Freelancer Interview Preparation Guide

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