How To Make The Most Of Traveling With Your Boss
6 ways to effectively use your one-on-one time to build a better working relationship
Use downtime to your benefit when on the road with your manager.
Business travel can be a welcome break from the day-to-day routine of the office. And if you’re hitting the road with your boss, you’ll find yourself in a unique position to log some hours with them in ways you wouldn’t normally—think flights, client dinners and cab rides. It can feel a bit awkward at first to spend time with a supervisor outside of the normal work environment (remember how weird it was to see your teachers outside of school?), but if you make the most of this travel time, it can go a long way in strengthening your relationship and proving your value.
If you have to book your own travel, discuss flight times with your boss before making a reservation. Consider booking the same flight or one close in timing so you can share a ride from the airport to the hotel and have some time for relaxed conversation before getting started on work.
When appropriate—such as in the car ride back to the hotel after a meeting—it doesn’t hurt to talk to your boss about weekend plans or each other’s interests outside of work. You shouldn’t open up to them like you do your best friend, but remember they’re human and have a life beyond the office. Friendly conversation may even lead you to realize the two of you have shared interests or goals, and it may even give you insight into how they approach their work.
Being on the road can sometimes mean fewer distractions and interruptions than on a typical day in the office. If it’s just you and your supervisor on the road, you’ll likely find time where you can communicate openly without worry of eavesdropping coworkers. Use the time to ask for advice, share progress updates or talk about your role. Communicating openly and with confidence can help build transparency and trust in your relationship with your boss.
If you’re looking to impress, try to stay a step ahead of your boss while you travel together. Before and during the trip, work to anticipate any challenges that might arise and be prepared with solutions. Not sure how you’ll project your presentation? Bring multiple port hookups. Will you be cutting it close going from your last event to the airport? Preschedule your ride with a taxi or ride-sharing service so there’s no waiting. Being prepared and taking initiative can help position you for advancement.
If you find yourself in over your head or stressed about being on the road, bring it up to your boss. Ask questions, get clarification and be proactive in asking for help. Most managers enjoy giving advice and want to help you succeed—especially while on the road and in high-stakes situations.
Find out what success for your trip looks like to your boss. Discuss this with them before and during the trip to ensure you’re hitting the mark. Being proactive, having periodic check-ins and ensuring goals are being met while on the road will show you are able to be responsible in a variety of business-related situations.
And remember, you should always follow basic business etiquette while on the road with your boss. That means:
- Avoid office gossip
- Work when your boss is working—on the plane, in the airport or at the hotel
- Stay off social media and personal email while at meetings or client events
- Dress professionally throughout your trip
- Avoid overindulging in alcohol
At the end of the day, be confident, follow basic etiquette and, of course, enjoy the trip—doing so will help you make the most of traveling with your boss.
Written by Emily Howard
Ready to travel? Explore our business tips and destinations..
More to Explore
Fly like a boss
Some helpful suggestions to remove some stress when your trip gets off the ground.