How Can We Ask Better Questions?

Previously, I wrote about my favourite TV talk show host — Craig Ferguson, and gave a little snippet of who he is. At that point in time when it was still airing, I thought The Late Late Show was purely entertainment for me. However, I soon realised that I was wrong. There is so much, but it is not all that there is. It wasn’t just entertainment, it was educational for me too. Craig Ferguson hosted the show for a decade, and over the years, he improved tremendously from his accent to the way he conducts his interview. Specifically, he became incredibly sharp with asking the right questions.

When his guests were nervous with the interview session, he would ask questions that were more personal and lighthearted to gradually ease them into the conversation. When his guests were comfortable with the setting, he wasn’t afraid to set up questions that were meant to cut through the clutter and allowed them to bring wisdom to the table. I was, and honestly still am amazed at how he was able to balance leaning on one and learning from the other. Craig Ferguson had a huge impact in changing the course of my life, at least in the area of having a decent conversation. He illustrated the power of asking the right questions, and I was drawn to it. How does that work for him?

More importantly, how can I tailor that for myself?

There are a few things to consider when we formulate questions, and one of them is to examine if the question we’re asking is one that can be answered relatively quickly. When we exercise, we start with warm ups before we plunge in the real deal. Similarly, when we have a conversation, we should start with questions that are relatively easy to answer first. Can he or she come up with a concrete answer in 5 seconds or less? If the answer is no, then we ought to alter the question. A bad example is — “What is your favourite book?” Chances are, people have read many books in their lifetime, and it takes a considerably amount of effort to filter through some of their favourites. Sometimes all we need is a little tweak.

Instead of asking — “What is your favourite book?”, we can switch it to — “What book or books have you gifted the most to other people?”

In comparison, the latter narrows down the search query to be more refined. I believe when we have our deep heart-to-heart talks with our friends, probably with a glass of wine under the starry night, we have encountered the question — “What makes you happy?” More often than not, our answers were vague and it seemed like we were getting nowhere. Instead of asking the prior question, perhaps we want to consider asking something along the lines of — “What makes you feel most relieved after work when you get home?” or “What activities or who are the people you want to surround yourself most with?”

Given the way that the question is phrased, the answer is short and sweet and much more actionable.

In the first few years of his hosting interview, Craig would normally ask — “What have you been up to recently?” There is nothing wrong with this question, however if he senses that the guest needs more time to think and there could be a potential awkward pause on the show, he would almost immediately sequence a second question to shorten the process — “Did you go shark diving?”

Initially, his questions were ridiculous to me. But I discovered that there was always an intent for most of his questions.

If we want to ask a question that can be kind of heavy, especially a technical question, we should not lead with it. We might be prepared and warmed up for the conversation, but who we are talking to might not. He or she may not even be in the mood to talk, much less to retrieve skills and blueprints in their head. So it is really important to start with small questions first, and gauge their responses to see if they are engaged and if the conversation is flowing coherently. Once we get that, we can ask the heavier questions. It seems intuitive and commonsensical, however we still often misjudge the pace of our conversation.

We are so hyped up on what we want to talk about, but it is in these moments that we tend to neglect how the other party feels.

In the art of asking questions, one of the things that Craig do very well is extracting little shred of personality from his guests. When we have a conversation with someone, it is interesting to know what is on their resume, but it is even more intriguing to know their backstory. We don’t just want to know their age, status and job position, we are eager to know their interests and perspectives too. However, it can be challenging to elicit personal answers than general ones. In order to bridge this gap, Craig would drop the heavy question, followed by a sharing of his own experience with the intent for his guests to listen and have some time to think about their answers. There was a guest who once asked Craig on tips in being a good interviewer, to which Craig answered — “Be genuinely curious in who you are talking with.” I was blown away by his answer. It was so simple, so utterly brilliant and I sincerely believe that is the hallmark of a good conversation.