Three Ways to Ask Better Questions

7 minute read

One of my favorite podcasts is by a historian who has an amazing ability to bring events to life.  He occasionally brings guests on his show to discuss specific periods or people in history. I’ve listened to many of his interviews with guests and almost felt bad for him…he has such brilliant guests, and I just wanted him to ask better questions.

Right now, you may be thinking, “What defines a bad question?”  

Now that is a good question!  

Here are the top three ways you’re probably asking bad questions right now.

They’re not actually questions

Sometimes people will “ask a question” that actually isn’t a question. It’s a statement or recommendation posing as a question. You’ve certainly heard (or said) things like this:

These are rhetorical questions…which aren’t actually questions at all. They are half-hearted suggestions that are dressed up as a question. This creates a disconnect because it can come across as condescending, leading, or fuzzy. When someone is already feeling pressure in a tough situation, and your intent is to provide assistance, these really don’t help.  

Here’s how to make those better: lay out two to three key facts and then clearly make your recommendation. You’re setting essential context and offering a different solution. You may also ask how others view your recommendation, providing space for people to tell you how they see it. Instead of saying, “Do you think we should start over?” you could say, “We’ve worked on this for three weeks without serious progress with this approach and have burned through 75 percent of our budget and time for this phase. I really recommend we start over with this. I know that’s hard to hear, and we’ll get further much faster that way.  What do you think?”

Poor questions are too limited or simplistic

This is the realm of yes/no questions…the daily grist of bad questions. These are usually way too limited to advance a conversation and usually require follow-up questions to make sense of the first one. And to get a good sense of a situation, you may end up asking a bunch of yes/no questions instead of one good question. Or, someone answers your yes/no question with what they’re guessing you want to know and may be totally missing the mark.

I remember 20ish years ago when I had a bad habit of asking yes/no questions, and someone answered my crappy question with a simple “yes.” I was expecting more and copped a bit of attitude. They looked at me and said, “Don’t get worked up. You asked a bad question, which I answered.  If you want a better answer, ask a better question.”  

BOOM!! That hit home and really stuck with me to this day. That guy wasn’t being difficult. I was the one using craptastic questions that weren’t accomplishing what I wanted and then getting spikey with him!

Yes/No questions are rarely useful since they pin things down to just one answer when there is tremendous grey space in the majority of situations.  

They are also too simplistic.

Consider these examples:

You may think that you’re reducing options with a yes/no question, which is true. You’re also doing all the work thinking through what could have happened to ask a bunch of crappy yes/no questions. This is tiring for you since you’re working to figure things out when you don’t know, and the other person is worn out from a blizzard of yes/no questions. 

You’re also probably doing way too much talking when you really want others to be talking. If you want to get others to share what happened or their ideas or recommendations, ask a good “what” or “how” question to hear from them, and then BE QUIET. 

Two simple examples are:

Bad questions lack a clear purpose

You’ve certainly seen parents—maybe even yourself—get peppered by non-stop questions from their children. It’s fantastic that kids can be curious, go in lots of different directions, and ask loads of questions…some of which are awkward or seemingly pointless. 

While this is understandable (though perhaps tiring), it’s not acceptable for adults to ask questions without a purpose. You’ve been in situations where someone is asking lots of questions, interspersed with their ideas, or asking run-on questions that get all tangled up. The podcaster I mentioned at the beginning of this blog will start asking one question, jump to another one, then keep rambling, inserting another one or two before he finishes his question monolog. Sometimes the guest will even stop and ask the host which question to answer… that would be the clue phone ringing that something is way off with his interview questions. 

Get clear on your intent before you ask. You may be getting more information, holding someone accountable, soliciting others’ ideas, or helping the team approach a problem from a different perspective. You may be doing multiple things at once. Whatever your intent is, be clear on it, and then create a good question to serve the purpose(s).

Practice, Practice, Practice

 This won’t come easily…you will slip into old habits. A few things you can do to help yourself:

It will take some work to shift your thoughtless habits around questions. The best way to do this is to practice daily. The leaders we work with say that spending 5-10 minutes each morning preparing questions for a few meetings later in the day is the most productive way to get ready. If you want big-time changes in your conversations, ask better questions… it’s totally worth it to you and those around you!