Making the First Move

Over December, I’m sure many of you will have endless engagements, be they work or personal. And at most of them, you’ve likely had to talk to someone you didn’t know.

Making the first move and introducing yourself is, for many, a terrifying situation. For some, just arriving at the event is a feat in itself.

Recently, I attended a local Women in Business event, my first one.

I did what I do for all new events and checked out the location in advance. I knew where to go, where to park, and how long it would take me to get there from home. I used my ‘pocket trick’ and held a power pose in the bathroom before I left, repeating the mantra - ‘you’ve got this’.

I was feeling alright until I turned into the venue and realised there were no parks left in the parking lot. The nerves grew. Instead, I followed all these women doing u-turns on a busy road to park on a large berm across the road. Getting my small car up the curb was challenge #1, parking successfully at a weird angle was challenge #2.

I arrived at the venue a little sweatier than anticipated (oh, and yes, I did wear my dress all morning to check if the sweat marks were showing) and joined the queue of women waiting to get name tags. The line was long, and many were in 2s or 3s, having come with colleagues.

I looked sideways, trying to figure out what to do next - take out my phone (no, I am actively trying not to do this) - so instead I turned to the closest person and said, “Did you manage to get a park?” hoping for a natural entry into conversation.

She replied, “Yes, I’ve been to these things before. They’re busy,” and then quickly looked past me with an enthusiastic “Hi, how are you?” to someone behind.

Sigh.This was going to be one of those events.

But here’s the thing: once you’re seated, once you’ve small-talked your way to a table, the room feels different. Warmer. More open. Suddenly, someone across the table says, “So what brought you here?” and a proper conversation begins.

And that - how you get from sweaty parking-lot chaos to a meaningful moment - is what this post is about.

Tips for Making the First Move and Starting a Conversation

Begin with something simple

It doesn’t have to be witty or impressive, it just needs to open the door.

When you’re introducing yourself, your job isn’t to perform; it’s to connect. And connection often starts with small conversational threads:

Parking.Weather.“Have you been to one of these before?”

It doesn’t matter what the thread is, only that the other person has something easy to respond to.

Building Rapport: Match → Mirror → Lead

Rapport isn’t luck, it’s something you can build, even in a crowded room full of strangers.

One of my favourite frameworks comes from Vinh Giang - you can watch his overview here:

Match → Mirror → Lead

Match: Start where they are. Meet their tone, pace, and energy.

Mirror: Gently align with their communication style. Not copying, just matching enough so they feel understood.

Lead: Once the connection is there, you can guide the conversation forward to shared interests, common ground, or something deeper.

No matter what, you will need to change your communication style depending on the situation you’re in.

Finding the Conversation Threads

We often rush to fill silence, but the real magic comes from noticing.

Try this:

• Listen for the hook. A detail, an interest, a challenge they mention lightly.

• Ask one step deeper. Instead of “What do you do?”, try “How did you get into that?”

• Share just enough of yourself. Not your whole story, just enough to build a bridge.

Great conversations grow from curiosity, not from rehearsed lines.

And the best moments often come from the unexpected, the person at the table you didn’t plan to sit beside, the offhand comment that turns into a shared story, the stranger who becomes something more than a stranger.

Your Turn

As we head into the silly season — parties, barbecues, networking events, and all the social gatherings in between — try this:

Match. Mirror. Lead.Find the thread.And open the door to the conversation.

You never know where it might lead, or who you might meet on the other side of it.

(Want more… Let’s chat.)

Ashleigh