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Better Conversations: from chit-chat to connections

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.” - Dale Carnegie


We’ve heard enough about the weather already. It’s time to charter into new and unknown topics – into conversations that are memorable, intellectually stimulating, and unforgettable. So how exactly do you walk away from an interaction feeling like you’re the Oprah Winfrey or Jimmy Fallon of conversation? Try these tips to get started:

1. A little give, a little take

Conversations are two-way, like a tennis match. They are about asking questions and about sharing information. Open up, and don’t just answer the question—elaborate a little, then ask a question back. After some good conversation, you should know something about the person and they should know something about you. If you don’t, you’ve either been interrogating the person (too many questions) or you’ve been talking all about yourself (which fails to impress).

2. Love the small talk

Drop the old “I hate small talk” adage. No, you don’t. Small talk is an essential part of a conversation, it’s how you break the ice and get comfortable in conversation. It’s the tasting spoon of gelato, to help you decide which flavour direction to take. It helps you find common ground and gives you clues and cues about the person you’re speaking to. Think current events, sports finals, the cool glasses frames/funky tie the other person is wearing, and what you do for work.

3. Find commonalities

As soon as you find SOME commonality—you’re both obsessed with salted caramel gelato, you’re closet Toronto Maple Leafs fans, you work in the same industry or on the same city block where the new poké bar just opened—you begin to make a deeper connection. Research tells us that we like people who are like us, so the key to great conversation is to find what you have in common. Once established, the conversation naturally moves from small talk and into forging a real connection.

4. Stay in the know

Upgrade from small talk to beefier conversations by being “in the know.” Read books, follow thought leaders, consume local and global news, attend movies/concerts/community events, and stay current on social media. You’re bound to find something to talk about (or never stop talking about) if you stay active on those fronts.

5. Ask great questions

People like to talk about what they know. Go in curious and ask great questions. What do you love most about your job?  What was your path to <<insert title here>>?  What was the best piece of advice you ever got? If you’re looking for great icebreakers, Peter Reek has compiled an impressive list of get-started questions to help you avoid the same old “hot enough for you?”


“Creativity is choosing the path of curiosity over fear. It's a way of living and your life becomes a work of art.” - Elizabeth Gilbert


Like public speaking, the only way to get comfortable with conversations is to have more conversations. Chit chat to discover common ground, and move from the tasting spoon to a full scoop (or two)!


Catherine Ducharme

Catherine Ducharme is Smart, Savvy + Associates; in-house queen of networking and communications professional. If you’ve ever had a conversation with Catherine, then you’ll know what we’re talking about. With decades of corporate communications and leadership experience, Catherine knows the industry—and is known in the industry—like no other.

Catherine Ducharme

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