Are You Asking Questions that Boost Conversation?

This type of question boosts conversation

“There is magic, but you have to be the magician. You have to make the magic happen.”


We all wish for a bit of magic in our social lives.

  • We hope that special someone appears.
  • We dream of spellbinding people quickly.
  • We desire to read thoughts and connect.

Real conversation isn’t quite so instant. But there is a technique that borders on conversational magic.

It hinges on the type of questions you’re asking. And, if you get this little bit of magic right, it compels the other person to talk more, reveal more and feel great about you.

The two types of questions

Most communication experts suggest asking questions to engage others in conversation. But the type of question you ask can make a BIG difference.

There are two types of questions:

  1. Close-ended
  2. Open-ended

Both have their place in conversation. But many people, especially those who are shy or not the best talkers, rely heavily on the close-ended variety.

This is a problem for two reasons:

  1. It promotes an interrogation-type conversation
  2. It draws out less free-information from your conversational partner

Close-Ended Questions

Ever been in a conversation like this?

Sally: How long have you been running?

Bob: I’d say about 10 years.

Sally: Wow, you must like it, huh?

Bob: Oh I love it.

Sally: Do you run often?

Bob: Fairly often.

Sally: That’s great…Do you do any other kind of workouts?

Bob: Yes, I go to the gym.

Sally: Oh really, where?

Bob: Mid-city.

This conversation is going nowhere because Sally is asking ALL close-ended questions. This is the interrogator version of a conversation because it’s just question after question after question.

It gets old real quick.

But Bob isn’t giving Sally much to comment on is he? Is that his fault?

Well maybe.

Thing is, Sally isn’t asking questions that encourage him to talk in detail. Close-ended questions are kind of like true/false or multiple-choice questions. They lead to only one or two word answers.

This can be useful, but only if it’s used together with open-ended questions.

Open-Ended Questions

If close-ended questions are true/false, open-ended questions are essay (I know, you loved those in school right?). Open-ended questions encourage longer, more thought out answers. They ask for elaboration and more information.

For example, in the above conversation, when Bob said he loved running, Sally could’ve followed with:

“That’s really awesome! What makes you love it so much?”


“What got you into running?”


“How do you find the motivation to run so often?”

See how these questions can’t be easily answered with only one or two words? They let the other person fill in the blanks and talk more extensively. Sally could’ve also asked for opinions or feelings:

“Tell me this, because I’m curious what a true runner thinks. How do you feel about those extreme competitions where people run 50 miles or more?”


How do you ask these questions?

As you can probably see, open-ended questions begin with some of the typical “W’s & an H” question words. However, some are better for open-ended questions than others.

Those are: Why? What? How? In what way?

Close-ended questions generally start with: When? Where? Who? Which? Are? Do?

'I sold art for a while on cruise ships. Open-ended questions are important in sales. They help you know what your client wants. In conversation, open-ended questions help you connect.'

I mentioned close-ended questions have their place in conversations and they do. In fact they’re unavoidable. Close-ended questions get people to reveal specific facts like where they’re from or what they enjoy doing. You can then follow-up with open-ended questions to delve into that subject in more detail.

But remember, as I mentioned in my post on how to start a conversation, an interaction is more than just questions. Be sure to make statements and comment too.

State your opinions and reveal something from your life that relates.

Benefits of Using Open-Ended Questions

  • It gets the other person more engaged. The more they talk and put effort into the conversation, the more engaged they become. If you’re the one initiating the conversation, then part of your goal is getting them more invested in the interaction.
  • They like you more. Dale Carnegie said to get others interested in you, first be interested in them. By offering the opportunity to talk about themselves, you make them feel listened to and special.
  • It gives you more to work with. The more they say, the more free-information they reveal. This gives you more opportunities to take the conversation in new directions.
  • You can talk less. If they talk more, you can talk less. As an introvert at heart, this is the BOMB-diggity!

Take Action

Consciously work to ask open-ended questions in appropriate situations. Even if it’s only once a day at first, eventually you’ll be able to do it without even thinking.

You’ll soon find that your conversations magically open up as if you’d uttered a well-placed chant of “Alohomora.”

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