The Power of Questions

Most of us don’t ask enough questions. In situations like job interviews, dating, or work meetings, we often overlook the power of questions in favor of talking about ourselves. It’s easy to fall into this trap. As humans I think we’re prone to always wanting to prove ourselves and our self-worth. Good questions, though, seem to achieve two really important things:

  1. Good questions signal that you’re interested in hearing what this person has to say, which makes them feel more important and helps establish rapport faster.
  2. Good questions help you unlock knowledge that you wouldn’t have otherwise known had you not asked. More knowledge helps us make better decisions.

Are there any bad questions? Yes, that’s why I emphasized “good questions” instead of just “questions”. In an interview with Patrick Bet-David, creator of Valuetainment on YouTube, Mark Cuban said that “questions you ask, tell me, tell whoever, more about you than anything else you do. In particular it tells me about your preparation”.

So how do we think more systematically about the questions we ask so that we’re not only just asking more questions, but better questions? One thing you can do is start to categorize them. By categorizing your questions you get a better sense of which questions to ask at which moments. It also forces you to anticipate the responses you might receive.

One thing you can do is start to categorize your questions. By categorizing your questions you get a better sense of which questions to ask at which moments.

I’m a big fan of the categories that I learned from Craig Wortmann, Clinical Professor of Entrepreneurship at Northwestern University’s Kellogg School of Management. In his online course, Mastering Sales: A Toolkit for Success, Professor Wortmann outlines the following types of questions:

  • Discovery Questions: seek new information and is the one we’re most familiar with. Discovery questions are typically asked first before any other type of question.
    • Example Discovery Questions:
      • Social: How are you?
      • Job interview: What does success look like in this role?
      • Work meeting: Could you provide some background on this process?
  • Qualifying Questions: qualify the person you’re talking to and whether you should continue talking to them. In sales that could mean whether this person has buying power. In job networking that could mean whether this person has hiring power.
    • Example Qualifying Questions:
      • Social: What are your hobbies outside of work?
      • Job interview: What is your timeline for filling this role?
      • Work meeting: What is your role in this process?
  • Follow-up Questions: seek additional information based on responses that were previously provided. These types of questions are usually spur of the moment unless you’re anticipating what the person will say prior to the conversation.
    • Example Follow-up Questions:
      • Social: So how did you like living in Austin?
      • Job interview: Earlier you mentioned that there was traveling associated with this role. How often is traveling required?
      • Work meeting: Based on what you’re telling me it seems like this process is very manual. How can we involve IT to help automate this for you?
  • Clarifying Questions: clarify information that has been previously provided. They are often more close-ended than follow-up questions.
    • Example Clarifying Questions:
      • Social: I’m actually not familiar with that place. Where is it located?
      • Job interview: Sorry I’m actually not familiar with that acronym. What is “FTT”?
      • Work meeting: Just so I understand you, after you wire the money it creates a journal entry that you then need to manually pair off. Is that correct?
  • Impact Questions: seek new information in a way that forces your listener to re-frame their view of the world. Impact questions are more thought-provoking and can help you stand out from others. You can often turn a discovery question into an impact question by asking “why”, forcing your listener to time travel, personalizing the question, or changing context with a leading “If” statement.
    • Example Impact Questions:
      • Social: What gives you the most joy where you currently live?
      • Job interview: Two years from now, how would you expect this role to have developed?
      • Work meeting: Why are you considering these other projects as higher priority?

Questions come in many different forms, and you may already have your own types of questions for specific situations. Cedric Chin from Commonplace for example talks about the value of head-fake questions when qualifying companies he interviews with. I would categorize this as a really good qualifying question which is why I’m a big fan of the categories Professor Wortmann created above – they’ll likely encapsulate the majority of questions you could ask in any situation.

So, which type of question should we ask the most? If you’re thinking impact questions, here’s why I disagree with you.

Impact questions are powerful because they are often head-turners, but a conversation with too many impact questions might also feel like an interrogation for your listener. In any given situation I would only ask one or two impact questions at most. Instead, focus more of your attention on follow-up questions. Harvard professors Alison Brooks and Leslie John wrote about the power of follow-up questions in a great article for HBR, and the reason they like follow-up questions more than others is because it signals to your counterpart that you’re listening and want to know more.

In my personal experience of trying to improve at asking good questions, I’ve observed that question-asking is as much an art in keeping the flow of a conversation going as it is the science of seeking and experimenting with new questions. Follow-up questions can dig deeper on a topic and will often branch your conversation into new territory. Knowing when that territory has been fully explored (thus giving you gateway to change context with a discovery or impact question) versus continuing to dig deeper (with more follow-up or clarifying questions) involve subtle conversation skills that can only be developed through – you guessed it – more conversation and question-asking.

Focus more of your attention on follow-up questions. Good follow-up questions signal that you’re listening and want to know more.

No matter how much you strategize about the questions you ask and the ways you can improve them, none of it will matter if you’re not listening.

So above all, be present. Listen. Breathe. You might just realize how much information you were missing in the first place.


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