How do you know whether to ask probing questions or open-ended ones? A good rule of thumb is to ask yourself, “What’s the most likely way I could fail to get the right information in this situation?” Generally, it will be obvious what the answer is: If you’re buying a used car, you’re most likely to fail by not discovering a flaw of the vehicle, or if you’re a vice president seeking feedback from factory workers, you’re most likely to fail by not uncovering what they really think. You can tailor your questions accordingly—more aggressive in the used-car negotiations and more open-ended with
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