It’s not unusual to do business on a plane these days. If you’re new to the world of business travel, or have been shy to strike up conversations with fellow passengers in the past, here’s a few suggestions to get you going.
Be Prepared
A little advance reconnaissance about your destination and the cities of any connecting flights can go a long way for initial small talk.
Learn about a great restaurant that just opened, a big company that’s opening a division in that locale, a museum exhibition, all of these things are ways to ask or suggest to your seat-mate: “Did you know, Have you seen, or  I’d love your feedback.”
Once the conversation is going, there will be organic opportunities to guide the topics to your advantage.
Body Language
It’s important to read the body language of the person to gauge if they want to carry on a conversation beyond the initial pleasantries one would exchange with a seat-mate.
If the person immediately puts on headphones or has a sleep mask at the ready, don’t make a move.
If they launch a movie, or order the featured film on the flight, then you’re not likely to get much going, unless you can start a chat after the film.
Devices and Reading Materials
The reading materials and devices the person sitting next to you are always a great clue.
iPad vs. Kindle = Kindles are usually reading books, vs. the iPad could be looking at anything and the conversation can start about technology and how do you use your device. Often clues about the person’s profession or vocation come up organically during a discussion about technology. Kindle users aren’t usually so tech savvy, although initially you could say the were early adaptors.
If the person is reading the Wall Street Journal, you know the individual has an interest in the big picture of the economy.
You might ask if you could read a section of the paper, most people will oblige. Conversation can begin about an article or news item.
Beverage Service
When the beverage service comes down the aisle is always a good time to start up a conversation.
If your seat mate is sleeping, let the flight attendant address the person, that way, you won’t be the pest that disturbed their nap.
If the person orders an alcoholic beverage, you might talk about your favorite scotch or the first time you had Vernors, try create a small talk opener.
Since you’re basically having lunch, it’s often easy to ask if you’re traveling for pleasure or business and guide the conversation from there.
You’d be surprised what you can find out. Those who master the art of small talk to connect the dots are going to have better luck.
For example, if they’re visiting a city for the first time and you have some great recommendations for them, offer to email the name of a great restaurant, car service, etc.
This is always a good excuse to exchange business cards, connect via Facebook or LinkedIn.
Look for the common threads in the conversations. Places to eat, business associates in similar fields, a project you worked on that could have used their expertise and vice versa.
First Class
There’s an assumption that if you’re in First Class, you’re successful in some way. There’s an air of privilege there.
I find that when the wine is flowing, the men, in particular, spread out, and will share anecdotes. I never interrupt anyone who is working unless it’s the beverage service, or they need to get by me to use the bathroom.
These are both opportunities to strike up a conversation.
Some of my “leads” are: ” Looks like you’re on deadline,” or “What program are you working in, I’ve tried X, but it doesn’t meet my / my companies’ needs.”
Men have the advantage of always being able to talk about sports or hobbies, and are usually more forthcoming about their work or business, and will usually always offer a business card. Over the years, I’ve dated two men I met on planes and forged a strategic alliance with another, and thirty years later, we are still collaborating on various projects.
I find that women talk about clothes, family, hobbies and business, not necessarily in that order.
You never know when you’re going to meet someone who will make a difference in your life. They say luck is preparedness meets opportunity.
Enjoy your flight, but should opportunity come knocking, be sure to answer the door.