Hello. Checking in?

How Hotels Win (or Lose) You Before You Reach the Elevator

Hotels, we are told, are places to sleep. This is by and large nonsense.

A road-side motel is a place to sleep. A good & proper hotel is something else entirely. It’s a stage set. A mood. A reason to get on that plane in the first place. People don’t fly halfway around the world for a mattress and a coffee maker…they go because a hotel promises a particular version of life. One with a moody bar, room service that understands hunger at odd hours, and a spa that makes you feel as if you’ve possibly been born again.

One thing we often gloss over though is how the entire experience can live or die in the first five minutes.

Check-in.

That moment when you arrive jet-lagged, perhaps slightly disheveled, mildly optimistic, and quietly judgmental…and the hotel has it’s first and most critical chance to show you whether it knows what it’s doing. When all of your anticipation either blooms into satisfaction or collapses like a badly made soufflé.

I’ve had some excellent check-ins. The sort that make you think, yes, this is going to be good.

In Mexico City, the Four Seasons doesn’t bother with the whole “stand here while we type” business. My experience involved getting whisked straight from the car to my room and deal with the details there. It’s confident hospitality. Assumptive, even. And it works. You don’t feel processed; you feel expected.

In St. Barths, at Gyp Sea, you’re eased onto a sofa and handed a cold glass of rosé while someone else quietly handles the paperwork. You’re not a guest at a counter; you’re a person who has clearly arrived somewhere pleasant and should sit down immediately to relax after a long journey.

Several years ago at Amangani, in Jackson Hole, the check-in was calm, measured, almost ceremonial. A proper desk. A proper conversation. No queue. No beeping computers. Just the gentle sense that everyone involved knows exactly what they’re doing and sees no reason to rush.

All very good. All memorable.

And yet, the check-in that sticks with me most is not one of those.

It’s in Amsterdam, a city I love visiting and almost indeed moved to, at a hotel I have stayed at perhaps two dozen times. Business trips. Leisure trips. Jet-lagged trips. Hungover trips. Same place. Same brand. Every single time, without fail, I’m asked:

“Is this your first time staying with us?”

At this point, it’s almost funny. A joke you’ve heard many times before but you still chuckle just before the punchline.

In this case the question doesn’t suggest forgetfulness: it suggests a specific brand of corporate indifference. A total surrender to the system. Despite loyalty programs, account numbers, years of data, and a multinational brand’s vast digital brain, no one knows, or seems to particularly care, who is standing in front of them.

True hospitality says, welcome back. Not, next in line.

That one question finally did what no oddly uncomfortable mattress or hour-and-a-half wait for room service ever could. It made me stop coming. Quietly. Permanently.

For all the talk of five-star service, marble bathrooms, and perfectly trimmed hedges, hotels are actually brutally simple operations. They either make you feel something…noticed and cared for…or they don’t. That feeling should be perhaps most notable upon arrival.

And that first moment, standing there with your bag, is the whole game. Get it right and you’ll forgive a lot of stuff. Get it wrong and no amount of cheap imitation champagne will save you.

Hotels don’t wholly reveal themselves at the bar, or the spa, or even in the room. They most often reveal themselves at “Hello. Checking in?” No matter your line of work or vocation, there is a big reminder for all of us in there…first impressions matter.

Let me know if you have any notable or favorite check-in experiences.