How to Interview Remote Workers and Freelancers

Do you look forward to the hiring process? If not, we don't blame you. There is much pressure to ensure you have a process that allows you to find the right person. As a result, it can be downright tough. However, what if another element was thrown into the mix? What if you had to conduct the interview process without a physical face-to-face interview?

Today, more and more hiring managers, CEOs, and HR professionals are having to deal with the reality that many of today's positions can be done remotely. Consequently, the hiring process itself also needs to be done primarily online and with the help of digital tools. How does this change the process of hiring, and what considerations do you have to make?

Here are what hiring managers, CEOs, and remote managers who hire remotely likely have to manage to find the right candidate:

• Finding and using the best technology necessary for video interviews.
• Having the ability to still pick up on critical verbal and physical cues.
• Managing time zone constraints and ensuring candidates are in places where day-to-day business can still be conducted.

These are just a few of the emerging considerations professionals are having to make when it comes to the hiring and interview process. Throw in the occasional technical malfunction, and you have what could be a recipe for disaster.

However, the world of remote work is here to stay. Consequently, the hiring process is going to have to continue to evolve with it. Don't think so? Check out these stats:

• Seventy percent of people globally working remotely at least once a week.
• Also, 73 percent of teams are projected to be remote in 2028.

If you and your organization have been hoping to avoid preparing for a remote hiring process, these numbers show that interacting with remote work is inevitable.

At the same time, part-time and full-time freelancing is also on the rise as companies understand they can benefit from non-traditional hiring arrangements.

So, why else is it important to learn the skill of effectively interviewing remote workers and freelancers? Take a look:

• More and more work candidates are expecting remote work as a perk, and are willing to find companies who offer it.
• The gig economy is growing, and more professionals are taking on freelancing side hustles to supplement income or start a full-fledged freelance business.

Kati, a co-founder of a startup, emphasizes the role side hustles and the gig economy as a whole have played in her career:

I was frustrated and wanted to make more money, so I created my own niche. Since then, I have always had a remote side hustle. Eventually, I was able to work remotely at least part of the time in my corporate jobs. Recently, I left the corporate world to pursue my own adventures remotely.

• Companies are figuring out that they can save money and time by hiring a part-time or full-time freelancer.
• Forward-thinking and innovative companies do not want to limit their talent pool by geography.
• If hiring professionals strategically plan for time zones, their companies can have remote teams working on projects throughout the day regardless of their location.

The future of work is now, and the sooner you begin to prepare to conduct an interview and hiring process without a physical in-person interview, the farther along you and your company will be to finding exceptional remote workers and freelancers. In the next section, we will offer practical and useful tips on how to interview remote workers and freelancers.

How to Interview Remote Workers and Freelancers

It may seem daunting to think about hiring someone an ocean or state away, and only interacting with them through video. However, there are some impactful ways to ensure you have the best strategy for finding exceptional talent. Take a look at these tips that you can begin to implement the next time you interview remote workers and freelancers.

Use Video Conferencing Software

Phone calls are great, but video can tell you more about physical cues and can give you better insight into what others are saying. Using video conferencing software during the interview process also allows you to see their aptitude for using this type of tool. You are likely going to want to have a variety of standup meetings, brainstorming sessions, and employee review meetings. So, the interview can also give you insight into whether they are prepared to handle most communications over video.

Find Common Ground

From ensuring the technology is working to the general stress associated with interviewing for a job, it is no secret that anxiety is heavily related to this process. Nevertheless, while stress is inevitable, there are some things you can do to ease the tension. Find a way to create common ground. Asking about the school they went to, or commenting on a hobby they are in can deflate the anxiousness and allow you both to be at ease during the situation. Ultimately, you want their best, and finding some common ground can help you both to calm down.

Ask About Previous Location Independent Experience

While you may not mind working with someone who does not have remote work experience, it is good to know this information ahead of time. For example, you would have to prepare for them to navigate a significant learning curve. They may not be aware of the importance of written communication or how to use specific technology tools. Whatever the situation is, you need to gauge their remote work and freelance aptitude to see if they can adjust to a location-independent situation. The last thing you want to do is to hire someone without remote work experience as an experiment.

Hrishikesh, CEO of Remote Tools and Flexiple, describes what he looks for when hiring a remote worker:

The challenges are multifold. It begins with hiring the right set of people who can comprehend extensive documentation and communicate (in written form) effectively in a remote setting. Once you have them on board, it is critical to have the right alignment from the beginning.

Inquire About Where They Would Work

Where they are planning to work can help you understand how much equipment they may need, and how much you may need to subsidize their tools. If they are planning to work from coffee shops or coworking spaces, then the tools they need will be drastically different when compared to if they had a home office. Knowing this will also allow you to see the things they need to excel as a remote worker. You may even want to make a few suggestions regarding where they work based on how often they may be required to join meetings, or if they will be participating in frequent real-time collaboration with teammates.

Study Their Resume And Ask Tailored Questions From It

While you should have general questions to ask every candidate, you will get to the heart of what they bring to your team by studying their resume. Look at their experience, decide on the information that is the most relevant to the position you are hiring for, and create questions that allow you to dig deeper into how these skills can benefit your company.

As an example, let's say that candidate A has managed a remote team and helped them complete a project under budget. Asking about the tactics they used to get their team to the finishing line may be a great approach in this situation. So, don't just gloss over someone's list of work experience, take out the details that are best suited for your needs, and ask about them.

Ask Pointed Questions About Their Portfolio

This one is very similar to the previous entry. However, you are now asking about the actual work they have completed. Again, look at their projects, see what is of interest, and then create questions that enable them to elaborate on their thought process. A portfolio also allows you to ask about the deliverable's purpose and the goals it met. Use this in combination with the resume to ask for details about the skill sets they bring to the position.

Ask Scenario-Based Questions

Every position brings with it specific scenarios that the potential candidate would experience. While every response or reaction cannot be predicted, you do want to get a feel for how they would handle the given situation. This is where questions regarding common scenarios that they may face in their role or during the project can help you decide if this person is the right fit.

This question requires detailed knowledge about the profession. Ensure you know what this employee would do daily and the types of situations they encounter. From there, you can create complete and informative scenario-based questions. You may even want to sit down with the current employees (who may be leaving the position) or someone who does this job (if this is the first time you are hiring for this position) to get a sense of what they would encounter.

Inquire About Their Ideal Work Environment

What drives this candidate? What do they look for in a work environment? Find out what helps them to be productive. Is it allowing them to work uninterrupted for a set period? Alternatively, is it the ability to work in the evenings instead of the day time? Find out how best they like to work, and how you can help to facilitate that (or if you even can).

For example, if you have an individual who does better working at night, but the position requires a professional to work during regular business hours, this arrangement is not going to be the best fit. Asking questions related to this topic allows you to clear up any miscommunications and discuss work-life expectations.

Include Information About Expectations

The previous entry leads into one of the most important topics you will discuss during the interview: expectations. What time do they need to be available for real-time communication? What is the timeline for a project to be completed? What tools should they use to interact with team members? Know what your expectations are, and communicate those during the interview.

Ask how the employee would handle these needs, and if they are even able to fulfill them. This question ensures that the candidate knows what they can expect if they accept the position or project. Also, with this job being handled remotely, discussing expectations is more critical than ever as this person cannot run to your office or HR to immediately clarify remote work policies. So, do all you can to inform them upfront.

Layout All The Tech

No remote work or freelance position can happen without the necessary tech tools. As a result, it is crucial that you are clear about the technology tools they need to be familiar with. If it is a situation—likely with a freelancer—where you do not have any tool preferences, discuss the apps and programs they plan to use anyway.

See if they are compatible with what you use and if you and your team understand how to use them. Different tools accomplish different things, depending on their function. So, be sure to be clear about what your expectations are regarding your remote or freelance tool stack.

Nathan and Connor, owners of Freeeup discuss how vital digital tools are to their remote work arrangements, and the staff they hire:

Skype chat can be the equivalent of stopping by someone's desk. Just have everyone on your team on Skype when they're working. Then that check-in is simple as a chat. Schedule weekly meetings where you meet with the entire team and then smaller groups of people. Do it in a Skype group chat or using a tool like Zoom.

Be Specific About Remote Work Arrangements

Remote work and freelancing come with much flexibility. However, you want to know how flexible they are looking to be. For example, are they going to travel as a digital nomad, or only be available during certain times of the day? You need to ensure that whatever their preference is that you can accommodate it.

If you require that your employees meet once every quarter for a strategy retreat and the candidate is a digital nomad that may be unable to make those meetings, then the person may not be the best fit. So, be sure to specifically ask where the person will be located while they work and what their remote work arrangement preferences are.

Additional Interview Tips

The tips above will give you a great start on how to conduct the actual interview. Below are some additional tips that can help you decide who the right candidate is.

• Record the interview – If you want to be able to compare interview answers between candidates later on, or show the conversation to relevant colleagues, then see about recording the interview. However, be sure to ask permission before filming and inform them of what you would be using the video for.

• Ask about why they decided to go remote – This question can help you determine if they are going remote or freelancing for reasons that align with why you offer location-independent positions. So, ask about why they wanted to get away from the traditional office. Knowing their motivations can help you see if this person will use this perk for the right reasons.

• Be transparent – Are there standup meetings every morning at 7 AM? Is there some weekend work involved? Be clear and open about all the less-than-favorable parts about the job so the candidate can make the best decision if you select them.

• Ask industry-specific questions – It helps to see how well-versed they are on industry trends. Whether it's related to SEO, human resources, software developers, the state of remote work, or general small business matters, be sure that the remote worker or freelancer knows the industry.

• Consider a paid project – Test their skills and see if they are the right fit by taking them on for a probationary period and having them complete a paid project. You get to see how they would fit into your company culture, and if their work is what your business needs.

• Focus on finding the right talent sources – Can you improve your talent funnels? Try to look out for the best talent sources in your industry. Gino, an entrepreneur, reveals how critical sourcing has been to find the best candidates:

Many recruiting managers overlook the importance of sourcing. They think it's a numbers game. I think the more effort you put into this stage, the more fruitful the rest of the recruiting process will be. If in the sourcing stage, you are putting low-quality candidates into the flow, the interviews themselves aren't going to do much to make them better candidates. A lot of recruiting companies and hiring teams place low-level team members on the sourcing side. That makes no sense to me.

Interviewing Remote Workers and Freelancers Doesn't Have to be Stressful

Hiring is never easy, but with the right questions and hiring structure, you can find the right fit. The key is to have goals for your recruitment and interview process and stick with them. Take time to know what you are looking for, whether it be regarding past experience or specific skill sets.

Once you have an idea of the ideal candidate, you can then create questions that help you find out who this person is. In addition to his, be as transparent as possible about your expectations for those working remotely. Also, be sure to share all remote work policies with them.

For some helpful insight into how other remote workers and freelancers handle hiring remote employees, check out our Interview page. We have interviewed a variety of CEOs and entrepreneurs who have shared their challenges in hiring and managing remote teams.

Lastly, if you are a remote team leader or CEO, and you are looking for capable candidates, we want to help! Feel free to contact us @remotehabits to send us your remote job posts, and we can get them up onto our RemoteHabits job page.

We wish you the best in your search for the best remote work candidate or freelancer.

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