It’s Not Enough To Ask The Question. It’s About Listening To The Answer.

Why the art of inquiry matters more than ever in the age of AI

I’ve never been someone who has had a problem asking questions. Despite my mother’s insistence that I asked her too many questions growing up, I’ve never stopped. It’s partly a combination of my New York roots and my Greek-American heritage. Plus I am a curious person. Curious people like to ask questions. They want to know more.

It turned out to be an asset when I got into media sales. An early boss told me if I learned to ask the right questions I would get all the information I needed to close a deal. He was right.

As a professor part of my job is to ask questions of my students but also to encourage them to ask questions of me. I am always surprised why so many of them have trouble asking. When I started to experiment with GenAI I was reminded why. It also reinforced how in a world where so much information is available to us any time we want it, question asking skills are more important than ever.

Talk to it like it’s a human

One of the first things I was told as I began my adventures with GenAI tools was that I needed to ask it questions as I would if I was conversing with a human being. If I did that I would get the best results. That sounds easy enough - especially for someone like me who likes to ask questions but it turns out it’s awkward. Very awkward.

Is “it”a he or a she or non-binary?

Does that even matter?

How can I ask a question when I can’t see a visual reaction of the person I am asking?

Once I got good at pretending I am conversing with a human it got easier. Maybe that’s why I like Claude so much. Claude is a human name so it is easier for me to transfer skills.

The point is that my lesson reminded me that not everyone is comfortable asking questions.

It’s not just about the questions. It’s about listening to the answers.

When that early boss told me if I asked the right questions I would get everything I needed to make my argument, he didn’t mean just rattling off a list of prepared questions. The implication was to listen to the answers I was getting and ask more questions based on what I was hearing.

In other words, practice the skill of critical thinking - something that seems to be harder and harder for people to grasp as we step deeper into this world where we can type a question into a search bar, get a quick answer and assume that answer is correct.

Whether it is AI or a human if you’re not getting what you want or understanding what you are getting, you need to ask more questions.

Asking better questions = getting better answers

Whether I am asking a question of Claude or one of my students if I don’t get the information I want the first time or if the answer I do get doesn’t feel right I first check in with myself to see if my question was specific enough. Then I keep asking.

The assumption that the first answer you get is 100% correct is never a good one. Like humans these tools make up answers on occasion. What I call lying they call hallucinating.

The more you ask, the better your question asking skills get

If you’re listening to the answers you are getting and asking more questions, your question asking skills are more likely to improve. Like anything practice is the only way you get close to perfect.

If you don’t ask, you don’t get - or you get something you didn’t want

Anyone who has ever sold anything - including themselves for a job knows that if you don’t ask, you don’t get. The other part of that is that if you don’t ask, you may wind up with something you didn’t want.

As I write this the stock market has been on a roller coaster ride since last week after the administration announced massive tariffs. Social media is flooded with accounts of people who say this is not what they voted for. They’re surprised at the chaos. But they shouldn’t be. Chaos is what they voted for.

Sometimes it’s the answer itself that needs to be questioned

One of three things likely happened. It’s possible they did not ask enough questions before they made their decision who to vote for. Another possibility is they were hearing the answers they were getting but not actually listening. There is a difference.

It’s also possible that they blindly accepted the answers they were given. They trusted without questioning - which does not make sense whether the conversation is with a human or AI.

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💭 If that doesn’t make sense maybe this does:

😡 Almost half of Americans say people have gotten ruder since the COVID-19 pandemic via Pew Internet Research

💯Action: Your Antidote to Anxiety and Other Ills via Gloria Feldt

📚What I’m Reading: I Am Maria by Maria Shriver

🤔How To Think Critically via Indeed