What to Consider Before Outsourcing Travel Bookings

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Strategic planning allows you to stay on track to meet your business goals. Here’s an overview of strategic planning and how to leverage it.

Whether you travel once a month or once a quarter, booking your plane tickets, hotel rooms and ground transportation can get very time-consuming.

But, because so much of it is based on personal preference, it can feel too difficult to outsource to a VA or personal assistant.

Rather than throw your hands in the air and commit to doing it all yourself all the time, start developing a process for booking travel so you can slowly outsource pieces of it as you get more comfortable. Before you know it, you’ll have the entire process streamlined and documented so you can easily and comfortably pass off the bulk of it.

And remember, even if you’re only outsourcing the initial research to start, you’re still saving time!


First, decide what your priority airlines will be. If you have two or three airlines you prefer to fly with they should always be the first ones you check for tickets.

Document what nearby airports you will and will not fly out of. If there are rules here like “I’ll fly out of JFK on Tuesday through Friday but not Saturday to Monday” then be sure to specify those.

Similarly, consider any connecting airports you prefer to avoid. For instance, I hate having layovers in San Francisco because there are such frequent weather issues. So, I avoid SFO layovers when booking flights if it all possible.

As for your destination airports, consider any restrictions or preferences as well, especially if it’s somewhere you travel to frequently.

Be sure to document any frequent flyer account information for your preferred Airlines as well as preferred departures and arrivals times. Your departure and arrival times may not always be feasible given other constraints, but if you’re adding a few buffer days before and after an event (which you definitely should!) they become much easier to accommodate.

Now to start, I’d recommend having an assistant do the initial research and narrow it down to three potential flights. You can then review and do the final booking. This will help avoid any unnecessary change fees.

Once you’ve found your groove thing, it may be entirely possible to pass the entire process off to your assistant.


You want to go through a similar process here. Consider your hotel preferences and any specific chains you prefer or want to avoid. Again make a note of any loyalty programs you participate in.

I would also recommend documenting room preferences. Think about things like:

  • view preference
  • floor preference
  • bed size
  • rooms set-up (i.e. Do you want sitting or working space?)
  • breakfast included

Location can also be very important, so consider how close you want to be to any events. This will likely tie directly into things like parking and your ground transportation, so you may need to stick with just the basics here.

Unless you’re booking a non-refundable room, it’s generally ok for your assistant to start booking reservations right away. If you end up needing to change the reservation, it’s usually at no charge until you get right up to the dates of your stay.

Ground Transportation

Start by identifying what your preference is for ground transportation.

When do you:

  • rent a car
  • arrange for a car service
  • use public transportation
  • use Uber, Lyft, a taxi, or a shuttle

If you need a rental car, again you want to document the companies you prefer or want to avoid. Document car preferences as well as any loyalty programs you participate in.

For a car service, think about what parameters are important to you. Is it price, wait time, or something else you care about?

If the trip lends itself to public transportation, consider what information you need to know upon arrival. I like to know things like the main line or stop closest to my destination, how I can pay (cash only or cards accepted), as well as my route to my hotel.

Again, if you’re booking a car rental or car service, your assistant can likely complete the process for you assuming there’s a free cancellation option.

All in all, with a little preparation and planning you can outsource your travel bookings with confidence. It doesn’t have to be an all-or-nothing process. So, even if you’re only comfortable with outsourcing the research stage at first that’s still a good place to start.

Before too long, your assistant will get comfortable with your preferences and eventually be able to book your travel with ease.


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