Our personal experience and market trends show us that more and more companies – big and small – are bringing on freelancers to help with growth and other business needs. It’s important to note that working with freelancers still takes a different approach than hiring someone in-house, as the working relationships are very different.  

For one, freelancers often work remotely, which requires a certain mindset and set of skills. It’s also much easier for either party to cancel the contract in a freelance relationship at any given point. Many freelance engagements are often pursued for short-term projects or for specialized help.

This all makes sense when you consider that companies often hire freelancers because they need someone who can hit the ground running — someone who is already experienced and skilled in the area they’re hired for. Freelancers are typically used to working with clients and managing their own time and workload. They need very little management to get the job done.

To help you decide if a freelancer has the qualities you need for them to work fast and help you accomplish your business goals, here’s 10 questions that are great to ask.

1) How long have you been freelancing?

We don’t encourage discounting new freelancers, as they can be equally or sometimes more equipped for the job at hand and managing their own work. But it’s still a good to know how much experience a freelancer has working with clients.

The more experienced someone is at freelancing, the more likely they are to have their own processes in place for how they operate, which can be beneficial if you’re still figuring out how to work with freelancers. 

2) Why do you freelance?

Freelancing requires a real hustler mentality and a whole lot of love for what you do. You want to look for a freelancer who’s doing it because they want to work on projects they’re passionate about or with people they enjoy working with.

Maybe a freelancer first started freelancing so they could be at home with a child or elderly parent, or so they could travel — that’s fine too. If that’s the case, ask them to explain why they stayed with it. If they fell in love with it for the work, freedom and flexibility, they’re likely in it for the long haul.

What you probably don’t want is someone who’s freelancing because they don’t like working with people or on teams. This is a sign that they might not be easiest to work with.

3) What type of projects have you worked on?

You’ve likely already reviewed their portfolio and are familiar with what a freelancer has worked on — it’s still important to have them walk you their history.

Pay attention to how they’re describing them. What are they focusing on — results achieved? The tasks at hand? Listen intently and notice what they get excited about when talking. You’ll get a good sense of whether or not they’ll be passionate about working with you on your project!

4) What specific results did you achieve for x campaign?

As a freelancer is walking you through specific clients, campaigns or projects they’ve worked on, ask them to share specific results achieved.

It’s one thing to say you worked on a Coca-Cola campaign, thousands of people worked on that campaign. Ask what they did, how they specifically moved the meter. Get them to dig into their experience. Their responses will help determine if they can really achieve the results you’re looking for.

5) How do you typically measure your results?

You’re not looking for specific tools here, but rather how the freelancer sets KPIs — how they determine what’s most important to measure when working on a project. The best answer is going to say something like “it depends on your goals, but in the past I have…” and then they break into specific examples of KPIs determined, how they set benchmarks and how they measured against them.

6) How do you communicate your results?

Being able to communicate one’s value as a freelancer is so important. You need a freelancer who will explain the results of their work, how and why something is or is not working, and what they plan to do next. This is a big reason why you hire a freelancer in the first place — so you don’t have to take the time to determine these things.

Not every freelancer has access to metrics for all jobs, so don’t hold it against them if they haven’t had the opportunity to do this. But if not, ask them how they would do it.

7) What would you do if you missed a deadline?

This question is really to determine how effective a freelancer is at communicating. A good freelancer over-communicates around deadlines. Shit happens, and sometimes they’ll miss one. You’ll want to work with someone who is upfront and honest about their timeline for when they’ll be providing any deliverables to you.

This is also an important question for anyone working remotely, as communication is crucial to remote work success. You need someone who’s comfortable speaking up through Slack or HipChat and who will ask for a call when they need answers quick. You’ll be able to glean how comfortable and confident someone is working remotely from this simple question.

8) Has a client ended a relationship abruptly – if so, why?

Before you ask for references, get a sense of the relationships that haven’t worked out for a freelancer. Try to not judge if a client wasn’t seeing the results they wanted, as you never know what their expectations were like. Instead, look for how the freelancer explains the situation and if they learned any lessons from. Look for someone who’s always able to take a lesson or action item from an experience.

9) What else are you passionate about outside of work?

Even if you’re only working with a freelancer on a short term project, their interests outside of work can help you know if you’ll enjoy working together. Bringing on freelancers isn’t like hiring full time employees: you don’t need to gauge them for a team culture fit. Even so, it’s always nice to get to know who you’ll be working with.

10) What tools do you use?

What tools a freelancer uses is a great indicator that they have processes in place and are focused on an effective and efficient workflow. Just as the best developers use the same tools, the best marketers use the same tools, etc. An experienced freelancer should know what tools will help them get the job done best.

A freelancer’s stack will likely include: Slack, Asana, Trello, Harvest, Google Office Suite; for marketing related – Buffer, Hootsuite, Google Analytics. If you’re looking for someone with some tech or dev experience, they should know Github and Bugspot, for example.

Final thoughts

Reviewing portfolios helps to narrow down who is best to work with for your current needs. Look at reviews, ratings, testimonials and referrals to get a sense of the freelancers’ past experience. From there, it’s awesome to set up short intro chats to touch base on any other questions you have for them. At the end, you’ll have a clear sense of how each freelancer manages their time and workload, how they communicate, if they’re results-oriented and if they’re excited to work with you!

Do you have other questions about hiring a freelancer? Leave them in the comments below and we’ll be happy to help!

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CloudPeeps Team
We match businesses with the world’s top freelance pros. We're creating the freedom to allow you to work the way you want, wherever you are!
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