The $10,000 upgrade that had nothing to do with money
Why hotels often save their best rooms for their nicest guests, not their richest ones.
Hi, my friend.
My friends Alison and Scott were staying at a resort in the Maldives, in one of those overwater huts like the one in the above picture. They hadn’t paid a dime for the room. They’d cobbled together every point they had between two credit cards just to cover it.
Early in their visit, they ended up making small talk with the property manager a few times. There was nothing strategic about it. Alison and Scott are just both social people, and they genuinely liked the guy, so they told him so.
Later in the trip, the manager showed up at their door and said he had bad news.
“He said, ‘I have bad news, I have to move you.’ And we’re like, ‘Oh, but we love this room.’ He goes, ‘Just trust me,’” Alison told me. “He said, ‘I double booked. We’re short on the type of rooms you have. These other people are giving me a really hard time. They’re being assholes, and you and your husband are really nice. So go enjoy three nights in the presidential suite on us. Thanks for being cool.’”
That’s the whole story.
The presidential suite. Four bedrooms. On the water. The kind of room that normally runs somewhere north of $10,000 a night. They didn’t ask for an upgrade. They didn’t complain their way into it. They just weren’t a pain to deal with, and when the hotel needed someone to offer its best inventory to, that mattered more than what they’d paid to be there.
Alison told me this in an interview I did with her for my book, back when I was gathering stories about the everyday power of just asking. While much of what we cover here is relatively small stuff — a $30 waived late fee here, a $45 food voucher there —this one is anything but.
It is also proof that sometimes you don’t even have to ask directly to get a break. Sometimes it is just about not being a jerk.
The pattern held in London too
It wasn’t a one-off either. A few months later she was in London with her mom for a milestone birthday, checking into a hotel that runs well north of a thousand dollars a night for its basic rooms. They’d booked the cheapest room available.
When they arrived, they mentioned at check-in that they were there celebrating her mom’s big day. The person at the desk told them their room wasn’t ready yet. When it was ready, they got a very big surprise.
“I just said, ‘We’re here for my mother’s 70th birthday, and she’s never been to London,’” she said. “We were sure to mention it was a special occasion, and when they came back to get us for the room, they upgraded us to a suite.”
This type of success isn’t super-common. Hotels aren’t just handing out suite upgrades to everyone who says they’re celebrating a birthday. However, the bigger lesson here is clear… It is almost always worth mentioning these sorts of things when you check in to a hotel or go to a restaurant.
You may just get a congratulations or a happy birthday greeting. Other times, however, you might get a free slice of cheesecake or $10 off an entree. Or one time you might even get a free upgrade to a $1,000 suite.
Either way, you won’t know if you don’t say anything.
The playbook
Obviously, these are two very high-end examples, but the truth is that your approach should be largely the same whether you’re staying at a five-star luxury resort or at a run-of-the-mill chain hotel off the interstate.
Here’s what Alison and Scott actually do every time they travel:
They dress as if they belong there. You don’t have to dress like you’re off to the Met Gala, but you probably shouldn’t look like you just rolled out of bed either.
If there’s an occasion, they mention it. They don’t mention it as a bid for a freebie, just as a fact. Whether you’re celebrating an anniversary, a birthday, a first trip somewhere or something else special, people who work in hospitality generally like being part of that moment. Plus, hotels know that if they treat you really well in an important moment, you’re a whole lot more likely to return.
When they want more than what they booked, they ask for it the easy way. They ask something like, “Any upgrades or extra perks available?” They’re not being pushy or obnoxious. They’re not acting entitled or haughty. They’re just asking nicely and politely to see what happens. And if they’re told no, they let go. There will be other days.
“They’re not gonna upgrade the jerk“
Niceness can unlock doors.
It sounds ridiculously simple. It may even sound a little outdated in a time when so many people are focused more on being an “alpha” than on being kind. However, it is true.
This certainly doesn’t mean niceness is a foolproof cheat code for getting free suite upgrades. Nor does it mean that there isn’t a time to be tough and stand up for yourself. Rather, it means that when a hotel does have something extra to give away, and they often do, they’re going to give it to the guest who was easy to deal with over the guest who made their day harder.
Alison said it best:
“If they’re gonna upgrade someone, they’re not gonna upgrade the jerk. They’re gonna upgrade the nice person 9 times out of 10.”
That’s worth remembering the next time you’re standing at a check-in desk deciding how much attitude to bring with you.
Ever gotten a great upgrade?
I love this story my friend Christine Burke shared about using her late father’s technique for getting upgrades. It’s such a simple and kinda goofy thing, but it certainly has worked for her, and it can probably do the same for you.
Got a great upgrade story? Share it in the comments below!
In other news… We’ve got a Dynamite weekend ahead!
This weekend, we’re taking my almost-80-year-old mom to see BTS — her favorite musical artist — for the first time. She’s going to absolutely go crazy.
It’ll be my first time seeing them as well. In fact, among my wife, son, sister and mom, I’m the only one who has never been to any K-Pop show before. I’m fascinated to see what it’ll be like.
But honestly, this is about my mom finally being able to see in person the group that has meant so much to her and helped her move forward after my dad passed away six years ago.
I wrote about it in the story below. If you’ve been an Ask, Save, Earn subscriber for a while, you might’ve read the story, but I always love sharing it.
Until next time!
Matt