5 Easy Ways You Can Turn Small Talk into Success!

Wes O'Donnell
7 min readMar 8, 2019

By Wes O’Donnell, Leadership Charisma Coach. Filmmaker. Enemy of the Oxford Comma.

From an uncomfortable seat on an airplane to the company holiday party, small talk is unavoidable.

For many of us, especially the more introverted, small talk is not only awkward, it’s painful! And while it may be more comfortable to say the bare minimum, you would be missing out on a huge opportunity to make new friends, reinforce old relationships and network.

Let’s face it, everyone says the same thing when engaging in small talk. But with a little verbal jiu-jitsu, you can not only appear more confident, charismatic and engaged but perhaps even create new business opportunities.

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I can often predict what someone will say when they sit down next to me on an airplane, if they say anything at all. Strangers who don’t initially make eye contact with you typically won’t say anything. For those that do, the first words for many are “How are you?”

According to Gary Burnison, “’How are you’ are the three most useless words in the world of communication. The person asking doesn’t really want to know, and the person responding doesn’t tell the truth. What follows is a lost opportunity and a meaningless exchange with zero connection.”

If you are meeting someone that you already know, perhaps at a company function, use your knowledge of the person to open with a more detailed greeting. For instance, “Hi Jennifer, great to see you! I bet your kids are getting big.”

Everyone loves to talk about themselves. It’s human nature. You will always come across as more charismatic when you take a genuine interest in the life of your conversation companion.

Opening with strangers is a little more difficult, but by no means hard. My favorite cold open is “Hi, you remind me of a famous actor [or actress], I just can’t put my finger on who. Is there anyone you relate to?” What follows is usually a humorous and authentic conversation.

I used this line on a gentleman while sandwiched between two strangers on a flight from Chicago to Detroit. The result was amazing. Once the conversation started, the woman on the other side of me joined in…

Wes O'Donnell

Army & Air Force Veteran | Global Security Wonk for War is Boring, GEN, OneZero, Soldier of Fortune | Law Student | TEDx Speaker | Founder of Warrior Lodge