life), what do you want to be famous for?
  • What’s getting in the way?
  • How do you know that for sure? (helpful when you or someone else is falling back on assumptions that may or may not be true.)
  • What’s the action you’re willing to take here to move forward?
  • What’s the question you’re afraid to answer?
  • What’s the question I should have asked?

YOUR TURN: How will you use good, Big Questions to satisfy your crazy curiosity? Try these out and tell us about it by leaving a comment below or sharing on Facebook!


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