This is the third in a series of articles for people who want help with the basics of making conversation confidently. That might not be you—but chances are, you know someone who struggles with what to say and when to say it. If so, feel free to pass this along!
You did it.
You started the conversation.
You smiled, said hello, asked a question—and now the person is looking right at you, ready to talk.
Cue the internal panic.
What do I say next?
If that’s a familiar feeling, you’re not alone. Starting a conversation is one hurdle. But continuing it? That can feel like wandering into the woods without a clue where to go.
That’s why I like to think of conversation like backpacking. When you head out on a hike, you don’t just walk aimlessly. You take a map and compass—a plan and a way to stay on course.
Turns out, that same idea can help you keep a conversation going smoothly, even if small talk isn’t your thing.
Step One: Know Where You’re Headed (using your Map)
Great hikers scan the landscape before they set out. They figure out which direction to go, and they’re ready for what’s ahead.
You can do the same with conversations.
Let’s say you’re headed to a social event or meeting someone for coffee. You can prepare ahead of time by thinking through three simple things:
- You – Be ready to introduce yourself
Have two quick ways to talk about who you are—one that includes your job, and one that doesn’t. Why both? Because conversations don’t always revolve around work.
If someone asks, “What do you do?” your 30-second job intro helps. But sometimes it’s better to say something like, “I’m a huge fan of local hikes and I’ve been trying to visit every trail in the area.”
That opens the door to shared interests—without turning the chat into a career monologue.
- Them – Be ready with a few good questions
Avoid the default, “So what do you do?” It’s not a bad question, but it can shut things down quickly if they’re between jobs, hate their work, or have a job you don’t understand (looking at you, cybersecurity specialists).
Instead, think of one or two non-work questions ahead of time. Here are some go-to examples:
- “What kind of stuff fills your time that you find interesting?”
- “What’s the best thing you’ve read, watched, or listened to recently?”
- “Did you grow up around here?”
If you know you’ll be seeing someone specific, think ahead—what do you already know about them? What might they be interested in?
- The Situation – Use what’s happening around you
This one’s simple: just talk about where you are. If you’re both at a conference, a birthday party, a sporting event, or even standing in line for coffee, that situation gives you a starting point.
“Have you been to this event (or coffee shop) before?” or “How do you know the host?” are natural, low-pressure openers.
Step Two: Stay on Track (using your Compass)
Even the best-laid plans can get you into unfamiliar territory. That’s when you need your conversational compass – something to help you keep moving forward when the path isn’t clear.
Here’s how:
- Keep it balanced. A conversation is like a seesaw—it works best when both people contribute. If you realize you’re doing all the talking (or none of it), shift the balance. Ask a follow-up question. Or, if you’ve been listening for a while, add a personal insight to keep it moving.
- Follow the trail markers. Listen for little cues—things they mention in passing. If they say, “We just got back from a trip,” ask about it. If they mention their kids, or a hobby, or a favorite show, that’s a direction worth exploring. You don’t need to change the subject – just keep following the clues.
- Be OK with short detours. Not every topic will lead somewhere amazing. If a question falls flat, it’s not a disaster. Shift to another topic. That’s part of the adventure.
Want to Practice?
Here are a few simple things you can do this week to grow your confidence:
- Before heading to any social setting (church, work event, party, etc.), think of two things you could ask or share in a conversation.
- Read one article or headline from each section of the news (sports, local, national, entertainment) so you’ve got a few talking points in your back pocket (but stay away from politics this early in your relationship).
- Pick a local event—a class, meetup, or even a city council meeting—and attend. It gives you more to talk about next time.
Final Thought: Don’t Wing It—Plan It
Most people think good conversationalists are just naturally gifted. But the truth? They prepare. Just like hikers plan their route, confident communicators take a few minutes to think ahead.
You don’t need to be clever or funny or fascinating. You just need to come in with a simple plan – a conversational map and compass. That’s what gives you the confidence to keep the interaction going, even when you don’t know exactly where it’s going to lead.
And sometimes, the best conversations come from a path you didn’t expect to take!
Next time – We’ll look at three other tools for exploring during a conversation. Don’t miss it!
And if you want to really work on your conversational confidence, pick up a copy of How to Communicate with Confidence – anywhere books are sold!