The Art of Asking Good Questions


You won’t have to hang around here long to discover one of my favorite soap boxes: that the world needs to learn to ask better questions… in life and ESPECIALLY at conferences.  Nothing is more maddening than a Q+A session that gets side tracked because someone at the mic ends up with “I guess, more of a comment than a question.” 

While asking good questions is truly at the core of the work I do today, it’s a skillset that all leaders can benefit from.  Whether you're leading a team, engaging at a presentation, or simply navigating everyday interactions, refining your questioning skills can profoundly impact the quality of communication and understanding.

So today, we’re taking it back to the basics and learning the art of asking good questions.

Ask

In its simplest form, a question is “a sentence worded or expressed so as to elicit information.”  I feel like it’s important to start with this basic premise because it’s common to use the guise of a question to express opinions or give answers instead. 

To get technical, there are generally four main types of questions.  Three of them elicit simple answers:

  • General yes/no questions (Do you have a dog?);

  • Choice questions (Do you prefer cats or dogs?);

  • Tag questions (That’s a dog, isn’t it?);

The fourth type, the real player in the question game as every journalist knows, is the “Wh-Questions” – who, what, when, where, why and how.  

Focusing on the open-ended questions (“why”, “how” and sometimes “what”) is where you get the most bang for your question buck.  Questions framed this way encourage exploration and diving deep. They can unveil insights and details that may not have been revealed otherwise. 

Try This: One of the most insightful exercises we did during executive coach training was spending a day asking only open-ended questions.  You’ll be surprised how often you frame questions in a yes/no/this/that format and how much more information you receive by creating an opportunity for it to be shared.  Most of us are familiar with Start with Why by Simon Sinek (if not, check out the Ted Talk), but that’s not the only way to explore this type of question.  Think “Did you do that” vs. “What are you doing” or “Why did you do that?” or “How did this happen?”

Answer 

Just as important as the question is the space that follows for the answer.  Once you have asked the question, stop talking.  It’s easy to fall into the trap of over-explaining or asking the question again in a different way.  Be thoughtful about how you’re asking the question on the front end and then lob the ball over the net to give the person you’re asking a chance to respond.  They’ll ask for clarification if they need it. 

One of the most powerful tools we have when asking questions is silence.  Once you’ve created a space for the answer – maximize it. Not only does it give the person you’ve asked the question to time to stop, think and provide a thoughtful answer, but by waiting it out instead of rushing on, you can often get more information than you would have originally.  My rule of thumb when asking tough questions is to wait a count of ten before reframing; during everyday conversation, a count of three seems to provide enough pause. 

Attention

Listen and pay attention to the answer.  If you don’t care about the response, don’t ask the question in the first place.  This is a key place where trust is built and trust is lost. Listen for information and once you’ve heard the answer, then frame the follow up.  

We live in a “Just the Facts, Jack” world and asking powerful questions, not to mention actively listening to the answers, takes time.  But one of the things I’ve loved the most about learning to ask good questions is that it’s really improved the caliber of answers I get.  The details provided are more vivid and nuanced, I better understand motives and inspiration, and as a bonus – the experience of the conversation is often more enjoyable for both people involved.

Bonus Tip: How to Ask a Good Question During a Presentation

I couldn’t close this post out without stepping on my soapbox for a moment to share a few tips on how to impress a room with your question asking skills. 

Make sure the question is relevant to the entire audience.  If it involves a situation with lots of specific details, it may be better addressed off line. 

  • Succinctly frame your question.  Think: two sentences or less. If it requires a backstory to set the stage, it also may be better addressed off line.

  • Make sure you’re seeking information.  If you want to debate a topic or point with the speaker or share your own experience, consider if the format lends itself to that type of exchange first. 

  • Write it down.  It’s easy to lose focus when the spotlight is on you.  Having your question written in advance can help keep you focused. 

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