The Key to Getting a Better Hotel Room

For those of you who missed my story in this Sunday’s Boston Globe, here’s the unabridged version on how to get a better hotel room:
After an exhausting 4-hour flight delay, you arrive at your hotel, only to wait on a long line at check in. You can’t help but take out your frustration on the person working the front desk. She smiles, types in your information, says, “Have a nice night” and hands you the key to the worst room in the property. You know, the one that’s next to the noisy ice machine a good quarter-mile from the elevators. 
Don’t underestimate the power of the front desk, notes Jacob Tomsky, author of the best-selling Heads in Beds (Doubleday), now available in paperback. Tomsky, 35, spent a decade in the hotel industry, 7 of those years manning the front desk at an upscale midtown Manhattan hotel. We caught up with him in New York to get some pointers. 
So how do you get the front desk to give you the best possible room?
Kindness and patience are always the best start. The front desk is doing their best to please everyone, so there’s no need to go overboard about that one special occasion that brought you there. The key here is to differentiate yourself from the 300 other people checking in that day. Providing a gratuity right away will go a lot farther than anything else. It’s a nice way to thank the agent for their hard work. It will also make them pause, look up and do everything to find you the best room and upgrade you. 
Was there ever a case when someone’s rude behavior resulted in a downgrading of a room? 
Absolutely. Almost daily. If you are demanding and say something terrible to me or my co-workers, then I’ll put you into a room that’s horrible, one that’s loud or has an obstructed view that doesn’t let in any sunlight. And the best part, you’ll never know. 
Is it better to book a room via a travel agent or calling the hotel directly than to reserve through websites like or Priceline? 
From a business standpoint, people who book through third-party travel sites are looking for a discount. The likelihood that they’ll return to your hotel is close to nil. So discount reservations are our last priority. Also, those third-party sites often don’t know the property. I once had someone checking into a midtown Manhattan who wanted a beach view. A good travel agent knows to call the hotel 2 to 3 days before you arrive to speak to the front desk or general manager. It’s a business of people serving people. The more you can connect with the hotel, the better your stay. 
Is it worthwhile to return to the same hotel in a city to hopefully get the best room?
Definitely. I had guests meet me just one time and then email me upon their return. I’ll go out of my way to ensure they have a nice room. The best time to get an employee’s name is not when something goes wrong, but when it goes right. When you return to the property, you can find that employee and pick-up where you left off. It’s all about relationships.