This is the fourth post in our series for anyone who wants to feel more confident making conversation. Last week, we introduced the first two tools you need to keep a conversation going—a map and compass. This week, we’re unpacking the other three tools you’ll want to carry on every conversational adventure: binoculars, a shovel, and pest repellent.
They’re simple, practical, and easy to put into practice—starting today.
Tool #3: Binoculars – Sharpen Your Observation Skills
Good conversation isn’t just about what you say—it’s about what you notice. The best conversationalists aren’t busy rehearsing their next line in their heads. They’re tuned in. They listen. They watch. They observe.
You can do this, too by being intentional about paying attention.
Here’s how:
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Listen beyond the words. When someone answers a question, they often reveal much more than what was asked.
Example: You ask, “Where did you grow up?” and they reply, “Mostly the East Coast, but we moved around a lot because my dad was in the military.” That opens up multiple directions: What branch was he in? Where did you live? What was it like moving often?
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Notice body language. Eye contact, posture, gestures—they give clues about what someone is really feeling. Are they leaning in, making eye contact, or backing off slightly? Those cues help you decide whether to engage more or start backing off.
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Look for environmental clues. A logo on a hoodie. A travel photo in someone’s office. A dog in their Zoom background. Each one is a conversation starting point—if you’re paying attention.
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Give genuine compliments. If you notice something they’re doing well or something that stands out (their sense of style, their kindness, their ability to make people feel welcome), say so. A simple, sincere compliment breaks the ice and often opens the door to deeper conversation.
The key? Stay curious. Most people will show you what they care about.
You just have to be intentionally looking for it!
Tool #4: A Shovel – Dig a Little Deeper
Once you’ve spotted something worth exploring, it’s time to dig in. Not in a pushy or nosy way—but with thoughtful questions and genuine curiosity.
Ask yourself this: What do they know or care about that I don’t?
Everyone is an expert in something. Maybe it’s their job, a personal interest, or a unique life experience. Your goal isn’t to interrogate them—it’s to discover the “treasure” they’re carrying.
You can try things like:
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“That’s really interesting—how did you get into that?”
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“So let me see if I got this right—you moved around every couple of years growing up?”
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“What’s something about that experience most people wouldn’t know?”
And when it’s your turn to share, keep it balanced. Offer a quick personal insight or experience that connects, but don’t take over and make it all about you. You’re not giving a TED Talk. You’re participating in a real conversation.
One last thing: don’t dive too deep, too soon. Oversharing with someone you just met can feel uncomfortable. Build trust gradually.
Think of it as a friendly hike—not a deep-sea dive.
Tool #5: Pest Repellent – Avoid the Bugs That Kill Conversation
You can have the best map, the sharpest binoculars, and the sturdiest shovel—but if bugs are biting, the experience is miserable.
The same goes for conversation. Here are a few “pests” to steer clear of:
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Jumping into controversial topics too early. Save politics, religion, and hot-button issues for later – after trust has been built.
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Making it all about work. Careers come up, sure – but that’s too easy. Try to learn who they are outside their job. You’ll likely find more meaningful connection there.
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Telling jokes. Humor is great—jokes can backfire (and almost always do). A light comment about your own day is safer than a punchline you’re not sure will land well.
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Faking it. Be yourself. People can sense when you’re putting on a front, and it can subtly create distance.
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Talking too much—or too little. Healthy conversation is a two-way street. If you’ve been silent, speak up. If you’ve been talking for a while, ask a question and invite the other person in.
Avoiding these bugs doesn’t require perfection. Just self-awareness. A little goes a long way.
One Final Thought
Good conversations don’t have to be long to be meaningful.
Even a brief exchange can brighten someone’s day—including yours.
Maybe it’s a comment to a cashier, a compliment to a coworker, or a quick question to the person sitting next to you. These small moments build connection—and your confidence.
Next time, we’ll talk about how to end a conversation well – and painlessly (yes, that’s a skill, too)!
Until then, keep your binoculars ready, your shovel handy, and your repellent close.
You’ve got this!
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!