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Planets are usually discovered by experienced astronomers, but 17-year-old Wolf Cukier did it in three days. Soon after starting his NASA internship, he noticed unusual light signals coming from an object 1,300 light-years away from Earth. He discovered the signals were coming from a planet, now called TOI 1338 b. Wolf’s remarkable discovery was the result of his ability to discern the right signals.

Similarly, your prospects are sending you signals during conversations and your ability to pick up on them can affect the quality of your conversations. It’s especially important to know the signals if a conversation is boring a prospect. Fortunately, there are ways to identify a dying conversation and it is possible to get it back on the right track.


First, Three Levels of Conversation

Have you ever met someone and in no time, you feel like you’re good friends? It’s a goal advisors strive for when meeting prospects, but how does it happen? It’s likely that their discussions move through three levels of conversation.

Level 1: Mundane – Think weather, sports, and traffic. This level is small talk where you talk about practical, factual information. It includes basic questions such as: Where do you work? Where do you live? How are you?

Level 2: Shared Interests – At this level, you discuss things you have in common, such as music, movies or TV shows, restaurants, family, books, mutual friends, hobbies, podcasts, technology, work, travel, community, and news (but not politics).

Level 3: Feelings – You talk about how each of you feel about level two topics. It may take more than one meeting to get this level.

Your goal is to get to level three, but many conversations get stuck at level one. Why? Small talk isn’t easy and because the topics are often mundane, it can get boring. When that happens, conversations fizzle out before they get to level two or three. So how can you recognize a dying conversation, and revive it to get to level three?


Second, How to Detect a Dying Conversation

When someone is bored with a conversation they’ll send signals, often without even knowing it. Watch for these clues to know if a conversation is dying.

  • Passive responses – You hear lots of routine responses, such as “Oh really?, wow, mm-hmm, yep, yeah, totally.”
  • Topic change – The person you’re speaking with abruptly changes the topic, e.g., you’re talking about a new restaurant and they say, “So, how’s work going?”
  • Wandering eyes – It’s a good sign if the person you’re speaking is maintaining eye contact. But if they look away or check their phone, your conversation may be dying. If their eyes glaze over or they’re half shut, that could also be a sign they’re bored.
  • Body position – If a person is engaged, they tend to stand with their head, shoulders, knees, and toes pointed towards you. Turning away or slouching could indicate they’re getting bored.
  • Yawning – Sure, people yawn because they’re tired, but also because they’re bored.
  • No Questions – If the other person isn’t asking you questions, your conversation may be dying.

Now that you’re aware of some signals that could indicate your conversation is dying, here are some tips to resuscitate it.


Third, How to Revive a Dying Conversation

We’ve all been in awkward conversations that feel like they’re going nowhere. If you pick up cues that your prospect is losing interest in a conversation, try some of these methods resuscitate it.

Word detective – Communication expert, Leil Lowndes, suggests listening to your prospect’s every word during small talk for clues to their preferred topic.1 For example, if you mention to a prospect how bad the traffic was today, they might say how that traffic caused them to miss a meeting at work. Since they mentioned “work,” that’s your clue. You could ask them where they work and what they’re excited about there.

Change the topic – If you’ve been talking about a topic and it feels like it’s not going anywhere, change the topic. There’s a misconception that it’s not polite to change the topic during a conversation. That’s not true. People tend to squeeze all the good stuff out of a topic pretty quickly.2 

Parroting – When speaking with a prospect, listen for their last few words and repeat it back to them in a questioning tone, passing it back to them to elaborate further. For example, if they say “I can’t wait to watch Netflix tonight.” You could say, “What are you watching on Netflix?” Use parroting when you want to get the other person talking more, or you want them to clarify what they mean. Don’t overuse this technique though. If it becomes obvious, you might be perceived as being manipulative.

Always follow up – Amateurs ask too many surface-level questions, such as “Where are you from?” and “What do you do?” These basic questions keep you in conversation level one. To get to levels two or three, listen closely, be curious, and ask more follow-up questions. For example, you: “Where do you live?” Prospect: “Pittsburgh” You: “How do you like it there?” When asking follow-up questions, try to use these keywords: who, what, how, why, where, and when. Also, occasionally try to weave in this question, “How do you feel about that?”

Does it work? A study of speed dating found that if a participant were to ask just one more follow-up question on each of the 20 dates, he or she would succeed in getting a “Yes, I want to see you again” on one more of the dates, on average.3

Back pocket questions – To get your conversation to levels two or three you need to have some good questions ready to go. Consider using some of these:4,5,6

  • Do you have any trips coming up?
  • What are you watching on Netflix?
  • Have you read any good books lately?
  • What was your dream job growing up?
  • How did you choose your profession?
  • What are you looking forward to?
  • What’s the best thing that happened to you this year?
  • Where did you grow up?
  • What do you do for fun?
  • Tell me about yourself.

Be vulnerable – Prospects are less likely to connect with people if they appear “perfect.” Therefore, share a non-work story about how you messed up recently. Or, share a work-related story about how you made a mistake earlier in your career, but leaned a valuable lesson as a result. Your vulnerability will be interesting to prospects and can draw them closer to you.


“What if I Try These Things and the Conversation Still Goes Nowhere?”

We’re typically our worst critic when we evaluate our conversations, especially initial ones. Therefore, we tend to think they’re worse than they really were. We think of all the things we could have done better. Was I boring? Did I talk too much? Did I make enough eye contact? However, a study has found that others usually don’t view our conversations as failures.7 It found that people underestimated how much their conversation partners liked them and enjoyed their company.


Remember 3 Things About Saving a Dying Conversation

First, remember the three levels of conversation. Your goal is to get beyond level one—small talk. Second, learn the cues to recognize a dying conversation. Third, if you realize you’re in a dying conversation, try some of the six methods to resuscitate it.


Sure, Small Talk Can Be Painful

Meeting people for the first time and struggling with small talk can feel awkward. One way to improve it is to recognize the signals that indicate a conversation is getting boring. Wolf Cukier’s sensitivity to signals helped him discover a new planet. Likewise, by being sensitive to the conversation signals others are sending and knowing reviving techniques, you can resuscitate dying conversations.


Next Steps

Review the cues in the section “How to Detect a Dying Conversation.” As you meet with prospects this week, be on the lookout for these signals. If you see these signals, try one or two of the methods in the third section, “How to Revive a Dying Conversation.”


How to Connect With Affluent Prospects >

1 Lowndes, Leil. How to Talk to Anyone. McGraw-Hill, 2003

2 “How to Not Be Boring.” Psychology Today, 10/29/19

3 “People Will Like You More If You Start Asking Follow up Questions.” Forbes, 10/30/17

4 “7 Questions Interesting People Always Ask in Conversations.” Inc., 6/6/17

5 “7 Conversation Starters Better Than ‘What Do You Do?’—And 7 That Are Even Worse.” Forbes, 4/15/16

6 “Turn Strangers Into Friends With 8 Great Questions From Harvard.” Forbes, 4/18/19

7 “Want to Seem More Likable? Try This.” The New York Times, 9/23/18



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