Beyond Small Talk

How to Talk to Anyone

The holidays are a time of warmth, cheer, and awkwardness. Here’s how to enjoy even the trickiest conversations.

Ross McCammon
Published in
4 min readNov 21, 2019
Illustration: Heeje Min Heo

This story is part of How to Talk to Anyone, Forge’s guide to moving past the chitchat and truly connecting.

IIt’s all about the first five minutes. This conversation is going to go a lot more smoothly if you treat your second cousin Jenna’s boyfriend as the most important person in the world for exactly that length of time. It’s long enough to take small talk to medium talk (holiday gatherings are festivals of medium talk), but not long enough to exhaust either you or Jenna’s boyfriend (it’s Kyle, right?).

Because, pace yourself. Holiday gatherings are marathons. They are rooms full of people you must talk to but aren’t necessarily equipped to talk to and maybe don’t even want to talk to. “How are you?” won’t get you far.

Awkwardness is a guarantee. And moving past it is going to require more than just warmth and cheer (and spiked punch). It’s going to require curiosity about whoever you encounter: your political opposite, the person four times your age, the painfully shy college student, that seven-year-old over there who has stared at you for easily 10 minutes straight. Easily.

These principles work anywhere: on a plane, at the grocery store checkout, in a waiting room. But they are crucial around the holidays, where you find yourself mingling with a group of people who would never otherwise end up at a party together.

It might help to approach the task like an interview. At first, your conversational partner should feel like a subject. Something to understand, to investigate. Put them in the spotlight and give them the space to spool out their own narrative.

You don’t have to be a particularly rigorous interviewer. Ask a question, and only follow up if they seem eager to keep going. Relate an anecdote about your own life for every two you draw out of them. Let any harmless mistruths slide by without comment. If you get stuck, triangulate! What is the deal with that painting over there, anyway?



Ross McCammon
Writer for

Author, Works Well With Others: Crucial Skills in Business No One Ever Teaches You // writing about creativity, work, and human behavior, in a useful way