Starting The Conversation

Let’s be honest—starting a conversation with someone you don’t know can be awkward. Whether it’s a cold call, an introduction at a networking event, or that moment at a conference where everyone else already seems to be deep in conversation, making the first move takes guts.

But here’s the truth: there is no courage without fear. That nervous energy you feel? It means you care. And learning how to start and build relationships from nothing is not just a business skill—it’s a life skill rooted in confidence, emotional intelligence, and the willingness to take a leap.

I once watched a video of Tony Robbins talking about confidence, and something stuck with me. Tony Robbins frequently discusses how people are more likely to be influenced by someone who speaks confidently, even if they're incorrect, than by someone who is right but communicates hesitantly. This underscores the importance of developing confidence and strong communication skills. That’s the power of presence. And when you’re initiating contact, presence matters as much as your words.

If you’ve been smart about timing and using your touchpoints wisely, there comes a moment where you just have to go for it. Scary? Always. But it helps if you keep it short and disarm the tension early.

One line I use all the time on the phone is:
“Hi, I’m Cheryl and I work at XYZ. We don’t know each other but…”
You can follow it with whatever makes sense—asking if you can send info, requesting a quick call, or even just saying you’d love to connect and learn more about their work.

And yes, it also works in person. Let’s say you’re at a cocktail hour during a conference, and everyone’s chatting in their cliques. Breaking in is tough. The trick? Keep it light. Keep it simple. Sometimes all it takes is a compliment:
“Hey, I just had to say—that’s a great jacket!”
No pitch. No pressure. Just human connection.

The goal here isn’t to close a deal in 30 seconds. It’s to be memorable, respectful of their time, and create a small, positive interaction that leaves the door open. You don’t want to be that person—the one who overstays their welcome like a waiter interrupting your table mid-story just to ask if you want a refill.

If the conversation continues, that’s fantastic. If it doesn’t, that’s also a win. Because you made the first move. You planted the seed.

Over time, with more touchpoints, more context, more seeds and more face-time, these micro-interactions start to grow. Maybe next time, they will remember your name. Maybe the conversation lasts longer. The timeline for this depends on your follow-up, opportunities to connect and your emotional intelligence—not just a sales script.

And yes, there are tools that help keep track of all this—who you talked to, what was said, when to follow up. (I dive into those in my CRM blog.) But no tool can replace the magic of genuine rapport and people skills.

That part? That’s all you!