I received a letter from a listener recently about something many people have trouble with. She wanted to know how to keep a conversation going.

Hi Lisa,

I am based in Melbourne, Australia and came across your pubic speaker material about 3 months ago. I can honestly say that putting into practice what I’ve learned on your podcast and smart talk interviews has had a massive impact on my life. I especially love how you frame questions to get people sharing so openly and with enthusiasm, and I wonder if you have some special tips about asking questions to keep a conversation going. Thanks so much.

Cheers,  Shannon

Shannon, thanks for your question. I think in-person conversation is quickly becoming a lost art! For many people, starting and maintaining a conversation is very uncomfortable, so they simply try to avoid them all together. In fact, I’ve even heard many people say, “I’d rather text than have a conversation!” So what is behind that statement? I think it’s because we like the ability to edit our words, to avoid awkward small talk, and to present our best selves. We like the fact that texting gives us time to create and sculpt responses. We can even consult with others before we respond. Of course, in-person conversation does not allow for that. In-person conversations require us to spontaneously engage with another person.   

I applaud you for how you framed your request to me because you obviously understand that a good conversation is about asking questions and sharing stories. People will feel immediately comfortable with you and will open up much more when they see that you’re truly interested in them. But keep in mind, the questions must not be an interrogation and they must be appropriate—at the right level for the conversation and for your relationship. Think of conversation depth as progressing from conversation about your immediate environment to roles and responsibilities to professional activities to personal activities to shared culture, goals, values, and emotions. To continue a conversation, you need to stay at the same level or go only one level deeper or one level higher. 

For some people they want specific words to say, so I’ve outlined a few of my favorite conversation continuers:

Conversation Continuers for Interviews

To continue conversation in an interview, you can ask things like:

• What are you looking for in the ideal candidate?
• Why was X a good fit for you?  
• How did you get into … ?
• What is the best part of working at X … ?
• What’s the biggest challenge of your current role … ?
• Or you can just say, “Ah, that’s interesting. Tell me more.”

Conversation Continuers when Meeting New People

When getting to know someone new, more wild questions can sometimes be appropriate. For instance, a friend of mine told me that on her second date with her now-husband, he ran out of things to say, so he asked her, “So … have you ever had any interesting pets?” She said she was embarrassed for him, but fortunately she had raised baby opossums. That certainly kept the conversation going for a while! When getting to know someone new, always strive to make it fun.

Some fun get-to-know-you questions might include:

• What did you want to be when you were a child?
• What is the most amazing place you’ve ever traveled to?
• What’s the best meal you’ve ever had?
• What would you do if you knew you only had a week to live?
• If you could talk to anyone (from history or today) who would it be?
• Are you more of a morning person or a night person?

Conversation Continuers for Networking

Much is said about conversation starters for networking, but little is said about conversation continuers, which are much more difficult. Once you’ve exchanged basic information, like who you both work for, what you do, and how good the hors d’oeuvres are, you need to make some deeper connection. I have found that listening carefully to your conversation partner and then moving to “so tell me,” combined with an interested and friendly demeanor, works really well:

• So tell me more about <current project>.
• So tell me about your role and responsibilities in <current role>.
• I’d love to learn about your experience with <anything they mentioned>.
• So tell me about the goals for <current project>.
• So tell me what’s the best part/most challenging part of working on <current project>.
• So tell me how you’re dealing with the current challenges of <insert project>.

Conversation Continuers for Business Meetings

Now that’s I’ve given you some specific things to say, I’d also like to give you some general question techniques that work really well in continuing conversations. They can help draw out crucial information and drive a meeting forward. When properly used, they can really increase productivity and deepen relationships.

Let’s look at my three favorite techniques …

Business Conversation Continuer #1 – Mirroring

The first technique is to mirror back what the person just said, with different wording. Often the person will add to what you have said, or further clarify. Even if he doesn’t need to add anything, it will be clear that you were listening and understood him, which will greatly increase trust and connection. You can then continue with one of the other questions. Some examples are:

• So the project is about…
• So your role is ____ and your main responsibilities are ____.
• Sounds like you’ve got three main objectives: A, B, and C.
• Sounds like your biggest challenges are ­­­­____.
• Sounds like you’re stuck because you’re waiting for input from the ABC team.

Business Conversation Continuer #2 – Nouning

This one’s called “nouning.” Continue with an open-ended question (not yes or no answers), repeating a noun from the person’s statement and using it in your follow-up question. The question could start with “What do you think?” or “How do you think?” or “Would you be willing to share your views on that?” You might say:

• So you’ll be doing the task X. What do you think will be the hardest part?
• So you’ve got experience with X. What do you think your approach will be?
• How will you approach objective X?
• How do you think you will be able to use X and Y?

Business Conversation Continuer #3 – Verbing

“Verbing” is similar to “nouning,” except you repeat a verb from the person’s statement and use it in your question. It might sound like this:

• So you’ll be managing. How many resources do you think you’ll need?
• So analysis, what approach might be best for <current project>?
• Not having enough resources is frustrating. What do you think you’re going to do?
• Hmmm … waiting. How long do you wait? What ideas do you have to speed things up?

So there you have it, some great practical words and techniques to keep a conversation going. I’ll admit it takes some practice, but this should prevent those awkward moments and improve any conversation! Shannon, good luck and let me know how it goes.  

This is Lisa B. Marshall helping you to lead and influence.  If you’d like to learn more about compelling communication, I invite you to read my bestselling books, Smart Talk and Ace Your Interview and listen to my other podcast, Smart Talk. As always, your success is my business.