10 Ways to Ask Great Questions

By Dennis McCafferty  |  Posted 01-23-2014 Email Print this article Print

Let's face it: Most of us love great interrogation scenes in movies or TV shows. From countless detective shows to 24 to the climax of A Few Good Men ("You can't handle the truth!"), we get a vicarious rush when we see a protagonist grasp the essence of reality under adverse conditions. In real life, of course, running an IT department is seldom this dramatic. However, CIOs need to routinely conduct inquiries in which actionable information is sought, which an often challenging pursuit. In the book Find Out Anything from Anyone, Anytime: Secrets of Calculated Questioning From a Veteran Interrogator (Career Press), author James O. Pyle (with co-author Maryann Karinch) reveals how the quality of your questions directly translates to the usefulness of the responses you receive. Combining the power of well-chosen words with techniques proven in military, intelligence and legal circles, Pyle illustrates how to make the most out of extended inquiries—whether during a job interview or a discovery effort to learn how a promising IT project failed. Pyle is a human intelligence training instructor who has served at multiple levels of the U.S. Army, including the United States Army Intelligence Center and School. For more about the book, click here.

  • Identify Your Discovery Roadmap

    Before launching the fact-finding session, determine the essential details you seek, and build each one into the ensuing discussion.
    Identify Your Discovery Roadmap
  • Limit Your Assumptions

    Remember: The more you think you know, the less you'll find out.
    Limit Your Assumptions
  • Ask Open-Ended Questions

    Open-ended questions which begin with words like "what," "how" and "why" will help eliminate dead-end "yes" or "no" responses and other unhelpful one-word replies.
    Ask Open-Ended Questions
  • Listen Actively

    That's when you physically engage the other person with eye contact, posture and comforting gestures to make them know that their input is important.
    Listen Actively
  • Don't Overwhelm

    Each question should address a singular line of inquiry, not three, four, etc.
    Don't Overwhelm
  • Reload the Question

    If you have suspicions about an earlier answer, repeat the same question with altered wording later in the conversation to see if the response remains consistent.
    Reload the Question
  • Don't Ask Leading Questions

    That's when you supply an answer that you think you're looking for. But you may prevent a more truthful and valuable narrative disclosure this way.
    Don't Ask Leading Questions
  • Embrace Smart Silence

    Not saying anything in a one-on-one conversation can cause the other person to keep talking, thereby dispensing useful information.
    Embrace Smart Silence
  • Always Opt for Face-to-Face

    Yes, you can get good information from a phone call or text, but you'll always get more in person.
    Always Opt for Face-to-Face
  • Eliminate Distractions

    Go somewhere where there will be no interruptions, with no computers in sight and smartphones turned off.
    Eliminate Distractions
Dennis McCafferty is a freelance writer for Baseline Magazine.


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