08/09/2013 07:31 am ET Updated Oct 09, 2013

Staying at a Hotel? Here's How to Get an Upgrade

When people discover I've spent 10 years in the hotel business, there is one question that seems to thrust itself to the forefront, one question everyone seems to want answered. They pause, throw a quick look around, lean in a centimeter, and then ask:

"How do you get upgraded?"

I intend, in this short little essay, to discuss ways in which one might secure this holy, coveted honor.

Hint: It's completely random.

Just kidding.

But I've heard it suggested that one might mention a special occasion. It's my anniversary! I just got a promotion! It's my birthday! I'm celebrating a divorce!

From my perspective, as a front desk agent, if you had to pick one of the above reasons, which do you think I'm most likely to respond to?

If you guessed "celebrating a divorce" you'd be correct.

Consider it from a dedicated front desk perspective: We can check in up to 250 guests a day. And of those 250 I would say at least 25 of them are celebrating a standard special occasion of some sort; anniversary, birthday, honeymoon. And business travelers, that staple, that corn meal of the hotel game, are always receiving promotions or involved in huge work events, during which an upgrade would come in pretty handy. I would estimate 10 guests a day ask for an upgrade based on business-related reasons. So, over the whole year, that's 2,000 standard special occasions and/or business travelers who need "special accommodations." Not sure that number means anything to anyone besides a front desk agent but, trust me, after your second year, when someone comes at you with one of these standard situations and it's the 4,000th time you've heard it, it really, does, lose, its, power.

But celebrating your divorce? Well, ma'am, I don't hear that one too often. I'll take care of it. Here you are: Upgraded corner suite with a tremendous view. Feel better.

Point is, your special occasion probably isn't that special, as far as a hotel employee is concerned. Hate to blow out your birthday candles like that, but it's kinda true. Apathy is an inevitable byproduct that comes from working a tough, hourly service job.

But let's discuss, for a moment, the possibility of tipping the front desk agent.

I've been a front desk agent, hourly, for longer than I have done anything in my life. And many, many guests used to tip me. I didn't ask for it. I didn't even know that was done until it was done unto me. But the first time I got tipped I was surprised and delighted! And the guests that started to tip me got special consideration, including upgrades.

Most people think it's a shady thing to do. But no one, in the history of tipping, has ever looked bad tipping.

I learned that. No one looks bad tipping.

Even those awkward pass offs, utilizing discretion, still look cool and even more philanthropic because of that funny use of unnecessary discretion. Even those still look cool.

And that's because tipping is kindness.

It's hard to express kindness in today's lightning-fast world. But generosity is infallible. Tipping is kindness converted into objective reality. It's like saying, "Here, this is some of the money I have earned and worked hard for. But you, giving you some of this might make you happy so... here."

And just like that, once a guest has definitively improved my life (I would spend my new-found tips on anything from a healthy lunch to rent) I would immediately set out to repay the favor and improve their life. Often with an upgrade. And if not that, the very best room in the category they have booked, because, believe me, there is always a nicer room. Or amenities! When they came back from a long day of earning that money, a bit of which they so generously handed to me, they would find a bottle of wine and fruit waiting for them in the room.

Point is, a hotel stay, in some ways, is a special occasion for every guest! It's an exciting time. But checking someone in is not an exciting time for a front desk agent. It's like herding cattle, some of whom are very rude and abusive and moo loudly right in your face. But receiving a little gratuity, something that makes my day better -- that's a special occasion to me. And if you are kind enough to give me that little gift then the least I can do is herd you into a room you'll love.