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Planning a Trip for Your Boss: The Checklist

Planning a Trip for Your Boss: The Checklist

Currin Berdine and Anna Yu / AdminSecret

Follow our four important steps to ensure planning a trip for your boss goes smoothly:

- Step 1: The Pre-Trip Discussion
- Step 2: Booking the Flight
- Step 3: Arranging the Hotel and Transportation
-The Final Step: Go Over the Details with Your Boss

Step 1: The Pre-Trip Discussion

When you start your administrative work for anyone, you need to find out about their travel habits and preferences. Even if your boss isn’t traveling anywhere for months, you should sit down and speak with them about arranging trips almost immediately. First, who knows if an unscheduled meeting across the country is going to pop up, and you need all their information immediately. Secondly, knowing your bosses’ preferences might give you insight to their overall work personality and procedures, which can come in handy with other situations. (For example, morning or night person? Is he always demanding first-class or is he stingy in coach? etc.) Every manager is different, so be sure to carefully note their tendencies.

What you should find out in the pre-trip meeting:

-When does he/she prefer to fly? Mornings? Early Afternoon? The red-eye?
-When does he/she prefer to arrive at a destination?
-Is he/she a member of any frequent flyer programs, special military groups, age groups, etc. that could alter the prices or arrangements of the flight?
-Do they have an overall preference for any particular airline?
-Does he/she always carry on their luggage or do they check it?
-Do they only want direct flights or do they mind layovers? Are there any airports they prefer to have a layover in (or ones they would rather avoid?)
-Do they have a preference as to modes of transportation? Meaning, would they rather travel in a commercial plane or a private plane? Also, once at their destination, do they prefer to ride in cabs, town cars, limos or rent their own car?
-Where do they like to sit on planes? Aisle, middle or window? First-class, business-class or economy?
-Do they have any requests for food preferences or allergies? Airlines today cater their meals to Kosher, Vegetarian, Vegan, Non-Dairy, etc.
-How much are they willing to pay/ how many frequent flyer miles are they willing to use to cater to all these preferences?

Similar questions should be asked regarding hotels and accommodation:

-Is he/she a member of any frequent guest programs, special military groups, age groups, etc. that could alter the prices or arrangements of the booking?
-Do they have an overall preference for any particular hotel?
-Do they request any specific amenities at the hotel? For example, do they need wireless access? A gym or pool? A restaurant or Continental breakfast?
-Do they have a preference as to modes of transportation? Once at their destination, do they prefer to ride in cabs, town cars, limos or rent their own car?
-Where do they like to stay within a hotel? Smoking or non-smoking room? On the first floor or the penthouse?
-How much are they willing to pay/ how many hotel program points are they willing to use to cater to all these preferences?

If you take the initiative to find out the answer to these important questions before your boss even asks you to book a trip, you are ahead of the game. It will not only show your dependability and responsibility, it will make your job a whole lot easier down the road.

Read all of our ‘Travel’ Articles

Step 2: Booking the Flight

The day has arrived – your boss has requested that you plan a business trip for him to Washington, D.C. He needs to be there for an important conference by Thursday the 8th.

Where do you go from there?

First, analyze what you know about the dates. If he needs to be there the morning of the 8th for something important, you should consider booking his flight to arrive in D.C. the night before. Yet, you don’t want to make him arrive too late, making him tired the next morning.

Second, take into account the departure and arrival locations. If your boss is flying out of New York City (JFK) and going to Washington, D.C. (IAD) the flight will only be about an hour and a half. But if your boss is flying out of Los Angeles (LAX) a direct flight last nearly 5 hours! That isn’t counting the time difference of three hours from LA to D.C. With stops, it could be a whole day of traveling for your boss.

If you boss is traveling for an important meeting and has to cross time zones and is flying for a long time, be sure he has plenty of time to relax and rest before the big day. Traveling can be exhausting, so take this into account.

Third, use a search engine to find flights that match your calculated schedule and also match your bosses’ preferences. The sooner you book the flight, the better times will be offered and the lower the cost. If your boss is a member of a frequent flyer program, give that airline preference – even if it costs a bit more money. finds the lowest prices of the major flight search engines. We also use because you can set your preferences for departure and arrival times very easily.

Fourth, once you book the flight, call the airline your boss will be flying with – especially if he/she is a member of a frequent flyer program. Be sure they have registered, that he/she will be flying with that airline and on what flight. If you boss prefers to fly first class, check how many miles he/she has available and how many it will take to upgrade. Most bosses allow you to do this at your discretion but you should have a good idea of what is appropriate.

Also during this call, be sure they are in the aisle or window, that their meal is catered to them, etc.

Read all of our ‘Travel’ Articles

Step 3: Arranging the Hotel and Transportation

First, take into account the purpose of the trip – going to an important conference. Check to see where the conference is located in Washington, D.C. Is it is Georgetown or in Bethesda? These areas are in completely different areas of the city, so be sure your bosses’ hotel is as close as possible to the venue.

Usually, this arrangement is the case. However, if you boss is very particular about where he likes to stay, then book him at that hotel. Be sure to let him know that the hotel is X number of miles from the conference, so he should plan that into his trip.

Additionally, if you boss is a member of a hotel rewards group, give preference to one of these hotels, unless there are none anywhere near the conference location.

Second, arrange transportation for your boss to and from: the airport, the hotel, the conference, and any other places they need to be. Depending on what your boss requests, this can vary greatly. Below are some of the options and how to manage the details:

Limo/ Personal Driver/ Town Car
If you boss already knows a company in the area, then get that information from him. If not, contact an admin at the company or organization to which your boss is traveling. Their administrative assistant can probably give you good references. If this fails, then try looking up a place on the internet and be sure it has excellent reviews across the board.

Call the limo company and explain to them your wishes. Give them an overview of your bosses’ itinerary with general locations and times. You will also want to explain that cost factors in or other requests. They should suggest to you the most reasonable service.

Just in case, you might want to shop around for this type of service. Call a couple of places and compare rates and transportation amenities.

Once you’ve found the best offer, finalize the details with the company. Send them your boss’s complete and detailed itinerary, including flight numbers, airlines, hotel location, etc. Find out the name of the driver(s) that will be transporting your boss and all of their contact information.

If your boss opts to hop in a cab, be sure he can do it easily. If he is going to large airport during normal flying hours, there should be plenty of cabs outside at the taxi stand. If he is traveling to a smaller airport, a small city or town, or during off-peak times, call a cab company the day before he is scheduled to arrive. Let them know when he should be coming out of the airport (take exiting the plane, getting luggage, etc. into account) and his full name. An hour or so before he is due to arrive, call the cab company again to confirm. Also, tell the dispatcher what terminal or baggage claim area he’ll be coming out from. Give the cab company your boss’s cell phone number so they can call him where they are waiting.

Renting a Car
If your boss wants his own wheels for the trip, then you should reserve an accommodating car. Go on a rental car company website and shop around for the best deals.

When deciding which car to order, consider the details. Does your boss choose safety over luxury or speed over a roomy interior? Think about the car he drives and what would make him most comfortable. Also, try to choose a color similar to the car he drives, because then he will instinctively be able to spot it in a parking lot.

Furthermore, think about the type of location where he’ll be driving. In a major city, opt for a smaller car where driving and parking will be easier. If he is going to Texas, however, nearly everyone drives an SUV so a bigger car might be more suitable. If your boss is traveling with a lot of luggage or has to accommodate other passengers, be sure the car has ample space.

The Final Step: Go Over the Details with Your Boss

Be sure every detail is printed off easily for your boss to read and take with him on the trip. Include:

-Airline: Carrier, terminal, gate, seat number, etc.
-Transportation: Any useful numbers, names, companies, etc.

Let your boss know he can call you anytime during his travels to help with whatever details he needs. Just because he isn’t in the office, you are still the support system, and should consider yourself the ultimate personal travel agent.

Bon voyage, boss!

Read all of our ‘Travel’ Articles
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