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Hack Your Business Trip to Make Your Hotel Stay Way Better

Even if your employer's paying for your stay, it's easy to secure perks and upgrades if you know who—and how—to ask.

Most business travelers are at the mercy of their employer's travel policies when it comes to where to stay. But once you get to your hotel, you'll need to impress a different power broker to make your visit as comfortable as you can: the front-desk agent. With a few keyboard taps, these often-forgotten employees can control whether you stay in a noisy closet-size room or get a primo suite for the same price, according to Jacob Tomsky, a former hotel front-desk agent and author of Heads in Beds: A Reckless Memoir of Hotels, Hustles, and So-Called Hospitality. 

Getting these people on your side can lead to a better room, better perks, and far better service. “Hotels seem impersonal, but they are very personal, and you're dealing with human beings who are making decisions about your stay,” said Tomsky. Here are his top tips for dealing with front-desk agents and getting their hotel to treat you like a VIP whether you're a grunt on a sales visit or a top executive.

Call before you arrive

Chances are, you didn’t have any contact with the actual hotel when your room was booked. Even if a travel agent or assistant didn’t book your stay, third-party booking apps such as HotelTonight and sites like Expedia have made the process almost as easy—and impersonal—as ordering an Uber.

According to Tomsky, actually calling the hotel the day you arrive or day before you arrive and making a human connection with an on-site agent can influence your stay, leading to more personal attention, possible perks, and the real likelihood of an upgrade.

“Call and say: ‘Hey, I’m arriving tomorrow and just want to check on my reservation and make sure everything is correct,’” Tomsky said. “You can also say: ‘Are you working tomorrow? I'd really like to thank you for taking care of my reservation.’ It’s an act of kindness, but it also makes the front-desk agent a little nervous in a good way, because it's like, ‘Oh, this person is coming, and they're going to make sure that I did a good job.’”

This phone call is also a good time to make any specific requests. If you need a room with a larger desk or a room suited for hosting meetings, mention it, Tomsky said. Also note: The number listed on most hotel sites leads to a centralized reservation line. To reach the front desk, Tomsky suggests looking up the property on Google Maps and calling the local number listed there. 

Pro tip: Tip everyone

While most travelers know to tip a bellman or valet, few leave anything for the front-desk agent—despite their enormous power to influence the quality of your stay.

“The front desk isn't a tipped position, so when you do tip, it makes them beholden to you,” Tomsky said. “It can be five dollars or twenty dollars, but it’s almost like they're so grateful that they feel they have to earn the money, and there’s a lot of creative ways a front-desk agent can do that by making your stay better.”

A small tip can easily lead to simple perks, such as a late checkout, breakfast certificates, a bottle of wine, fruit baskets, or waived minibar charges—as well as major room upgrades that could be worth far more than the Jackson you threw down, Tomsky said.

Tomsky’s advice for slipping the bill: Place it on the counter along with your credit card and ID and say something simple, such as: “This is for whatever you can do, but I just appreciate all your hard work and hope you're having a good day.” Do it casually, with a smile, and don’t be put off if the agent can’t actually give you that upgrade you’re hoping for.

Offer to wait

For a hotel’s staff, check-in time can be utter chaos. While housekeeping races to prep rooms for the hordes of incoming guests, front-desk agents have to deal with just-off-the-plane travelers who are more than happy to turn them into verbal punching bags for a long-haul flight’s worth of accumulated stress.

Tomsky says that subtly signaling that you’re on their side and won't create trouble can often lead to a better stay. While simply keeping your cool and offering pleasantries and a smile can go a long way, if things are particularly hectic and you’re not in a huge rush, letting the agent know that you’re happy to wait a bit can often lead to a much better room—especially if you’re staying for multiple nights.

“You want to be the 1 percent of guests that the front-desk agent loves,” said Tomsky. “Say something like: ‘I’m in no rush, and I’m here for a week, so if anything better will be opening up later today, I’m happy to store my luggage and come back.” When you do, you might find yourself in a far nicer room.

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