freelancer interview questions


When you write up freelancer interview questions, you shouldn’t feel like you’re just rolling the dice. Hiring freelancers might seem just like a risky game of chance most of the time, but it doesn’t have to be that way.

How do you come up with freelancer interview questions that can accurately determine a potential freelancer’s skillset, attitude, and communication style while still keeping the interview from dragging on forever?

FreeeUp founders Nate Hirsch and Connor Gillivan recently sat down in a live chat to discuss the best freelancer interview questions. We’ve summarized their thoughts here, based on years of experience hiring freelancers for their businesses. With their sound advice, you can start interviewing with purpose to hire with confidence.

Before You Begin

freelancer interview questions

Make sure you know what you want to hear in response to your questions. For instance:

  • What weekly hours are you asking for?
  • Do you want the freelancer to work on specific days or certain times of the day?
  • What kind of work ethic does your company demand?
  • What are your expected turnaround times?

If you know the answers you want, then you’ll be able to easily recognize them in the interview. It also makes it easier to spot any red flags.

So without further ado, here are the 12 freelancer interview questions that you should never forget to ask a potential hire:

1. What kind of outside commitments do you have?

freelancer interview questions

According to Nate and Connor, this is the first question you should ask any shortlisted candidate. It’s the best way to determine a freelancer’s current availability, since it goes beyond work commitments alone.

You need to not only determine how much time a freelancer is spending on other clients, but also whether they have other responsibilities such as school or childcare, as well as hobbies or other activities that take up their time.

It doesn’t matter if a freelancer is perfectly qualified in every other way. If they cannot be available when you need them, it’s better to move on immediately. It is even suggested that you simply skip the rest of the interview if you don’t find a good fit here.

2. How do you see this position long term?

This question will help you determine whether the freelancer is interested in making a lengthy commitment. This is important because it affects your turnover rate, which affects overall productivity and expenses.

Is contract work just a means to an end for the candidate, or are they passionate about growing their own business? How likely are they to stick with you for a year? For five?

This is something that most people may not be entirely honest about, but it’s still worth asking. If you craft your questions carefully, you can glean more from their answer in combination with how they responded to the first question.

3. What time zone are you working in?

freelancer interview questions

This is an easily skipped question, but it’s important to talk to freelancers about it. If they live overseas, it’s absolutely essential.

Nate and Connor recommend asking it multiple times, and even setting a calendar date during the interview for a future meeting. This is to make sure that the differing time zones are clearly understood and accurately reflect what the freelancer expects and is willing to make adjustments for.

Hiring a freelancer from overseas can mean a dramatic discount on cost, but their time zone might prove a detriment. If you need them from 9AM to 5PM in the western hemisphere, triple check that they understand what time this equates to in their part of the world.

You need to make sure they can sign on for what might mean odd hours or all-night work. Have they ever worked overnight before? What were their experiences? All of this information should factor into your final decision.

4. How did you get into this type of work?

freelancer interview questions

This question helps reveal things about the freelancer’s natural talents and passions as well as their attitude and work ethic, among other important freelancer characteristics.

Often, when you hear their story, you can determine their primary motivation for entering a specific field of work. Are they a software engineer because that’s what their parents wanted them to study? Or did they get into advertising because they took a class in college and realized how much they loved it?

You really want to find someone who loves what they do. It will mean a lot more positive energy infused into each task and result in much better work.

5. What is your experience in this position?

Asking about general work experience is far less important than asking what experience they have in the specific position you are looking for.

Connor cautions against hiring someone who is spread too thin, experience wise. It’s better to find someone who is great at the one or two things you need and who can specialize in those things, rather than someone who has tried a little bit of everything but doesn’t have true expertise in any area.

The next two freelancer interview questions make great follow-ups to this point. They will allow you to better see the freelancer’s true colors in case they have not been honest about their experience.

6. Rate your skills in these areas from 1-10 and explain your ratings.

freelancer interview questions

This question has two primary benefits. First, it’s a great way to hone in on experience. A specific rating, and a reason why, forces the freelancer to explain more as they justify their score. They will have to think harder and base their responses on real examples from their work history.

Second, this question is a good way to catch some red flags. For example, if a freelancer rates each skill as a 10, but only has a few months of experience in each category, then they may have an inflated ego that indicates that they will be difficult to work with. If a freelancer gives a low score in a category they’ve worked in forever, this tends to mean that they either struggle to pick up new things or are timid, which likely also means they lack initiative.

Basically, look for any discrepancies between scores and actual amount of experience. If something doesn’t sound right, ask them to expound on their answers.

7. What would you do in this situation?

Giving someone a specific scenario is another great way of truly determining their level of experience.

For example, if you’re hiring a content writer who specializes in Amazon, you could show them a product page and ask what steps they would take to boost sales for that product. The specialist should be able to quickly and easily pinpoint problems with the page and give you at least some basic ideas for how to improve them. By the same token, you could have a salesperson review a pitch, or ask a designer how they might improve your website home page.

Creating a specific scenario means circumventing pre-rehearsed answers. You will be able to see how the freelancer thinks about an actual problem, and how familiar they are with the necessary tools and processes to solve it.

8. What is your biggest strength for this role?

freelancer interview questions

As mentioned above, you should be targeting the one or two skills that you most need the freelancer to have. Asking about their strengths is a great way to make sure that their skills align with your most important needs. It’s also a great way to verify that their ratings and experience tie in nicely together.

This freelancer interview question is also a nice way to set standards for their future work with you. As you near the end of the interview, it is a natural shift from past work towards this new role.

For example, if a freelancer mentions that they are very hardworking and will produce a ton of work in a short amount of time, you can hold them to it. You can take their original responses as promises they made you and being able to cite them is an excellent way to provide motivation. It’s also a completely fair reason to let them go, if they are not meeting the expectations that they themselves set up.

9. How much would you like to be paid for this work?

freelancer interview questions

When asking freelancer interview questions, many business owners tend to either ask this question upfront or leave it until the very end. We believe the perfect time to bring up price is right after you talk about experience. This provides grounding to the conversation.

Before you interview, always research the fair market rate for someone in the same field of work and location with the same level of experience you are looking for. That will help you be prepared to negotiate. Don’t offer more than the freelancer is worth based on their experience, but don’t lowball them either.

Lowballing freelancers is an especially dangerous game. It shows the person that you do not value them. This can immediately hurt whatever motivation they have to work with you. They will also tend to have less loyalty and commitment to you if they do decide to stick with it, which means that they will not hesitate to terminate your agreement if someone offers them what they’re worth.

10. How do you communicate?

freelancer interview questions

Get ultra-specific with this question. Do they usually communicate with clients by calling them on the phone? Do they prefer to text or Skype? Is email the most convenient means of communicating for them? Or do they use social media channels or CRMs to ask questions and give updates?

If none of the channels they are accustomed to using work well for you, make sure to ask them if they are comfortable with your preferred methods of communication. Even if the rest of the freelancer interview questions yielded impressive results, this candidate may not be a good fit if you foresee a problem with communication down the line.

11. When can you get started?

This is one of the most easily missed freelancer interview questions although it should never be set aside. Unlike most full-time job-seekers, freelancers aren’t always available to start right away, particularly if you’re hiring for more than 20 hours a week.

The best freelancers will often have current clients and previous commitments that aren’t quite complete yet. In an ideal world, they would have checked your ticked details, but in case they missed it or your needs have changed, you need to confirm this with them.

If the freelancer can’t get started right away, decide whether it’s worth it to wait. Don’t pressure them into starting early. They likely have a lot on their plate already, which means the work they deliver will be rushed and not up to standard.

In the same vein, for longer-term work, ask them if they have any big vacations coming up in the next few months. You need to know immediately about anything that is going to affect the amount of work they can deliver from day to day or week to week.

12. What questions do you have for me?

freelancer interview questions

If the freelancer has a genuine interest in working with you, then they will likely have questions about you and your business. They will want to know specifics about the arrangement, just like you do. This portion of the interview gives them an opportunity to clarify things that you may not have thought about.

Giving them the stage also sets a good tone for the end of the interview. It shows them that the relationship is give and take, and not dictatorial in nature. Freelancers are business owners like you, not yes-men who are only good for doing what they’re told. You want to be able to take advantage of their experience and passion, and giving them some power is how this happens.

If a freelancer doesn’t have anything specific in mind at the time of the interview, go ahead and share information about your business. Let them know about the culture, goals, management style – anything that’s important to establishing and growing a good working relationship.

Then you can end the interview on a positive note, letting the freelancer know when you’ll make your final decision if you haven’t decided to hire them on the spot.

Final Thoughts

Sometimes, a freelancer might realize on their own at some point during the interview that they are not a good fit, and let you know. This is actually a good thing since it goes a long way towards saving everyone’s time. If that happens, ask them their reasons. Then thank them for their time and honesty and move on to the next candidate armed with this additional information.

Always be ready to ask “why?” and “can you expand on that?” When you dig deeper into one point, it’s harder and harder for the freelancer to give rote, ready-to-please answers. You are ideally looking for the best fit, and you need more specific responses to determine who that is.

With this new set of freelancer interview questions in your arsenal, you should be well on your way to hiring the best fits for your needs. If you’d like to learn more about optimal hiring, be sure to check out our book, Free Up Your Business, which discusses these concepts at length.

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