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Freelancers

List of interview questions when hiring freelancers for your company

Here is a list of interview questions when speaking with freelancers to help you make the right decision.

Now that you’ve established that you want to hire freelancers to complement your existing talent pool. Here are a few key interview questions that you should consider asking when looking for your next freelancer.

Motivation and Interest

It’s important to ensure freelancers feel connected to the projects that they’re working on. Whilst you don’t have to manage their career development, ensuring the deliverables are of a high standard is crucial so that your other team members feel supported and that they don’t have to fix anything. It’s also likely that the freelancer would need to ask questions from your team occasionally so ensuring they’re easy to work with and are interested in the project is important.

What made you want to become a freelancer? What do you like most about it?

As part of establishing a relationship with the freelancer, it’s important to set the right tone with each other, it’s always a good start to learn more about the freelancer's motivation. You’ll get to better understand what’s important to the freelancer and be more mindful on how to best work with them in the future.

What was your most favorite project to work on previously? Why was it your favorite?

Even though freelancers are contractors and their projects are of a finite duration, it is important to provide a positive work environment for your contractors. Think of them as a way to supplement your team and create a team of flexible A+ talent when you need it will only make things easier for you at your job.

By setting the right expectations early on on both sides, it will make any project go smoothly. This includes understanding your contractors personality, working style and also their interests. By showing that you care about them, even when they’re not a full time employee goes a long way. Freelancer also has a strong network that they work with, if you trust your freelancer, know that their referrals will be really helpful going forward.


Skills and Expertise

What skills are you most proficient in?

Many freelancers tend to see themselves as generalists who can do everything. This is probably pretty rare in real life. It’s good to figure out what the freelancer is truly an expert at (and enjoy doing the job) so that you can complement that person with other folks in your team or other contractors. You probably would want to work with someone who is truly honest with their skillset to get quality work. 


What technology tools do you like to use?

Experienced freelancers can adapt to different client needs and as such, would probably have been exposed to a variety of tools in the market. By asking your freelancer to explain the tools that they find most useful will give you a sense on their ability to pick up new tools and also how they think about productivity when working with clients. It’s also a really good way for you to learn from your freelancer too and adopt new workflows / tools going forward.

What was the outcome / results of your last project? How did you measure it?

This is a good way to better understand how thoughtful your freelancer is when it comes to the projects. A great freelancer considers or asks questions on how the work impacts the overall business even if it is a small project. It illustrates that they are diligent with their work and don’t waste extra hours on tasks that may not have an impact on the overall KPI. If they’re excellent at their job, they will provide recommendations on how to approach things differently to achieve maximum results vs just doing what they’re been told to do.


Communication and Organization

Since most freelancers work remotely due to the flexibility in lifestyle, it’s even more important to ensure the freelancer has strong communication and organization skills. Depending on the project, it’s a good idea to potentially work with the freelancer on a smaller pilot to better understand each other’s working style. Note that the freelancer is not a full time employee so there needs to be some flexibility involved on both sides since the incentives will not be as aligned as someone who has worked with you and the company for many years.


How do you like to communicate with your clients?

Establishing a cadence of regular communication and updates is important especially since the freelancer is most likely not available specifically based on your availability and you won’t see them at the office. It’s important for them to be proactive and follow through on any action items without you needing to chase them up. Setting clear milestones, deadlines and deliverables are important to ensure there are no confusion.

An experienced freelancer knows when to ask questions, ask for help and ensure they get what they need to meet their deadlines. They want to keep the relationship with you going so they are top of mind whenever you have new projects. 


How do you like to manage your workflow?

Experienced freelancers should be proactive in their updates and questions for you. You should listen for the freelancer's ability to be open to feedback, ask you questions for direction and be willing to collaborate with your team. Ultimately, you want to work with someone who is flexible, open minded and understand how to be most productive and effective when working with clients. 

Project specific

Outside of the typical questions that you want to ask on your specific project (e.g. have you done this type of projects previously and can you provide a portfolio / case study of the work, can I contact your previous clients for a review), it’s also important to get a sense on how prepared and ready the freelancer is to take on your project.


What do you need from me to get started?

If the freelancer is well prepared and experienced working with clients, then they should have a checklist of items that they need from you to get started (e.g. brand assets, previous reports, templates etc). It also indicates much how they’ve understood the project scope and should be asking you questions at this point (vs needing you to tell them everything). 

What is your capacity at the moment?

Many freelancers like to take on multiple projects at the same time especially if it’s an expertise that they have and therefore is able to do that. This generally is not a problem especially if they’re really good at their job but it’s good to set the right expectations upfront which says alot about the transparency and working relationship you want to establish. It’s also a good sense check to see if the milestones / deadlines you proposed are realistic.


Any other questions you would ask during the interview process? If you want to chat with us about how to establish freelancer programs for your company, let us know here! .



Winson Wong
Hi! I'm Winson, Founder of Wattle. I'm a fourth culture nomad, born in Hong Kong with Taiwanese roots, spent most of my life in Australia before embarking on a professional career in the US. Having spent most of my career in product management and business development across a variety of startups, consulting firms and corporates, I realized that I'm most passionate in helping people achieve their dreams. I'm a builder and operator at heart which is why I want to create a long term sustainable company. Some of my personal values include going the extra mile to drive impact, to give more than take and be openly compassionate and vulnerable, all of which I am still working on!

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