15 Interview Questions to Ask Your Next Freelancer

Chloe Brooks
7 min readApr 4, 2019


Even gig workers need to go through a vetting process

Every hiring manager knows how important it is to interview potential candidates to find the right one for the job.

But with the rise of the gig economy, today’s candidate pool isn’t quite what it used to be. More than one-third of U.S. workers freelance now, and many companies are changing their hiring policies in response to this shift.

Just because freelancers aren’t your traditional job candidates doesn’t mean you don’t have to vet them thoroughly. In fact, it may be MORE important to interview freelancers than other candidates, and the questions you ask should be even more comprehensive.

Ready to hire freelancers, but aren’t sure where to start? Here are 15 freelance-friendly interview questions for you to use.

1. Why do you freelance?

No matter what position you’re looking to fill, it’s important to know why each candidate was drawn to it. And since 61% of freelancers work for themselves by choice rather than necessity, you’re bound to hear a variety of answers to this question.

A 2018 study by The Freelancers Union and Upwork found that the top reasons most freelancers chose that career path are to be their own boss, to have more flexibility in their schedule, and to be able to work from anywhere.

The key is to look for passion in their response. If they went freelance to be able to choose their own projects, what kind of projects do they love working on now? If they wanted to be able to work from anywhere, where do they choose to work now?

Honing in on what drives people will help you get a feel for whether they’re a good fit for your company and role and may help you identify new ways that they can be a benefit to your company.

2. What experience do you have in my industry?

Just because a freelancer hasn’t worked in your industry doesn’t mean they’re not a good fit for your company. Many freelancers work with multiple industries at a time and are adept at learning on the fly.

However, if you do choose a freelancer who is new to your field, you may need to be prepared to give a little extra training or brace yourself for a steeper learning curve on their part. Weigh the benefits of each before making your hiring decision.

3. May I see samples of your work?

A freelancer who knows what they’re doing should be able to provide you with samples of work they’ve completed for past clients or employers. Be sure to ask to take a look, as the samples in their portfolio show you know what style and quality of work to expect from them.

4. How many clients do you typically work with at once?

Depending on what services your freelancers offer, they may be able to handle more or fewer clients at a time. Knowing how much is usually on their plate gives you a feel for how much time and attention to expect from them during an average week.

5. Do you have the capacity to take on this project right now?

Too often, newer or less experienced freelancers take on any project that comes their way simply because they need the money. Unfortunately, freelancers who do this often overcommit themselves and wind up with more work than they can handle within a reasonable timeframe.

Ask any freelancers you interview whether they have the capacity in their schedule to take on your project. If need be, phrase the question a few ways throughout the interview and gauge how they respond.

6. Is the proposed timeline long enough for this project?

Sometimes a freelancer will have the availability to take on your project, just not necessarily by the deadline you hoped. Ask freelance candidates upfront whether the due date you’ve assigned is reasonable or not. Experienced freelancers will let you know the answer right away.

7. What would you do if you missed a deadline?

At some point or other, every freelancer misses a deadline. They’re only human, after all, and mistakes happen. But when you’re hiring freelancers, you want to find someone who is upfront and proactive — not someone who leaves you wondering for months if they’re still alive.

Ask candidates what they would do if they missed a deadline, and listen to their answer carefully. Would they reach out to you before the deadline to let you know they couldn’t make it? Or would they simply try to make things better after the fact? Find someone who falls into the former category, not the latter.

8. What do your clients like most about working with you?

A good way to get a feel for what it’s like to work with a certain freelancer is to ask what their current and past clients like most about working with them. Unless you’re speaking to a first-time freelancer — i.e., you would be their first client ever — everyone should be able to answer this question.

Listen for evidence of a freelancer who provides great customer service, like:

  • Fast responses
  • Little to no revisions
  • Quality work
  • Great results
  • Cheerful demeanor
  • Etc.

9. How do you deal with unhappy clients?

A freelancer’s answer to this question tells you a lot about how they run their business and can help you identify freelancers who aren’t so great at handling client issues.

Once again, look for evidence that they will be proactive and service-oriented when dealing with unhappy clients. And if they tell you they’ve never had an unhappy client, they’re either new to freelancing or lying to you.

10. Has a client ever ended their relationship with you abruptly? If so, why?

While not every freelancer has been in this situation before, plenty of us have been, so there’s a good chance that any freelancer you interview has an experience like this that they can draw from to answer this question.

Keep an eye out for red flags in their answer, like placing all of the blame on the client, or phrasing that shows they’re still angry or resentful about the situation.

11. May I contact past or current clients for a reference?

Every freelancer worth their salt should have at least one client they know they can count on for a good review. If they can’t come up with someone, run!

When you do contact the references they provide, be sure to ask them some of the same questions as numbers 8–10: What did they like most about working with that freelancer, how did they handle uncomfortable situations, and what was the reason for ending the relationship?

Cross-check these answers with what the freelancer told you to be sure you know what you’re getting into.

12. How will you invoice this project?

If you’re new to working with freelancers, you may not yet have a system in place for paying contractors. In this case, look for a freelancer who already has this process down to a science.

Pay special attention to freelancers who include fees for things like late payments and early cancellations. Often, freelancers who have these policies in place are a bit more experienced and conscientious about their work.

13. How do you prefer to communicate?

Knowing from Day 1 whether your communication styles are compatible or not is a crucial part of finding the freelancer who will perfectly complement your existing team.

For instance, if you like to have daily video check-ins but your freelancer prefers weekly phone calls, you could be in for a tough working relationship.

14. What are your normal business hours?

Freelancers’ schedules can vary wildly from contractor to contractor — one may have another job or classes, while another may take Mondays and Fridays to work on their own business.

If your freelancer tends to work later in the day but you’re an early bird, you may not be able to communicate with them as well. Hire someone whose business hours line up with your own as closely as possible to avoid unnecessary tension down the road.

15. What do you need from me?

Before starting work, your freelancer may need a contract, brand assets, more information about your company, or even patience from you while they put together a quote. Ask them up front what they’ll need so there won’t be any surprises down the road.

Leave the interviewing to us!

These interview questions will go a long way toward helping you find the best freelancer to add to your team. But the absolute best way to narrow your candidate pool is to let us do it for you.

Every freelancer here at Collabos has gone through a rigorous, multi-stage screening process to ensure that only the very best designers, developers, and other creatives ever touch your project. We take care of all of the hiring and management so all you have to do is request work and pay for completed tasks.

Ready to get started? Request your free quote below.



Chloe Brooks

Helping you heal and prevent burnout with the #AntiBurnoutLifestyle. More about me: www.chloerbrooks.com