Ask An Assertive Person, Vol 1: Discounts

Dear Assertive Person,

When is it appropriate to ask for a discount on a purchase or service? I especially feel weird doing this when I don’t see anything wrong with whatever I’m buying, and I’m not convinced by This American Life’s claims that the “good guy discount” doesn’t make me sound like a douchebag. For example, does visiting his shop every week for a year entitle me to expect a discount from the guy at my local empanada place? From my barber? What if my bank has made a wrong transaction and offers a refund — should I ask for something extra on top? Or what if a bartender has obviously made my drink wrong? Clearly, we’re not talking about haggling over furniture from Craigslist. Where can I draw the line, and how, as an introvert, do I steer the conversation in the right direction?

Sincerely, Diffident in DC

Dear Diffident in DC,

You bring up two situations where being assertive can lead to saving money: when you merit a reward, and when someone else messes up. Let’s start with the more cut-and-dried of the two.

If your bartender messes up your drink, your server double-charges your meal, or your cashier gives you incorrect change, it is your right to ask for the mistake to be corrected. This can be a little less comfortable in person than over the phone, but odds are the accidental offender will apologize and reverse the error. I work for a bank, and noticed they had charged me a transaction fee that they usually waive for employees. I stopped by a branch on my way home from work, explained the situation, and asked for the refund. Easy peasy.

But you also bring up what I like to call the “apology discount”: a free drink after a botched first attempt, comped dessert after an undercooked main course, free shipping on your next order after a late delivery. These are courtesies extended to you by merchants who want to retain your business after a mistake, since you can always take your money elsewhere. I generally do not ask for courtesies like these, since more often than not they’ll be offered to me before I get the chance. However, if the mistake is big enough, I will sometimes nudge the server or sales rep toward offering me something extra by asking if there’s “anything else we can do” to expedite shipping or salvage my meal. 

Recently I moved into a new apartment after my real estate agency dropped the ball and failed to renew the lease on my old place. They helped me find a new apartment by giving me the first look at places as they became available to rent, which was nice — but I was losing my apartment, and I wanted a little more from them. I negotiated down the broker’s fee by asking if they could “work with me” and “extend a courtesy.” Sure enough, we managed to negotiate down by nearly half of the original sum they quoted.

Let’s consider another example: when no one does anything wrong, but you still get screwed over. Earlier this month I bought a beautiful rug from a big-box retailer’s website, only to see it go on sale the following week. I called the help line, politely asked to be refunded the difference between the price I paid and the one the rug was now going for, and three days later received a $30 credit to my card. Was it the site’s fault that the item went on sale after I bought it? Nope. Was it my fault for not predicting the sale? Nope. But common sense and the sheer volume of the business — they can afford to eat $30 on an order every so often — allowed me to get a refund anyway.

Retailers, restaurants, and other big companies have a process in place for dealing with dissatisfied customers that often includes financial incentives. They’d rather you walk away happy, having spent a little less money than you otherwise would have, than never come back again. For this reason I’m unafraid to ask for student discounts, corporate discounts, damaged-item discounts, and the nebulous “Is there any way to get a better price on this item?” discount at chain stores and other places that I suspect will want to accommodate me.

+ Ask the cashier if she can try your expired coupon [hint: those barcodes very rarely expire]

+ Call the customer service hotline of a website and ask if they’ll honor two discount codes that the website refuses to combine

+ Always negotiate rates with cable and cell phone companies.

The bigger and more soulless-seeming the company, the greater the odds that they have an “appease the customer” slush fund. Someone is going to benefit from these kinds of policies. It might as well be you.

What, then, of your local empanadería? It is my humble opinion that words like “entitle” and “expect” have no place in the world of discounts. Reversing mistakes is one thing, but giving repeat customers a break every now and again is a courtesy, nothing more. Remember too that discounts and freebies are two of many ways that proprietors can acknowledge customer loyalty. Your empanada guy might give you a friendly smile; your barber might take extra care on your shave; the owner of your local bodega might let you choose from freshly delivered flowers in the back of the store instead of the ones that have been wilting out front all day. These gestures are less obvious and less quantifiable than a 10% standing discount, but in my opinion they’re more meaningful. Asking for the discount would void the charm, not to mention decrease your odds of getting it again.




The Billfold’s resident Assertive Person is Amanda McLoughlin, a writer from New York with a day job in finance. She is the eldest child in a big family, a former stage manager, and always the one to divide the check at group dinners. Find her on Twitter, Tumblr, Instagram, and YouTube.

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