12 Must Ask Freelancer Interview Questions

Feb 27, 2019

Guest Blog from Nathan Hirsch (freeeup.com), written by Emily Bell


12 Must Ask Freelancer Interview Questions

12 Must Ask Freelancer Interview Questions

When you write up freelancer interview questions, you shouldn’t feel like you are rolling dice. It might seem just like that most of the time, though. How do you come up with questions that can accurately determine a potential worker’s skillset, attitude, and communication style, and still keep the interview from dragging on forever?

At FreeeUp, we’re here to help. Our 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, so you can start hiring with confidence.

Freelancer Interview Questions

Tip: Make sure you know the answers you want to hear. What hours are you asking for? What kind of work ethic does your company demand? If you know the answers you want, then you’ll be ready to recognize them in the interview, as well as any red flags.

1. What kind of outside commitments do you have?

According to Nate and Connor, this is the first question you should ask. It’s the best way to determine a worker’s current availability, since it goes beyond just work commitments. You need to not only determine how much time they are spending on other clients, but also whether they have school, childcare, or hobby-related responsibilities.

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. We might suggest simply skipping 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, which will affect your turnover rate. Is contract work just a means to an end for them, or are they passionate about growing their own business? How likely are they to stick with you for a year? For five? This is a question that people may not be entirely honest about, but it’s still worth asking.

3. What time zone are you working in?

This is an easily skipped question, but it’s important to talk to freelancers about it. And if they are overseas workers, it’s absolutely essential. Nate and Connor recommend asking it multiple times, and even setting a calendar date for a future meeting during the interview, to make sure the differing time zones accurately reflect what the freelancer expects.

Using an overseas worker can mean a dramatic discount on cost, but their time zone might prove a detriment. If you need them for a 9-5 job in the western hemisphere, triple check that they understand what you are asking for.

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

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

The next two freelancer interview questions we’ve listed below make great followups to this point. Followups are so important because they let you better see a person’s true colors. 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.

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

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 worker to explain more as they justify their score. They will have to give examples from their own work history.

Second, this question is a good way to catch some red flags. For example, if a person gives themselves all 10s, but only has a few months of experience in each category, then they may have an inflated ego that’s difficult to work with.

Or perhaps they give themselves a low score in a category they’ve worked in forever, which means they might struggle to pick up new things. Basically, look for any discrepancies between scores and actual amount of experience.

6. 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, you could show an Amazon content specialist a product page and ask what steps they would take to boost sales for that product. The specialist should be able to pinpoint problems with the page and how to improve them. By the same token, you could have a salesperson review a pitch, or ask a designer how they might improve a website home page you show them.

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.

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

When asking freelancer interview questions, many interviewers aren’t sure when to bring up price. We believe the perfect time is right after you talk about their level of experience. This provides grounding to the conversation. Before you interview, always research the fair market rate for someone in the field you are considering.

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 and can immediately hurt their motivation. They also have less commitment to you than a full-time worker, which means that if someone offers them more, they are free to make a quick exit.

8. What is your biggest strength for this role?

Since you should be looking for the 1 or 2 skills you need most, this is a great way to see if their skills align with your most important needs. It is also a nice way to set standards for their future work with you.

For example, if the interviewee mentions that they are very hardworking and will turn around a ton of work in a short amount of time, you can hold them to it. Being able to cite their original interview and the promises they made you 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 they set up themselves.

9. When can you get started?

This is an easily missed interview question for freelancers, but you should never set it aside. Unlike your typical full-time job-seeker, freelancers aren’t always interested in starting right away. They often have previous commitments to other clients. In an ideal world, they should let you know this unprompted, but since there’s no guarantee of that, you need to ask them so that you are not left in the dark.

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, ask them if they have any big vacations coming up in the next couple months. Anything that is going to affect the amount of work they can deliver, you should know about.

10. How did you get into what you’re doing?

This question helps reveal things about the freelancer’s attitude. Often, when you hear their story, you can determine their level of passion for their work. Are they a software engineer because that’s what their parents wanted them to do? 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 bring up the energy of each worker, and result in better work.

11. How do you communicate?

Get ultra specific with this one. What methods of communication do they use: phone, text, email, skype, social media? What do they use most frequently with their clients? Are they comfortable with your preferred methods of communication? Even if the rest is a good fit, a problem here can break a client-contractor relationship down the line.

12. What questions do you have for me?

If the freelancer has a genuine interest in and passion for working with you, then they will likely have questions. But even if they happen to clam up, share information about your own company freely. Let them know about the culture, the company’s goals, and the management style. Sometimes, the freelancer might realize on their own that they are not a good fit, and let you know. This goes a long way in saving everyone’s time.

With this new set of freelancer interview questions in your arsenal, you should be well on your way to hiring skilled workers.

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.