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!