7+ Ways to Get Better at Small Talk – and Why Startup Founders Should Care

by rshafir | September 23, 2025 | Blog, Entrepreneurship, Uncategorized

Kyle, a fintech founder near Salt Lake City, recently wrote:

“Rebecca, my startup is gradually picking up new clients but at a very slow rate. I’ve been advised to double down on networking, but I hate small talk—probably because I’m terrible at it. Can you give me some ways of getting better?”

If you’re nodding along, you’re not alone. Many founders find small talk awkward. But the ability to start and sustain casual conversations is essential to building the trust and connections your startup needs.

Here are some practical ways to improve:

✅ Accept it. Small talk is an essential communication skill for founders. Think of it as a bridge to learning something new, deeper conversations and future opportunities.

✅ Reframe it as a treasure hunt. Be curious: “What brings you to this event?” or “Where are you in your startup journey?” Avoid tired topics like the weather. Make it a goal to leave an event learning at least three things about the other attendants. Not all conversations will yield treasure, but that’s what makes networking a hunt.

✅ Answer with substance. When asked, “How’s your day?” go beyond “Good.” Try: “Much better now that interest rates dropped—what’s your take on that?”

✅ Notice and ask. “I see you’re using a Remarkable tablet—how do you like it?” Or offer a genuine compliment that sparks more dialogue: Your comment to the speaker was spot on. That’s been my experience too.

✅ Limit self-talk. Keep your story to 30 seconds. Then, as I emphasize in my book The Zen of Listening, shift fully into their “movie.” Put aside your agenda to imagine how they see the world. Folks can tell when you’re thinking about what you’re going to say next instead of really listening to them.

✅ Exit gracefully. Wrap up a conversation with: “It’s been great talking with you (use their name) —I don’t want to monopolize your time. Best of luck with [their project].” If that is difficult for you, as it is for many folks, practice your exit line in front of the mirror until you’re comfortable saying it.

✅ Practice in safe spaces. Try out small talk with Uber drivers, waiters, or baristas—low-stakes reps make you more confident at events. Use people’s names if available and create a personal connection.

Two extra tips just for founders:

✅ Prepare 2–3 “go-to” openers (“What’s been the highlight of your week?”). This prevents awkward silences.

✅ Use follow-up as small talk’s secret weapon for contacts that you sincerely appreciate. Send a short note the next day referencing something they mentioned. It shows you listened—and builds credibility.

If you want to dig deeper, research backs this up: small talk enhances both trust and wellbeing. (Harvard Business Review, Psychology Today).

Need practice? I offer single-session coaching for founders who want to sharpen their small-talk and listening skills. Reach me at Rebecca@MindfulCommunication.com.