insi-ded: Customer horror stories

3 Min Read

Customer horror stories: The unlucky customer

Our inSi-DED series is back! This week, an anonymous contributor shares a story that I’m sure we can all relate to. It’s about that one account, that one customer, where everything just seems to go wrong.

If you want to submit your own CS or community horror story, do so here. (And just like this contributor, you can choose to be completely anonymous!)

Have you ever had a just plain unlucky customer? It’s the customer who must have purchased on Friday the 13th after crossing paths with a black cat, walking under a ladder, spilling salt, stepping on a crack – you name it.

I discovered the unlucky customer phenomenon with a customer we’ll call Dan. Dan, through no fault of his own, has been a party to every mistake, human error, product bug, billing overage, that you can think of. His experience is by no means common at our company; it’s so out of the realm of normal that it’s become a running joke to our team.

With Dan, we started off on the wrong foot with the very first customer interaction when somehow the calendar appointment didn’t sync to his calendar and he didn’t show up.

Then, in a subsequent conversation, confusing information around our contract document was given to the customer that caused him to second-guess renewing his contract for two years. We sent over a clarification email, but accidentally wrote up the clarification based on a completely different part of the contract document that he had no issue with – thus causing even more confusion. Oh, lawrd.

Once we straightened it out, the customer signed up for two years. Hooray!

But… the billing information was entered incorrectly and he was then overcharged. Oh no!

When we refunded the overcharge and in the next month’s billing, the customer hit a bug and was overcharged again. ARE. YOU. KIDDING. ME?

We fixed that and the customer was excited about turning on a few integrations and requested a dev environment for testing. That’s great! But the dev environment encountered a previously unknown product bug. SERIOUSLY?!

We corrected that bug very quickly. Great job team! But then we sent out an incorrect automated email about his upcoming renewal, not scheduled for another year and a half.


Here’s what we’ve learned in our interactions with Dan, the unluckiest customer around:

Inevitably mistakes happen. Hopefully not all to the same customer. But mistakes give us, as the CS team and the face of the company, the opportunity to showcase our human-ness in front of our customers and how we react when things don’t go perfectly. Customers are reassured to know that when things don’t go as planned, there is a real human at the company who cares deeply about making it right.

That’s our superpower as CSMs.

Don’t forget to subscribe to our blog or check back next week for another hair-raising story.