Freelancer Interview Preparation Guide

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An experienced professional should be able to share samples of their work or tell you about projects they've worked on. Use your best judgement about this based on how they've represented themselves: Some types of work aren't always public or easily shared, for example, and someone with years of experience may not have a big portfolio if they've recently made the move to self employment.

☛ Things to listen for: Quality. Does their work represent the skill level and attention to detail you're looking for?

☛ Follow-up question: "What was your approach to this project?" This question will help give you more insight into how they collaborated with others, addressed the client's needs, met challenges, or exceeded expectations.

This is a standard way to close an interview, giving the contractor the opportunity to ask any questions you haven't covered.

☛ Things to listen for: If you've communicated your needs well, or if the project isn't very complex, they may not have any follow-up questions. Even so, questions about your organization or your next steps in the selection process show an active interest in your project.

Reporting and 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.

If someone doesn't have a working process they are either brand new or unorganized. Either way, move on.

The last thing you want is to hire a freelancer who is so unorganized that they can barely remember their own name let alone the project you're working on.

The flip side is the person who has a process that's too time consuming. If you are required to be involved with every little aspect of the project then you're talking with someone who is afraid to make decisions. They lack confidence and it will show in their work. You need to work with a professional who is confident (not arrogant or proud, but confident).

Ask yourself this, "Would you trust a doctor who was always asking your feedback on a procedure? "So, do you concur?"
Now I realize copy writing or graphic design isn't the same as practicing medicine but I think you get the point. The freelancer should be an expert in his or her field and therefore be bold enough to say, "This would work best."

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, make sure they 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 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.

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 should 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.

If you have a tight timeline, you need to know right away whether the freelancer has a conflict. Most freelancers often manage multiple projects; this doesn't mean they aren't the right fit for your project, but it does mean that they need to be able to balance your project against the needs of their other clients.

☛ Things to listen for: Project management skills. Are they confident about their ability to meet your milestones? What's their approach to juggling multiple projects?

☛ Follow-up question: "Is this timeline realistic?" An experienced freelancer should know whether you've allocated enough time, missed key steps, or aren't leaving enough "buffer" for challenges that are likely to arise.

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. Hire someone who will give you sufficient notice and explain why and when the deadline will be met.

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.

Get your prospective freelancer on the phone. There's so much you can learn from a phone call. And it starts before they say the first word… if they keep their word and call you at the appointed time that's a good sign. People who are punctual are generally always on time. Same goes for those who not.

Not only can you find out if this person is punctual or not but you can also get a feel for who they are by talking to them on the phone. Do they sound professional? Is there loud music blaring in the background? Are they a good listener?

Remember, a mark of a good listener is the ability to paraphrase you. Not in an annoying recorder-like-fashion but in a here's-what-I-hear-you-saying-main-points way.

People work differently and projects work best when people agree on a working style. This is especially true when collaboration is paramount. Make sure that the freelancer you hire shares your expectations about working remotely and believes in your choice of communication whether the choice is email, text, Skype chat, Google Hangouts or phone calls.

Another part of this question can involve discussing the various tools that will need to be used on the project. If you use Todoist for project to-do lists, but your freelancer uses Evernote then you will need to come to an agreement on which platform to use if your project involves shared lists. If your project requires extensive use of Hootsuite or Omnifocus, then you will most likely want a freelancer who has extensive experience using those apps or platforms

If you've written a good job post, and if they've responded with a thoughtful proposal, these core skills may have already been identified.

☛ Things to listen for: Understanding. Do they really understand your project? Core skills aren't necessarily technical skills, and it's possible a freelancer will list skills that aren't reflected in the description or the proposal. However, their response should show a firm understanding of your project or issues they may encounter.

☛ Follow-up question: "Of the three, which would you describe as your strongest skill? Your weakest?"

All good freelancers who have worked for over a year should be able to provide you with at least one reference. References, whether you actually contact them or not, can offer reassurance that the freelancer is a worthwhile investment. If you do contact the freelancer's references, you can also ask questions about what it was like to work with the freelancer. This will offer yet another perspective on whether or not the freelancer is a good fit for your project and your personal working style.

Many freelancers, like those who work on the Upwork platform, have testimonials and client feedback they can share with you.

☛ Things to listen or watch for: Highlighted qualities. Does the freelancer deliver quality work? Do they communicate effectively? Are any problems identified? Working relationships aren't always flawless, but you should feel comfortable that any issues were isolated or have otherwise been addressed.

☛ Follow-up question: "What are your top strengths and weaknesses?" or "What worked well and what did not work well in past projects?" This classic interview question gives freelancers an open-ended opportunity to be genuine while also positioning themselves as a great fit for your work. You could also ask for references.

Ask the freelancer what experience he or she has in your industry. While you may be willing to hire someone new to the industry, choosing someone with experience can make your outsourcing experience run smoothly.

Follow up with questions specifically about the freelancer's experiences that relate to your project in theme and concept. Look for ways in which the freelancer has approached similar tasks in the past.

You'd be surprised how many hiring managers skip this question. We don't encourage discounting new freelancers, as they can be equally or sometimes more equipped for the job at hand and even 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. More experienced freelancers are also used to more varied forms and levels of feedback. So if someone is newer to freelancing, try to put extra effort into sharing effective feedback in a constructive manner.

Whether you're a freelancer or looking for a full-time job, this interview question can uncover whether or not you're staying busy and working on projects to improve your craft. Use your answer to speak to your ambition, expertise and motivation.

Different people thrive in different situations. What elements of this recent project helped them excel, and what can you do to replicate them?

☛ Things to listen for: Work style. Are they able to work independently? Are they good at prioritizing? Consider how their preferred work habits fit your project.

☛ Follow-up question: "Considering that same project, what do you feel could have been improved?" As above, listen for clues that indicate their work habits.

This question cannot always be asked, particularly if you have not laid out the details or scope of work in the job description. However, this question is a great question to ask when possible because it allows you to look at the way that the freelancer approaches work. It will give you a glimpse into the freelancer's time management and organizational skills.

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 team they worked with? 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 happy working in your industry or with your team, or with you!

A formal bid letter is a great way to avoid any confusion over what's involved in the project. A phone call - which we'll talk about next - can help accomplish this also but there's too much risk for misunderstanding when it's not in writing.

And as the one hiring it's your job to communicate exactly what you need done. If you need someone to write all the copy for your site don't just say, "How much would you charge to write the copy for my website?"
A better way to ask this would be, "I need copy written for the following pages: Home, About, Services, Our Team. I need headlines on each page and will also need meta-descriptions written for each page using our keywords of Muscle Cars for Sale."

Be specific. And get it in writing.

Not all freelancers are available on a full-time basis, and if this hasn't already been discussed, it's important for you to know their availability. Many people have successful freelance businesses in addition to other employment, and you should feel comfortable that your expectations will still be met.

☛ Things to listen for: Time management. Confirm that they can meet your deadlines and communicate in a timely manner.

☛ Follow-up question: "What time zone are you in?" There are benefits to working across time zones, and often the impact is minimal. However, this will help set expectations; it's also helpful to identify hours that overlap so you know when you're both available to connect live.

You should always ask at the end of the interview whether or not the freelancer has any questions. Do not be alarmed if there are no questions. If you do a good job of explaining the scope of the project or state that details will be shared after the hiring decision has been made, then do not expect any questions. At the same time, if a freelancer asks a pertinent question that is interesting and shows that they have thoughtfully considered the project, then that freelancer should be highly considered.

Remember to add a few of your own questions and personalize the interview process. Be as thorough as possible and you will find the freelancer who is the perfect fit for your project.

► How do you think the project went?
► Do you have any suggestions?
► Do you anticipate having any other projects based on this one?
► Will this project need to be updated or revised at some point?
► If the project needs updating, do you consider the updating or revisions to be a separate project?
► Are there any other projects that I can do for you?
► How often do you need the services of a (writer/web designer/programmer/consultant)? (Choose one.)
► Can I use this project as an example on my portfolio? (If the project has gone well.)
► Would you be willing to give a testimonial on my work for my web page? (If the client is pleased.)

► What kind of business is your company in?
► How long has your company been in business?
► What is the size of your company?
► What is the company's reputation?
► What is your typical customer like?
► Who are your competitors?
► What is your address?
► What is your phone number?
► What is your e-mail address?
► What is the best way to contact you?

► What is the budget for this project?
► Who will own the intellectual rights to the finished project?
► What is the deadline for this project?
► How will you be making your payment?
► When will you pay?