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: