Hiring freelancers is not the same as hiring full-time employees, and the approach to interviewing and assessing them needs to reflect that difference. Adhering to lengthy and multiple interviews, long-timelines and cumbersome internal processes will ensure you lose out on the best talent. Why? Top-tier independent talent is in demand and are likely fielding multiple projects at the same time. Assessing them quickly and effectively is key to securing the cream of the crop.
Today, we’re chatting with Karabo Mahlakwane, who manages the Africa team at Outsized responsible for curating and vetting freelance talent. We will be sharing best practices when it comes to assessing talent and a behind the scenes look at how we approach this important part of the process at Outsized.
The early bird gets the worm. Quality independent talent is often in high demand and won’t wait for lengthy hiring processes. Their business depends on securing new projects quickly, so organizations must streamline their hiring processes to attract and retain top independent professionals. In the two maybe three weeks it takes you to get back to a prospect, they may have already accepted an offer from a competitor.
It is important to note that independent contractors and consultants see themselves as entrepreneurs. They are always looking out for the next and best opportunity. Setting up a streamlined and fast assessment process is key to making sure you have a chance of securing your top choice.
Many hiring managers, who are used to a slower-paced hiring process are resistant to making a speedy decision. The main reason for this is they see it as risky. The good news here is that hiring an independent is significantly less risky than hiring a full-time employee. Many of the contracts we facilitate at Outsized have a 30 day termination clause, so if for whatever reason, the hire doesn’t pan out, organisations can legally end the arrangement.
D: Karabo, thanks for taking the time to talk with me. Let’s start with the basics—how do you prepare to interview a freelancer?
K: It all starts with understanding the project requirements. Before we even begin interviewing, we need to have a clear picture of what the project needs. This isn’t just about the technical skills—although those are crucial—but also the specific expertise and experience that will make someone the right fit for the job. For instance, if you’re looking for a developer, it’s not enough to know they can code; you need to know if they’ve worked on similar projects and understand the tools your team uses.
To make this happen, we hold close consultations with our clients. In fact the process starts with our client- we interview them first in a way. In some cases that conversation leads to more clarity and our clients realise that in fact they are looking for two different roles. We are there for them in an advisory capacity too.
D: Great. So once you’ve got a handle on the project needs and have consulted with the client in depth, how do you tailor the interview to a freelancer versus a traditional hire?
K: That’s a great question. Interviewing a freelancer is really different from interviewing someone for a full-time role. With a permanent hire, you’re often thinking about their long-term potential, how they might grow with the company. But with freelancers, the focus is on what they can deliver right now. We’re looking at their project-specific skills, their past performance, and how well they can fit into the team culture—even if it’s just for a short while.
So the focus is really on deliverables. We look at the specific needs of the role and we make sure that we double check their capabilities. Oftentimes CVs don’t tell the whole story, or aren’t specific enough. We get really targeted with our questions.
D: What are the key areas you assess when interviewing a freelancer?
K: There are a few critical areas. First, of course, are their technical skills and expertise. We use practical tests or review their portfolio to see if they really have the skills they claim to have. But technical ability isn’t everything. We also need to understand how they solve problems and adapt to changing project needs. This is where scenario-based questions come in handy—they help us see how the freelancer approaches challenges.
Of course it’s hard to test for this via interview questions, so we do recommend that for more technical roles, clients set up a real-world assessment that allows a candidate to show rather than tell.
D: Communication must be important too, especially with more freelancers working remotely.
K: Absolutely. Communication is key, particularly in remote settings. We assess their ability to communicate clearly and work well with a team, even if they’re not in the same location. This ties into cultural fit and work ethic too. Even though freelancers might not be with the company long-term, they still need to align with the company’s values and work culture to some extent, otherwise, the collaboration might not be as smooth. These days, most of our talent is working both in office and remotely within a hybrid arrangement, so fit is an important part of the screening and we share our findings openly and transparently with clients. For example, if we know that the requirement of a role will be client-facing, then communication skills, eloquence and some of the softer skills are equally important to our client.
D: When it comes to conducting the interview, what kind of questions should you ask?
K: You want to ask questions that dig into their work style and past experiences. For example, we might ask them to walk us through a previous project that’s similar to what they’d be working on with us. It’s also important to get to the core of their capabilities quickly—time is often of the essence when hiring freelancers, so the more specific and targeted you can be with your questions the better. I would avoid generic questions and be more direct.
D: Do you assess their work beyond the interview?
K: Reviewing their portfolio or work samples is crucial. You’re looking for quality and relevance to your project. But beyond that, it’s a good idea to involve all team members who will work closely with the freelancer in the interview process. This helps ensure that the freelancer is not only technically capable but also a good fit for the team’s dynamics.
We recommend that you keep it to one interview and make sure that all relevant stakeholders are in the meeting. That includes hiring managers, but also members of the team who will be working directly with the freelancer. This saves a huge amount of time and makes sure that nothing is missed in the assessment.
D: It sounds like speed and efficiency are really important in this process.
K: Definitely. When a client comes to us, they often need someone who can start immediately and contribute from day one. They don’t have time to go through lengthy recruitment processes that can take months to complete.
We pride ourselves on moving quickly, often getting qualified candidates placed in a week or two from our first conversation with a client. Because of our accelerated assessment process by the time a freelancer’s profile lands on a client’s desk, we’re confident they can do the job.
We also advise clients to move quickly in the interview process—good freelancers are in demand and won’t stay available for long.
D: That makes a lot of sense. To wrap up, what’s the key takeaway for hiring managers when it comes to interviewing and assessing freelancers?
K: The main thing is to focus on the immediate fit—can this person deliver what you need right now? By clearly defining your project needs, asking the right questions, and involving the right stakeholders, you can ensure you’re selecting the best freelancer for the job. And of course, if you want to save time and ensure quality, consider working with a talent partner like Outsized, where we’ve already done a lot of the heavy lifting for you.
D: Thanks so much, Karabo. This has been really insightful.
K: My pleasure.
Before you start interviewing freelancers, it’s crucial to clearly define the scope of your project. This means identifying not just the technical skills required but also the specific expertise and experience necessary to achieve your project goals. The clearer you are on your requirements the higher your chances of finding the perfect fit candidate quickly.
Freelancer interviews should focus on project-specific skills, past performance, and cultural fit. Unlike full-time hires, you’re not looking for someone to grow with the company long-term; you need someone who can hit the ground running. Here is a quick checklist:
Focus on questions that reveal their work style, past experiences, and problem-solving abilities. For example, you might ask about their experience with similar projects or how they handle tight deadlines.
Look for quality, relevance, and creativity in their previous work. This review should give you a clear indication of whether they can meet your project’s demands.
Involve all team members who will work closely with the freelancer in the interview process. This collaborative approach helps ensure that the freelancer not only has the right skills but also meshes well with the team dynamics.
Navigating the freelance talent market requires a different approach, one that prioritizes speed, precision, and a deep understanding of project-specific needs. As we’ve discussed, the stakes are high—top-tier freelancers are in demand, and lengthy, traditional hiring processes can result in losing out on the best talent.
Working with the right talent partner can be extremely helpful in situations where speed, agility and industry expertise are required.