Repeat After Me: You Don’t Get If You Don’t Ask

The four most important words in travel are Hang Up, Call Back.

When you’re tempted not to follow that advice, do it anyway. Odds on you may be given the wrong answer the first time or two times, or get an unhelpful agent, or maybe even be given the right answer when what you want is the wrong one. That’s why you need agent to play roulette, eventually you will win.

A related lesson is You Don’t Get If You Don’t Ask. Sometimes you just need someone to help you get something you’re entitled to or at least not unentitled to. Other times you need someone to bend the rules, or go out of your way.

Airline agents are busy. Hotel agents have lots of things on their plate. They may not volunteer what you need or want. They may not stop to think about your needs, and what you might want. They may not have any idea how to be helpful, and not stop to consider it unless you let them know you are in need.

That’s why you need to ask.

A few years ago I used to have great luck converting prepaid, non-cancellable hotel reservations into fully cancellable ones. I’d call the reservation line, say something like “I booked the wrong rate and am going to get in trouble at work, we’re supposed to book the full daily rate and I somehow booked a cheaper non-cancellable one. Could you help me upgrade my booking to a more expensive one?” Sometimes it would take a few tries, but eventually they would do it. Then I could cancel.

I was caught in an ice storm at one point and I wound up cancelling a booking for the destination I wasn’t making it to…

  • on the day I was supposed to arrive, after the cancellation deadline
  • and again the next day, because my delayed arrival was delayed again

I called the hotel directly and they were happy to be accommodating since I had a reasonable story. That’s happened to me many time.

I was standing in an airline customer service line behind a woman who was misconnecting and lives an hour and a half from the airport she was flying into. She wanted the airline to pay for her ground transportation home and for meals while she was at the airport. The agent wouldn’t give her anything but called a supervisor. She was sympathetic and nice, and it was the holidays. The supervisor declared “it’s not my money.” So he gave her what she wanted.

You don’t get everything just by asking. Hotels are more flexible than airlines and agents there have more discretion. Upgrades are in almost all cases assigned based on an algorithm not by an agent who likes you, who thinks you’re well dressed. You can ask for upgrades all day long but if you aren’t next in line based on priority or the upgrade instrument you’re using you’re unlikely to be successful.

You may not always get what you want for free either, but might get it at a substantial discount to retail. Always know what you want, and ask for it. (And know what it’s worth to you, and what discount you’d be willing to pay.)

There are a few principles that make it more likely you’ll succeed when you do ask.

  • Be sympathetic. Be someone the agent wants to help, not someone pushing them to give you something they don’t think you deserve. Be nice. Build a rapport — commiserate over the tough day they’re having, share something personal about yours, be thankful and tell them how grateful you are (for help you haven’t yet received).

  • Know who has discretion, and for what. Don’t ask for things the agent can’t give, and don’t ask agents who can’t give it. Call the hotel directly for exceptions to policy that a chain reservations agent can’t offer, but if you want the heft or influence of the chain based on your status or other complaints then ask the chain to intervene on your behalf. What is in the agent’s purview? If you don’t know for sure, ask them! It does no good to ask the impossible, but if it’s possible then if the agent wishes they can give it.

  • You get numerous bites at the apple. Just because you get shot down, ask ask again — over the phone, at the check-in desk, in a club lounge, of anyone who will listen to your story.

You know how your travel day can be made better, and if you’re kind and friendly then the people with the power to grant an improvement in your day may just give it to you — if they know what you want, and only you can help enlighten them!

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. “A few years ago I used to have great luck converting prepaid, non-cancellable hotel reservations into fully cancellable ones. I’d call the reservation line, say something like “I booked the wrong rate and am going to get in trouble at work, we’re supposed to book the full daily rate and I somehow booked a cheaper non-cancellable one. Could you help me upgrade my booking to a more expensive one?” Sometimes it would take a few tries, but eventually they would do it. Then I could cancel.”

    So you mean….lie?

  2. It also depends on how bad a situation is…..For me, it was that wonderful Icelandic volcano in 2010. Our trip to Europe was delayed and delayed. We finally gave up and re-scheduled for the next Sept. Every travel supplier was overwhelmingly helpful. Except one, yeah, Disneyland Paris. And if I wasn’t a stockholder, I’m sure they would have screwed my family over. But every other supplier made all kinds of accommodations that were not expected, and mostly not requested. We didn’t have trip insurance and there should have been cancellation fees on everything. We didn’t lose one penny.

  3. I also had that flash in my mind as I read the article: it assumes you are prepared to confect a story to get what you want. I could not do this.

  4. Lying is not the point of this blog post, so calm down people! The point is that if you don’t ask, you won’t get. I’m one of those people who generally “suck it up” and accept whatever the rule is. I tend not to stand up for myself. There’s no harm in giving it a shot and I for one appreciate Gary’s encouragement!

  5. There sure are a lot of goody two shoes on here. Who is harmed by doing things like Gary mentioned? I live by the “no harm, no foul” rule, personally.

    I canceled Barclay’s Aviator card a few months back but still keep it in my travel wallet. For the times I’m not in F and get a lousy boarding group/zone I go to the gate agent, show her my card and feign ignorance about why I’m not in Group 1 or Zone 2. Never failed at having them allow me priority boarding. Obviously this is deceitful but who’s actually harmed? I also don’t ever try to use it to get out of paying for checked bags which would be cheating the airline out of money and over the line for me.

    I do actually plan on getting a new AA credit card but I’m holding out for Citi to create a new product like the Aviator Silver that earns EQMs but doesn’t include Admirals Club membership.

  6. Who is actually harmed?

    How about the person you jump in front of who now has to check their bag.

    I can understand trying to screw over a corporation (my moral compass doesn’t permit it)….but screwing over other passengers for your own benefit? Scummy.

  7. Rules are for sheeple like you and me to keep us in line, while the 1% lobbies and gets laws written just for their benefit. It had been more profitable to break laws than to follow them. Be an illegal immigrant instead of going back home and you have more chances of becoming a citizen than the guy who followed the law. Buy a big house you can’t afford and then cry and see your loan written down. If you have been paying your mortgage diligently, no such luck.

    Most of the time people are pretending to themselves they are law abiding just to take the moral high ground. They would break the law if they had reasonable expectation of not being caught and reward was lucrative enough.

  8. Lots of rationalizing going on. Society is evil so it doesn’t matter what I do to get an advantage over fellow travelers? I’m glad there are plenty of great opportunities out there to get good things honestly. On the other hand, it’s just a blog. Take the good ideas, and ignore the dishonorable ones.

  9. “I booked the wrong rate and am going to get in trouble at work, we’re supposed to book the full daily rate and I somehow booked a cheaper non-cancellable one.” Wow – must be nice to have an employer that tolerates this type of deception in their name.

  10. One can just request a date change for next month, then cancel if your plans change. No need to come up with a story.

  11. A practical question: So, there are no on-line notes being taken? No history pops up attached to my reservation? I would have thought there would be notes like “Guest requested view; advised not available for P&C reservation.” Nothing like that is following my reservation? Are you sure? Same with applications–I find it hard to believe no one is recording what happens as I call.

  12. ““I booked the wrong rate and am going to get in trouble at work, we’re supposed to book the full daily rate and I somehow booked a cheaper non-cancellable one.” Wow – must be nice to have an employer that tolerates this type of deception in their name.”

    The blogger is self-employed. I’m pretty sure his boss is quite tolerant of dishonesty and deception. (Come to think of it, isn’t that how bloggers make their living?)

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