How to Hire the Right Remote Worker for Your Needs


You’ve made the decision to seek a remote freelancer to help your business. Now, you need to find the right remote freelancer. But how do you know which candidate(s) will best suit your company’s needs?

Read on for some questions to ask yourself before getting started in your hunt for great talent. These questions can help you define what you’re looking for in the right remote freelancer for you, and ultimately help you narrow your search before you even begin, saving you time and money.

Are you looking for someone to work independently with minimal input on projects, or someone to work with on projects who can take direction regularly?

Determining the type of work a remote hire will be doing can make a significant difference in the type of candidate you seek. Just like in-house hires in a typical office setting, the right remote freelancer is best suited to different management styles based on their experience, aptitudes and working styles. For example, an entry-level in a traditional office will likely receive more guidance from management on how the company produces materials or communicates with customers, while someone who’s been with the company for some time won’t need this same attention.

This same principle applies to remote hires. If you’re searching for someone who fits the first criteria mentioned above (an independent self-starter), you might consider a freelancer with more experience.

The right remote freelancer is more experienced and won’t need as much supervision or guidance if the project is similar to others in their portfolio. They will be able to produce quality work without as much direction since they’ve been through the process before. Their experience will also allow them to complete the required work with minimal supervision. Supply them with the information they need to get started and they’ll be able to get to work on their own.

If you’re looking for someone who fits the second criteria mentioned above (more of an assistant to work with you hand-in-hand), the right remote freelancer will be someone who is prepared to work together closely on all aspects of a project. Since you will be working with them on a regular basis, you can provide the direction they need to produce the results you desire, so they might not need as much as experience as someone who could work independently.

Will you need someone to work during a specific time every day, or will the work allow for flexibility in completion?

This is an important question to consider and can lead you to certain candidates while steering you away from others. For example, if you’re looking for someone to work during certain hours each day, then you can narrow the candidates to only those available during those times. If you need someone during your own typical working hours, keep in mind time zones and whether a remote hire is international or domestic. If you work from 9am-5pm Eastern Standard Time, then be sure to advertise that information when soliciting candidates so they can adjust accordingly.

If you expect the hire to work with you during the day, then the right remote freelancer might not be one who is overseas. That would require them to work odd hours during their days or nights. However, if they’re available and willing, be sure to outline the expectations regarding working hours so there’s no confusion later.

Keep in mind that wanting a freelancer to work specific hours might rule out candidates who have other obligations throughout the day such as other work, parenting, or caring for elderly relatives. For example, many remote freelancers are stay-at-home parents who put in hours while children are in school and then finish when they’re asleep for the night.

If the hours you offer will be flexible, you can consider a wider range of candidates. Sticking with the example of stay-at-home parents, there is a significant percentage of highly qualified women who exit the workplace or take a break for a period of time once they have children—women who could contribute their time and talents from home as freelancers.

Flexible working hours also further opens up the candidate pool to international remote freelancers who can get work done during the evening and nighttime hours. This can be helpful if the work is building upon what you’ve done during the day—essentially keeping your business running around the clock.

Will your projects be time sensitive and need immediate attention, or will there be a longer turnaround time?

In addition to considering the time requirements, you need to consider the time sensitivity of the work you need completed. There are several factors to consider when picking a candidate whose work will be time sensitive. When there are time constraints, the right remote freelancer will complete the tasks quickly and reliably.

You might consider asking in depth questions about their work environment, such as the reliability of their internet service provider, etc. If they rely on the local coffee shop’s internet which is spotty, they aren’t going to be the best choice for your projects with a deadline.

You will also need to consider a candidate’s availability. Do you need a remote hire to dedicate a set number of hours to your work to ensure that deadlines are met? Outline your expectations in the beginning to ensure both you and the freelancer are on the same page. This will help eliminate any surprises once you make a hire and begin working with the right remote freelancer for your projects.

In addition, you can also ask questions about a candidate’s experience in other fast-paced work environments to gauge how they respond in those work situations. When on a deadline, you need a candidate who can work under pressure. To gather an accurate impression of their capabilities, try to avoid asking leading questions. Ask probing questions instead to see how they’ve reacted to time sensitive projects in the past.

An interview might take longer when you ask probing questions, but you’ll get a better idea of the candidate’s experience. For example, you might ask, “When was the last time you missed a deadline?” Then follow up with other questions like, “What happened?” or “What did you do after missing the deadline?” The answers will tell you when they last failed to complete a project on time as well as how they dealt with the situation afterward. This information can help you understand their ability to work under pressure (and give insight into their problem-solving abilities).

If your projects aren’t time sensitive, you might be able to negotiate a better wage due to the flexibility. You may also be able to select a candidate who is less experienced (and less expensive) who might need more time to complete given tasks. Longer turnaround times can also open your projects to more qualified candidates who are in-demand and have other commitments that limit their availability.

Are you looking for someone to interact with customers and clients, or will their interaction be solely with you or one of your managers?

Aside from time commitments and requirements, consider the level of interaction a freelancer will have within the business. Will they interact with your customers? If yes, then be sure to screen freelancers for additional qualifications. When picking a remote hire that will be interacting with your customers and clientele, you will need to consider their communication and customer service skills.

Do they speak English fluently? Are their communications via email clear and easy to understand? These are some questions you’ll need to answer as you consider who would be best as a point of contact with the customers that make up your business’ clientele. Thankfully, some of that legwork is done for you when working with certain third party freelancer suppliers—candidate vetting has already been completed.

You can also determine much of a candidate’s communication skills through your own interactions with them. During a phone call or video interview, you can determine whether they can verbally communicate effectively. During your conversations, are they easy to talk to? Are they courteous and informative? Would you want to deal with them on a customer service issue? The answers to these questions can help you select someone who can best represent your company.

For written communications, you can request further information or writing samples via email to measure the effectiveness of their writing.

To evaluate a candidate’s customer service skills, you can ask about their previous customer service roles, gather insight from their references, or even give them mock situations to see how they respond. This information can help you form an idea of how they will react when faced with similar situations with your own customers.

When asking about their previous customer service experience, use probing questions again to correctly access their skills. You might say, “Tell me about a challenging/dissatisfied/upset customer you had to interact with.” Then follow up with questions like, “What was the problem?” and “What did you do or say that worked or didn’t work in resolving the issue?” Answers to these questions can guide you to someone who best fits your customer service goals.

If a freelancer won’t be interacting with customers, then you can focus more on other qualifications that suit them to the position you’re trying to fill.


Before you start searching for the right remote freelancer, clearly define what type of candidate you’re looking for to fill the position. Try to be as detailed as possible. Make a list of key qualifications as well as the requirements of the tasks, such as availability and time input required. This will help you assemble the best pool of candidates to choose from. Then sign up with FreeeUp and submit a freelancer request to meet suitable candidates and make the hire.


Rachel Stones


Rachel writes business and human resources articles for Built for Teams, an innovative HR software package that allows businesses to track PTO, manage employee vacation requests and more, created by Objective AWS Consultants. Rachel also enjoys spending time with her family and curling up with a good book during her free time.  


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