Hi there, my friend.
We love a good success story here at Ask, Save, Earn. You might’ve seen these stories in the past month…
However, we also aren’t afraid to share our failures. And my goodness, there have been plenty of those, including one this week that forced my family to change some travel plans.
Why share when things don’t go our way? Because that’s when the learning happens. (Yeah, it is a cliché spewed by parents, teachers and coaches everywhere, but it is 100% true.)
The question I should have asked
My latest failure came at the hands of an Airbnb owner.
My mother is turning 80 later this year, and we’re planning a family trip to Virginia to celebrate her big day with friends and family. For any number of reasons, it didn’t make sense to do this as a surprise party, so my sister and I have been working with my mom on logistics. Lately, our primary focus has been figuring out where to stay.
The three of us agreed pretty quickly that a rental home, not a hotel, felt like the best fit for the trip. We then scoured various websites looking for the right place — reasonably close to the city, at least three bedrooms, at least two bathrooms, at least one bedroom on ground level, with personality but not too much personality. After several days of texts and a few emails, we landed on a choice that we would all be happy with.
Or so we thought, until my wife asked me this.
“Have you checked the cancellation policy?”
The October problem
My wife and I don’t mess around when it comes to cancellation policies. As our family and friends age, life is simply too unpredictable and chaotic. (Heck, we even have a 16-year-old diabetic dog to take care of. My wife will skip my mom’s trip to watch over him.) That’s why we tend to assume any plans we make are written in pencil. This trip would be no exception.
Still, I didn’t anticipate any issues. I’ve traveled enough over the years to know that while cancellation policies can certainly vary, there was no reason to expect this charming little house on the river in Virginia would have an egregiously ridiculous cancellation policy.
I was wrong.
Full refund before October 11. No refund at all after October 11.
Mind you, we’re not traveling until mid-December.
It was a complete outlier from other properties we were looking at, all of which had policies similar to this:
Full refund until November 10. Partial refund until November 26. No refund after November 26.
So what did I do next? Mr. Ask, Save, Earn asked.
Worth a shot
Following my own advice, I messaged the owner.
I mentioned that we’d be traveling for my mom’s 80th birthday. I mentioned that other rentals in the area allowed for later cancellations. I mentioned that we’d likely book the house in short order if they could be flexible with the policy. Then I hit Send.
The next day, I got my answer.
“[The rental] stays very busy and we have the cancellation policy in place so that others have time to book in case of a cancellation. Thank you for understanding.”
Shot down. Attempt failed.
The good news, however, was that we didn’t need to go fully back to the drawing board. My mom, sister and I did a little more searching, exchanged a few more texts and emails and settled on a new option — with a perfectly acceptable cancellation policy that we hope we never have to think about again.
The message I’d send again
Even though my request didn’t work, it wasn’t because of anything I did. If I ran into the same issue tomorrow, I’d send basically the same message.
Here’s roughly what I sent, in case you find yourself in a similar situation:
Good morning! I’m very interested in renting your place. [If a special occasion, mention it in a sentence or two here.] However, I’m reluctant to make the reservation because of your cancellation policy.
We’re considering a few other places and they all have similar policies, allowing a partial refund closer to the booking date. Would you consider amending your policy to be something similar? If so, we’d likely book today or tomorrow. I appreciate your consideration.
Thank you!
There’s no guarantee it will work for you either — the rental owners don’t have to budge — but asking politely gives you a chance to find out.
My ask flopped. But my wife's question, the one I didn't think to ask, might have saved us a much bigger headache in December. So before you book the flight, sign the contract, buy the car, reserve the house or agree to the deal, ask yourself this:
What’s the question I haven’t thought to ask yet?
Until next time!
Matt