Illustration by Erik Blad

A Customer Service Advice Column for Actual Humans

Long-time customer service professional Mat “Patto” Patterson answers readers’ most challenging customer support delivery, leadership, and career questions.

Balancing soft-skills with technical ability

Dear Patto,

How can I hire people for my customer service team who are strong in soft skills but are also capable of learning the more technical aspects of our complex product? What’s the best way to identify the right people without making the application process too onerous for them?

Simone, a SaaS Support Soft-Skill Seeker

Hello Simone!

Finding the right balance of excellent soft skills and just enough technical aptitude is a challenge, and I can tell you from personal experience that failing that challenge sucks for everyone involved. But the good news is that I learned from my failure, and so can you.

First, you need to understand how much technical skill is enough for your team. What sort of questions will they need to answer? Do you expect every team member to reach the same level of technical skill, or could you have a tiered team with different levels of knowledge?

Second, form an honest opinion about the resources you have on hand. What training materials do you already have, and how much time is realistically available to help people develop their skills?

Those two points will help you understand where to set your bar of technical capability. Your next challenge is to find promising candidates and to discover through the process whether they will be able to clear that bar and succeed in your role.

That begins with a good role description. You want to attract people who have the soft skills you need, but you should also be clear that they are expected to continually increase their technical knowledge.

Your best candidates will be excited to stretch themselves, and they may even have some background with more technical work but be looking for a change. These people do exist — I myself was a web designer before moving into SaaS support, and I know there are plenty of others like me.

Have a question for Patto?

Have a question for Patto?

Create opportunities to assess technical competence as people move through their application stages. At Help Scout, our support hiring process includes a short paid project which has folks demonstrate understanding and explain some technical issues. I appreciate that you don’t want to be too burdensome, but you may be able to tweak an existing step to draw out those skills earlier.

Ask customer service interview questions that dig into their attitude toward learning technical topics. A question like, “In your family, are you the one who gets a call when the printer breaks? How do you help?” can offer a low-key entry into a conversation about their troubleshooting approach.

Look for evidence of the ability to pick up new technical skills: Have they taught themselves CSS or taken a coding bootcamp? Ask about times they were faced with a question outside their expertise and what steps they took to resolve it.

The key for your situation will be finding people who are adaptable and resilient, with enough existing technical skill to build upon. My guide to hiring for customer service may help, too.

Best of luck with your soft-skill shuffle,

mathew patterson's photo and signatureillustration of eight question mark bubbles in various positions

Breaking into SaaS support

Dear Patto,

How can I move into a SaaS customer service role? All of my past jobs were customer-facing, but I don’t have the 1-2 years of SaaS experience that everybody seems to be asking for. Is it even worth me applying for those roles?

Thanks for any advice,

Dear Cortney,

First let me encourage you: Software companies will absolutely hire customer service reps who don’t have SaaS experience. I’ve done it myself. Even those asking for 1-2 years of experience are often just trying to filter out more experienced (and therefore more expensive) people.

Research has also shown that men are more likely to apply to and be hired into roles where they don’t meet the stated requirements. So you can confidently apply in those same situations.

Now, how to book those interviews and, ultimately, a job offer? Since you don’t have prior SaaS experience to point to, you’re going to have to work a little bit harder to show how the experience you do have will apply in those roles.

Start by thinking back over your previous work. You’re looking for great stories you can tell about how you helped customers in difficult circumstances, handled inter-personal conflict, or went above and beyond to solve a tricky dilemma. Those skills will all transfer well to online support.

When looking for potential roles, start with companies that might value your previous industry experience. For example, even though I was not a customer service pro at the time, my web design skills were highly valued by Campaign Monitor (who were then selling email marketing software specifically to web designers). If you can bring relevant domain knowledge to a role, it will count for a lot.

Your real goal is to build confidence in the hiring manager that yes, Cortney could do this job well if we gave her a chance. That starts right from your application letter, where you will directly address your lack of experience.

Let them know that you’ve read the requirements, acknowledge you don’t technically meet them, and explain how the skills and experience you do have will make you a great candidate. Highlight other skills you have learned as evidence that you could get up to speed quickly.

Our article on how to craft your customer service resume is worth a read; be sure to tweak your resume each time to reflect the priorities of the role you are applying for.

Once you book an interview, take some time to prepare. Sign up for a free account, try out whatever you can, and read through the support documentation and any customer forums. Write down a few thoughtful questions that you can ask during your interview. Our customer service interview questions are a handy way to think through potential answers.

In the meantime, consider joining a customer service community like Support Driven. It’s a great place to learn, find jobs, and be encouraged in your journey toward a new career.

Finally, we’ve got a bunch more tips for you in these articles: 7 Tips for Becoming a SaaS Support Professional and How to Snag a Remote Customer Service Job.

If you can get through a few interviews, you’ll find your confidence increasing, and I know you will find the right match before too long.

Best of luck getting SaaSy,

mathew patterson's photo and signature

P.S. If you’re a hiring manager reading this who’s open to hiring a skilled-but-inexperienced customer service team member, let us know! We will put you in touch with Cortney.

illustration of eight question mark bubbles in various positions

The best role for a second customer service hire

Dear Patto,

I lead Support & Success at my company, and we're getting ready to start scaling up our business teams early this year. I handle the full customer life cycle — everything from pre-sales through onboarding, support, and renewals! I’m getting ready to hire someone to help me, but my question is: What is the best role for that second customer service/success hire?

So very busy,

Dear Georgia,

Busy is right! Reading your list of responsibilities reminded me of The Cat in the Hat balancing everything from a cake to a fishbowl while standing on a ball. Small companies can be like that, and it’s often customer service folks who end up taking on every “well, someone just needs to do it” job.

In the story, of course, juggling one item too many brings the Cat and all the items crashing down. I’m glad that your company is looking to hire some help before that happens to you. Who should that next hire be? I see two main options for you.

The first option is human cloning (or as close to it as science — and the law — currently allows). If you can find another Georgia-type person, someone who can learn to do all the same things you do, you will buy yourself time and space to step away, plan, and prepare for the next stage of growth. That’s what I did when I faced a very similar situation. You can’t keep doing it forever, but in the short term it can really keep things moving.

The second option will cost less in salary but more in time: hiring a more junior person and training them up. You’d start by giving them the parts of your work that are fairly simple but time consuming and still important. Training up a junior will be more upfront time and effort, but you can develop their skills into exactly what you need and eventually reclaim a lot of your time for the work only you can do.

Which option is best? To decide, sit down with your manager and really dig into where you spend your time. What parts of your role do you want to hold onto as you grow? What should eventually be a separate team? Do you have capacity to train a junior now, or do you need someone to come in and be immediately productive? How long could “two Georgias” keep up, given your company’s trajectory?

Whichever way you go, now is the time to start documenting processes and getting information out of your head and into places where someone else could learn from it. The sooner you can do that, the easier it will be to hand off work to whoever joins your team.

Good luck Georgia, and keep serving those customers,

mathew patterson's photo and signatureillustration of eight question mark bubbles in various positions

Avoiding cherry-picking in the support queue

Dear Patto,

Our support team is going to grow quite quickly, and we want to minimize the chance of people cherry-picking tickets. The obvious answer is assigning out every incoming ticket automatically, but I would rather avoid that if I can.

I am already exploring skills-based routing, but here's my main question:

What triggers cherry-picking, and how can I encourage my team to take ownership of all kinds of tickets without having to force it on them?

Sarah Betts,
Agent Relationships at Openly

Dear Sarah,

Cherries are delicious, and picking them should be greatly encouraged.

Best regards,

Well all right, by “cherry-picking,” we’re really talking about customer service folks browsing a busy support inbox and picking out the conversations that are simpler or faster for them to resolve.

Customers with more complex, unclear, or tricky questions are left languishing in the queue like Brussels sprouts at the budget buffet. It’s a poor customer experience, and the older those questions get, the less appealing they look to the support team.

As you mention, having every conversation automatically routed to a support person does remove the cherry-picking aspect, but it can feel heavy handed — it’s enforcement, not encouragement.

I think you’re looking for a way to minimize the problem while holding onto those small team strengths of flexibility and personality. I have two ideas for you.

The first is to reduce opportunities for cherry-picking. Automatically assigning every conversation, whether by round-robin, capacity, or other system, will certainly remove the time lost to browsing the queue.

You don’t have to go that far, though. There are many other ways to reduce the need to browse the queue. The skills-based routing you’re looking at is one. Another is assigning some people to answer the oldest questions first and others the newest, rotating folks through those roles for variety.

Personally, my ownership over the toughest questions came from being a solo support agent with no other option. You might try creating a version of that experience by categorizing incoming support questions using tags or workflows and assigning folks to own sub-queues based on those categories.

My second suggestion is to find ways to encourage your team to challenge themselves. I am certain you already have a supportive work environment, but I bet there are some tweaks you can make to encourage that sense of ownership. It helps to know that cherry-picking is often less about taking the easy conversations and more about avoiding the difficult ones.

I’ve got three suggestions to help your support team make the harder choice. First, consider how they are being measured. Is their work success mostly about the speed and volume of conversations they handle? Could you measure their skill development and willingness to engage, too?

Second, encourage knowledge sharing. Newer people may not yet be confident enough to answer complex questions, but they want to learn. Use something like Help Scout’s “follow” feature so they can watch how the experienced team members answer (and reward them for teaching their colleagues.)

Finally, add in some incentives for taking ownership. For example, imagine if your team could rise up tiers by proving they had been successful with certain types of complex cases? Or if you celebrated those people already taking the harder cases with some public praise or perhaps a custom bobble head doll depicting them as a queue gardener? Two good options right there.

I know you will pick the right combination of changes and greatly reduce any cherry-picking without needing to become Sarah Iron-Fist, Destroyer of Cherries.

Keep serving those customers,

mathew patterson's photo and signature
Mathew Patterson
Mathew Patterson

After running a support team for years, Mat joined the marketing team at Help Scout, where we make excellent customer service achievable for companies of all sizes. Connect with him on Twitter and LinkedIn.

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