Want Better Conversations? Learn to Craft Intentional Questions.

Which questions do you ask the most in casual conversations?

Are they, more or less, the same questions that most people ask?

If so, you can likely benefit from learning the art of asking intentional questions. And the good news is that this is actually pretty easy to master once you've done the groundwork.

All it requires is a little bit of preparation and an idea of what kind of conversations you want to have.

You see, most people ask the same standard questions over and over again.

• "Where are you from?"
• "What do you do for fun?"
• "What do you do for work?"

And while there’s nothing wrong with asking these questions when you have a genuine curiosity and interest in them, they otherwise rarely create sparkling conversations.

In fact, most people tend to reply to these autopilot questions with autopilot answers by regurgitating the same words they've said tons of times before. And it might even make them mentally check out of the conversation because it feels like one they’ve had countless times before.

So how do we avoid this in favor of genuinely interesting conversations?

Well, we simply have to replace our autopilot questions with intentional questions.

What are Intentional Questions?

Intentional questions are questions that you’ve intentionally crafted (duh;) because they’re likely to spark conversations about things that you are genuinely interested in.

They can still be generic, appropriate for most people in most situations, and even fairly broad. The important thing is that they stand out from the autopilot questions most people ask, and that they increase the likelihood of getting answers that you find interesting.

Some of my personal favorites include:

• “What’s exciting in your life these days?”
• “What kind of things are you interested in?
• “What goals or passion projects are you working on these days?”
• “What are your favorite things to do when you have the time and energy?”

When I ask questions like these, most people have to pause for a moment and think about what to answer. When they do, their autopilot will turn off, and they'll tend to tune in to the conversation more fully.

The simple fact that these questions are unexpected means that they have to be present in the conversation with me to answer them. And the fact that they are unusual makes the conversation stand out from all the others they’ve had.

How to come up with your own intentional questions.

Coming up with intentional questions is easier than most people think.

The first step is to decide what kind of conversations you want to have. If you’re not sure, you can usually figure this out by asking yourself questions like:

• "Which topics do I like discussing?"
• "What do I like learning about other people?"
• "Which parts of people’s lives am I curious about?"
• "Which types of conversations tend to be most interesting?"

Personally, for example, I enjoy conversations about positive or aspirational topics, so questions about positive events in people's lives or their ambitions or goals tend to work well for me.

Someone who enjoys discussing current events might ask something like, “What have you been following in the news lately?” And someone who likes discussing entertainment might ask about which movies or shows people enjoy or if they’ve discovered any new music lately.

So, what do you enjoy talking about?

Write an extensive list, and select the ones that feel most fitting for most of the conversations you tend to have.

Once you have that list, all you have to do is come up with a handful of questions related to those topics and memorize them. (It’s not a bad idea to write them down in your phone so you can easily remind yourself during social situations.)

Then, practice.

Start asking those questions in conversations every day. Ask friends, acquaintances, colleagues, strangers - it really doesn’t matter.

Once it becomes as natural for you to ask these intentional questions as it has been to ask the standard ones in the past, you’ll far more often find yourself in conversations that are both more enjoyable and connected.

So, what kinds of conversations do you enjoy having? Let me know in the comments!

Also, want to learn more about turning dull small talk into something valuable, interesting, and enjoyable?

Check out my Small Talk for Introverts course here for free (and don’t worry, extroverts, the techniques in there will work for you too!)