Blogs & Comment

How to make it slightly less hellish to travel with your colleagues

You don’t truly know your colleagues until you’ve tried to clear airport security with them. Here’s how to keep things together on those out-of-office jaunts

Workish: Corporate culture. Career advancement. Welcome to the office.

Man looking at his watch at an airport

According to unconfirmed statistics hidden in the lyrics of Air Canada’s hold music, business travel is at an all-time high. And as methods of transportation evolve, it’s important to understand the unwritten rules of jet-setting with co-workers.

Whether you’re riding horseback to the CEO’s fireside chat in Muskoka or paddle boarding in the IT department’s “Race for RAM” on English Bay, heed these Fundamentals of Etiquette when globetrotting with colleagues. After all, unspoken regulations are known to change at the drop of a hat…three ounces or less.


Invented by the Wright brothers as a psychological experiment to test the boundaries of human patience and basic comfort, airplanes are the in-demand, out-of-shape transportation of the future. And though the value of the WestJet Dollar hasn’t adjusted for inflation since 1903, airline formalities have upgraded in priority.

When traversing an airport with a co-worker, remember that security lines are like the neutral zones of Star Trek: buffer sectors requiring careful navigation. Save time by researching new TSA restrictions for Adobe Acrobat downloads before you arrive. During unexpected bag checks in the presence of your boss, get brownie points by packing a 3-ring binder labeled “Ideas to Build Revenue.”

After passing through an over-branded jet way from HSBC, choosing in-flight content can be a trickier than a $19 book of puzzles from Relay. Acceptable magazines include Fast Company and the industry-agnostic Periodontology This Week. Watch on-demand videos like Too Big To Fail, and crack-open a pre-highlighted book written by your CEO. If you absolutely have to sleep, cover your head in an Ostrich pillow and tape your mouth shut.


Originally designed as a pre-fabricated excuse for employees running late to work, today’s trains are used exclusively for downtown commutes, and in some cases, between Toronto and Montreal.

Though railroads once separated Snowpiercer-like first class benefits, today’s public transit amenities are available to all. When loudly discussing trade secrets while riding the rails, enjoy Standing Room Only, No A/C, and Four Seconds of WiFi at Bloor-Yonge.


Aside from cost-saving measures like staying near The Four Seasons, the most expensive portion of a business trip is often the overnight stay. And though new mobile-based services like Airbnb and Kindle Motel with Free HBO! are disrupting the hotel industry, elemental rules remain the same.

Upon check-in, exchange 500 loyalty points for a bottle of Aquafina, then announce a last-minute call and head to your room. Take this newfound Zen-like “you time” to charge the iPad you don’t need and stack business cards you’ll never use. Confidential to hotel gym power-users: Treadmills Only.


When rolling with fellow road warriors from HQ, remember that regardless of who’s driving, the renter of the car is the keeper of the radio conch. Instead of polling passengers for music suggestions, recite a sales training audiobook as it plays in synchronicity. On long trips across the highway, steer clear of Fury Road by jumpstarting conversations on politics and religion.

Riding in Ubers requires a different set of dialogue chops: when banter lulls, be the first person on the planet to ask the Uber driver if it’s fun to drive for Uber.

Sandy Marshall has almost reached silver status, and can be unfollowed on Twitter at @MarshallSandy.