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Ask Help Scout: A Customer Service Advice Column

Long-time customer service professional Mat “Patto” Patterson answers readers’ most challenging customer support delivery, leadership, and career questions. If you have a question you’d love Patto to answer, send it to

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
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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