Regardless of what industry you’re in, it has never been easier to hire freelance employees to support and grow your business. Freelancers can help you reduce costs, improve efficiency, and allow existing employees to focus on core goals and tasks. It’s not hard to see why freelancers could represent 80% of the global workforce by 2030. Despite this, it’s still possible to land yourself in a freelancing nightmare if you don’t hire correctly.

If you are embarking on your outsourcing journey, a structured hiring process — including background screening and interviews — will help you filter through the best candidates. Asking the right questions during the interview process is critical in helping you navigate the freelance space. Here are some essential questions to ask any freelancer before you commit to hiring, as well as some common red and green flags to look out for along the way.  

1. What is your ideal client relationship? 

When bringing a freelancer on board, it’s vital to build a robust and positive relationship. Outsourced staff members must have an equal understanding of expectations and communication pathways. Make sure you ask questions that will provide you with a sense of how the freelancer works individually and in a team. Being on the same page is critical for a flourishing business partnership and a good way of avoiding any potential problems.

As freelancers become an integral part of your team, we understand how important it is to forge meaningful connections. Unlike traditional freelance agreements, which operate on a per-project basis, our Virtual Associate program offers more permanent arrangements with freelance lawyers so that you can retain your best talent. Signing up is easy — simply list your project and requirements, and we will match you with the best virtual associates for your business.

Green Flags: 

  • “Timely and efficient communication.”

  • “One that feels honest and comfortable.”

Red Flags:

  • “Independent work over collaboration.”

  • “As long as it’s providing cash flow, it doesn’t matter.”


2. What experience do you have? 

This should be one of the questions on the top of your list during the hiring process. It’s important to know whether a freelancer has worked in a team before and how they have performed.  Similarly, understanding how long they have been freelancing and whether it suits them helps judge their ability to work well in this type of environment.

You should also ask about their specialist knowledge and skills to see if they will be adequately suited to the role. Knowing the clients and companies they have worked for is a valuable indicator of their reputation, skills, and expertise.

Green Flags:

  • “I have experience working as a freelancer and in the past, a team.”

  • “I have skills in specialized areas such as….”

Red Flags:

  • “I am very new to working as a freelancer.”

  • “I haven’t worked for any major companies before.”


3. What is your current schedule?

Time may be tight, and deadlines might be on your mind. If you are looking to hire a freelancer to ease this pressure, it is essential to understand what projects they are currently working on to determine whether they can meet your needs. Enquiring about their current schedule will also indicate how in-demand (or not) they are and how likely they are to over-commit themselves; this can become a problem for you when they miss deadlines or are unresponsive to messages.

Green Flags:

  • “I follow a weekly schedule that I create around my clients.”

  • “I am busy enough but have some spare space in my schedule for extra work.”

Red Flags:

  • “My schedule is completely open.”

  • “I am at capacity, but I can try and squeeze you in.”


4. Do you have any samples of your work? 

Obtaining samples of a prospective freelancer’s work will allow you to better understand the quality and accuracy you can expect and whether this will suit your business and your goals. If you are comparing various candidates, reviewing samples of their work may help you separate them and, therefore, make the right choice.

Green Flags:

  • “Yes, here is my portfolio.”

Red Flags:

  • “I don’t have any samples to give you right now.”

  • “Here is some of my work, but it’s from a while ago, so it isn’t my best.”


5. Why do you freelance? 

Sometimes, narrowing in on what drives someone will help you understand whether they will be a good fit for your business; this is especially true if your business centers around a specific team culture or has a particular ethos. For example, if passion over expertise is something you’re looking for, this may be an excellent question to ask. Enquiring why they choose to freelance can also help gauge how suited someone is to the freelancing lifestyle and how comfortable they are working in this capacity.

Green Flags:

  • “I freelance because it suits my lifestyle and working capabilities.”

  • “I have been freelancing for a long time and feel comfortable supporting myself as a freelancer.”

  • “I have developed systems that help me work in a freelancing environment.”

Red Flags:

  • “I don’t know why I freelance.” 

  • “I have just started freelancing because I wanted to try something new.” 


6. Can you tell us about your current client relationships?

Asking a question like this allows for a more thorough understanding of their experience and work schedule. Request detailed examples to gain insight into how they work and communicate with clients. A clear image of their practice is also extra helpful in identifying any green or red flags. If you are passionate about moving your business in a particular direction and prioritize the importance of client relationships, this is a valuable question to ask.

Green Flags:

  • “I have a positive and professional relationship with my current clients.”

  • “We have great communication.”

  • “We have established a cohesive routine.”

Red Flags:

  • “We don’t communicate much.”

  • “I prefer to work autonomously.”


7. How do you like to communicate? 

Communication is one of the fundamental driving forces of success in any business. If you decide to hire a freelancer, you must establish clear lines of communication, especially as they will most likely be working remotely and could be in a different time zone. If you already use a messaging or conferencing tool within the business, make sure the freelancer is also comfortable using this channel. Be sure to get a sense of how responsive the freelancer is and their preferred methods of communication.

Green Flags:

  • “I like having an instant messaging platform so we can easily communicate.”

  • “Regular catch-ups are something I prioritize.”

  • “I like to schedule regular weekly or biweekly status meetings with clients so we stay on track with our work.”

Red Flags:

  • “I leave it up to the client.”

  • “Whatever works, as long as I get the work done.”


8. What are your usual working hours?

The global nature of the freelance workforce can create obstacles to conventional working hours. Typically, you and the freelancer will need to communicate during working days to ensure projects are staying on track and deadlines are being met. If being online at similar hours is something you deem necessary, you will need to make sure your freelancer will be available to respond and have meetings when you are working. If they are overseas, they may have to be willing to work irregular hours.

Green Flags:

  • “I work around my clients’ preferred days and times.”

Red Flags:

  • “I work around my own schedule.”

Get support with hiring freelancers

Freelancers can be a vital asset to your team, and hiring the right people is critical. Whichever industry you operate in, it’s essential to choose a hiring partner who can offer support and guidance throughout the process. LAWCLERK provides access to thousands of quality freelance lawyers who can ease caseload and increase billable hours for legal firms. We also offer assistance throughout the screening, interviewing, and hiring process so you can find the best possible talent for your team.

Find your perfect freelancer

A successful business requires good client relationships and a cohesive team. We believe that asking the right questions during the recruitment process is one of the best ways to find the right talent for your business. At LAWCLERK, we are committed to supporting hiring attorneys to source quality freelance lawyers who can add value to their business, whether that’s on a per-project basis or as a virtual associate. For more information on how we can assist with your legal outsourcing requirements, please get in touch today.

Kristin Tyler, Co-Founder Lawclerk

Kristin Tyler, Co-Founder Lawclerk


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