Four Ways To Master The Art Of Small Conversation Skills

Broadly speaking, I have observed that I tend to have way better conversations with older people. You could say that it’s because of their life experience or general relaxed attitude – after all, chances are they’re retired.

But the data tells us that millennials are more confident, self-expressive, and upbeat than generations past. How does that add up to flat banter?

I went to a screening last Friday and plopped down next to a young woman sitting alone. My guess is she was in her mid-20s. I lobbed her a few niceties as she focused on her phone. And she put her phone away, seemingly intent on engaging with me.

Then the strangest thing happened.

She never returned my serve. I would inquire about her work and goals, she would answer, but then abstain from asking me anything. It was exhausting. I eventually gave up and she responded by talking. There is something to be said about people wanting what they can’t have.

Since then, it’s occurred to me that this may be the first generation whose primary communication tool is not a conversation. It’s a screen. And we all know how much can be lost in mere text.

Despite her desire to have a real conversation, it struck me that this particular woman was at a loss over how to small talk at a professional event. So with holiday parties and uncomfortable family get togethers just around the corner, here is refresher on how to chat for all ages.

Set Low Expectations

When it comes to light conversation, throw your vision board away. Company parties may be the ideal time to charm your boss for that extra bonus. But don’t bet on it. The last time that happened to me, he was pretending to listen while eying everyone who was walking past behind me.

Same rule applies when you see your family. It’s natural to seek approval and hope to heal past wounds. But sometimes it’s better if your goal is to get a good movie recommendation. And be surprisingly satisfied.

Refrain from “I”

Using “I” statements is a best practice in conflict resolution, but this is not applicable when aspiring to light banter. Notice how you feel if somebody keeps saying “I” all the time in conversation. Especially if you don’t know them, it can come off as a little self-important.

It signals to the other person that what you’re saying has nothing to do with them. It’s you talking about you – and you will probably lose them.

Remember in conversation, the objective is to have a back-and-forth. By steering clear of “I”, your conversation will naturally veer to the other person. They will pay attention more and likely talk about themselves: a surefire way to have a good conversation.

Be Curious

Find some angle to start the conversation. They can be as universal or unique as you can muster. Have fun with it and try to be genuinely curious.

Here are a dozen of our favorite starters:

1. What area or group are you with?
2. Oh, how long have you been there?
3. That sounds so cool. How did you get that job?
4. What’s it like working for __________?
5. Traffic (or subways) were brutal. How did you fare?
6. This place is so cool/ugly/bizarre/crazy. Have you been here before?
7. What movie/TV/streaming show are you dying to see?
8. Did you grow up around here? (Or seasonally) Going home for the holidays?
9. What are you looking forward to this week?
10. Great jacket/ring/shirt. Where did you get it?
11. Did you hear about [insert news headline]?
12. If you could live anywhere, where would it be?

It goes without saying that you should be actively listening to what the other person has to say. In a world with so much noise, people cherish the opportunity to be heard.

Also please avoid “What do you do?” at all costs. This is such a cliché and makes most people cringe when asked. You have my permission to cringe when you hear it.

Have An Exit Strategy

Not everybody will be as versed in conversation as you are right now after reading this. So be prepared to disengage as the conversation wanes. You will know. Or it will be made clear to you by the other person’s actions.

Stepping away to take a call or return an “emergency” email is an acceptable failsafe. So is refilling a drink or feeling hungry. Or if, like me, you were stuck sitting in a crowded theater, simply be silent. Sometimes it’s the only thing to say.

“Silence is one of the great arts of conversation.”

-Cicero