Interviews with CEOs: The Top 6 Recruiting Tips for Companies Hiring Remote Workers

As an entrepreneur I can acknowledge that recruiting the right team is challenging. Yet, anyone can tell you, it’s one of the most critical factors in determining the future success of your business.

Your business is only as good as the people you employ.

Which means recruiting is a necessary task that should be based on thoughtful processes, personal time investments and the right resources.

I spoke with a number of successful CEOs who run nearly 100% remote teams, I’ve learned some of their most interesting and actionable tips that other employers, whether fulfilling distributed teams or not, can benefit from.

Below are the 6 most thoughtful tips I’ve learned about recruiting a remote team.

1. Search for Flexibility, Test for Resourcefulness and Consider Paying Weekly to Start

Isaac Kohen of Teramind manages a talented group of highly skilled, distributed workers. As the founder and CFO of an employee monitoring, and insider threat prevention platform, his focus is to hire candidates who are more than just skilled programmers, but also practical, resourceful problem solvers.

Because the qualifications he seeks are highly specific, he’s developed a recruiting funnel. His funnel starts with a Google form that asks for the candidates technical qualifications and salary expectations. This lends to a first interview via video chat, at which time he conducts a face-to-face speed test to test for the candidates resourcefulness and practical knowledge.

“As far as programming goes, there are some people who excel in languages skills and have mediocre problem solving skills, which is not less important than knowing transaction theory” Notes Kohen.

They’re initially paid on a weekly basis and then graduate to a monthly to ensure the partnership is optimal for both parties, and that lower risk for everyone.

2. All Things Being Equal, Hire for Fit Rather Than Skill and Run a Hiring “Trial Period”

Almost two decades into entrepreneurship, Mark Faggiano of 100% remote TaxJar is able to share his personal insight into his best practices for recruiting a remote team.

Having started more than 6 businesses, he’s learned from personal trial and error what types of candidates and particular characteristics that will likely lead to success in their work environment.

Faggiano’s strategy is quite formulaic in that he’s developed specific steps of the interview process that test partially for skill and partially for cultural fit.

Though the process with the hiring manager is primarily skills testing, he says, they’re looking as much for fit (the ability to do great work in a 100% remote environment) as dexterity, adding “we’ll take fit over skill all day long.”

That being said, once a candidate is chosen, they go through what Faggiano calls a “Mutual Trial.” This period, between 30–90 days allows both the candidate and the employer to determine whether or not they’re actually right for each other.

Faggiano understands that although the candidate might have done well in the interview, they still need to know if they can really do the work. “Can you walk the walk? Can you excel in the environment? How do you treat people? Are you someone that can deliver and work at the pace that we work at?”

Furthermore, this period allows for the candidate to determine if the role was everything he thought it would be. If they like the team and the problem they’re trying to solve, and if they’re “excited to get out of bed in the morning.”

At my current companies, we use Remo our online workspace (emphases on audio/video communication vs. text) to conduct 7-14 day trials, where they work in our workspace. We have a lot of transparency of what they are doing and how they communicate to get a better feel for who they are and how they work.

3. Develop a Test to Filter Out Candidates Who Otherwise Wouldn’t Put in the Work

As the second employee, and Vice President of Operations at Customer Bloom, Chase Buckner has had plenty of experience in hiring. His company, a full service digital marketing agency has worked to streamline the process of reputation management, SEO, UX/UI and even social media.

Since their employees are chosen based on talent rather than location, the biggest challenge has been identifying who the best candidates are and spending the least amount of time funneling through applicants who don’t fit their criteria.

Through his experience, Buckner found that devising a test for potential applicants has yielded the best results. An example he gave to me that his firm successfully implemented, “film a screen recording of you building an ad set for this product and walk me through the targeting that you setup.” I implemented this technique as well asking the candidate to record a screen share with Loom, walking through how they used data to choose a new anchor blog post for our blog, what research they read, and what their process in writing it. I found it very effective to test logic, communication, and creativity.

Though he notes many candidates won’t take the time to make the video, he’s also been able to effectively filter the go-getters from those who wouldn’t be as effective with their autonomy.

4. Have an Honest and Open Conversation About How They Feel About Isolation

True to the values of the open-source community, Addison Berry talked to me about having a transparent conversation about the concerns and challenges of a distributed environment.

Berry is the CEO of Lullabot Education, an educational platform for individuals who want to learn Drupal (an open source CMS). Though Drupal developers themselves tend to be familiar with the online space, other impactful roles surrounding the industry are less so.

Rather than searching for people who have experience in a remote environment, Berry prefers to prompt conversations about how candidates will overcome the adversity of a lack of social interaction.

Questions like, “how social are you at the office now?” and “Are you looking for a space to have a quiet escape, or do you love the social momentum?”

Delving further, she asks each candidate how they’ll be able to satisfy those needs without an office full of people to socialize with. She notes that although sociable employees can thrive in a remote working environment, they need to be aware and consider the actions they’ll need to take to satisfy their fill of human interaction.

5. Forget Resume’s and Focus More On Test Based Hiring

Head of Marketing, Dunja Lazic understands the importance of quality hires when it comes to remote working. Her company Sked Social, a leading tool for scheduling and planning on instagram, has remote workers in 5 continents.

In order to hire quality candidates, without extensive time commitment, Schedugram relies on Hundred5 for candidate screening, and then concentrates primarily on test based hiring to asses the candidates aptitude for the role.

“I strongly believe resumes are outdated and hardly a representation of skills and culture fit which is why I rely on testing.” Says Lazic, “It’s also important to interview people with a few members of your team just to see how they fit in”

Ensuring that ultimately the potential employee is the right fit for their new environment and that it’s a collaborative decision allows Schedugram to create a better remote working culture and more collaborative and communicative digital workplace.

6. Find Out If They’ve Worked Remote, and Try Hiring a Contract Project First

The tricky part about getting into remote work is the self-discovery of your social needs. Michal Watson, both COO & CFO of Treehouse explains that he works to identify if a candidate can be successful in the role, by learning whether or not they’ve worked remote and what capacity they have to be successful if it’s their first time.

Watson, who’s had quite a bit of experience with distributed work explains how Treehouse, the affordable technology education website, has had remote hiring in it’s DNA since the day founder Ryan Carson (based in the UK) hired his first two employees in Florida.

He told me that often times a best practice is screening and confirming that even when someone looks great on paper you get to know their working style. Noting that some people need an office environment to succeed.

“There’s a lot of humans who need to have regular social interactions. And there have been people on teams who’ve left and said ‘You know, I just need to work in an office again, staying at home isn’t for me’”

Asking thorough questions surrounding their experience and capacity to succeed in distributed working, you can avoid the lost time and resources in the future.


Overall, the methods and specific tools each company use may vary, the consensus is along the same lines:

  1. Do not solely rely on resumes or interviews, they are not a strong indicator of performance
  2. Take the recruitment one step at a time, from a small test, to a paid test week, to a 1 month trial

Are you looking for hiring process templates or example tests?

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