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Dear Yanni...Any tips for booking on behalf of my boss?

Dear Yanni...Any tips for booking on behalf of my boss?

In this week's column, Yanni addresses how to handle booking travel for a manager.

My new boss travels all the time and I’ve never really booked travel for anyone- I don’t want to mess anything up for her- what should I do to make sure I get things right, where do I start?

Heads up, this topic is a bit of a beast. TL/DR – Ask your manager about their rewards programs, preferences for hotels and flights, and time constraints. Make sure you have easy access to the necessary information you need to book their travel. For extra credit, consider their personality when choosing a hotel.

First things first, good on you for wanting to get things right. Planning travel is already tricky enough, let alone for a frequent traveler and a new boss. Not to worry, there are a few ways to easily get started. 

A good proxy for understanding how to prioritize where to stay and how to get there is to ask about loyalty. You may already have a list of loyalty accounts for your boss or not, but find out which frequent flyer or hotel loyalty programs matter the most to her, does she have any type of elite status or some status goals? If, for example, she is already Diamond Medallion with Delta, that means things like complimentary upgrades and priority boarding, along with access to lounges along the journey. This is important to keep in mind if company policy keeps certain flights to economy and the pricing is similar across carriers as someone’s status can get them a better experience for the same price. The best thing to do is ask, as most frequent travelers have some strong preferences. This wouldn’t be showing your novice side, it would show that you are read in to prioritizing her needs. 

It’s also important to ask about some of the small stuff that can really matter, like preferences for seating (aisle, window, nearest to the front/back, emergency rows), time of day to travel, if she prefers to check bags, and even if she prefers specific airports (e.g. never wishes to connect via Cleveland). This will help you to whittle down the right options and action preferences along the way. Ask about the needs around flexibility as well, do meetings or travel needs often change? Are last minute travel changes required because of it? This will prepare you to select the right options for that flexibility. There are flights that are fully refundable up until the last minute, and some hotels that will let you cancel without penalty up until the day of travel, but always read the fine print. If your boss knows that more flexibility is needed when traveling to Los Angeles versus Atlanta, this can help to make the right decision when booking. 

For extra credit, take time to understand her personality and preferences around things like food, fitness and culture. For the times you have personally traveled, you may have researched places you’d like to see or restaurants you’d like to try. It can be a really nice touch to let her know that near a hotel there’s a particular artist on loan for an exhibit, or that there’s a great option for her taste nearby to have a client dinner. These sorts of things keep folks happy when away from home and infuse a bit of joy into the travel experience. 

You’ve done the right thing by asking and being mindful of what your boss may need. The best piece of advice is to find the right balance for both of you, and this will take time as you get to know each other. Be prepared for delays and cancellations along the way, don’t stress or blame yourself and take a moment to always find what it is that can make travel a bit more fun.  


About the Author: Yanni Poulakos
Yanni has had the travel bug from a young age. From traveling to over 50 countries and stints spent living in Asia, South America, Europe and the Caribbean, his insights into hacking personal and business travel are grounded in first-hand experience. As a former road warrior, he once covered every province in Italy in 6 weeks by car, served as a travel manager for dozens of colleagues across the US and Europe while leading a fundraising team, and customized exclusive travel experiences for a smattering of politicians and celebrities. No matter whether at home or on the road, Yanni stringently adheres to his approaches to nutrition and self-care, with a fervent commitment to help others do the same.