Traveling with your boss is an opportunity not to be wasted. Private 1:1 time with the one who controls your future can be incredibly useful for your career or could have devastating consequences. If you are the employee who gets wasted on the flight – not ideal. Alternatively, if you are inquisitive, knowledgeable and interested in the broader business it could be a career boon.
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
Let’s dig in to the 11 tips for traveling with your boss. We want you to learn how to make the most of this great opportunity.
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 apologist.
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Do you know how to behave in public? Do you remember your table manners? All of these things matter as your boss continues for an impression of who you are (and are not) as a person and employee.
The story he/she forms will be the narrative helps determine future opportunities (or lack thereof).
3) Avoid politics and religion (or at least be very careful)
I happen to be a bit on the conservative side of the political spectrum (more of a moderate conservative, really). During dinner with several junior staff members politics (tax policy, specifically) came up and I neutrally mentioned I tend towards fiscal conservatism.
One employee (although not my employee) sensing (incorrectly) that he had a dark red fellow brethren at the table with him he pivoted the conversation into more radical directions – eventually going on a 5-min diatribe about homosexuals and gay marriage.
We hardly knew each other…and it was entirely inappropriate for work conservation.
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 is. 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 (like I want to stay at the Red Roof In..lol #hardpass). 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. If you are like me, I’d rather throw my headphones on 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 bosses executive admin or another employee for suggestions. Or just ask your boss.
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 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. I was traveling with our COO once. A very nice lady and a road warrior. At the time, I’d not yet have TSA Precheck. She did. I queried her on the process, value, etc. It was great info and put me over the line to finally go get it myself.
And 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. So, don’t get into a Mexican standoff (who’s gonna talk…lol), but if/where appropriate let them opine.
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
One way you can show your boss your worth your salt is by asking smart questions. Asking great questions is a good way to show your worth.
For example, you might ask what the business motivation behind a new marketing campaign was, or maybe where do you 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 just 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, etc.
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 him/her.
Do some extra research before your trip. Brush up on market reports and conditions. Refresh your understanding of your customers 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 I started doing for my boss many years ago. When traveling with my boss to a customer site I built a one-sheeter that described the key pieces of information my 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, I made a point of making sure my boss at least appeared like they knew everything there was to know about the customer we were 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).
My bosses always LOVED it.
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:
Bonus Tip for Traveling with Your Boss: Avoid rumors, backstabbing and bitching
It might be tempting to let your trip with the boss devolve into a bitch 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!
By the way, if you are interested in more travel tips and travel advice, you might like these great articles:
- Best Career Advice: Do Something Even if it’s Wrong!
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- The Ultimate List of the Best Travel Blogs 2019 Edition
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