I’m writing this at a Starbucks near my house. There are 12 customers:
- An older couple are sitting together. He’s quietly eating a breakfast sandwich, and she’s talking to him nonstop.
- One guy is reading his Bible.
- Five people are sitting alone at separate tables – three staring at their phones, one on a laptop and another juggling both.
- Four people are standing at the counter, waiting for their drinks. They’re not talking – just waiting.
If I wanted to start a conversation. Who would I approach?
- Probably not the couple. Even though they seem friendly, I’d feel like I was interrupting.
- Not the people on their laptops. They seem focused, and I wouldn’t want to be interrupted if I were working.
- The ones on their phones? Maybe. They might just be scrolling, open to a brief interaction.
- I’d probably pick someone waiting for their drink. They’re not busy, and I could make a casual comment to test the waters:
“I’ve never had that drink before – What is it? Worth trying?”
“Pretty quick service today!” or, “Do you always come to this location?”
But here’s the catch: I’m making assumptions. I’m deciding who’s approachable based on what I think they’re feeling. That means I might be missing out on a great conversation simply because I made up a story about them.
It makes me wonder what they assume about me.
Probably nothing.
They’re not thinking about me at all.
If they wanted to start a conversation, I likely wouldn’t be their first pick. I’m just the guy focused on his laptop.
6 Assumptions that Get in the Way of Genuine Connection
When it comes to starting conversations, there are two basic approaches:
- Wait for someone to approach you.
- Take the initiative to approach them.
Most introverts choose the first option. If someone else starts the conversation, it must mean they’re interested – right?
The problem is that waiting gives you zero control. And if no one approaches, it reinforces feelings of inadequacy.
Extroverts tend to take Option #2. They’re not thinking as much about how they’re being perceived, so they’re quick to approach others. It’s second nature for them to simply start a conversation with anybody.
Quiet people might find that approach more threatening, so they don’t consider it. But they often hesitate because of these false assumptions:
Assumption #1: “I don’t want to intrude.”
We worry that approaching someone might annoy them. But think about the last time somebody started a conversation with you – were you offended? Probably not. More likely, you were grateful that they took the initiative so you didn’t have to!
If someone is standing alone, there’s a great chance they’ll welcome the chance to talk. And if not? You’ll know quickly and can move on.
Assumption #2: “They might not like me or think I’m interesting.”
That’s insecurity talking – bad self-talk.
If we see ourselves as boring, we assume they’re thinking, “Oh, great. Look who I’m getting stuck with.”
Most people give the benefit of the doubt. They assume that someone approaching them is interesting – at least enough for a conversation. First impressions form fast, but they can change just as quickly once you start talking.
Assumption #3: “They’re more confident than I am.”
People often look confident on the outside, but feel just as uncertain as you do. We all crave connection. When you initiate a conversation, you’re making it easier for the other person, too.
Assumption #4: They’re standing alone because they want to be alone.”
Not necessarily. If they really wanted to be alone, they would have stayed home. More often, they’re just waiting – hoping someone will approach them.
If you take the initiative, they’ll be relieved.
Assumption #5: “I don’t know them, so I don’t know what they’d like to talk about.”
That’s actually an advantage. It means you don’t have to have a script or a bunch of ideas to talk about.
Just a simple question like “How do you know the host?” or “First time here?” can open the door to a bigger conversation.
Assumption #6: “I’ll feel like a failure if we don’t have a great conversation.”
That puts all the responsibility on you for a good conversation.
Not every interaction will be amazing. Some will be short, while others will be deep.
The goal isn’t to impress – it’s to connect.
And that’s a two-way street.
The Best Part of Taking Initiative
When you start the conversation, you’re in control. You get to decide who you talk to.
You’re not waiting, hoping for connection – you’re creating it. And with every conversation, it gets easier.
Next time you’re in a coffee shop, a waiting room or a social event, give it a try. Just a simple comment or a curious question.
You never know where it might lead!
This is part of a series on “How to Start, Continue and End a Conversation.” Next time, we’ll get really practical about the starting process – and how to make it easy and non-threatening for anyone.
It’s based on some of the principles found in my little book, One-Minute Tips for Confident Communication. It’s a great resource for anyone who either needs a tune-up for their conversational skills, or someone who’s just learning the basics (think: College student or recent high school grad).
Check it out here – and it costs just about the same as a Venti latte!