Matthew Ramirez September 22nd, 2022

Best Practices When Interviewing Freelancers

Regardless of your company’s size, hiring freelancers is often a great choice because they are more flexible and can work on projects both large and small. To work effectively with freelancers, you need to know how to properly vet the ones you've chosen to interview. Doing the right prep work and asking the right questions during the interview process will ensure that you are hiring the freelancer that best fits your needs. 

Review their portfolio beforehand

Be sure to look over their portfolio before the interview. Not all clients post their work publicly, and you might have to dig a little bit to get a good idea of what they are capable of. You don’t want to lead the interview with vague, uninformed questions. 

Send an overview of the work involved before the interview

Before interviewing a freelancer, make sure the job description is clear and detailed. By having a clear job description, you can ensure that the freelancer is a good fit for the job and you can avoid any misunderstandings about the work that will be done. This also gives them an opportunity to voice any concerns or back out before you commit to spending time on a call or in person with them.

Make plenty of time for the interview

Another tip is to make sure that there is plenty of time for the interview. An interview should allow both the freelancer and the hiring company enough time to ask questions and get to know each other. You also want to account for possible technical snafus, such as spotty wifi, troublesome video and voice call software, and computer audio issues.

See if they can connect their portfolio to the work you need done

When interviewing a freelancer, ask to see some of their past work. One of the best ways to gauge the quality of a freelancer is to look at the work they’ve done in the past from their perspective. If possible, ask to see work that is similar to what you’d like them to do for you. This also helps test their understanding of what the job will entail. If they have no relevant experience, they may not be the best fit for you. 

Understand how they work

When interviewing a freelance worker, it is important to ask them how they work. This can include questions such as how many hours a day or a week they work and what their process is. Ask them to walk you through their typical day or task if they're already familiar with your industry. If they’re not yet familiar with your industry, ask them how they plan to get up to speed. Ask them what tools they plan to use and whether they’ll be working remotely or in person. And finally, be sure to ask how they’ll stay up to date in your industry and how they’ll ensure that they’re delivering the best quality work. By asking these questions, it can help give insight into whether or not the freelancer is a good fit for the company. 

Give a small task in the interview

When you interview a freelancer, you want to be sure they are competent in the skills they claim to possess. To test this, provide a small task that the freelancer must complete. This could be as simple as having them write a short paragraph, or it could be something more advanced, such as designing a website mockup. By having the freelancer complete a small task during the interview, you can test their skills and ensure that the person you hire is capable of performing the duties required of them. 

Ask about any negative reviews

As a small business owner, you want to hire the best talent possible and that’s exactly what you should do. If any of the freelancer’s previous clients left a negative review, try to find out what happened there. When you ask, does the freelancer blame the client entirely, or are they fair in their response? Have they learned from what happened? This is your opportunity to assess how the freelancer handles criticism and conflict; it also tells you a lot about their level of professionalism.

Make sure they can write

A good test of a freelancer’s writing and ability to communicate clearly is to have them write a short piece for you. You can ask them to write anything they think will help you determine whether they are a good fit for your business needs, or you can direct them to write a specific piece, such as a short blog post, email newsletter, or press release. When you receive their work, you can evaluate it for grammar, punctuation, and whether it is easy to understand. You can also assess whether their writing style matches your company’s tone and voice. 

Even if you are hiring for a technical role, if the freelancer can’t write at least adequately or paraphrase so their peers can understand them, you may experience communication issues down the road.

Ask for references

When hiring a freelancer, it is important to ask for past references. If a freelancer is serious about their business, they should be able to provide you with a few people that can refer them and why they’ve chosen those references. If they are unable to do so, this could be a red flag. You want to ensure that the freelancer is professional and has a good reputation in the industry. By asking for references, you can put your mind at ease and know that you are choosing a reputable professional. 

Assess how they will fit with your company culture

One best practice when interviewing freelancers is to make sure they are a good fit for your company’s culture. Getting to know the candidate’s work ethic, attitude, and communication skills is important, but so is finding out if they will mesh with the rest of your team. It’s also worth noting that since freelancers work remotely, their availability and responsiveness will play a bigger role in whether or not they are a good fit for your company than if you were hiring an in-house employee. 

Get ahead of workflow problems

One of the most common problems that can emerge in working with a freelancer is either you blocking their work or them blocking your work. To prevent such problems, ask your potential freelancer to describe their ideal workflow and make sure that your workflow is close to theirs. It is also advisable to set up a working schedule and make sure that both parties stick to it. Finally, make sure that your communication style is similar to or can accommodate your potential freelancer’s communication style. If you do not have much experience in hiring and working with freelancers, you should work with only a few tools, such as Slack and Trello, to ensure freelancer communication and task management respectively.

Matthew Ramirez

Matthew Ramirez is a serial entrepreneur and investor. He grew and sold his first company, WriteLab, to Chegg (NYSE: CHGG) in 2018, where he worked for three years as Director of Product. He is now the founder of Paraphrase Tool, which helps authors create compelling and varied content for their audiences.

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