How to Approach a Group of Strangers

I was running a workshop the other day when someone asked me, “What’s the best way to approach a group of strangers?”

Immediately, I thought of one trick that makes approaching and starting a conversation with a group much easier: beginning the interaction with an open-ended question.

An open-ended question should be two things:

Engaging
Relevant

Engaging Questions

By engaging, I mean that when you ask the question, it should elicit more than a yes, no, or even a short response.

For example, “Where are you from?” is a bad question to use when starting a conversation with a group. This is because the response will almost always end in the name of a place – a closed answer.

Unless you are either able to (A) think of something to say to keep the conversation going, or (B) lucky enough to have approached a group where one of the members takes up this conversational burden, it will die out quickly.

Instead, start the conversation with something that takes a little more thought to respond to.

In one of my recent dating bootcamps, one of the guys approached a group of women and started the conversation with, “What do you think of traveling alone?” He had planned a trip to Rio for Carnival, and all his friends had canceled on him. He was trying to decide whether he should still go.

Although most of the responses were short, he was able to follow-up with three natural questions that came from their responses:

Have any of you ever traveled alone?
What was that like?
Why?

These gave the conversation a natural flow, and it took off from there.

Relevant Questions

The second thing an open ended question should be is relevant.

When I say relevant, that doesn’t mean that it has to be relevant to something in the environment, although it could be. What it does mean is that there should be a context for what you’re asking.

In the example from my workshop, the guy mentioned to the group that his friends had canceled on their trip to Carnival, and he was undecided on whether he should still go. The background gave the question a context, and made it relevant.

This is important because it anticipates the most common question that will come from the members of the group that you’ve approached: “Why are you asking?”

Answering this question in a natural way will help you build trust with the group, and thus make continuing the conversation easier.

Feel free to post an open-ended question with a brief story for context in the comment section below. I’ll be happy to give you feedback!