8 Questions to Ask Any Freelancer Before You Hire Them

12 min read

Small businesses rely on freelancers for many projects and tasks. A great freelancer is excellent and delivers solid content for a fraction of the cost of hiring an employee. But many small-business owners have at least one freelancer horror story.

The trick to avoiding a horror story yourself is to carefully vet freelancers before you hire them. Beyond the usual questions about qualifications and references, here are 8 interview questions to ask a potential freelancer!

What Is Your Ideal Client Relationship?

The answer to this question should tell you three things about a potential freelancer.

First, it will give you an idea of how much real experience they’ve had. A newly minted freelancer won’t be able to answer this question because they haven’t had enough client relationships to form an opinion. By contrast, freelancers with wide and varied experiences will have formed not just a wish list of relationship attributes, but also a set of operating procedures that help make them a reality.

Second, it can help you determine how good of a match this freelancer’s work style is for your company culture and your team procedures. Some work styles will be a better fit for your company than others.

Finally, this question helps spot freelancers who might be hard to work with. Listen during the answer for whether they are willing to adjust their expectations to work with a client, or whether they’re likely to be demanding and inflexible.

How Many Projects Are You Working On Right Now?

Unless you’re offering a temporary full-time assignment to a freelancer, it’s unfair to expect that you’ll have their undivided attention. However, many freelancers fall into the trap of accepting all work that comes in for fear of missing out on income and opportunities. This question helps you gauge whether or not they have enough bandwidth to take on the work.

Unfortunately, there isn’t a universal formula to tell whether or not a freelancer has too many tasks to treat your project with the attention needed. However, you can ask several follow-up questions to get an idea of whether or not the freelancer feels overwhelmed and how they balance multiple projects at one time.

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What Experience Do You Have With (Insert Tool Here)?

Whichever app, platform, or software you used to communicate and track workflow, you should ask a potential freelancer how much experience they have with it. If they have no experience with that particular tool, find out how many different tools they have worked with.

For example, if you are hiring a freelancer to help you with your Ecwid store or help manage your business. They should have a background in e-commerce terms, programs, and tools.

Ideally, a candidate will have extensive experience with the tools your team uses on a day-to-day basis. Alternatively, a candidate who has experience with enough platforms should have no problem learning an additional one.

That said, most freelancers are good at picking up new systems and tasks. It’s one of the core competencies of successful freelancing. It’s best to consider this question a tie-breaker between two candidates with similar qualifications, rather than a deal-breaker.

How Would You Prefer We Measure Your Results?

This is a weeding-out question. If the candidate is confused by the question or appears to be making up an answer off the top of their head, they’re probably not the best option for the job. Not understanding that results should be measured, or being unfamiliar with the concept, indicates they’re not professionally ready for your project.

If a candidate gives a knowledgeable, detail-oriented answer, they’re most likely worth considering. It doesn’t really matter what the answer is, as long as they’re willing to alter how they measure results to match the metrics and analytical tools you use. What’s important here is that they understand the importance and the best practices of objectively measuring performance.

As a bonus, the answer to this question gives you a head start on finalizing project details with whichever candidate you ultimately decide to go with.

What Happened the Last Time You Missed a Deadline?

Everybody misses deadlines once in a while. You do. Your team does. Your company does. It’s not fair to disqualify every potential freelancer who admits to having missed a deadline. Instead, this question is about how well the candidate solves problems and how honest they are.

If a freelance candidate with more than three years of experience tells you they’ve never, ever missed a deadline, they may have an honesty issue. At the very least, you need to check with their references to confirm this track record.

When a candidate admits to missing a deadline, listen for how they handled the situation. Do they acknowledge their role in missing the deadline, or do they blame everybody else? Do they have a personal plan in place for finishing work quickly if they miss a deadline? Are they cavalier about deadlines in general? Listen to the substance of the answer, as well as to how they talk about deadlines and timelines in general.

What Else Do You Do for Work?

Most questions you want to ask candidates, whether for regular employment or a freelance arrangement, should be open-ended, with no clear right or wrong answer, as a way to gather information. This is not one of those questions.

There are two kinds of freelancers: professionals who rely on freelance work for their full-time living, and those who do a bit of freelance work on the side for extra money. If the candidate has a full-time job, their work for you will be a second, third, or even fourth priority.

That’s not to say part-time freelancers with talent and potential don’t exist. But most will be more problematic than those who treat their freelancing as a full-time profession. If you find a part-timer who otherwise checks all of your boxes, give them a shot, but set workflow and a contract that makes certain you stay top of their priority queue.

Why Do You Freelance?

The best professionals in any field are those who got there on purpose and who value their position. They are passionate and motivated because they do what they do for well-understood reasons.

If you asked multiple freelancers why they freelance, you would get an array of answers. Some of these answers suggest a particular candidate will be excellent, while others are bright red flags.

The answers you’re looking for will center around how much the person cares about freelancing. They will tell you if the candidate is knowledgeable about the type of work you need. Suppose you need extra help managing your business, whether it be marketing or e-commerce. Make sure the freelancer shares the same passion for your business!

If you get answers about how easy freelancing is, or how the candidate just “sort of fell into” the job, consider other applicants. If the candidate doesn’t care very much about their own freelancing business overall, it’s unlikely they will care about your particular place in it.

How Do You Manage Your Freelancing Business?

Much like the question about measuring performance, this question reveals the professionals in your candidate pool. A professional freelancer spends time on managing their freelance business. They think and care about the business aspects of their career. Such a freelancer will be able to answer this question briefly and intelligently.

If a candidate doesn’t have an answer to this question or seems unprepared to answer it, it’s an indication of a lack of professionalism. If they don’t manage their business well, they’re unlikely to manage yours any better.

Among the applicants who do have a strong answer to this question, look for those with management practices that best match your company’s. There are many right ways to manage a freelancing business, but some of those ways are better suited to working with how you run your company.

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Bonus Question

This final question isn’t for the freelancer themself, but for the references they give you. Ask each reference if they know anybody else who has worked with that freelancer. Most candidates will give you the references who are happiest with their work (or are related to them or friends). This is what scientists call a “selection bias,” and it may or may not reflect the most common experience with that freelancer.

But if you ask for other people who’ve worked with them, and then ask those people for more names, eventually you’ll get a sense of the average experience. That’s the information you want to base your final decision on.

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Sep 8, 2020

About the author

Robert Tulley is a former human resources manager at a Fortune 500, where he used to hire freelancers, part-timers, and full-time staff members. Now, he’s on the other side of the equation and freelancers for numerous companies.