Q&A: Customer Service Thought Leader Jenny Dempsey

December 20, 2017

jenny2_480.jpgWe write a lot about women in tech, breaking barriers and how women can influence the industries they work in. In October, we interviewed one such woman, Jenny Dempsey, customer service pro and co-founder of customer service blog, Customer Service Life. It’s no surprise that in the time it took Language I/O’s marketing manager to write this blog, call center and customer service expert IMCI named Dempsey one of the industry’s top 50 influencers on Twitter. 

In addition to running her blog and working as social media and customer experience manager for, Dempsey started a customer service podcast called “Breaking the Ice,” a weekly banter between Dempsey and her Customer Service Life Co-Founder Jeremy Watkin. Today, in addition to working, blogging and podcasting, Dempsey also runs Dempsey Wellness Center and is training to be an integrative nutrition health coach. 

Here’s a little insight into one of customer service’s best and brightest.

Q. How did you go from English major to customer service expert?

A. I fell into a customer service job by accident while I was in college. I ended up doing really well and elements of my English major—writing and composition—played a part. 

I was surprised by how much psychology is involved in customer service and ended up wishing I had taken more psychology classes. I was also surprised by how exhausting customer service can be on your emotional and mental self. 

Q. What was your biggest customer service fail?

A. The one that stands out the most happened when I was communicating with a customer via email. The customer was very aggravated. I kept trying to explain the same thing over and over and finally he replied by saying, “listen Mrs. Dumpsey,” which really triggered a response from me. When I was a kid, people called me Dumpsey so that really pushed my buttons. I ended up forwarding the email to my manager—or so I thought. The email actually went to the customer—I’d accidentally hit reply—and so he saw my reaction. 

Q. What’s your biggest customer service success?

A. This might not be my biggest success, but it’s one of my favorite stories. I helped a customer answer a really simple question. They were so grateful that they wrote a song about the experience. It was just a few guys being goofy with a guitar, but I responded with a song back that basically said you’re welcome. It was the coolest customer interaction. 

Q. Why did you start the Customer Service Life?

A. I started the blog in 2012 with my former boss, Jeremy Watkin, because we wanted to talk about customer service. Our friends and family were tired of hearing about it all the time, but we wanted to share what we had been learning. That was the foundation for Customer Service Life. It’s taken us to some really interesting places. We’ve had a lot of exposure and a following through social media. We have met authors, been interviewed by traditional media and met some really interesting people in customer service. It sort of took off. 

Q. What about women in customer service? Do you see roles shifting there?

A. In my experience, customer service has always been very respectful of women. Where I’ve seen bias is with the customers, not the employers. When I first started working in customer service, I worked for a web host domain registration company and there were a couple of times where I’d be talking to a customer and they’d say, “wait, I need to talk to a man. Get me a guy on the phone.” It happened a lot, like they didn’t feel that women were capable of knowing about the technical stuff. I haven’t seen it as much now, but it is very confusing and frustrating.

Q. What do you love about customer service?

A. I love helping people and working in customer service has given me the opportunity to help people in a variety of ways. 

Q. Tell us about “Breaking the Ice” and your top must-see episodes

A. I love “Breaking the Ice.” Jeremy and I actually started breaking the ice in a more literally sense off-line when we worked together. We’d start every customer service team meeting with an ice breaker question. We took that concept online with “Breaking the Ice,” which asks various leaders in the customer service community ice breaker questions and see where they go with it. Ice breakers are great because they set the tone for how agents interact with their customers. It makes them feel comfortable in their work environment and lets the agents get to know each other, too. 

I love the episode that starts with the ice breaker, “do you like cheese?” People either love or hate cheese. This is an ice breaker that I use at networking events and it’s one of my favorites.

Q. How have language barriers affected call centers?

A. I remember that when I first work in customer service, we had one Spanish speaking agent so if anyone called speaking Spanish, they had to talk to them or they couldn’t communicate. Today, I think the biggest struggle across the board is being able to read exchanges with customers who do not speak English. 

Q. What can employers do to make their customer service agents’ lives easier?

A. The easiest thing companies could do to make agents’ lives easier is to ask what they need. Sometimes agents are too intimidated to go to their boss and say, “we could do this better.” Feedback that is given doesn’t always get to the person who can make the change. Companies could also put a system in place where this feedback gets to the right person. 

Follow Jenny @jennysuedempsey