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Dos and don’ts for building a remote team: Lessons from a hiring manager

Mandy Smith
August 14, 2019

Most of us have had at least one bad hiring experience — a recruiter who got too aggressive (or, conversely, ghosted), an interviewer who showed up unprepared, or even an unpleasant post-hire moment when we realized the job wasn’t what we’d been led to believe. But as someone who’s been part of this process for more than a decade, I’m still shocked by some of my friends’ and colleagues’ hiring horror stories. Who are these people, I wonder, who are so blasé about hiring? Do they not understand the stakes?

As someone who’s been part of this process for more than a decade, I’m still shocked by some of my friends’ and colleagues’ hiring horror stories.

For a job candidate, the hiring process is the first impression of a company’s values, ways of working, and approach to supporting and caring for employees. For a company, it’s a means (often the only means, beyond scanning a resumé) of learning about a candidate’s personality, professional style, and strengths and weaknesses with respect to a role. It culminates in both company and candidate making a huge investment of time, money (the cost of hiring and onboarding a new employee is about $4,000), energy, and trust.

My goal is to make prospective employees feel welcome, respected, and excited about working with us.

“Finding qualified employees” is one of the top ten concerns for today’s small business owners. At a small company like Olark, a new hire might be one of just 4 or 5 people on a functional team, and they’ll interact almost daily with everyone who works here. The right person can lift the entire company up, and a bad fit can bring everyone down. That profound impact is part of what makes hiring my favorite part of being Olark’s Director of People Operations — and it’s also the reason I take hiring very, very seriously.

The right person can lift the entire company up, and a bad fit can bring everyone down.

Hiring at Olark is challenging and high-stakes not only because we’re small, but also because we’re remote. When I applied for my role back in 2015, the process took several months and culminated in an in-person interview. It was a great experience; I made genuine connections with everyone I met, and was inspired by the team’s energy and enthusiasm. After I started, however, I began thinking about how we could make hiring even better — and the in-person component nagged at me. I understood why a face-to-face meeting felt important, but it was also costly and time-consuming, and didn’t mimic the way the new hire would be working with us on a daily basis. So I took a deep breath, and scrapped it.

We’ve been hiring and onboarding new employees 100% remotely for several years now. It’s not always easy, but it has taught me a lot about what’s truly important, especially when bringing new members into a small, close-knit team. As we’ve refined our system, I’ve compiled a list of dos and don’ts that I hope will help all small companies — remote-first, remote-friendly, remote-curious, or happily co-located — develop more effective hiring processes. There’s a lot here, but my tips really boil down to building a process that’s genuine, transparent, and respectful of every candidate’s time and talents.


Do: Keep it real

During my first phone interview with Mark (now one of Olark’s senior backend engineers), my doorbell rang. Surprise — the dryer I’d ordered had arrived early. Mark and I were having a great chat, and I didn’t want to cut it off, but now I had a large appliance sitting on my porch. So I just got real with him: “This is weird, but I need to get this dryer installed. Is it okay if I call you back in 5 minutes?” We both laughed about it, and after the dryer was installed (unsuccessfully, but that’s a story for another day), we hopped back on the phone and finished our interview.

Mark was hired a few weeks later, and the dryer incident is still one of my favorite interviewing memories. It was a great reminder of the fact that life happens — and when you work remotely, life can happen unexpectedly, at your front door, smack in the middle of the workday. If a candidate gets a glimpse of your real life during the interview process — or if you get a glimpse of theirs — it’s really only a good thing. Take it in stride and work around it as you would with any friend or colleague.

Do: Provide a “day in the life” experience

The problem with most interview settings is that they’re, well…fake. Most people can practice their way into nailing an interview, and hiring managers can know interview questions front to back. But are you getting actual data on how well the applicant can do the job? Or are you both just doing the interview tango?

The only way to really know if someone can do what you need them to do, with the team they’ll actually be working with, is to put them in the real situation. This has become a non-negotiable step in our interview process. Final-round candidates at Olark complete a full-day “work-along”, during which they meet with teammates, dive into a project, present their work, and answer questions.

Are you getting actual data on how well the applicant can do the job? Or are you both just doing the interview tango?

The work-along has never failed us. By the end of the day, it’s 100% clear if an applicant is the right fit. The applicant also knows exactly what they’re signing up for — they’ve had a taste, they’ve seen the inner workings, and they know how our workflows operate. It’s truly a win/win.

Make sure you involve folks from other departments in the work-along, too. In a small company, collaboration across teams is the day-to-day norm; for example, a new Customer Service team member will be working with engineers, marketers, product analysts, and designers, so members of those teams should have an opportunity to meet candidates and weigh in. I often have Olarkers from different departments conduct non-technical interviews, meet with candidates informally, or to sit in on presentations. Diverse involvement gives us a wide range of perspectives on each candidate — and it gives candidates a much clearer picture of what it’s really like to work here.

Don’t: Be too rigid

Plan your interviews carefully, but don’t try to stick to a script. As long as you get the baseline data you need, there is absolutely nothing wrong with going off on a tangent or allowing a candidate to elaborate on something they’re passionate about. If you’re too focused on keeping an interview “on track”, you won’t learn anything about what it’s like to have a normal conversation with the candidate — the kind of conversation they’ll be having with you and your teammates every day if they’re hired.

Of course, to have a normal conversation, you need to make sure you’ve put the candidate at ease. Almost everyone gets at least a little nervous in an interview, but I’ve found that kicking things off with a simple “let’s keep this informal — I want to get to know you” goes a long way toward bringing out the real human.


Do: Discuss salary right away

I get a lot of raised eyebrows when I say this, but I firmly believe you should set salary expectations in the first interview. We all care about money — it’s a part of life. As a small company, Olark has a fixed budget for each new hire, and sharing that information upfront helps us ensure that we’re not wasting anyone’s time. We’d rather lose a great candidate on the first call than go through a month-long interview process only to learn that we can’t possibly pay them what they’re expecting.

We all care about money — it’s a part of life. Sharing salary information upfront helps us ensure that we’re not wasting anyone’s time.

Setting salary expectations up front also helps us keep salaries equitable, since we make it clear that we’re not open to negotiating big changes. My role as an HR and hiring manager includes compensation research, inclusion, and benefits planning — which means that knowing our salaries are fair compared to the market, that we prioritize gender equality, and that we’re up front about all of these factors is enormously important to me.

Do: Be upfront about the interview process and expectations

Although we no longer require an in-person interview, hiring at Olark is an involved process, and it can be a little intense at times. The last thing I want is for a candidate to be surprised by how long things are taking or what’s being asked of them, so I explain the process in the first interview, and give estimates for the time required of the candidate at each step as well as for our overall timeline for making a hire. That way, the candidate goes in clear-eyed and has a chance to let me know about any potential conflicts (upcoming vacations, etc.) — and they can bow out with no hard feelings if they’re uncomfortable with our timeline or process for any reason.

Do: Talk about the challenges

No job is 100% rainbows and sunshine. If it were easy, or you had it all figured out, you wouldn’t be hiring someone new to take it on. When candidates ask about the tough, ambiguous, or tedious parts of a role, or about the department’s or company’s general struggles and weaknesses, be completely honest. If they’re a good fit, they’ll see those challenges as opportunities.

For example, everyone at Olark periodically chips in on tasks outside their core areas of expertise. We’re very upfront about those “all hands on deck” moments in our interview process, and we learn a lot from candidates’ reactions. Someone who sees pinch-hitting as a downside of the job probably isn’t the best fit for us. On the other hand, many candidates are excited about learning and contributing in different areas, and those are the folks we want to move on to the next stage.


Do: Take time to review applications thoroughly

Olark receives hundreds of applications for every position we post. Apart from the fact that we’re awesome (yes, I’m biased), being remote significantly expands our applicant pool.

What happens with that stack of applications? Well, I read them. And I don’t just mean “I scan them quickly for keywords.” I spend the ten minutes it takes to digest each candidate’s information, and to think critically about whether they’re a potential fit. I also read and consider their answers to the application questions — open-ended questions related to the specific role and our core values are a key part of our application, and allow me to gauge a candidate’s interest, knowledge, and written communication abilities before deciding whether to move them to a phone screen.

For some roles, reading applications takes a full week of my time. But it’s worth it, because the most important qualities we’re looking for — creativity, empathy, ability to adapt and learn — can’t be captured in a six-word headline. Some of our top employees come from non-traditional backgrounds, and probably would have been dismissed in a traditional “filtering” process.

The most important qualities we’re looking for — creativity, empathy, ability to adapt and learn — can’t be captured in a six-word headline.

If you’re hiring for a very specific, static skill set, you might be able to get away with just scanning resumes. But very few small companies are in that position. If you want someone who can grow with your business and contribute in a variety of ways, you owe your candidates (and yourself) the time it takes to read every word.

Do: Pay for any project-based or lengthy activity

For most positions, we ask applicants to complete two lengthy activities (2–3 hours or more) into the interview process. We pay $100-$250 per activity, because we want candidates to know we respect and value their time. A homework assignment might eat into an evening or weekend that an applicant would otherwise have spent with family; a full-day work-along will probably require them to take a vacation day, find a babysitter, etc. It’s important to us that prospective employees know we don’t take those things lightly, and that if they do join our team, we’ll respect their lives and commitments outside of work.

Don’t: Waste someone’s time

Don’t string people along. If a candidate clearly isn’t a good fit, tell them right away so they can move on and pursue other opportunities. It’s no fun letting someone down, but it’s much, much easier if you do it quickly and cleanly, before they’ve invested too much time in your process.

Similarly, don’t disappear from the process. If you say you’re going to get back to a candidate within a certain period of time, do it. If it’s been more than two weeks since you’ve updated them, update them. Ghosting after a first date is bad — ghosting after a first interview is literally the worst, and sets an especially bad precedent in a remote setting, where everyone is highly reliant on consistent, predictable communication. We’re all busy, but even a one-line email is better than radio silence.

And finally…

Do: Share your experiences

We just covered a ton of ground — but really, these dos and don’ts only scratch the surface of what it takes to build a great team. If you have tips of insights that might benefit other small businesses (remote or otherwise), let us know! You can comment on this post or drop us a line on Facebook, Twitter, or LinkedIn. We’d love to learn more about what works for you.

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