A Customer Service Advice Column for Actual Humans

Mathew Patterson | October 22, 2021

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

Annual planning as a new customer support leader

Dear Patto,

I was recently promoted to Head of Customer Service for my six-person team. I’m excited about the chance to do some real planning for the next year, but I’ve never done it before. How should I get started, and where can I learn more?

Max Pankov

Dear Max,

Congratulations on the promotion! Planning as a leader for the first time can feel overwhelming (it sure did for me), but the good news is you’re starting with a lot of advantages.

Since you’ve been working in the queue with your colleagues, you already know what is working well, where the rough edges are, and what some of the challenges your team is facing are. Your work for the next year can be divided into three key areas: yourself, your team, and your company.

I’ll start with the company, because that encompasses the annual planning you’re most interested in.

Successful planning starts with understanding where your company is going, what the company goals are, and how your team is going to help meet them. Once you understand what your company really cares about, you can develop goals for your own team that will align well.

My Foundations of Great Service course will walk you through defining your team values, setting relevant goals, and planning for team and company growth. It’s worth working through, even though you have an existing team. The really short version is this:

  • Understand where you are today by collecting some baseline metrics so you can tell later what has changed.
  • Referring to your values, set some ambitious goals for your team to reach, imagining what it would look like if everything went perfectly. Maybe that’s about increasing speed or quality, opening new channels, or developing a closer relationship with internal decision-makers.
  • Then, select some metrics that will measure the behaviors and results most likely to move you toward those goals. Finally, work with your team on plans to hit your targets. Remember, data is a customer service manager’s best friend.

Good planning is essential, but you’ll still face some other challenges as you work to deliver on the plan. The biggest one will be making the team-member-to-leader shift. A caterpillar who has become a butterfly can’t keep crawling around eating and pretending to be bird poop. It must learn to fly, defend its territory, and bask glamorously in the sun.

Have a question for Patto?

And you, Max, must do the same. OK, this analogy isn’t perfect, but you get my point. When you’re a leader, you need to work differently than the queueterpillar you were before, because they are two different jobs with different goals.

Understand that your job now is to help your team succeed — not to do the work for them. In my experience, making that mental shift will require repeated attempts. So start with some habits to rethink when you become a manager, learn lessons for new managers, and maybe read The Making of a Manager.

Your team is the final element in your success in this new role — work to understand who they are as people, their goals, their challenges, and what they need from you to succeed. You know them as colleagues, and now you need to develop a relationship with them as their leader. Set up some effective one-on-one meetings, and keep at it.

Best of luck in the new role, Max. Can’t wait to see your butterfly wings!

What should I include in my cover letter?

Dear Patto,

For the last year I’ve been applying for remote support jobs with no success, and I am wondering if a stronger cover letter could make the difference. Do you have advice on what to include (or not include)?

Build Bella a Better Letter?

Hello Bella,

Job hunting can be so exhausting, and I sympathize with you. In the resume you shared with me, I see solid experience in customer service roles, so you have proven capability to do the work. That’s huge.

There’s plenty of advice on cover letters out there (and on customer service resumes), and I could offer some help there … but I won’t. It’s not because I am the Grinch of advice columns, but because I suspect your biggest challenge is not in the cover letter area.

I see you are based outside of the U.S. (like me!). Unfortunately, that can eliminate you from some roles immediately, and for other roles it may introduce a new complication that a business would rather not deal with.

My suggestion is to target roles where your location becomes a benefit to the hiring company. For example, look to a U.S.-based SaaS company that has a growing number of customers in EMEA (Europe, Middle East, and Africa) and needs to expand their support coverage.

Suddenly, as an experienced support professional who can work daytime hours in the right time zone and who has worked with U.S. companies before, you are a really strong candidate.

Then all your cover letter needs to do is get that across quickly. Your pitch should be, “I’ve done this before, I am a safe bet, and I will represent your company well if you give me the chance.” If you have particular past experiences of working across time zones or with distributed teams, mention that, too.

I know from personal experience that as a busy hiring manager, those are the applicants you get excited about — the ones who solve problems for you instead of creating new complications.

So how do you find those roles? Here’s our general advice for finding remote work. Start in the SaaS support communities and the remote work Slack communities, and don’t be shy about mentioning your availability. These roles do come up, so you want people to know about you and the work you can do.

You can even try putting together a single-page website with your pitch as, “I am your first EMEA-based customer service person.”

By starting off your application process from that position of strength, you’re more likely to find the type of remote work you’re looking for.

Best of luck, from one excluded by “remote (U.S. only)” person to another,

Telling my boss about my true career goals

Dear Patto,

I’m on day two of my new job, and my manager just asked me about my career goals. I want to have fun, make things, and do good work while keeping enough time and energy to fully enjoy life beyond my job. How can I be honest about that without seeming unmotivated or disengaged?

Not Just a Worker Bee

Dear Bee,

Congratulations on finding a manager who cares about your career progress! I’m certain you know that is not always the case.

Like a lot of business practices, career goal discussions have been defined and promoted by the type of people who are seemingly born with a 78-year-long career plan, plopping out into the doctor’s hands while simultaneously checking “☑full term delivery (natural)” off said list.

Not everyone is made that way (I’m certainly not). There’s no need to pretend to be passionate about whatever business your company is in or about climbing a specific career ladder.

What your manager is (probably) actually looking for is something more prosaic. They want you to perform well at your job, contribute to the company’s success, and stick around for a while so they don’t have to go out and replace you. It’s their job to figure out how best to use all the various resources they have on their team to meet their own goals.

So your role in this discussion is to figure out what you want to get from this job, what you can give, and to let your manager know that.

For example, you mention wanting to make things. I bet you’d hate to see a fun, creative project get handed to someone else because your manager didn’t know you’d be interested, right? So let them know what does grab your interest and which new skills you’d love to have. Focus on those things, and in that discussion you can share the engagement and motivation you obviously have in your life.

Here at Help Scout, one of our customer service professionals, Kristi, has been able to contribute to company-wide culture-building projects. She shared her interest with her manager, and they spotted an opportunity for her to take on.

There are limited spots for leadership in any company, but there are plenty more spots for hard working people who want to do good work at work and then go home without having to think about their job until the next day.

Best of luck achieving that balance!

P.S. Even in a role like customer service there are plenty of different paths to follow, and great teams need both players and coaches.

Being pushed to offer Service Level Agreements too soon

Dear Patto,

The sales team at my company is working on signing up a big potential customer, and to help land it they want to offer this prospect a Service Level Agreement — they think it will be a deal breaker not to offer one. The problem is my support/success team is only two people, and we just don’t have the capacity to deliver on an SLA.

How can I push back on this request effectively?

Service Level Disagreement

Dear SLD,

A sales team trying to sell something that doesn’t actually exist yet? Unheard of! I jest, of course, and it’s not unreasonable for a sales team to ask about offering SLAs. It’s actually a positive sign that your sales folks see customer service as being of real value.

What would be unreasonable is signing a contract which includes a service that just can’t be delivered on. It sounds like the customer hasn’t demanded an SLA yet, but your team thinks they might require it later in the deal process.

So what to do? First, when your colleagues ask about Service Level Agreements, what are they imagining? There’s a big difference between “I need a 20-minute response time 24/7” and “I want a number for an account manager I can call if things go wrong,” so a good place to start is by being explicit about the expected level of service.

Once you understand the expectations, you can work out what resources would be needed to deliver them and talk them through with the sales team and perhaps your executives. That way you’re saying “Here’s what we would need” instead of “No, we can’t do it.” Now it’s a conversation where you’re both on the same side, lined up against the oncoming forces of budgets and priorities.

It may be that you can work together on some alternate options to achieve your shared goal, which is probably building this potential customer’s confidence that they will be promptly looked after if something goes wrong.

One option might be a VIP support tier that isn’t a strict SLA but more a package of services. These might include a priority support email address, a named account manager, or an emergency escalation number. That could build peace of mind, even if it’s actually close to the support level you offer to all your customers.

Or perhaps your company really wants to go after those big customers and is willing to pay for the support coverage that would be needed — either using internal staff or with the help of an outsourced first-tier service, for example.

Whatever the case, telling your sales team that you can help and you’d like to talk about what that means is a good practice, and it will help you build mutual trust and respect that you may need in later conversations or disagreements.

If all that fails and you’re expected to offer real SLAs with no extra help, then there’s only one option. To slightly mangle that famously abusive sales speech from Glengarry Glen Ross: Always Be Cloning.

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.

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,

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,

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.

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,

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

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.