Follow-Up Questions That Make People Want to Keep Talking

Do you struggle to ask follow-up questions without making conversations awkward? Most people either ask surface-level questions or dig so deep they create tension. This video breaks down a simple conversation technique for asking better questions—one that lets you zoom in and out of topics naturally, understand what someone’s really thinking, and keep momentum going instead of hitting dead air. Learn how to structure your questions using chunking so conversations feel like genuine exploration, not interrogation. Master the flow between light and deep questions to keep people engaged.

Behavioral Tells: Read the Hidden Signals Behind Every Action. What People Reveal Without Saying a Word. (How to be More Likable and Charismatic Book 46)

By Patrick King

Behavioral Tells: Read the Hidden Signals Behind Every Action. What People Reveal Without Saying a Word. (How to be More Likable and Charismatic Book 46)

By Patrick King

In this episode, Patrick King dives into the art of asking better questions to enhance your conversations and deepen connections with others. From mastering the chunking technique for smoother conversation flow to learning how to craft follow-up questions that lead to meaningful exchanges, you’ll pick up valuable skills for improving communication and understanding people on a deeper level.

Chunking Up and Chunking Down
“Chunking” = putting together or breaking up information or data into bigger or smaller pieces.
In conversation, chunking is a way to ask questions or organize ideas so as to reach an agreement or gain clarification. But the way that people use chunking in their own speech can tell you interesting things about them as people-if you pay attention!
• “Chunking up” is when you move from specific and detailed information to more general or abstract information.
◦ How and why questions tend to lead to chunking up.
• “Chunking down” goes the other way and happens whenever we move from broad generalizations and abstractions down to finer specifics.
◦ Where, what, when, and who questions tend to lead to chunking down.
When you chunk up, it is as though you are zooming out of the conversation to gain a broad, top-down overview of it, or as though you were getting a larger and more general “map” of the conversation terrain.
When you chunk down, it’s like taking a deep dive or getting stuck back into the nitty-gritty level, filling in the inevitable gaps you have on a more abstract overview.
Understanding how chunking works can help you in three ways:
1. It can help you structure your own questions so that you zoom in and out of the topic appropriately, helping you gain a broad yet detailed understanding of what the other person is trying to share with you.
2. It can help you understand how the other person is using chunking, and what this implies about how they’re structuring their own mental maps.
3. It can help you identify differences in chunking styles-typically, misunderstandings and conflicts arise from a mismatch of chunking styles. Making sure that chunking styles are balanced and aligned can smooth over conversational difficulties.
So how do you use chunking in a conversation where you’re trying to learn more about a person?
First, chunking up questions will help you zoom out and find commonality, look for themes, or help you summarize what you’ve been told so you can reflect it, showing that you understand and are paying attention.
Example:
A: “So after we lived in Puerto Rico for a while, we found ourselves back in Italy, but within just two months, because of work, we found ourselves pulling the kids out of school again and doing a year-long stint in France. We wanted to come back to Puerto Rico, but… oh well, long story short, we’re here in New Zealand instead!”
B: “Wow, what a whirlwind! So overall you moved, what, four times in one year?!”
A: “Pretty much.”
B: “What toll do you think all that had on you?”
A: “Well, it was hard, but we all learned a lot, I will say that.”
Speaker B above has asked two chunking up questions:
• The first (“You moved four times?”) more or less summarizes the key theme of the story (“a whirlwind!”)
• The second (“what was the toll on you?”) probes a little for bigger overarching themes that connect all these disparate travel experiences. The question itself is looking for a broader, more abstract analysis, rather than further details about what happened in each particular country, or the exact dates they went there.
If Speaker B continues asking these kinds of chunking up questions, eventually the pair might find themselves having a very detached and abstracted conversation, indeed, about how humankind has always been nomadic, the resilience of children, globalization, the philosophical and political implications of being dislocated from the land, etc.
If A and B are enjoying this, it may be a good conversation, but it probably won’t be a conversation in which they learn much about one another as people!
Adding some chunking down questions will not only make for a more balanced and comfortable conversation, it will also allow more personal and detailed information to come through.
The devil is in the details, but so are people’s more interesting idiosyncrasies!
• A good rule of thumb: Stick to no more than three questions of one type in a row.
If you ask three chunking up questions, switch to a chunking down question to drill down a little more deeply into a specific idea or detail. But don’t stay there too long or you’ll risk getting “caught in the weeds.” Come up for air after a few chunking down questions to get a breather and a bird’s-eye view:
B: “What toll do you think all that had on you?”
A: “Well, it was hard, but we all learned a lot, I will say that.”
B: “So be honest, which country was your favorite?”
A: “Hm… honestly? I thought I’d love France, but it was nothing like I’d imagined. I’m really loving New Zealand, which I never expected to.”
B: “What surprised you most about France?”
You can almost imagine zooming in on the mental map, from countries  favorite countries  France  something specific about France.
But if Speaker A had said, “You know what, they all drink too much!” and Speaker B had another fifty questions about what kind of wine, the conversation would not only stall, but they’d stop gaining further insight into Speaker A.
Here are some examples of chunking-up-style questions (importantly, these are not necessarily verbatim):
• What do you think that means?
• Why did that happen?
• So in the bigger picture…?
• Is that connected to…?
• What do you think that says about…?
• How do all these things connect?
• What do you think of…?
• How do you make sense of…?
Here are some examples of chunking-down-style questions:
• How did you like that?
• What happened?
• What happened next?
• When…?
• Who did that?
• Tell me more about…
If you make sure to balance the ratio of chunking up and chunking down questions in any conversation, you’ll likely keep things moving along at an enjoyable and balanced pace.
But remember to pay attention to learn more about your conversation partner.
Do they continually ask chunking up questions themselves and respond most enthusiastically to chunking up questions from you?
This could mean a few things:
• Organizing, analytical, and pattern-seeking questions typically show intelligence, awareness, and mastery of a topic.
• This pattern can also hint at a desire to be personally and emotionally distant from a certain topic.
If you’re having a heated conversation with someone and they suddenly seem to retreat into lofty abstractions about nobody in particular, ask whether you’ve struck a nerve and if chunking up is serving as an evasive maneuver.
Do they continually ask chunking down questions or respond most enthusiastically to yours?
This could indicate a narrow, focused, or even enthusiastic sense of attention to concrete matters, but it can also signal a lack of insight and critical thinking. People who are most comfortable continually chunking down might be:
• Running the procedural meta-program.
• Bored or lost in a conversation that doesn’t anchor directly onto something in their literal lives in that moment.
• Signaling that they are interested not in the topic at hand, but in you. You’ll notice that people who flirt, for example, are seldom having a deep and meaningful conversation!
Finally, if you do notice that someone prefers chunking down, pay attention to the kind of questions they ask to gain insight into what they’re primarily focused on.
• Are they more interested in people, places, what happened, the prices of things, family connections, the sequence of events?
• If you’re talking very generally, notice what triggers people to dive deeper into detail.
• They are communicating what inspires and excites them. By the same token, someone who repeatedly chunks up while you’re trying to chunk down might be telling you that they don’t find that particular topic very interesting!
You may be wondering if every question is potentially a chunking up or chunking down question.
The answer is yes!
That said, there are also questions you could ask that act to keep the conversation at more or less the same level of depth-i.e., they neither chunk up or down but stay at that level of focus.
At the end of the day, it’s not any particular question itself that will yield greater or lesser insight into someone’s character.
Rather, it’s how that question is used.
This is why it’s important to create hypotheses in your mind to explain your perceptions and observations. That way, you “test” that observation through targeted questions. At the same time, you listen to their questions, what they are probing for, what they are focusing on, and what that tells you about their motivations, priorities, and thinking style.
We’ve discussed a few methods so far:
• Listening for Word Clues
• Identifying meta-programs
• Noticing overall language use
But each of these is relatively weak on its own. When combined, they become incredibly powerful.
Have you ever heard people say that they’ve spoken to someone for hours, or even known them for years, and yet they know nothing about them? That’s because their conversation lacked strategy and focus.
With a little practice and awareness, though, you can be the opposite-you will be able to talk to people for an astonishingly short amount of time, yet see more clearly into the depths of who they are as a person.
Here are a few last hints and tips for asking questions that will help you fine-tune your people-reading skills:
• As a rule, begin with open-ended questions and lead to more closed ones once the flow of conversation is established.
◦ This neatly maps on to the habit of asking more chunking up questions first, and then after you’ve gained an overview (and the person is more comfortable with you), you can drill a little deeper with a closed question that probes for a specific, detailed answer.
• Be careful not to ask too many questions (of any kind). It will feel like an interview or interrogation, and the person will definitely register that the exchange of information is imbalanced.
• Try posing some questions as statements-for example, “You’re one of those super smart people, so I bet you learned all sorts of amazing things while living there.”
◦ Such statements act as questions since they spur conversation and inspire the other person to tell you what you want to know. Extra points if you can be a little unexpected or controversial-the way people jump in to respond tells you a lot about where they are psychologically: “Smart!? Well, I certainly didn’t feel that way at the time. Quite the opposite, actually . . .”
Finally, one final tip is to work on the delivery of questions.
When you ask:
• Use a friendly, relaxed tone of voice.
• Don’t use eye contact.
• Only once you’ve asked the question, pause and then make eye contact-this body language acts like a nonverbal invitation for them to speak, and communicates your respectful interest in their answer, without being pushy.
Finally, pay attention to their eye contact. Avoiding your gaze or looking away may suggest their desire to avoid that question!