Asking and Responding to Tough Questions

Linda Dulye's picture

raise hand.jpg"I try to give them a question that feels like a two-by-four between the eyes." How would you like that in your next job interview or performance review? That's the approach used by Kevin O'Connor, chief executive of, a comparison search engine. In an interview with The New York Times, he shared his leadership approach, including one of the tough questions he asks: "How smart are you?"

People get really uncomfortable. They don't know what to do, and they don't know how to answer it. They know it's kind of a trick, and it flusters them. Or I'll take a look at something that they did, and I'll tell them it's a big mistake and then just see how they react. Do they start crying? Do they get in a terrible rage and argue with you, or do they come back and systematically tell you why you're wrong, or perhaps agree with you on certain areas? So, I'm looking for that.

Are you prepared if someone drops a doozy like that on you? If you're like most, the answer is probably an emphatic no. But you can be ready by simply taking a breath, giving it some thought and offering a sound answer. This applies not only to the "two-by-four between the eyes" variety questions but also those that are asked in team meetings or during a phone call. Just because it took a few seconds to ask the tough question doesn't mean you have to answer it quickly. Now, what about those tough questions that you have the luxury of time to ponder?

  • Tap your social network. If you belong to LinkedIn, for example, post a question for some of your trusted contacts to weigh in on.



  • Do some research. Go online to learn more about the topic. Talk to subject matter experts that you respect. Backed by solid facts and trusted opinions, you can shape your answer.

Answering tough questions isn't easy. But with practice you can be prepared for when they come up and create your own internal process for offering answers.


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