6 Ways to Use Questions as Jedi Mind Tricks

In one of my favorite scenes from the TV show The Office, Robert California (the boss after Michael Scott) is able to start a conversation with the normal, “How are you today?” and then use someone’s response of “Fine” to get them to reveal one of their darkest fears with just a few, powerful follow-up questions. As coworkers stand around awkwardly, he turns to the next person and asks, “And how are you?”

“Just great!” is the quick reply.

You might know someone like this who can direct a conversation almost miraculously. Like a Jedi master, they ask a question with a wave of their hand and suddenly reality bends to their will. I know several people who excel at this, and I’m always amazed at what they can accomplish in a short dialogue. The management guru Peter Drucker was famous for helping clients clarify and simplify their thinking. He said, “My greatest strength as a consultant is to be ignorant and ask a few questions.”

The good news is that asking questions is a learned skill, and like all skills it takes practice. Here are 6 ways to use questions to your advantage:

  1. Answer a question with a question. When someone asks you a question, resist the urge to immediately launch into a lengthy explanation. Your answer may be off-point and you would have no idea. I’m always surprised by how long people can ramble after an open-ended question like, “So tell me about yourself [or your company].” Instead of taking the plunge, ask in return, “Sure! What would you like to know?” Questions like, “Why do you ask?” or, “Why, what have you heard?” are great for finding out how people will respond before you’ve even given them an answer.
  1. Ask a clarifying question to buy yourself time. Ever been put on the spot? No one likes to look like a fool, so give yourself more time to think with a follow-up question. More than once I’ve had a moment of panic when a client asked me something, and I didn’t have any idea what to say. By asking them to clarify, I was able to either figure out what they were asking… or at least give myself a minute more to think of a response.
  2. Pitch a question instead of an idea. If there’s something you think your company or team should try, don’t launch straight into the pitch and risk being immediately shut down before the idea is considered. Alternatively, ask, “Have we ever tried a different approach?” Or, “What do you think could happen if we….?”
  3. Ask a disruptive question to reframe a conversation. If you feel like a conversation is stuck and you’re not getting anywhere, a disruptive question can shake things up by allowing everyone to take a step back and look at a problem with fresh eyes. The idea of a disruptive question is that it’s unexpected or hasn’t been clarified before. Some even use “shocking” questions, but that isn’t usually necessary. It could be something as simple as, “Why do you think this is so important to you?” Or, “What would we do if this wasn’t an option anymore?”
  4. Ask for a description instead of an explanation. This tool is helpful if the person you’re talking to is having trouble explaining themselves. Counselors ask questions like this to help make a vague idea concrete. Instead of, “Why don’t you think your marriage is working?” the question would be, “If you were to wake up tomorrow morning and the problem was ‘fixed’, what would happen differently throughout the day?”
  5. Use silence to prevent jumping the gun. This technique isn’t a question, but it’s just as powerful after one. Interrupting someone is not only rude, it can also cut you off from important information that was coming next. If someone doesn’t answer a question immediately, it’s normal to want to fill the void by rephrasing the question. A silent pause can feel awkward. But this awkwardness can say much. After someone has answered a hard question, I frequently leave a 10 second pause to make sure they’re finished. More often than not, they start talking through their answer again before I reply. You’d be surprised how critical the information after the silence can be.

Andrew Sobel writes, “Good questions are often far more powerful than answers.” In a knowledge-crazed world where everyone is constantly looking for better answers, perhaps it’s time you started to look for better questions.


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