Want to improve your social skills?
Talk to strangers.
If you learn how to talk to strangers, you can talk with pretty much anyone.
Now here’s the “secret”:
Not all strangers are made equal.
Some strangers are just a lot less intimidating to talk with.
Enter retail store owners!
Their job is to make sure that you have a great time at their business, after all.
While they definitely want you to buy a thing or two, many of them also enjoy connecting with people.
I’ve chatted up all kinds of retail store owners — from bookstore owners to kiosk owners — and here are a few tips that have worked best. You will notice that most of these tips are really, really simple, and I will explain why that’s the case.
Say hi and smile
A big mistake most folks make is skipping the small talk, or trying to be too clever in small talk.
Yes, you can be creative, but when you’re nervous, it’s way easier to keep things simple and direct.
Saying hi also helps you gauge early on if they are open to chatting a bit more.
Comment on their day
Another way to test if they’re open to chatting?
Ask them about their day. There are many ways to go about it, depending on the crowd and time of day:
- “Quiet [afternoon/evening] so far?”
- “Looks like it’s a busy day/evening for you?”
- “Wow, didn’t expect that many people today/tonight.”
If they brush off the comment, that’s OK — give them space and approach them on another day.
Ask for their recommendations
Whatever store they’re running, ask them to recommend something based on your goals or preferences. For example:
- If you’re looking for a book, say: “What [genre name] book would you recommend reading?”
- If you’re looking for a dress, say: “I’m going to [event type e.g. party] – what dress would you recommend for me?”
- If you’re looking for a game, say: “I want to play some [genre name] games – what would you recommend?”
Alternatively, you could name a specific item they would have in their store and get their feedback on whether you should get it or not.
Getting their input helps you make a better buying decision, it also helps you understand them better without having to get too personal — which is ideal for initial interaction.
Ask what their name is
“What’s your name?”
If they have a name tag, ask them how to pronounce their names correctly. (Exception: if the name is a simple one like John…)
- “How do I pronounce your name?”
- “[their name] – did I say it right?”
You could also be curious and ask “so what does your name mean?”
This sounds like such a basic tip, but it’s underrated. Why? From my experience, once they’re willing to disclose their names —something small about themselves— it’s a lot easier to get them to share other things. (This is known as the foot-in-the-door effect in psychology.)
Make it a point to remember their name, and call them by their name when you visit next time — you will get better service and better conversations.
Compliment them personally
What do you compliment them on?
Not their looks, please.
Here are a few things I’d look out for:
- If they have a cool hair color or hairstyle (appearance-related, but still OK to say based on my experience)
- If they’re wearing an interesting personal accessory, for example an old watch or a colorful brooch
- If they have tattoos (tattoos are typically imbued with meaning)
Your compliment can be as easy as “nice [thing you noticed]”. Specific enough to make an impression, but not too specific that it comes across as awkward or creepy.
Ask them about their entrepreneurship journey
I’ve collaborated with entrepreneurs all my life so I’m probably biased… but it’s so fascinating to learn about why someone took the leap of faith.
Once you’ve broken the ice, here are a few questions that you can ask:
- What made you start the store?
- What was the biggest challenge when starting the store?
- What do you enjoy the most about running the store?
Here are more career journey questions.
Alternate between asking questions and talking, so that they don’t feel pressured to answer one question after another 🙂
Ask them non-work questions
Once they get comfortable talking with you, you can open up the conversation and start getting to know them personally.
Make sure that there aren’t other customers waiting to be served — they are there to run a business after all.
There are too many ways to continue the conversation from here, so I’m not gonna try… but here are two helpful resources:
- Lists of conversation starters (organized by topic)
- 25 useful phrases to keep a conversation going (and avoid awkward silence)
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