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How to Get Free Stuff (Hint: Ask Nicely)

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A few years ago, I flew from Chennai, India, to New York. To say I was not looking forward to the twenty-plus hours of air travel ahead of me would have been a criminal understatement. I had made the flight before and knew all about the back pain, body odor, and less-than-appetizing choice between chicken and curry I had in store. My mother was traveling with me, and we were joined at the airport by a German friend, a woman who had worked years earlier for the airline we were flying. “Let me see what I can do,” she said. She made no promises, but approached the ticket counter. It was late, maybe 1 a.m., and we were already tired from a three-and-a-half-hour taxi ride through the Indian countryside. Our hopes were not high. We could already smell the stale cabin air as we slumped on our baggage.

No more than fifteen minutes later, she returned. She needed our passports and tickets. We were being bumped up to business class for the first leg of our flight. My jaw dropped. I had never flown business before, let alone on a transcontinental flight. Then again, I had never asked.

The experience was a learning one for me. Not just because I now know what fully reclining seats and warm hand towels can do for a travel-wearied body, but because I learned that sometimes, if you ask nicely, you get things—free things. Really great free things. Maybe it’s a lower price on your cable package or a hotel room with a better view. Maybe it’s a comped dessert after a lackluster meal or a big discount for buying in bulk. Either way, you’ll never know if you don’t try. Next time you’re stuck in metaphorical coach, try these tips for getting more, better, and free stuff you really don’t deserve:

It never hurts to ask.
For years I thought my friend was the luckiest person in the world. Everywhere he goes, he’s showered with upgrades and freebies and perks. Then I realized he isn’t lucky, he just isn’t afraid to ask for the things he wants. What’s the worst that can happen? They say no, probably with a smile. Hardly something to cry over.

Don’t silence your dissatisfaction.
How many times have I stewed at a restaurant because some aspect of my meal didn’t live up to my expectations? I’ve vowed never to return when, in many instances, if I had just spoken up, the situation might have been rectified and then some. As my “lucky” friend points out, “Their job is to be a kick-ass experience.” If they’re not doing their job, say something. Restaurants, hotels—any business with customers—should be open to constructive criticism. If they’re not, don’t be afraid to tell them you’ll share your experience on user-review sites like Yelp and Citysearch.

Ask nicely.
The old adage is you’ll catch more flies with honey than vinegar. The trick to asking for anything is to ask firmly but nicely, just the way you would want to be asked. Customer service representatives deal with disgruntled people all day. They’re not going to respond to browbeating. Treat them courteously and with respect for their jobs, and they’ll be more likely to help you.

Don’t bluff.
While it may be tempting to threaten to leave or never use their business again, this often backfires. If you’re not going to come back, why should they bend over backward to make things right or better? You can let them know you’re looking elsewhere and ask them to compete (this has lowered my Internet bill a couple times), but only threaten to walk if you’re really prepared to do it.

Negotiate.
Don’t just say what you’re not happy about; be prepared to ask specifically for what you want. Be direct and shoot higher than what you think you might get. Don’t be afraid to go to the top. Ask for a manager. It might be that only a higher-up is allowed to make those decisions, and sometimes just the fear of calling the boss will nudge customer service in your favor. As my friend says, “Low-level folks have the fear of God put in them that a call to the C-suite will get them in trouble, so they respond.”

Be a V.I.P.
Many stores and businesses now have rewards programs or club cards that offer discounts, deals, and perks to members or frequent customers. If you are a returning customer, mention it. If you are a new customer, make it clear that you want to be a returning customer. Give them your loyalty, and they’ll give you the goods.

Name drop.
Beyond knowing someone personally—or someone’s boss personally—there are other affiliations that can be useful in getting deals. Some credit card companies, like American Express, have special relationships with retailers. Small, independent businesses often give discounts to neighbors. And at some restaurants, college students, faculty, and alumni get special deals.

Make what’s good for you good for them.
Take a minute to look at it from their perspective. Is what you’re asking for potentially advantageous to them? Hoping to upgrade your balcony seats? Remind the box office that it looks good to have front rows filled. Hoping your florist will beef up a flower arrangement? Mention that you put the flowers in your reception area where potential customers will see it. Have a food blog? That’s free advertising for the restaurant. Make your request feel like a partnership and less like a favor.

Buy in bulk.
Kind of like being a regular, the more valuable you make yourself to a company, the better they will treat you. Buying in bulk often brings a discount. Even if a bulk policy isn’t advertised, ask about one. Wine and liquor stores, grocery stores, and websites will often throw in a discount or a freebie or two. It’s the classic baker’s dozen.

Price match.
Most companies want to be competitive. If you saw a similar good or service offered elsewhere at a better price or under better conditions, ask if they will beat or match it, even if they don’t have an advertised price-match guarantee. Try it with electronics stores, car rental agencies, and hotels. Again, go to a manager if necessary.

Request a sample.
Free samples are meant to get you hooked, but showing interest in a company’s product also has a psychological impact on the owners, triggering a sense of pride or ownership. Make the salesperson want to prove that what they are selling is worth buying. Ask questions. Taste the wine before you order a glass. Check out the sample or travel sizes at the beauty and makeup counter. Try the cheese before buying a pound. If you take the bait, both parties are happy.  

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