There are many books out about the "perfect interview" questions, but I think you will improve your skills in this area if you simply try to be more like Barbara Walters.
Her interviews are conversations. She gets people to open up, to reveal their true selves because they don't feel like she is firing questions at them (even though she is). They relax and simply engage in the discussion with her. That discussion is organic—one response leads to Barbara taking a path to another topic that you sense was not pre-planned, but was rather inspired by the dialog. This seemingly casual, yet very organic process, consistently results in a meaningful and insightful discussion.
I say “seemingly casual,” because I believe that Barbara enters into her interviews like a good interviewer enters into a discussion with a candidate. Not with a full list of pre-planned questions, but with a discussion plan that is based on the candidate's resume, their experience, and the qualities and characteristics that will enable that candidate to be successful in the new role. When entering a discussion with this broader outline rather than with a script of questions, you, like Barbara, will more likely discover the essence of the person. You will not only learn what they have done in their career, but equally important, you will discover why and how they did it.
One more important piece of the equation—in having a conversation versus an inquisition, you are more likely to discover (through the enthusiasm in their voice tone, for example) where the candidate's true passions lie.
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