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11 Tips on Traveling with your boss – don’t miss this career opportunity

by Jeremy B

Don’t waste the opportunity to travel with your boss. Private 1:1 time with the one who controls your future can be incredibly useful for your career or could have devastating consequences. Learn our 11 tips for traveling with your boss.

If you are the employee who gets wasted on the flight – not ideal. Are you not sure what to talk about with your boss? Missed opportunity. Unable to show up at breakfast on time each morning? Ick. Love opining about your political views? Yikes.

Alternatively, if you are inquisitive, knowledgeable, and interested in the broader business it could be a career boon. If you learn how to travel efficiently and hold a conversation with your boss you might find an edge for that next promotion.

In this article, we examine the idea of traveling with your boss and share 11 tips on how to make the most of this great career opportunity.

Traveling with your boss: 11 tips to make the most of it!

Traveling with your boss is an opportunity not to be wasted.

Let’s dig into the 11 tips for traveling with your boss. We want you to learn how to make the most of this great opportunity.

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1) Jump at the opportunity

First off, instead of being anxious, you should be jumping at the opportunity to spend some quality time with your boss.

This is your opportunity to shine. If you do this right, your career might be greatly enhanced. Don’t overthink it, of course, but see this for what it is and be prepared.

2) Every interaction matters (when traveling with your boss)

While traveling with your boss can be a great thing, you also need to be on point. Remember, every interaction matters. How nice/rude are you to the wait staff? Do you tip the shuttle driver? Do you order one drink too many with dinner? Or pop off about your political views?

Or, are you more measured? If politics comes up, you have a reasonable response that doesn’t betray your ethics/positions but doesn’t come across like a far-left/right extremist.

Do you know how to behave in public? Do you remember your table manners? All of these things matter as your boss continues to build their impression of who you are (and are not) as a person and employee.

11 tips for traveling with the boss

The story they form will be the narrative that helps determine future opportunities (or lack thereof).

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3) Avoid politics and religion (or at least be very careful)

No politics! That’s the rule if you can help it.

However, they do come up from time to time and understanding how to navigate this world is important. Here’s a real-world example.

During dinner with several junior staff members, politics (tax policy, specifically) came up and the boss neutrally mentioned she tends toward fiscal conservatism. One employee sensing (incorrectly) that he had a dark red partner at the table with him pivoted the conversation into more radical directions – eventually going on a 5-min diatribe about homosexuals and gay marriage.

They hardly knew each other…and it was entirely inappropriate for work conservation.

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As a general rule, try to keep divisive political opinions to yourself, and if you do feel the need to share them do so in a professional manner. Remember, it’s work.

If your boss, God forbid, takes the conversation in an inappropriate direction or goes off the deep end politically, take the high road. Demure, be neutral, and stand your ground only if clearly out of bounds per your company’s work policy. If your boss has a difficult political view than you – that’s their prerogative. You don’t have to be aligned on everything your boss says, is, or agrees with. They shouldn’t have brought it up,  but it’s still their opinion.

If it’s truly atrocious (and violates your company policy) file a complaint with HR…and perhaps consider a different job.

4) Defer to their travel preferences (e.g. their preferred hotel, airline, etc)

Unless it’s a totally obscene request, defer to their hotel choices (unless they want to stay at the Red Roof Inn. That’s a nope!). For example, if you are a Marriott person, but they prefer Hiltons, and it would be inconvenient for you to stay at different hotels, stay at the Hilton.

Don’t be fussy and make the trip an inconvenience for your boss just so you get your points.

5) No need to sit next to them on the plane…unless it makes sense (e.g. you board at the same time on a Southwest flight), but also don’t be adverse to sitting next to them

This is a little tricky. Some bosses would rather throw on their headphones and watch a movie (and not talk) for 2 hours. The same thing might be true for your boss.

You don’t necessarily have to sit right next to them on the flight – although your boss may actually want you to. You might have to use your intuition here and/or ask your boss’s executive admin or another employee for suggestions. Or just ask your boss.

people sitting on plane chairs
Photo by Johannes Rapprich on Pexels.com

Unless I know that we have something specific to work on / discuss I assume we will sit separately. If you are traveling on an airline like Southwest maybe you take different sides of the aisle – near each other but not on top of each other.

If you have assigned seating, it’s likely a non-issue. If it’s important you sit together, you’d have likely coordinated it already (in theory).

6) Ask them for travel advice (they likely travel more than you…)

Many bosses travel quite a bit – especially senior management. Ask them for some travel tips (if you are a newbie, anyways). If you are a pro already, then maybe you want to keep your “dumb” questions to yourself.

Here’s a good example of a question to ask. The author was traveling with his COO once. A very nice lady and a road warrior. At the time (many years ago, mind you) the author did not yet have TSA Precheck. She did. After querying her on the process, value, etc, the author learned some great info and it was enough to put him over the line to finally go get it. Good conversation fodder.

Besides, the COO liked it too. She got “tutor” a youngin’.

7) Let them do most of the talking (some bosses love to talk…)

If they are a great boss they will let YOU do the talking. The smart ones always do this (and even help the conversation along). This is an opportunity to maybe see behind the curtain on the business, see how the sausage gets made if you will. Let them show you.

Listen attentively, ask good questions (see below for more on this), and learn.

8) Ask smart questions (strategy, business, market) when traveling with your boss

You can show your boss your worth by asking smart questions. Asking great questions is a good way to demonstrate you are interested in the business and are worth his or her time.

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Photo by rawpixel.com on Pexels.com

For example, you might ask what the business motivation behind a new marketing campaign was, maybe where do they see the business in the next 3 years, or what are the major risks to a new product’s success, etc.

Don’t limit your questions to simply your swim lane (e.g. if you are a salesperson don’t just ask sales questions). Ask questions about other parts of the business, the broader market, and so on.

This demonstrates to your boss that you have a big-picture view of the universe.

9) Be informed (market, business, customer, etc)

Good employees should be doing this anyway, but when you are traveling with your boss, it’s a great opportunity to demonstrate this to them.

person using laptop computer on brown wooden table
Photo by rawpixel.com on Pexels.com

Do some additional research before your trip. Brush up on market reports and conditions. Refresh your understanding of your customer’s concerns, or new trends. Even company issues or opportunities.

Show your worth by showing your knowledge.

10) Pre-brief them when applicable (e.g. customer one sheet)

This is something great employees do for their boss. For example, when traveling to a customer site the boss might want to learn a little bit about the account and what they are walking into. Why not build them a short one-sheeter that describes the key pieces of information your boss might need to know?

Things like

  • Current Products
  • Current Business Challenges
  • Last Sale (date and size)
  • Future Sales opportunities
  • Key decision makers (and any tidbits of useful info about them)
  • Any existing problems/concerns about our products

You get it. In other words, consider the value in helping your boss at least appear like they knew everything there was to know about the customer you are visiting.

As the boss, it can be hard to keep track of every customer and issue. By refreshing their memory and giving them a current lay of the land they can walk in with confidence. This helps you in that your boss can “do his/her job” onsite and further cement that relationship.

And when traveling with your boss you can use the flight, or breakfast at the hotel to go over with them.  It shows you are prepared and that you want THEM to be prepared (and successful).

11) Think about things FROM their point of view

As the “boss,” you have an entirely different perspective. You may have a different view of the business, different motivations, different concerns, etc than a line worker.

Try to think about things from their point of view when engaging in conversations while traveling with your boss.

You  might be interested in the Best Career Advice Ever:

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Bonus Tip for Traveling with Your Boss: Avoid rumors, backstabbing, and complaining

It might be tempting to let your trip with the boss devolve into a gripe session about how the service department is dropping the ball, or how Jimmy in accounting is a pain in the arse. Resist that urge. Take the high road.

You can certainly air grievances if and when appropriate, but keep it professional, not bitchy/whiny, and focused on business outcomes. Avoid the urge to dime out other employees – even if prompted.

Final Thoughts on Traveling with Your Boss

Traveling with your boss is a great opportunity so don’t be anxious. Instead, be prepared. If done correctly, it can be a major boon to your career. Your boss will see you as an informed, intelligent, and prepared employee and perhaps someone worth promoting in the future.

What’s your favorite tip for traveling with your boss? Do you have a horror story? We’d love to hear it! Leave us a comment or tweet us!

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traveling with the boss - 11 important tips

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1 comment

D.A. September 11, 2023 - 8:29 am

Much like traveling with your s.o., always offer them your upgrade.


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