The following is a guest post from Chase Clemons, Customer Support Pro at Basecamp, the guy behind SupportOps and a co-organizer of the Support Driven community.

Hiring the right person for your customer support team is the single, biggest thing you’ll do for your customers. They’ll be your company’s face, the very first person a customer interacts with. Get it right and customers will love you. Get it wrong and you’ll end up with a mess.

But how do you find the right person? When applications start pouring in from your job posting, it’ll feel like you’re looking for that proverbial needle in the haystack. It’ll also take up a ton of your limited time.

With this post, we’ll look at all the things involved with hiring. I’ve talked with three different people, all experts in finding and hiring the right person. They’ve figured out how to comb through that haystack and are ready to share that with you. We’ll walk through each stage of the hiring process from crafting the job posting to picking the final candidates. But first, let’s meet our experts.

Meet our Experts

Diana Potter heads up the customer success team at, a product that helps web and mobile apps send smarter emails. As the team lead, she’s been around the hiring block a few times.

Varun Shoor is the founder and CEO of Kayako, a simple customer service app that scales with your business. He’s had a hand in hiring for his company from day one.

Micah Bennett is the Support Lead at Zapier, a tool that connects the web apps you use so you can easily move data between them and automate tedious tasks. He’s done his fair share of hiring for the team.

Job Posting

First things first – the job posting. This is where you announce to the world that you’re looking for a person to join your team.

Diana – Be specific but not too specific! So many job postings either go crazy “you must know x, y, and z” or they’re completely fluffy and nebulous “we’re a family and you must be part of that. Be nice, that’s all we want.” Give an idea about what the day-to-day job is, what kinds of skills they might need, what they’d be learning (wait, your job never involves learning anything? Time for some introspection there).

Varun – The smartest candidates have their pick of the litter. If you want the awesome problem of having lots of great candidates lining up to build your company, your job listing is your big (and sometimes only) chance to show them how you’ll help them build their career.

Micah – I think the biggest thing to keep in mind is to write the post so that your ideal candidate would be interested. That seems like obvious advice, but so many job postings are weighed down with stilted language that serves as a red flag for job seekers. On the other side of the coin, we include a handful of carefully chosen questions that we ask each applicant to answer. This helps us to be able to measure applicants on consistent criteria and criteria that are closely matched to the qualities we look for in a candidate.


As you’re putting together the job post, you’ll want to be thinking about what you’re looking for in a good candidate. What qualities should you be looking for in a person?

Diana – “That kind of nebulous ability to put themselves in someone else’s shoes. Not quite empathy (though that’s part of it), but more thinking like a customer. Where could someone get stuck? How can I explain this that makes the most sense for this person?”

Varun – Two big things: we look for inquisitive people ready to ride a steep learning curve and we look for cultural fit. Everything else can be taught.

Micah – ”App Curiosity” along with clear and concise writing. At Zapier we constantly work with hundreds of different web apps, so an interest and proficiency with them is crucial. Having that sixth sense for both how to get apps to do what you want and the familiarity from hours spent playing with such apps is a huge help in troubleshooting.

Support is also a lot of writing, and as such we need to be great at communicating with our words. Word choices are crucial in advising what users need to do, and also in a way that doesn’t confuse them or waste their time. This is even more important in a remote team like Zapier is, because those words are the primary form of communication within our team as well.

Resume, Writing Samples, Etc.

The traditional resume seems to be going the way of the dodo bird these days. What should candidates be offering up instead?

Diana – I really could not care less about a resume, it’s all about the cover letter. Writing samples are great, but in reality the cover letter is where it is at. Sell yourself to me. The resume might give me a little bit of background, but I’d prefer not to have to open it until I’m ready to interview them (I like to know a bit about their background, but a good cover letter should cover that :-D).

Varun – We want to see the best you in action. If you’re a writer, include links to your blog. If you’re a dev or a designer, include your Github, Behance, or another appropriate platform.

For marketing and community manager positions, you should be able to write a killer introduction email. A big plus if you’re able to adapt your messaging appropriately to each platform (e.g. forums, Twitter, LinkedIn, etc.)

Micah – Because we specifically ask questions of applicants in our job listing, everything else is less important. If they point us to a URL to their writing or pass along their formal resume we’ll take a quick glance, but that’s very much secondary to the rest of their application.

Working Through the Candidates

At this point, you’ve got a ton of applications to go through. How do you start to separate out the good ones from the bad?

Diana – Discard anyone without a cover letter. Then discard anyone with a short cover letter or who started “dear sir/madam” or anything along those lines. You’ll be down to 5-10% of the applications and can actually take some time to read them. From that point I sent some follow up questions out. Sample support questions for the most part. That allowed me to discard probably another 50% of people (those who didn’t reply or who sent in horrible replies).

Varun – We go through each application looking for well-rounded people who are curious, have worked on interesting projects, seem to enjoy learning and have active side projects and hobbies. Those are the candidates we pass onto the next stage.

Micah – We use a Trello board that shows all applicants and their stage in the hiring process, a trick we borrowed from DoSomething. From there, everyone on the support team takes a look at candidate applications and adds their two cents. Typically a good number will be easy nos, and a few will definitely stand out relative to the others. Having the whole team do this helps remove some biases, since everyone’s top picks won’t always match exactly.

Top Picks

With the best applications in hand, it’s time to set up some interviews. What’s an interview with you look like?

Diana – From the sample questions round it went to a phone interview. A 30 minute chat to get a handle for how they handle things, what their personality is like, etc. I cut it short if things weren’t going anywhere (everyone was told a 15-20 minute chat, it went over when the conversation was flowing, was cut short or kept to the exact time limit when it wasn’t). I probably talked on the phone with a lot more people than other people would. I spent a lot of my time on that, because it’s something I found valuable. Your mileage may vary. I probably did about 13 initial phone interviews (cut down from about 75 applicants).

Varun – We throw out mock scenarios and ask candidates to draft responses to both emails and chats. We toss out a variety of hard situations: customers who are really pissed off, customers giving poor feedback or who want to cancel. Aside from the obvious communication skills, we’re looking for candidates who can handle these with empathy.

Micah – Our first step after filtering applications is a 1-on-1 phone interview, this is typically to validate our initial impression of the candidate and make sure we didn’t completely miss the mark in our evaluation of that candidate.

Favorite Interview Questions

Everyone has a few favorite interview questions. What’s the best ones that we should all be asking?

Diana – Have you ever taught yourself how to do something? What was it? (try and get a conversation going). It’s the most cliche question ever, but where do you see yourself in 5 years? (again, shoot for a conversation). Why? (I like to see what they say here just because it’s fascinating. You can often tell if someone has a path in mind, or if they’re just interested in this job for specific perks and not the job itself, or if they want to use it as a stepping stone to another role, etc).

Varun – What book do you think everyone you meet should read? Tell me about the time you felt company leadership was wrong, what did you do?

Micah – What’s your personal opinion on refunds? I like this question because it helps to suss out if the person is both independent and empathetic/customer focused. Someone who’s not independent will defer to company policy and base their answer on that, and someone who isn’t empathetic will approach the question from the perspective of protecting the company rather than helping the user.

Another good one – what are you better at than most people? I like this question because it forces people to be specific about why they’re good at what they do, but more than anything what is not said in response is just as telling. Someone who talks about how they’re world class at hopscotch rather than something applicable to doing the job may not be a strong candidate. Similarly, someone who speaks very generally about a skill without examples or specifics may not be as much an expert as they think/say.

The Final Candidates

The interviews are done and the final candidate selected. How do you hone in on the best hire if you’ve got a few final candidates?

Diana – If they make it past the first phone call, they get another round of support questions (the first round is just 1 or two questions that more judge basic skills, the second round judges more technical skills). From there the top 3 candidates head off for another phone call with someone else on the team and hopefully can be narrowed down to 1 from there, but if not 1 or 2 might get another phone call with me wherein I’ll finally make the decision and then a job offer.

Varun – If we have to choose between a few people for a position, the one with most creativity and curiosity generally wins.

Micah – Once we’ve decided to go forward with a candidate, hiring for support is a 3 step process. A 1-on-1 phone interview, a Google Hangout interview with the support team, and then a GoToMeeting with the whole Zapier team where you do a quick lightning talk and ask/receive questions from everyone(and OF everyone). We filter candidates at each step so that only the truly top candidates are meeting with the whole team.

The Empathy Test

I’ll leave you with an amazing story from Diana. Yes – this actually happened to her during one of her interviews.

Diana – For bonus points, use my newly made up interview question/test that I call “the empathy test”. Now it takes a fair bit of set up, but it’s worth it.

What you have to do:
1. Make sure you’re using an inflatable balance ball for your office chair.
2. Work from home.
3. Have cats with sharp claws that enjoy spending time in your office.

Now, while you’re in the middle of a video interview with someone, have one of your cats decide they want to join the interview (bonus, you can show your interviewee how you handle interruptions) and to get your attention casually walk by and jab their claws into your chair. See how your interviewee reacts as you slowly but surely start sinking out of their view as your ball deflates before their very eyes and you eventually THUMP against the floor.

Do they ask if you’re okay? Do they find it utterly hilarious while also being completely shocked and want to make sure you’re fine? Do they just laugh? There is no way someone can practice their response to something like that. That’s a true test of both their empathy AND their sense of humor AND how they react to weird unpredictable situations.

Do you have some lingering questions around hiring? Join the Support Driven chat and ask the community!

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