Planning the Perfect Business Trip for Your Boss

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By Liz Carisone

Planning any business trip can be stressful, but the pressure is even greater for an administrative professional when you’re making those plans for your boss. With the ability to make or break an out-of-town meeting, arranging travel is a serious responsibility that takes a good deal of intentionality and foresight. Despite the stress, planning a trip can be a great opportunity to show your company your capabilities and skills, potentially earning the confidence of your superiors. If your job responsibilities include managing business travel arrangements, use these tips to plan a trip for your boss that is sure to impress.


Communicate Well
One of the most important things to keep in mind when planning a trip for your boss is to never make assumptions. When you’re assigned the task of taking care of business travel details, write down all of the information that you’re given and ask for additional details as needed. Know the budget that you’re working with and be sure you don’t go over it. While you want to make sure that your boss is comfortable, your company likely won’t appreciate it if you spend more money than you were assigned.

It’s also helpful to find out right away if your boss has any specific preferences or has any ties to specific loyalty programs/travel brands. You don’t want to make reservations at the Hyatt only to discover that your boss prefers to stay at a Marriott. It’s hard to meet your boss’s expectations if you don’t actually know what they are, so be sure to find out in advance what those preferences and expectations are.

Once you have all of the information that you need, make a checklist of everything that you have to do before the trip. Put a date next to each item to remind yourself when the task needs to be accomplished. Entrepreneur magazine reported that checklists are an effective way to optimize performance and ensure that nothing gets forgotten, so you should consider using this strategy even if you aren’t typically a “list person.”

Plan for the Unexpected
While your boss’s time is valuable, always plan for the unexpected when it comes to booking flights. If the day’s first meeting is at 10 a.m., don’t book a flight that lands at 9 a.m. Flight delays could completely throw off the schedule that you planned. Before you purchase the tickets, budget in some extra time for delays on the day of travel.

You never know when your boss is going to need to impress a client, so it doesn’t hurt to make reservations at an upscale restaurant far in advance. It’s much easier to cancel a reservation than to try to find a table at the last minute. Keep in mind that dinner reservations aren’t the only area that will benefit from a bit of foresight. According to USA Today, making business travel plans as early as possible is a good strategy for every step of the process.

Before your boss leaves the office, make sure that you have forwarded them any confirmation emails, and that you print out extra hard copies just in case.

Arrange for Exemplary Transportation
An often over looked item in planning travel for your boss is having ground transportation pre-arranged for every step of their business trip. Even though your boss might claim he or she can handle this portion of the trip on their own, on the ground, they will appreciate that you have taken the initiative to make sure they’re not wasting time in a long taxi line, desperately searching for a last-minute on-demand option or trying to navigate the public transportation system in an unfamiliar city.

It’s important to find a reliable provider that offers an on time, every time pickup guarantee, scheduled service, and places a priority on safety and security (duty of care). In other words, they only hire professional drivers who are properly screened, licensed and insured. You want to seek out a company that not only features the latest technology (including booking through a mobile app or website), but also gives you the option to talk to a live person when needed. This way you can easily communicate with the provider any last minute changes.

Also look for a ground transportation provider that offers transparent pricing so there are no surprises at the completion of your boss’ trip. It’s also smart to find a company that provides the ability for you as the travel arranger to track your boss’s ride, and it is especially helpful if they provide access to a dashboard that shows all of your boss’ ride history and e-receipts for easy expense reporting.

With a bit of advance planning and foresight and attention to detail, you are sure to impress your boss and earn the confidence within your company as the “go-to” when it comes time to book the next important trip for one of the company’s top executives.

About The Author:
Liz Carisone is the CEO of GroundLink, a leading global tech-enabled, black car service with operations in more than 100 countries throughout the world. You can reach Liz at


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