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Last week you may have read my blog about saying The Third Thing.  If not, you might want to circle back. It offers some excellent advice to those of us who tend to blurt out the very first thing that comes to mind in our conversations or written exchanges. As you’ll see (or may have learned the hard way), the first thing may not be…the best thing. (No judgment here. Lots of us do this in our fast-paced world. It’s just a habit, but one we could probably do without.)

Today, as promised, I’m going to share with you another conversation trick involving the number three. This one is called “Going Three Deep.”  I’ve seen Oprah, one of the world’s most gifted and engaging interviewers and conversationalists, write about this technique. Other communication experts I know and respect suggest this technique as well.

It’s a crowd-pleaser that can revolutionize your conversations and networking. And it’s really rather simple.

When you find yourself in conversation and are practicing the vital art of asking good questions, don’t just ask your conversation partner a series of rapid-fire random queries. Doing this could make you sound like you’re: a) desperate to keep the conversation going at any cost or b) an aggressive interrogator. Neither of these sound fun or engaging.

Instead, try staying on the same topic and go deeper with each of three questions. 

Need an example?  Let’s say you’re at a business mix-and-mingle event at a local watering hole put on by a professional organization or your company. Your vision for success is that you’ll enjoy yourself and make a few new connections. You’ve just walked up to someone standing by the bar and introduced yourself (which, as you may know, is your social duty and responsibility).  Here’s what the initial conversation might sound like:

You:  So, what made you decide to attend this event this evening?

Them:  I try to make as many of these as possible because they’re a great way to meet other people in the organization / industry. And it’s a setting away from the office.  Plus, I love the local lager they have on tap here.

You:  I’m a local beer fan, too. (Note: the mutual interest in local beer is a topic you can expand on later.) You mean you’ve actually connected with some interesting people at events like this one?

Them:  Yes, absolutely.

You:  Are there any people here you’d be willing to introduce to me?

Them:  Sure. I see my friend Jose over there. Let’s grab you that beer and then go over to say hi.

Bam!  You’ve just made not one, but likely two new contacts. Maybe more if the evening continues in this fashion.  And you can always compare notes on favorite local brews and build on other topics that come up as well.  Just keep Going Three Deep when it seems right.

Here’s another example. Say you’re out having coffee with someone you met at an event like the one I’ve described above.  It’s a get-to-know-each-other-better meeting.

You:  I’d love to hear more about what you do. (Note: Okay, that’s not technically a question, but it’s still an inquiry. )

Them:  [They spend a few minutes describing their job / business while you listen.]

You:  How did you end up doing this kind of work?

Them:  [They spend a few more minutes telling you that story. Again, you listen.]

You:  So, do you love it? I mean, what’s most meaningful to you about what you do?

Them:  [They tell you that story.]

Do you see how you’ve not only learned more about the person’s work, but also the how and the why behind it?  That’s a lot deeper than a lot of coffee conversations go.  The trick is to keep asking and listening without going all over the place.

Your task:  Figure out ways to Go Three Deep in your everyday conversations. And for sure, resist the urge to bring the conversation back to you before the other person barely gets started. You’ll learn a lot more about the other person, build a stronger connection, and….be remembered as a fascinating conversation partner!

Want more ideas on how to enjoy better conversations?  My new book “More Than Just Talk” is loaded with them.   It’s available on Amazon, at BookPeople in Austin, Texas, and via other online book retailers.   Have a question or want to discuss how we can work together?  Email me at