Inside Learn Something Days: The Help Scout Support Team

Time away from the support queue is considered a luxury for many support folks out there, which can make finding time for professional development a challenge. Thankfully at Help Scout, learning isn’t just encouraged — it’s built into the job.

Since 2015, team members have received (after six months of employment) an annual stipend that they can use for any learning opportunity, from purchasing books and professional memberships to taking online courses, attending conferences, or getting certifications. 

“We believe that investing in learning is good for our people because employees want to work for a company that genuinely cares about their development,” said Heidi Harris, who heads up learning and development at Help Scout. “It’s also good for business. When team members are learning and continually improving, then they’re equipped to contribute even more impact to help us succeed.”

We’ve shared about our Learn Something program at the company-wide level in previous posts, but today I want to dive into how our support team uses this time as well as provide some inspiration for implementing a Learn Something program with your own team.

What does a Learn Something Day look like? 

Given how busy life in the queue can be, you might be wondering how we're able to focus on growth and professional development during the regular workweek.

Since we can’t all be away from customer conversations at the same time, every support team member gets one day each month to spend away from regular work, plus use of the company’s annual stipend to develop a new skill and invest in their growth.

One of the things I really love about our Learn Something Days is how flexible they are. There’s no requirement to turn in a full report or account for every minute — it’s all about making space to grow. Essentially, as long as what you’re doing helps you better support customers, it’s a valid way to spend the day. 

To give you an idea of how this looks in practice, here are just a few ways our team has used Learn Something Days to help level up both our own individual skills and the skills of the support team as a whole. 

Sharpen your spidey senses

SaaS support relies heavily on strong documentation, and for good reason. We aren’t robots, and we can’t be expected to have every possible answer to a problem memorized. Although it isn’t realistic to expect a support pro to know everything, building your institutional knowledge by reviewing internal documentation can help sharpen your instincts, so when something looks off, your “spidey senses” kick in. Over time, you’ll start to recognize common issues faster and feel more confident navigating tricky situations.

When I'm planning to dig into existing documentation during my Learn Something Day, here’s how I structure my time:

• Pick a topic or area of focus. I’ll typically start by picking an area of the product that I’m not super familiar with or a topic that’s just too big to know everything about — something like integrations, as an example.

• Dig into documentation. Then I’ll go through the internal documentation around the topic, slowly and carefully, taking notes, jotting down questions, and flagging anything that feels unclear or confusing.

• Review past conversations. After that, I jump into the support queue and search for past conversations related to my topic. I look at how common issues were handled and whether anything tricky or unexpected came up. 

• Compare and contrast. Next, I compare those real-world cases to what the docs said. Were they in sync? Was something missing or outdated?

Not only does this type of practice help me get a better grasp on the topic, but it also often leads to suggestions for improving the documentation for everyone else.

Give yourself (and your team) the answers to the test 

Speaking of documentation…have you ever found yourself answering the same question over and over and thought, “I really wish there was a saved reply for this”? Or maybe you’ve searched the knowledge base for a customer-facing guide on a specific feature and come up empty. Or worse, you go to your internal knowledge base and find outdated information. A Learn Something Day is the perfect opportunity to fill in those gaps — both for your team and your future self.

A perfect example of this:

Technical Support Specialist Kelly Herring recently finished a huge saved reply maintenance project. She used her Learn Something time to comb through our hundreds of saved replies, checking for tone and content, updating any outdated links, and adding links to related feature requests or bug cards in our Linear account. 

Small improvements add up, and contributions like these will continue paying off long after a Learn Something Day is over.

Empathy in action 

One of the most effective ways to build empathy as a support professional is to use your own product just like a customer would. Putting yourself in their shoes helps you see the experience from their perspective — what’s intuitive, what’s confusing, and where there might be friction — so you’re better equipped to recognize and explain pain points when customers reach out or even flag improvement opportunities for the product team to review.

For example, during my last Learn Something Day, I experimented with using ChatGPT to help build a Python script that could create a Docs structure via our Docs API. The script itself isn’t polished enough to share broadly (AI or not, I am still decidedly not a developer!), but the process was incredibly valuable. I got much more familiar with how the Docs API works, uncovered a few quirks, and walked away with a stronger foundation for future projects. 

How you do this type of learning will depend on the type of support you provide. But whatever your product or service, using it like a customer would is a simple but powerful way to learn and support with greater empathy.

Read a book (or a blog, or take a course)

How can you be a better advocate for your customers? How can you connect your work more directly to your company’s business goals? How can you grow in your role or take steps toward the next one? These are all big, important questions, and you shouldn’t have to figure them out on your own time.

Using a Learn Something Day could mean something as straightforward as picking up a business book you’ve been meaning to read (here are a few books to check out if you need some inspo) or even diving into our archive of The Supportive newsletter.

You can also tailor your day to your interests. Want to learn something technical? Take a course! Technical Support Specialist Cameron Mitchell once used his Learn Something Day to take a JavaScript course on Codeacademy. 

Curious about improving your writing or communication? Senior Technical Support Specialist Sarah-Mei Estrada used a Learn Something Day to take a writing course — our job is mostly writing, after all! 

Whatever you choose, use the time to focus on something that matters to you. It’s a few hours to step back, zoom out, and think about what’s next for you and your career.

Learn Something Days can lead to career growth 

Over the years, several folks from our support team have transitioned into new roles across the company, bringing their deep understanding of our customers along with them. 

Justin Wolfe joined Help Scout as a member of our support team and is now a JavaScript engineer in our experience org. While on the support team, Justin spent time flexing his engineering muscles during his days out of the queue:

I've always been a person who prefers to learn by doing, so I like to treat Learn Something Days as solo mini hackathons. When I was working in support, I would often use those days to build internal tools for our team.

One of my first tasks as a fledgling product support engineer at Help Scout was taking one of those internal tools and translating its functionality into the public Beacon('info') method in our Beacon API.

Justin Wolfe

JavaScript Engineer

Another former member of our team, K’Shelle Waller, is now a product manager at Help Scout. K’Shelle used her Learn Something Days to attend product-related webinars, take e-learning courses, and attend conferences like Afro Tech to help prepare her for a career on the product side of the house. 

Whether it’s digging into something technical, leveling up communication skills, or just getting curious about how another part of the company works, that dedicated time has helped people like Justin and K’Shelle take real steps forward in their careers. It’s also been good for business: By hiring internally, Help Scout is able to retain institutional knowledge, reduce ramp-up time, and invest in talent we already know and trust.

Create a Learn Something Day program for your team

Of course, programs like this do come with some trade-offs — there’s the cost of the stipend and taking time away from the queue, as well as the challenge of balancing support coverage.

To give you a peek at how we’ve made it work, our Director of Support, Katie Harlow, shared a few thoughts on how we approach guidelines and expectations around Learn Something Days:  

As a front-line support team, we want to be sure that we’re still providing our customers with a consistently wonderful experience, so we’ve implemented guidelines around the team requesting their monthly day out of the queue. This ensures that we’ve got the coverage we need to meet our customers’ expectations.

We looked at our team’s other PTO and found that the most common days that people requested off were Mondays and Fridays, so we made a blanket rule to not have the team take their Learn Something Day on these days. This way, we have more room for long weekends and disconnecting from work fully.

We also make sure that only one person is taking a Learn Something Day at a time — this works well for us, but a different limit might make sense for a larger team.

Katie Harlow

Director of Support

As Katie mentions, depending on your team size and industry, a Learn Something program might look a little different from what we've set up here at Help Scout.

Maybe the frequency that works for your team is once a quarter instead of every month, or maybe you aren’t able to add a stipend just yet. That’s OK! The important thing here is to be intentional. Set guidelines that work for your team, encourage participation, and prioritize setting time aside for your team's development.

Happy learning!