What goes on behind the scenes of your hotel? A former hotel clerk tells all

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He's not only checking you in, he's checking you out. With his personable, advice-filled book Heads in Beds, one-time hotel front-desker Jacob Tomsky gives the lowdown on the "hospitality" business and what the workers really think of you, the paying guest.

Often in a movie, there's the scene when someone checks into a hotel room, and there's the awkward moment when the bellman waits for his tip. Is that a Hollywood cliché, or does it happen that way?

That moment of uncomfortableness is a very powerful tool for a bellman or a doorman. That skilled lingering is an art form. The moment lasts five seconds more than it should, and suddenly "tip" pops into your brain. Doormen do it even more than bellmen, because not everyone thinks to tip the doorman. So he will stand there and just linger, and you can feel the guest having that uncomfortable feeling that there is a gentleman behind their back, floating about.

I never know how much to tip. You mention $2 in the book, but that is that enough?

The bellman would have no anger at $2 a bag. But I would say tipping less than $5 would not be that helpful. So, even if you have two bags, you should round up to $5.

You advise never to tip with loose change. But in Canada, we have dollar coins and two-dollar coins. Would a hotel worker be offended if I flipped them a two-dollar coin with my thumb?

Yeah, you would kind of look like a jerk there. Unless he's a 10-year-old newsie who just sold you a newspaper and who's going doff his cap to you and head on down the road. I don't think an adult is going to want to catch the money you're throwing at them.

Do you find that guests who book through Expedia or Priceline.com are cheap with the tips? Do you treat them with less appreciation?

The bellman and the doorman are very much aware that discount-seeking guests are not guests who tip.

On the other hand, if I see someone who books through the hotel website, I know they want to stay here and I'll definitely pay more attention to them, as a valued guest.

But even if you book through a discount bulk-rate service, there are ways a guest can get upgrades or better treatment, right?

Absolutely. If you get thrown onto a property through Priceline.com for example, you should find that hotel and call them. Front desk will call up your reservation, and now you're speaking to a human being who can find out exactly what room you have. Then, when you come into the hotel, you're not just one of 56 bulk reservations.

You're the one who called a week ago. You've made a personal connection.

There's the often told story about hotel guests getting their vacation photos back and finding photographs involving their toothbrushes being used, shall we say, in a non-traditional and unsanitary manner. Is that just an urban myth?

I've honestly never done that, but I've known hotel workers who have done some pretty disgusting stuff. Would 99 per cent of hotel employees ever consider doing that? No. But there are some really weird people out there in the world. I firmly believe that anything that you can imagine happening in a hotel has happened in a hotel. If you can imagine an employee doing something nasty to your toothbrush, there is a time when that happened.

In your book, you begin in New Orleans as an enthusiastic hotel employee. Things soured by the time you ended your career in New York though. How do you feel about the hotel business now that you're out of it?

I miss all my co-workers. You spend more time with them than you do with your family. I miss the excitement of the job. But the reason I was working in the hotel was so I could pay rent, which allowed me to write. Today, with the publishing of my first book, is the greatest day of my life.

So, it's bittersweet. I miss my friends. But I hope people really enjoy my book, and I hope they learn from it and it makes them laugh.

This interview has been edited and condensed.

BOOK EXCERPT

Want to raid the minibar – for free? Hotel clerk turned author Jacob Tomsky shares one (highly unethical) way to do it in Heads in Beds: A Reckless Memoir of Hotels, Hustles, and So-Called Hospitality by Jacob Tomsky (Knopf Doubleday).

Here is the plan. Check in at the desk and make a strong request for a non-smoking room, possibly mentioning allergies (but don't go overboard and annoy the agent, please). Refuse help from the bellman (that shouldn't be hard for your cheap ass), and go up to your room unaccompanied. Immediately open the minibar and shove every god-damn item into your suitcase. Take it all. Then smoke a cigarette on the bed and gaze out the window. Afterward, call down to the desk and complain about the heavy smoke smell in the room. Request to be moved. I mean, it smells like something just smoked in here. The front desk will send a bellman up with your new keys, and – not that he has been informed, nor would he care – should he pop his head in, he too will smell the odour. Go to your new room, close the door, and get fat and salty and drunk on your suitcase of snacks. The hotel will never trace that minibar to you. Moving rooms in the system, when it's done the same day you check in, leaves almost no trace, no overnight confirmation that you actually ever occupied the suite.