The Top Customer Service Challenges Reps Face [& How to Solve Them], According to Experts

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Rebecca Riserbato
Rebecca Riserbato


Without good customer service, your company would cease to exist. That might sound dramatic, but it's not (okay, maybe a little).

Customer support rep on a difficult phone call

Support reps are on the front lines, providing an excellent customer experience that develops your relationship with your customers. Without that relationship and customer loyalty, then it'd be hard to turn a profit.

Your customers' success starts with your customer service organization -- and the happiness and empowerment of those employees.

However, despite its importance, many businesses have high turnover rates in their support department. To learn why that is, we wanted to know the top challenges that customer support reps face and how you can solve these challenges and enable success for your support team.

In this post, let's learn from some of HubSpot's expert customer support specialists about the top challenges facing customer service reps.

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1. Having many conversations at once.

As the customer service industry continues to grow, there are more and more channels where you need dedicated support reps. This could mean live chat, social media chat, phones, emails, and more. With a growing amount of channels, support reps can be spread thin.

Haley Burgess, a senior customer support specialist at HubSpot, says, "I'm primarily on the chat channel. I think one of the challenges we see as chat grows and becomes a primary channel for our customers is working to multi-task. You could be on anywhere from 1-3 chats at once, which makes it challenging to go back and forth."

To solve this issue, Burgess recommends keeping an organized desktop and organized tabs to make it easier to manage multiple conversations at once.

2. Complex questions.

As customers become more knowledgeable, the questions people ask get more and more complex.

Burgess adds, "Another challenge we see as the chat channel grows and customers prefer this channel is the questions can sometimes be very complex. Because we are not on the phones, it is really important to make sure to align with the customer and have a good understanding of what the issue is."

While customers love communicating via live chat, it can be hard to describe an issue and a solution over text.

Burgess recommends asking many follow-up questions, so you can have an understanding and foundation of the issue to effectively solve for the customer.

3. Product knowledge.

One of the many growing pains of working in customer support is product knowledge. Your product goes through updates and changes regularly, which means your customer support reps need to know how to solve new bugs regularly.

Burgess says, "One challenge is the consistent growth of product knowledge. Because reps are customer-facing roles, it can be overwhelming to keep up-to-date with the many product updates and changes. I think to mediate this, it is really important for companies to offer consistent training for reps so they have the product knowledge to be able to troubleshoot effectively."

4. Product improvement requests.

As a customer support rep, you'll talk to customers who are having issues with the product or service your company sells. Sometimes it can be hard to manage requests for product improvement since the customer support department isn't responsible for product upgrades.

Kristen Von Loesecke, a senior customer support specialist at HubSpot, says, "A customer reaches out with a feature request, and I politely, but firmly respond that the function currently doesn't exist in HubSpot and offer workarounds when available. I either get a negative response or a low NPS score with a comment about our product instead of the service provided. As software companies scale and take on more Enterprise level customers, customer expectations become higher for a software's functionalities, and this can translate to a low NPS score."

So, what does this mean for support reps? How can you have a high NPS when you can't necessarily fix the issues that customers are facing?

"My advice to other support representatives is to be fully transparent with a customer, letting them know that support can't make changes to the functionality without the Engineering/UX Team making an update to the product. Customers often don't realize that the support team doesn't have the power to update a tool," Von Loesecke recommends.

5. Burnout.

Burnout is a challenge in any job, but particularly with customer support reps.

Julia Gentillo, a senior customer support specialist at HubSpot, says, "I think the biggest challenge of my day-to-day is how repetitive some of the work can be. It has been super rewarding for me to work on some of the challenging cases and help out our customers but sometimes answering the same types of questions every day can become uninteresting and get tiring over time."

To solve for this, Gentillo says, "The HubSpot support organization provides us with numerous extra opportunities to tackle during our day to help break up some of the repetitiveness. In addition, having a great support system at work between my manager, team lead and colleagues has been a lifesaver!"

Ademole Fasanmade, another customer support specialist at Hubspot, agrees that managing burnout as a support rep is one of the biggest challenges in his job.

Fasanmade has a few strategies to overcome this challenge: create bookends, take carpe-diem to heart, and minimize assumptions.

"When you finish a task, reflect and move on rather than revisiting," the support rep adds. "Take Carpe-Diem to heart. The urge for someone to make the most of the present time and give little thought to the future. I combine this with creating mental bookends. This mental model helps me stop focusing on individual tasks after I finish. It requires me to set boundaries around my work."

Additionally, Fasanmade also focuses on minimizing assumptions when problem-solving. He says, "The principle of Occam's razor (attributed to William of Occam) is that in explaining a thing, no more assumptions should be made than are necessary. Don't overthink things. Apply a methodical approach and avoid overcomplicating because it has been proven to distort issues and increase work-related stress; stepping back will prevent getting lost within."

6. Separating user errors from system bugs.

Another challenge, according to Fasanmade, is separating user error from system bugs.

He adds, "If you can't clone or replicate what a customer is doing, it's typically a user error. If you can, then it is probably a system bug. Human error is always a factor that should be considered while solving for your customers, so the challenge here is to make sure to start fresh and try to replicate the issue on their end if you cannot reproduce it on yours. It's essential to help the customer understand when they're using your product or service incorrectly, while still leaving them happy and satisfied with your customer service."

Essentially, to solve this, don't assume the customer is always right because it could end up hindering your troubleshooting efforts. If you can't replicate an issue, it's a red flag.

7. Simplifying the question.

When a customer is facing a problem, they usually end up thinking they've uncovered a really unique problem. This means that the questions they ask get complicated.

Fasanmade reminds support reps to simplify the question. He says, "The most common answer is usually the correct one when troubleshooting. However, customers often think they've encountered a unique issue when facing a problem. It is vital to troubleshoot based on the factual information of the situation and avoid going down the wrong rabbit holes. Here as well, it's important to guide the customer to the correct solution in an empathic manner."

Solving for this challenge, Fasanmade says, "having empathy is essential in every step of the process. It is vital that you have empathy and troubleshoots based on factual information instead of how the customer feels should work. Since most issues are common, it is crucial to address the obvious and most common reasons why this issue is happened before looking into the obscure."

Always ask yourself, "Is this the easiest way to do this?"

8. Growth and career mobility.

Silver Li-Situ, a senior customer support specialist at Hubspot, says, "I think being a support rep is a challenging job. We provide delightful customer experiences, partner with the internal team to troubleshoot complex issues, and meet the department standards."

However, customer service is a hard industry to grow in. Li-Situ adds, "One of the biggest challenges for me is career mobility. I seldomly get a chance to connect with people outside of support or customer success since I don't work with them directly. Gaining exposure to other departments such as Marketing, Finance, and Engineering could help me understand the bigger picture of how the business operates and lead to potential career opportunities."

To solve this challenge, Li-Situ thinks that companies should have a program where support reps can meet with colleagues from different departments informally. This would give support reps a chance to grow and collaborate with other teams.

So, now you know what challenges HubSpot support reps face. But, we're curious, what are the top challenges for your customer support team?


Customer service is an exciting, evolving industry. However, it's important for companies to be aware of the challenges that front-line support reps face so they can provide the best customer experience.

Editor's note: This post was originally published in March 2018 and has been updated for comprehensiveness.

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