How to Ask a Business for a Favor

I have mixed feelings about asking retailers and service providers for discounts/deals you didn’t claim in time/special treatment of any kind. When I was a service rep at a web-based company, I HATED 99% of the people who asked me to bend the rules for them.

But I just had a really great, “I might as well ask,” experience. And friends, there is a right way to make these types of requests, and I would like to spread the gospel of not being a jerk when asking for special treatment.


1. Be patient. Unless something is extremely time-sensitive, send your request via email or contact form. Getting it in writing puts a timestamp and paper trail on your request and it can be kicked to a manager very easily if it’s in digital form. Service reps DO read and respond to these, so don’t be the ~*squeaky wheel*~ and don’t ever say to a service rep on the phone, “You guys NEVER respond to emails or pick up the phone so I called until you did!” Follow-up with caution. Silence means no. You’re biting your nails, but giving out free stuff is low on their list of priorities.

2. Provide documentation. Include a booking or order number or the email address you used to make your purchase or reservation. If you don’t think you have a reference number of some sort, you are wrong. They provided it. They sent it to you. I promise. If you can’t find it: admit it, don’t accuse them of having not provided it, and they’ll tell you what information they need to find your record.

3. Be friendly. Say hello, say thank you, be chill. Say you’d love/appreciate/enjoy/whatever the additional service/discount/feature rather than just “CAN I HAVE IT” Darrell style. “I’d love to stay another night,” is just as direct but significantly less blunt than, “Can I have a free night?” If you’re that comfortable being blunt, don’t be surprised when their response is a blunt, “No, I can’t extend that offer.”

4. Be brief. Provide only the most necessary information, and they will ask if they need or want to know more. Don’t tell your life story of even the story of that hour or the fact that you’re flustered or so embarrassed to ask or OMG planning a vacation is crazy or you wouldn’t ask except for this thing that happened in your personal life. Don’t ever tell a service provider a story. You’re already asking for a favor, so do them the favor of not wasting their time. People who would never get to the point- the point being that they wanted a discount or a free service and we both knew that’s where the conversation was headed- were the absolute worst when I was an operator. They know as soon as you start talking that you want something special. Spit it out.

5. Don’t threaten or try to get the upper hand or leverage. Don’t come right out with, “I’m gonna have to cancel if not,” and don’t act like it’s unfair that you didn’t see the deal in time or didn’t review their terms of service/delivery times/whatever so they ~*SHOULD*~ do the thing for you. Don’t say it’s “good service” to give you special treatment. It’s not. It’s an investment of time that muddies their standard operations. If you threaten to take your business elsewhere/trash them if they don’t give you a deal, they are praying to every deity and planet that you’re telling the truth and will never come back. No order is worth a customer like this.

6. Accept no. Make sure your message conveys that you’re actually asking, in that their no will be the end of the conversation, and a complete sentence.

7. If they decline and it really is a dealbreaker: thank them for reading your message and politely ask how to cancel your order/booking. That’s it. If you’ve been polite and cooperative throughout the entire interaction, you have proven yourself a valuable potential customer, and they’re more likely to help you out. They may end up giving you the deal, a discount on your next order, or waiving a cancellation fee. They will happily cancel an order and lose someone who has been obnoxious but go the extra mile and be flexible for a nice, polite person. That is how service reps make 99% of these judgment calls, cetirus paribus.

8. If they decline and it’s not a dealbreaker: thank them for reading your message and ask whatever questions you need to in order to make sure you don’t make that mistake again. They will likely point you in the right direction to get a better deal next time, they may very well give you a discount or promo code for a future order, and they will happily answer your questions. You’re also establishing rapport for the next time you need help. That’s what they are there for. Do everything you can to prove that you will be a well-behaved AND paying customer.

9. If they give you the deal, say thanks! Don’t ever assume it will happen again! Leave positive reviews and feedback and this is the ultra super mega pro tip: DO NOT announce that they bent the rules for you. Don’t. DON’T. Instead, mention in reviews and feedback that the staff was accommodating and helpful with getting the service/order you wanted. Do not set off an avalanche of people calling in and saying, “BUT YOU DID THE THING FOR A STRANGER ON YELP.”

10. They don’t owe you any special treatment. They don’t owe you an incentive. They don’t have to play ball with you. They don’t, they don’t, they don’t. I am not saying that service providers and retailers are cold, unfeeling Gods doling out judgments to customers as if they are insects and that they don’t care if you have a good experience or not, but rather that all businesses have rules, terms, and standard procedures, and breaking from those when a customer doesn’t like them is not “good service.”

I had a lot of people tell me, when I was a service rep, that eating a loss, discounting a normal product, or offering free solutions in situations clearly defined by our terms and in which problems were of the customers own making, would be “good customer service.” NOPE. That is a LUDICROUS expectation of service. Good customer service is being polite and available, and helping people use a service within its proper, pre-disclosed terms. You may not like a company’s terms and offerings, but you are The Worst if you expect a company break their own rules, in the name of “good customer service,” just because you don’t like them.

My situation:

I had booked a hostel via Airbnb, then saw that it was cheaper to book directly on their site. I cancelled and ate the $5 Airbnb fee to save a bunch of cash on booking directly with the hostel. I booked the second I saw that, and to get the best price (by all of like €4), I opted for the cheapest type of room and the non-refundable, no changes allowed, final sale reservation. I then got to perusing the website and saw that they were running a promotion offering three nights at the price of two. This promo displayed automatically if you booked three nights, but I had only booked two nights, so I never saw it. Had I known a third night would be free, I’d have planned for three nights.

Because I opted for obnoxiously cheap, final sale, nonrefundable reservations, it seemed unlikely they’d extend the offer to me. Isn’t that the difference that €4 makes? I sent this message via their contact form and provided all the information they requested on the form.

“Hi! I have flexible travel dates and just saw your free night deal for three nights at the price of two. I already booked my two nights but if the third night is covered I’d love to stay another day. Can that be manually added to my reservation? Reservation #XXXX”

There it is. There’s all of the above in action. Within twelve hours, the manager had replied sure, cheers, here’s your new reservation. This was an admittedly small request, but I’m sure it won’t be the last time I mess up and humbly request a little mercy from a hostel or service provider.

Do you have a success story about asking for a deal? Please share!


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