Freelance

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.

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.

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.

Many employers believe that people who are passionate about interests outside the office typically perform better on the job. Hiring managers want to know what drives you - whether it's mentoring kids or making cootie catchers. Who knows, maybe you'll have a hobby or interest in common.

This question will help you understand how the freelancer works and how you can help the freelancer excel on your project. Pay attention to what the freelancer liked about the project and the style of working. If you can mimic the working environment and add the same sensibility or creativity to your own project, then you are more likely to receive the freelancer's best work.

To follow up, ask the freelancer what they might have changed if they were given more time or if they were able to revisit the project? It is always interesting to see what a freelancer might have done differently on a project whose outcome they already love.

This question is less about specific tasks and more about how they approach and prioritize the work.

☛ Things to listen for: Organization and consistency. Their response should reflect your earlier discussion including their project management skills, understanding of your project, and ability to prioritize.

☛ Follow-up question: "Given your understanding of the project, are there any potential problems we might run into and how would you address them?"

You're going to be working with this person for a given amount of time, so you should enjoy working with them. Having common or complementary interests make this easier. Get to know what makes your freelancer happy, what they enjoy doing and how they spend their time outside of work. You'll want to hire someone who has a healthy sense of work-life balance so that they don't burnout and have to quit.

Everyone has a different approach to getting work done, particularly when you aren't working face-to-face. Are your priorities in sync?

☛ Things to listen for: Communication style. Does their response reflect an understanding of remote work? For example, collaboration, good communication, and accountability can be critical in any freelancer-client relationship. How do they manage these challenges?

☛ Follow-up question: "What tools do you use to manage your work?" There are many different tools available and you'll want to rely on your freelancer to determine and provide the tools needed to get your work done efficiently

This question is an excellent question because it allows freelancers to share their most valuable skills, but in relation to the scope of your project. Freelancers should be able to describe how they can help you and your project succeed through their skill set.

We like this question because it gives you an opportunity to differentiate between candidates and to see whether or not the freelancer understands what it is that you need in the project. In some cases, you may even learn about new skills that you did not know the freelancer possessed. Ask the freelancer to describe the skills and to detail why those skills would be useful throughout the project.

When you hire a freelancer, you are hiring someone who works on an as-needed basis for a number of clients. It is unlikely that you will be the freelancer's only employer and it is wise to make sure that the freelancer has enough time for your project. If the freelancer wavers while answering this question or is unable to commit to the timeline then you may want to look elsewhere.

With that said, you may find that the top tier freelancers are booked several months in advance. If your deadline can be extended or is not written in stone, then you should consider these freelancers. This is especially true for projects that require freelancers with more than a decade of experience.

If the answer is "no," then perhaps it would be better to part ways sooner rather than later. However, if you know that you can perform well on the project, tell them how and give specific examples of how you have performed on similar projects in the past.

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.

Hiring managers want to know that you have done your research and are familiar with their work - and that you have an educated opinion. Share your honest thoughts clearly, tactfully and succinctly.

In addition to revealing your approach to creative work, your answer can show how you view yourself, how you think others perceive you and where you think you fit within an organization. How you describe your style - quirky, clean, bold - also can help hiring managers determine if your design aesthetic will complement (or clash with) the company's branding.

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.