The examples below work as starting points for messages or one-on-one video chats. Adapt them to what the person actually says instead of reading them as a script.
Follow One Detail Instead of Changing the Subject
A broad answer often contains a smaller topic you can explore. Listen for an activity, a feeling, or something the person chose to mention.
Example conversation
You: “What’s been keeping you busy this week?”
Them: “Work, mostly. I finally finished a difficult project.”
You: “What made it difficult?”
Them: “It was my first time leading the team.”
You: “Was leading people different from what you expected?”
The follow-up comes from their answer. Asking “What music do you like?” immediately after the project story could work, but it drops a topic they have already offered.
Keep the question small enough to answer comfortably. “How did that go?” is easier to respond to than asking for their entire career history.
Adjust When You Get a Short Answer
A short answer can mean many things: the question was too broad, the person is distracted, or they do not want to discuss that topic. It is not a puzzle you must solve by asking more personal questions.
| Their answer | A reasonable next step | Example |
|---|---|---|
| “Not much.” | Offer a small topic of your own | “I’m deciding what to watch tonight. Have you seen anything you liked lately?” |
| “I don’t really know.” | Make the question easier or change topics | “Fair enough. Would you rather have a quiet evening or go somewhere new?” |
| “I’d rather not say.” | Accept the boundary | “Of course. We can talk about something else.” |
| Several short answers | Leave room to finish | “No worries if now isn’t a good time. It was nice meeting you.” |
These are options, not a sequence to push through until someone engages. A conversation needs willingness from both people.
Handle Quiet Moments on Video
On a video call, a pause may be thinking time or a connection delay. If the sound seems interrupted, check the connection before assuming the other person has lost interest.
You can ask, “Did my audio cut out?” If you both started speaking at once, stop and say, “Go ahead—I was listening.”
If the connection is fine, give the pause a moment. You can return to an earlier detail: “You mentioned you were learning something new. How’s that going?” Avoid pointing out every silence with “This is awkward,” which gives the other person another thing to manage.
Change Topics or End Without Forcing It
A natural topic change can acknowledge the previous subject: “Speaking of weekends, do you have anything planned?” You can also be direct: “Can I ask you something different?”
When you want to finish, a clear, friendly sentence is enough: “I need to go, but I enjoyed talking with you.” You do not have to invent a reason or promise another call.
If someone ends the conversation, respect that choice. Keeping a conversation going means making room for an exchange, not preventing the other person from leaving.
Starting from the first hello? Read How to Talk to Strangers.
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