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How to Ask Better Questions

credit: Cherie Cullen (US Army/DOD)

And Get Smarter and More Effective in the Process

The best way to get smarter is to ask questions — a lot of them. When we ask questions, we open ourselves up to collecting more information — information that we wouldn’t necessarily get otherwise. That’s largely because when we ask questions — if we do it right — we are admitting that we don’t know, and we are removing the bias and pretense about the subject of the question that we normally carry.

Unfortunately, we don’t ask questions correctly. Most of the time, when we ask questions, we are not really opening ourselves up to the answers. Often times, we ask questions with some idea of either what we think the answer is, or what we would like the answer to be. Our questions, then, end up being more of a tool for guiding conversations and investigations toward a conclusion that we already favor. But when questions do that, we’ve effectively watered down the potency of questions — they become far less powerful. We end up being mistaken, or just plain waisting our time because we don’t bother to learn anything.

It’s not really our fault. We tend to ask questions with the goal of getting answers, and getting answers right away. It’s no different than the many things we do each day where we look for instant gratification. But like anything else, the good stuff doesn’t happen instantly, it takes time, it takes patience, and it often takes more work than the instant stuff.

How to Ask Questions More Effectively

So here’s a tip that I stumbled across to help ask more effective questions. It’s simple, but it is by no means easy.

Ask a question with the intent to ask at least a new follow-up question based on the answer you get.

When you ask a question, and someone gives you an answer, you will often get the urge to accept the answer, note it, and move on. Resist this urge. Resist it because the more professional or high-stakes the situation, the less likely the person answering your question will give you the whole truth at the outset. It’s not always that people are trying to hide things, more often it’s because they are answering off-the-cuff; they haven’t thought through an answer. They haven’t been asked for all of the information, or had it made clear what is important.

So, to make questions work more effectively try this instead: take in what the answer to the question is, and try for a few seconds to formulate a follow-up question. Here are a few easy examples of general follow-up questions that you can fine-tune, depending on the situation.

  • What makes you think that? This is a great follow-up because it makes it much easier to filter out gossip and speculation. There’s a famous motto at the C-suite that goes: “In God we trust. All others, bring data.”
  • Where did you hear that?/Who did you hear that from? Nearly everyone makes the mistake of taking what are essentially rumors and accepting them at face value. Questions about where the person heard something can get both of you to take a minute to examine the source of the information that was being passed along as something like fact.
  • Could you explain what you mean by that? (best for short expressions of opinion) I, just like many people, will often say something that sounds good in my head, but upon examination is a bit vague. Don’t make the mistake of assuming that you can tie up the speaker’s loose ends by drawing your own conclusion. Have them explain what they mean; have them make the vague more precise. That can rarely be a bad thing.
  • No, I’m not familiar with that (person/theory/event/etc.), could you fill me in? Look, we all want to appear smart, and often one way to do that is to be charitable to ourselves in the things we know about. Sometimes we overshoot (as happened in this great clip from Jimmy Kimmel), and pretend to know stuff we obviously don’t — to save face. Doing that is a surefire way to lose something in translation. Err on the side of appearing to know less than you do when you’re trying to get information from someone. It can help you by getting more information out there, and helping you make connections in your own mental web a lot better.

Questions are like a bladed weapon. When sharp and used correctly, they are extremely precise and effective. When dull and fumbled, they are useless and possibly harmful to the user.

Go forth with better questions, and ask not to get a quick answer, but to ask even more questions. The difference in your level of understanding might amaze you.

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