Learning to do customer support is like learning any skill: you master it by doing it. Reading books is helpful, the same way watching someone swim gives you an idea for emulation. But if you don't get some water in your nose, no amount of reading will save you from drowning.

At Help Scout, we have a practice where every week a team member jumps into the support queue and answers some of the more challenging inquiries.

As part of the content team, I was encouraged to jump into support so that I could learn the product, and in turn, understand customers’ challenges. This would ultimately help me devise my essays accordingly—but the fear of failure kept me back.

Left to our own whims, we will pick the lowest hanging fruits and avoid the more difficult inquiries that are usually handled by the veterans. However, this doesn’t help accumulate the skills and knowledge that we need to fulfill our obligations.

Lessons are learned the way muscles are built: no resistance, no growth.

Whether you’re a new hire learning customer support or simply interested in getting better at it, here are some lessons and tactics I learned along the way.

Seek (and Soothe) Discomfort

It was a sudden flash of self-awareness: I clicked on the email, read the body—the customer was leaving another service and was inquiring to see if we were a good fit—and I immediately went back and searched for another question.

Realizing what I’d done, I stopped to think for a moment. Why did I just ignore that email? What about it made me feel uncomfortable? Why wasn’t I confident to answer this question with enthusiasm?

In short, it was a lack of confidence, which derived from a lack of experience. And what obstructs us from experience?


The more resistance you feel in facing a difficult question, the more compelled you should be to answer it. Suddenly, feeling a sense of discomfort is natural. What matters is how you respond.

Jumping head first into support is scary because relationships are on the line and you don’t want to be the person who severs them. Like a child who is excited to jump into the deep end of the pool where all the adults play, there should be someone watching over you.

When I felt discomfort in the queue, here’s how I alleviated it:

  • I searched all closed conversations and looked up anything that was similar. Had our customer champions responded to similar inquiries? How did they answer?
  • I searched our knowledge base to see if I could find any insights that would benefit this conversation.
  • I wrote my response and saved it as a draft.
  • I pinged Justin—one of our customer champions—on Slack, and I notified him of my draft.
  • He reviewed it and added some notes, giving me pointers on how to reword specific phrases and add helpful links for the customers to explore.
  • I revised and sent the response.
  • The potential customer was delighted by the timeliness and information, which sparked a follow-up conversation and a demo of our product.

This oversight mitigated any potential mistakes. Justin’s coaching helped me become familiar with the unfamiliar. This was now one more type of inquiry that I was comfortable dealing with.

Rinse and repeat.

Play with Varsity

I love the story about the CEO of Yahoo, Marissa Mayer, and her 2% chance of getting a job at Google early in her career versus the 12 other job offers that she had. She retells what she calls the “Laura Beckman story”—a story about the daughter of her middle school piano teacher.

“Laura tried out for the volleyball team her junior year at high school,” said Mayer. “At the end of the tryouts, she was given a hard choice: bench on varsity, or start on JV.”

The more alluring choice would be to play JV. Laura chose the opposite and was benched the whole season. Why Laura did this was simple: she knew if she practiced with better players, she’d become a better player herself.

The moral of the story is to surround yourself with people who will challenge you to learn and grow (which is why Mayer went to Google).

Willfully seeking discomfort in the queue—not just dipping your toes—is a difficult desire to muster on your own. But understand that this sudden leap gets you practicing with varsity.

Don’t “try” to do support; you will actually end up not doing any of it. You have to jump in and purposely seek discomfort.

Build a Habit to Keep Your Focus

Trying to be everywhere gets you nowhere.

If answering support emails is only part of your duties, it’s vital to have a schedule or a routine where your responsibilities aren’t being stretched too thin.

While my schedule and tactics are idiosyncratic, my advice is to carve out blocks of time—perhaps in the morning and then again later in the afternoon—where your mind is fresh and you can fully immerse yourself in high-priority work.

The inbox can turn into a kind of black hole where you get sucked in without realizing it. Understanding your rhythm and energy levels is vital for continuously producing high quality work while also being attentive to your customers’ needs.

This is a tough balancing act, because on one hand we need to do our work and we need blocks of time to focus; on the other hand, we want to respond to our customers quickly.

This is a skill that gets honed over time, especially if you’re a non-support person learning to do support. Experiment with your schedule. Don’t try to answer all the inquiries on your own; if you have to, break it down into smaller chunks.

You find your balance by losing your balance.

A Wellspring of Customer Insight

There are myriad benefits of non-support people doing support.

Marketers can empathize and gain customer insights to improve their efforts; engineers can figure out what features or tools need tinkering; CEOs can turn assumptions in improving the business into an actual plan based on feedback; product managers can turn their theories into experiments based on what customers are saying, and experiments will turn into reality.

Up until this recent change, most of my insight came from books and a variety of other sources—in fact, not enough of it was coming from the lifeblood of the business: the customers.

In just one short week, I gained richer insight about our customers and how they view and use our product; this post is a reflection and digestion of that week.

By stepping into the queue and engaging with customers, you learn an indispensable style of communication that goes beyond a business context; you gain rich insights that will complement your work and stretch your creativity; and ultimately, you overcome fear and actualize your potential.

All this just for doing support? Worth every minute.

Paul Jun
Paul Jun

Paul is head of content at CreativeMornings and a Help Scout alum. Connect with him on Twitter and LinkedIn.