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A Tip on Tipping: Go Big to Get What You Want
Thursday, November 29, 2018 -- Travel editor Jeanne LeBlanc once offered some sage counsel: Tip bigger on the road because it works and because it is the right thing to do.

I've always said the same thing albeit more crassly and with less social justice fervor: Money talks, more money talks louder and it talks loudest to the underpaid travel-industry workers who can make our lives on the road easier, more comfortable and more productive.

The best lesson I ever learned about the relationship between tipping and the quality of our lives came decades ago, long before I became a business traveler. And it's a lesson about using a tip as a way to get what you want.

I don't remember why my friend James and I decided to go to a sold-out baseball game one evening, but we arrived at the stadium and I instinctively made a beeline for the easy-to-spot scalpers. Not James. He went to a will-call window, slid a $100 bill under the cage and said, "I need two on the third-base side."

"Sold out," said the grim-looking fellow in the booth as he turned away and fluffed some papers.

James was as resolute as I was perplexed. A hundred bucks bought a lot of scalper tickets in those days and this grease-the-functionary approach seemed bizarre and fruitless.

"Hey, pal," I recall James saying as he pushed the $100 bill further into the cage. "I need two."

The man in the booth eyed us suspiciously and made the hundred disappear. Then he produced two prime tickets, slid them to James' hand and said loudly: "Sorry, sir, sold out."

Still, I'm a slow learner. Years later, now a supposedly savvy business traveler, I found myself in the bowels of the Vatican being escorted by a private guide from one sanctum sanctorum to another: rooms where the jewels and ceremonial chalices were kept; a relic cabinet storing bits of the "true cross" and "bones" of the saints; the Pope's private elevator. I got to wave from the papal balcony overlooking St. Peter's Square. I was even taken into the Sistine Chapel via a side door and given 15 minutes alone to wander.

"How do you get this kind of access?" I dumbfoundedly asked my guide, who, by the way, had parked his black Mercedes right in St. Peter's Square.

"You make the right contributions to the right people," he said matter-of-factly.

Get it? Money talks, even to the guardians of sold-old baseball games and the religious pezzonovante. Needless to say, it will do wonders at airports, restaurants, hotels--and anywhere a harried business traveler needs a little extra traction to get what's needed.

For all the discomfort over appropriate amounts and the social mores--Martin Deutsch covered that in Argosy magazine as far back as 1964--the ground rules of tipping are easily found. I've always admired Susan Breslow Sardone's terrific traveler tipping tip sheet. An exhaustive guide to the global greasing of palms seems regularly updated at Conde Nast Traveler. And someone is always calculating the basics of baksheesh, something we explored last year.

Allow me to offer these key additions. Tipping--hell, lavishly over-tipping--these folks is crucial to improving your life on the road. And remember: Consider a tip as a means to your end, not as a payoff for "good" service rendered.

THE SECRET SKYMASTERS
Forget about that dollar-or-two-a-bag tip that some suggest is appropriate for skycaps. I say always seek out a skycap, take out a big bill and put yourself in his amazingly powerful hands. (And why are there no female skycaps?) Assuming you can still find a skycap at our increasingly self-service airports, checking bags is the least important thing he can do for you. He can snag you a better seat assignment, issue a new boarding pass and shepherd you to an expedited position at security. I use skycaps even when I'm traveling on premium class tickets or when I don't have luggage to check. They just seem to be able to get things done faster, better and with less hassle. Don't skimp: Put at least a $20 next to your paperwork and photo ID and you'll be thrilled with how fast your curb-to-gate experience can be. If you actually have scads of luggage to check, tip more and do it in advance.

TAKE A SHINE TO THESE GUYS
Shoeshine guys have a cinematic reputation as sources of inside info (and horse touts) thanks to those cheesy old private eye and film noir flicks. Airports are one of the few places where you can still find a bootblack and guess what? If you want to know about what's happening at the airport--where to eat, where to hang, what to avoid--the shine guy still seems to be the guy in the know. (And, hey, I have seen some shine gals in recent years!) Tip him or her at least the posted cost of the shine and you'll be surprised by what you'll learn. Besides, your footwear probably need the servicing.

NAMING NAMES, IF NOT TITLES
As upmarket hotels and resorts ditch traditional check-in formalities, the new king of "customer-facing" lodging interaction is the person who guides you to your room and offers the ongoing litany of products and services available. They don't even have a name--hotels variously call them assistant managers, rooms executives, "hosts" or the ever-popular "associate"--and there is no accepted wisdom on whether these people should be tipped.

I say tip them--and tip them big. Get their name and ask them when they'll be on-duty. If they say they won't be around for most of your visit, find out who their replacement might be. Thank them effusively for the help and start with a crisp $20 bill. Then use that person as your point of contact for the rest of your stay. You'll be stunned at how fast and how good the service is if you've tipped "Anthony" or "Jessica" at the start of your visit and then call down and ask them for something later. Your generosity will not be a secret: These people talk amongst themselves and better service goes to the guest with the reputation as a good tipper.

If your hotel is less fancy and still has "front desk" types, catch their name and address them by it. If you need something later, call down and ask for the person who checked you in. They'll be jazzed that you remembered them and will be extra helpful when you need something. Just also remember to stop by the desk and throw 'em a sawbuck (in an envelope, please) as a thank-you gesture for their help.

HOUSEKEEPING ON HOUSEKEEPERS
The older I get, the more I tip the housekeeping staff. I know the concept remains controversial--some business travelers are still pissed about Marriott's tip envelopes--but I can't imagine not spiffing these people generously. The strikes against some Hyatt and Marriott properties this year finally were settled, but housekeepers are severely overworked and badly underpaid even with the newly negotiated wage scales.

I never leave less than $10--every morning, on the pillow of my bed. Since I frequently work in my room and don't want to be bothered during traditional housekeeping hours, I tend to be one of those "special needs" guests. I try to respond in kind. I'll tip more if I've been particularly messy or if I've stretched their working hours to match my schedule.

I will go further, too. Whenever I run into a housekeeper in a corridor, I introduce myself and ask about their schedule. This not only means I know the person I'm tipping, it also means the housekeeper knows I value the work. Treating housekeepers well financially has never gone wrong for me. I get lightning-fast service if ever I need more pillows, towels or robes--or an extra of some particularly nice bath amenity the hotel may be placing in the room.

DELIVERING THE DENOUEMENT
Finally, a service category that business travelers too often forget: The postal and courier people who deliver packages and mail to your home and office. If you're on the road a lot, these people will be extra helpful if you remember them during the holidays. Fifty bucks a year--come on, folks, that's just a buck a week--virtually assures that your mail and parcels will find you no matter how frequently you're not around to take possession of them.

This column is Copyright 2018 by Joe Brancatelli. JoeSentMe.com is Copyright 2018 by Joe Brancatelli. All rights reserved. All of the opinions and material in this column are the sole property and responsibility of Joe Brancatelli. This material may not be reproduced in any form without his express written permission.