questions to ask freelancers


Before you can start working with a freelancer, you have to find the right one for the job. When you’ve identified a freelancer (or a few) you think may be a fit for the project you have in mind, scheduling a call or meeting to get a feel for who they are and how they work is an important part of the process.

This initial meeting is your chance to figure out everything you need to know to make an informed hiring decision. But before you take the step of hiring them, it’s crucial to ask the right questions now to avoid potential issues later.

9 Questions to Ask a Prospective Freelance Hire

  1. Can you provide relevant work samples?

The best way to get an idea of the quality of a freelancer’s work is to look at the work they’ve already done. If you’re hiring a freelancer for a creative role, they should be able to provide a portfolio of their work. If you can find it, be sure to browse their portfolio before you get to the point of a phone call.

But if you’d like to see samples that are more in line with the type of project you’re hiring for or that relate more closely to your industry, just ask. If they don’t have that specific type of experience yet, that’s good to know (although it doesn’t necessarily mean they can’t do the job). If they do, you can get a better picture of the kind of work they’ll do for you.

  1. What’s your typical turnaround time?

When a freelancer’s late on a deliverable, it can hold up your whole project or screw up your content calendar. Maureen Jann, founder and managing director of Super Deluxe Marketing, cites this as one of the biggest problems to be on the lookout for in a freelance relationship.

“Hashing out what they will deliver when and ensuring they stick to that timeline is critical to having a good working relationship,” she explains. “If there is a lack of baseline respect for timelines and quality metrics, I question the entire relationship.”

She suggests that one of the most important questions to ask a freelancer is their typical turnaround time. And find out what specific deadlines they can commit to for your project.

  1. Can you provide references from past clients?

Great writing samples can show you their skill level, but finding out what a freelancer is like to work with is equally important. Their answers to the other questions on this list should help with that, but the usefulness of what you learn depends on their honesty.

It’s bad business for a freelancer to lie to potential clients, but that doesn’t mean it never happens. To make sure what they tell you matches what you can expect when working with them, ask for references. Check with one or two past clients to learn a little about what the working relationship looked like and if there’s anything you should be aware of going into it.

  1. What’s your typical working style?

For freelancers, one of the benefits of the gig is the ability to set up schedules and working habits in whatever way they work best. That means if someone gets their best work hours in at night and likes to sleep most of the day, you can’t count on having calls with them in the afternoon. If they insist on planning their schedule at least a month in advance, they won’t be a good fit for rush work.

Different freelancers have different preferences for when and how they get their work done. Figure out if their preferences match up with the way you work. Someone can be talented and have a great track record, but if their working style doesn’t mesh with yours, they’re not the best hire for you.

  1. What are your communication preferences?

This is part of working style, but a big enough issue to mention on its own. Some freelancers are happy to come onsite for in-person meetings, while others will insist on emails and phone calls only. Some are fine with being available on Skype or Gchat throughout the day, and others find that disruptive to their work.

If you have a strong preference for doing all your communication with colleagues over the phone and a freelancer you hire prefers to stick with emails, you’ll end up getting frustrated with each other pretty quickly. Discuss upfront how you prefer to communicate and find out if it matches their preferences.

  1. What’s your availability?

When you choose to go with a freelancer rather than an employee, one of the tradeoffs is getting only a certain portion of their time. They have other clients and responsibilities to attend to, so you have to be realistic about how much time to expect them to spend on your project. Without trying to control their schedule, you still need to know enough to be sure they can accomplish the work they commit to.

Carol Raym of Custom Blend Communications recommends asking a freelancer “how many hours a week, ballpark, he or she will be able to devote to your business while handling multiple clients.”

When you know how much time they have available, you gain a better idea of how much work you can reasonably assign them. Alternately, some freelancers will prefer to talk in terms of deliverables rather than time – letting you know the number of assignments they can commit to in a week or month. Either way, having this discussion upfront can prevent potential disappointment down the line.

  1. How do you handle unexpected challenges?

Just like anyone, freelancers have days where they come down with the flu or face family emergencies that disrupt their work life. Even a freelancer that manages to meet deadlines 95% of the time is going to have life get in the way at some point. What really makes a difference here is how the freelancer handles those issues.

Maureen Jann describes it as a respect issue. “We’re all humans and life happens, but keeping partners and clients apprised of those changes is just good business. What happens all too often is that people no-show or fail to deliver on the day committed, and then active management needs to happen by the other parties.”

Someone that’s comfortable communicating when their work is falling behind and they’ll need more time allows you time to adjust plans as needed to keep your schedule intact.

  1. What do your rates include?

Freelancers are all too familiar with the concept of “scope creep” – the idea that if the terms and scope of the project aren’t clearly defined (or sometimes even if they are), clients may continue to keep asking for and expecting more. If both you and the person you hire aren’t on the same page when it comes to the details of the project and you end up expecting more than they think they’ve agreed to provide – nobody will be happy. Rather than risk being told a couple of months into the project that something you want will cost more, clarify at the start what their rate covers so you can plan your budget accordingly.

  1. What do you need from me?

Marketing Consultant Erika Heald has experience both working as a freelancer and hiring them, so her perspective takes into account what works best on both sides of the relationship. “The one question I am never asked as a freelancer but should be is, ‘What will you need from us to deliver this project?’” she says.

For a freelancer to fully understand your brand, your audience, and the type and style of work you want from them, they need clear information from you. “I proactively ask new clients for a copy of their brand guidelines, content style guide, brand voice chart, and their three biggest competitors.”

Asking this question will increase your chances of getting deliverables from them that match your expectations and require less work from both of you in the revision process.

Pay Attention to What They Ask You

With these questions, you’ll learn the most important information you need to hire the right freelancer and make sure the relationship will be a good one. But Carol Raym points out that your questions aren’t all that matters in the first interview.

“I’d twist this slightly and say pay attention to the questions the freelancer asks you, to see if they’re really in tune with your goals, audience, way of working, etc.,” she explains.

Knowing the right questions to ask is a good way for a freelancer to demonstrate expertise. Do they grill you on your unique value proposition? Ask about your main goals for the project? Request details about your target audience? You can learn a lot about how well a freelancer knows their job based on what they ask you during the interview.


Working with a freelancer can be a catastrophe where everyone feels unsatisfied or an equally rewarding experience for both parties for years to come. So much of which experience you’ll have depends on making sure the freelancer you hire is the right fit for your project – and that you’re on the same page from the start.

Kristen Hicks