Ask Away

4 Simple Tips To Help You Level Up Your Conversation Skills

It’s all about asking the right questions.

Originally Published: 
two adult male friends having happy conversation over coffee

Questions don’t need any campaign to publicize their upside. You ask something. You find out something, like whether this seat is taken or if this is the end of the line. But more than getting information, questions start conversations, which connect people, which gets you more happiness.

And you might already know this and ask questions to your neighbors or fellow parents, but a common occurrence is that every conversation feels the same. Nothing gets deeper, and you’re unsatisfied. The reason could be the questions. They may be honest and well-intentioned, but they could also be boring, giving the person nowhere to go except a one-word answer.

So here’s a question: Can you ask better ones?

The short answer is yes, of course. With a little intent, you can make your asks organic without coming off as strained.

But first a couple of rules. There are no magic questions. The best questions can go nowhere; the worst can lead to great exchanges. The X factor is always how chatty the other person feels, something you can’t and will never control.

The trick is to make them want to talk. One way is to stay away from questions about feelings. It asks for the other person to examine their behavior and most people would rather not.

“They get frustrated because they can’t answer,” says Elizabeth Keating, professor of anthropology at University of Texas and author of The Essential Questions. “When you want to get to know another person, you don’t want to frustrate them.”

There’s the foundation. The following advice might help with specifics:

1. Share Something About Yourself Before Asking Someone Else to Share

There are the people you don’t really know but you see enough that you want to ask something. On Monday morning at the crosswalk, it’s always, “How was the weekend?” That, per Keating, is a terrible question. It’s akin to, “How are you?” Do you really want a health report? No. You want to hear “OK” and move on.

It’s the same thing with this question, but it can be easily tweaked. Keating says to give a quick preamble. We discovered an amazing show from Ireland on Saturday night. What did you guys get up to?” Share first, then ask about their weekend. You’ve offered some momentum and a subject to latch onto, making it all easier for them to follow suit.

2. Instead of “How Was Your Day?” Ask “How’s Your Day So Far?”

Another go-nowhere question, “How’s your day?” It’s too vague, so the usual response is, “Fine.” Instead, ask, “How’s your day so far?” Those last two words make it sound different.

“It makes the listener think and it gets past the surface,” says Dean Nelson, director of the journalism program at Point Loma Nazarene University and author of Talk to Me. It also cuts down the expectations. In a way, you’re asking for a highlight or lowlight, and it focuses the person.

3. Play Off Context To Elicit Better Responses

Sometimes your interaction will last longer, like on the sideline of your kid’s soccer game. What works here is what works for any question. Play off the context. Nelson says that it never hurts to notice hats, shoes, or cars. They often are distinguishing, so you can ask, “Why the Red Wings?,” or you could go purely functional and ask, “How do you like those boots?” The former taps into a love that they’re displaying. The latter plays into a person’s expertise and asking for advice shifts the power dynamic to them and most often gets a conversation going.

Or you ask something based on the event, like, “Have you ever been a referee?” It could be answered with one word, but more likely it would get some empathy and maybe start a conversation about the level of play. Or you just state, “I can’t believe that with 10 kids on the court, none are wearing the same sneakers.” It’s not a question, but an assessment does the same thing. It stimulates a response and “gets an agreement or an upgrade,” Keating says.

And if it’s picked up, you can follow it with, “What was the sneaker of your youth?” Overall, anything that touches on childhood topics — favorite candy, biggest celebrity crush, first concert — taps into a time when you made goofy choices that aren’t embarrassing anymore. The other part is the question has a specific answer, and because it’s fun, it gets a person relaxed and a relaxed person is more likely to keep talking.

4. Show You Were Paying Attention

The above are good approaches for anybody, but then there are the people who you’d mark as a “friend” but that’s on the Busy Dad Curve. You’d like to remove the quotation marks and talk about slightly more substantial things. Do that by asking something that refers to a previous conversation. “What happened with your brother’s visit?” “Did you ever find that garage door opener?” “How did the work phone call turn out?”

Keating says that leading with, “What happened …,” is hard to answer with less than three words, but more than that, it conveys genuine interest and that you’ve been paying attention. That makes anyone feel pretty good. As Nelson adds, “It says, ‘I remember you. I see you. You’re not a role player in my neighborhood.’”

This also is a delicate space, because you’re trying to shift the relationship. It’s a scary move, one that you don’t have a complete say on, but it’s unavoidable. “Risk is part of the magic of friendship,” Keating says. But once you break through that, the trust grows and the anxiety lessens.

One question that might be able to serve as a bridge is, “What’s the most unimportant thing you did today?” The “unimportant” makes it stand out. It doesn’t ask for much but some existing relationship helps because you’re asking the person to consider their life and judge their activities. They could say playing Phoodle or reading minor league scouting reports, but it’s like with any question. They decide where it goes and you follow.

“The answer doesn’t matter,” Nelson says. “It’s the ‘and then and then and then.’ That’s when we’re peeling back those layers of vulnerability.”

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