7 Ridiculous Real-Life Customer Conversations

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People will continually surprise you, especially when you work with the public. I asked customer support folks, CEOs, and consultants about their most ridiculous, can’t-be-real conversations with clients and customers. Here are my seven favorites:

1. Give me a free meal, or I’ll attack your political beliefs

From Doug Sands of Restaurants Client Magnet, a consulting firm.

“You have no idea,” Sands said. “We work with many clients AND we often deal with their negative customer reviews. Here’s the transcript of a Facebook conversation we had with one negative customer.”

Customer: This is b@#$t. I waited ten minutes for my food at [name omitted] today before I stomped out without getting a refund. What kind of customer service is that?? Talk about a B.S.. Fast Food joint.

RCM: We’re sorry you had a bad experience, [name omitted]. Unfortunately, we’re not technically a fast food place. Our customers typically wait 15 minutes, because that’s how long it takes to cook our fresh dough. The wait is simply for your safety, sir.

Customer: Still B.S. Where’s my free coupon?

RCM: Sorry?

Customer: I’m not eating again at [name omitted] unless you get me a free meal coupon. And I’m gonna tell my friends about it, and their friends, and we’re gonna blow up your Facebook page.

RCM: Sir, there’s really no need for that. We’re not giving you a free coupon.

Customer: Fine. Just wait and see how many friends I can get together to BRING YOU DOWN. We’re gonna grind your nasty restaurant into the dirt. We’ll post fake reviews, launch nasty emails, and attack your political beliefs. And we’ll start a boycott too. Better stop me. But now it’ll take THREE free lunch coupons.

The rep went on to inform the angry customer that the threatening message had been logged for police records. It’s a good idea to keep a record of every transaction, so you have a paper trail in case a customer starts to make threats.

2. A piping hot dish

This one is also from Sands:

Customer: Hi! My name is [redacted], and I’m writing to say that [restaurant name omitted]’s front man is really cute. Like, really really cute. Is he single? I wanted to know if you could get me his number…

RCM: Uh, we’re not really authorized to do that, but he was single the last time we checked. If you see him in the restaurant, you’ll have to ask him in person. Hint: He likes basketball and chocolate milkshakes. Best of luck!

3. I’m going to sue you for $22

From Bryan Clayton, CEO of GreenPal, which he calls “Uber for lawn care.”

“Our customer support team is the backbone of our company,” Clayton says. “As CEO of the company I dedicate myself to do at least one hour of customer support each day, so I always have firsthand experience for the voice of the customer.

“I tell my customer support team that arguing with fools proves there are two. Last week I was doing my support box duty, and a gentleman in Tampa, Florida, who has been a user of our service for three months, started a conversation with us in our in chat app that he had thought he had canceled service and was not going to pay for the last lawnmowing that he got.

“After explaining to him that unfortunately we couldn’t refund his money, he said he was going to have his attorney contact us about a $22 refund.

“I just blew it off and helped him cancel the rest of his appointments but we did not process the refund.

“Sure enough less than a week later we got a letter from his attorney demanding the $22 refund, or they were going to take our company to small claims court.

“At that point I felt that the $22 was worth the laugh they gave us, so we mailed them a check.

“95% of people are pleasant to deal with, it’s the 5% of the general public that makes customer service one of the more difficult jobs in any organiztion.”

Customers never want to feel blown off, even if their requests are unreasonable. It’s a good idea to try to explain why your policy is what it is. And consider going above-and-beyond the policy if it will make them very happy and won’t cost you very much.

4. Serge loves user testing a little too much

From Skot Carruth, CEO of digital innovation firm Philosophie.

“Customer conversations are a central part of our design process,” Carruth told me. “We try to talk to end users weekly, so over the years we’ve collected some outlandish experiences.

“About a year ago we were conducting a usability test for a fintech client. In the middle of the test, the woman lifted her leg, [broke wind] audibly, and went on with the test pretending nothing happened. As you can imagine, it was challenging for the team to stay professional.

“Another story comes from our New York office. When we work on brand new products, we recruit people who fit our target audience, sometimes using classified ads and Craigslist posts. Eventually, it came to light that the same guy named ‘Serge’ kept showing up, even when we had very specific requirements like, ‘must work as a field service technician.’ He must have really loved participating in our tests. Fortunately we caught on to him and started improving our screening process!”

Always take user feedback with a grain of salt!

5. They aren’t using that marble anyway

From Sam Carter, Sales Manager at Challenge Coins 4 U, a commemorative coin company.

“A few months ago I had a very unusual conversation with a customer,” Carter told me. “Since Memorial Day was approaching, he said that we should make our coins out of the ‘marble that is used in the Arlington Cemetery.’

“I thought he was joking but he was serious. He thought that if we did that, then our product would be a hit.

“I did not even hear any humor or sarcasm in his voice. I asked him why that is, and he said that by showing customers that we make challenge coins out of the very same marble found in Arlington Cemetery, that we would be honoring those that have fallen.

I told him it wasn’t feasible and thanked him for his unusual suggestion (I was being polite).

He later told me that he would have no problem getting that same marble for us to design the coins with from another cemetery (we learned he used to work in a funeral home). I quickly told him ‘No thanks’ and to have a great day and to let us know if there is anything we can do for him.”

Customers don’t always have the best ideas, but it’s wise to show appreciation for them anyway.

6. All bark, no bite

From Inna Barratt, Merchandiser & Client Relations Manager for Full Disclosure, an online luxury lingerie, swimwear and sleepwear boutique.

“As Merchandiser & Client Relations Manager, I also act as a personal shopper assisting and advise customers via live chat, Regpack, a registration software provider and Capterra vendor (read their reviews!)

“Our registration software can be embedded into a client’s website so it sits on their website and not ours,” Sam told me. “The embed process is pretty simply, just copying and pasting a snippet of code.

“When one of our project managers explained the ‘copy and paste’ procedure to a client, he responded ‘The only thing I am pasting is a glass of wine to my lips.’

“Well, ok then sir!”

On the client’s five-year anniversary with Regpack, they should send him a bottle!

In sum

That you can’t always predict what a customer will say next is what makes customer service and support fun, and also what makes it a challenge. Good customer service will always require agents and reps who are good at thinking on their feet. It also requires investing in good tools. Check out our customer service software directory to compare your options and narrow them down by features.

Looking for Customer Service software? Check out Capterra's list of the best Customer Service software solutions.

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About the Author


Cathy Reisenwitz

Cathy Reisenwitz is a former Capterra analyst.


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