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4 Types of Interview Questions to Vet Freelancers

Executive Summary

In this new corporate landscape, there has been a significant change in the way companies and employees partner together. With this comes a necessary shift in the hiring process.

  • Today, 53 million Americans, one in three workers, are considered Freelancers.
  • Utilizing independent contractors may bring flexibility and cost savings to employers, but it also comes with its own set of challenges.
  • Before onboarding a freelancer, make sure to take your time to understand their availability, background, willingness to collaborate, time management skills, and communication skills. Asking the right interview questions will tell you if they’re a solid fit for your company and your project’s needs.

It’s been called the on-demand economy, the 1099 economy, the peer-to-peer economy, and freelance nation, but both the government and commerce sectors seem to be settling in on the term gig economy to describe the large-scale trends in employment that are defining the current generation. You’ll hear terms like solopreneurs, free-range humans, and portfolio careers. Whatever nomenclature you opt for, this tectonic shift in the social contract between workers and the companies that employ them could be viewed as either inherently freeing and positive or insecure, vulnerable, and downright scary. What we do know is that some 53 million Americans—one in three workers—derive some form of income outside of the traditional nine-to-five setting and are considered Freelancers.

The first picture these terms conjure up is of skilled professionals opting to pick and choose the work they engage in: well-educated millennials looking for creative outlets for their productive talents and measuring themselves in terms of their concrete contributions and results; individuals willing to forego job security for the possibility to choose where, when, and how they work, while having enough time and opportunity to travel and otherwise disengage from the workplace. This optimistic snapshot of solo contributors feeling fully engaged in their work and making just-in-time, creative contributions to the employers they choose to support is accurate for some. The counterreality is that far too many U.S. workers were displaced after the Great Recession of 2008 and are having tremendous difficulty regaining traction in their careers because of massive cuts in middle-class jobs—traditional roles that defined prior generations and that offered job security, benefits, and retirement options that have now disappeared due to outsourcing, offshoring, and mergers and acquisitions, created primarily by technological advances and globalization.

However you define it, freelancing is part of a huge economic and cultural shift. Whether you see this as helping U.S. businesses or gutting the fabric of American society, this part-time work model and on-demand workforce is a new fact of life and force to be reckoned with.

Depending on the types of projects you need completed and the types of independent contractors you may need to bring aboard temporarily in order to complete your project or at least particular aspects of it, employ some of the following questions to help you define and determine who might best meet your project-specific needs on a finite, short-term basis.


  • How much time do you have to dedicate to the project demands of a program like this?
  • In terms of your availability, do you anticipate having any competing projects or priorities while working with us over the next [ninety] days?
  • Based on your understanding of our needs, how can you help our project succeed and what, if any, obstacles or roadblocks can you foresee?
  • What is your general approach toward launching a project in terms of strategy, effectiveness, and efficiency?
  • What’s the typical-size company you support, and what niches (types of industries, nonprofit, international, startup, and the like) do you generally serve?
  • Which elements from your portfolio bear closest resemblance to the project we’ll need you to work on for us?
  • What do you think of the current marketing and creative materials on our website?


  • How do you ensure that communication, collaboration, and accountability are part of the freelancer-client relationship?
  • If you win this project, what will be your general approach to crafting a roadmap to success? What would you do on your first day of work for us?
  • How would you describe your design style? How do you help clients determine if your design aesthetic will complement the organization’s branding?
  • How would you generally handle it if you suspected that you might miss a deadline? How much advance notice can we expect? Likewise, do you feel our timeline is realistic?
  • How do you typically measure and communicate results, especially in terms of key performance indicators (KPIs) and intermittent milestones that you set for yourself?
  • How would prior clients grade you in terms of your balance between quality and volume? How about your working relationships and communication style?


  • Of all the projects you’ve worked on, which one mirrors this one most closely? What were the end results of that particular project, and what types of similar challenges could we expect?
  • On a scale of one to ten, ten being the highest, how challenging is this project relative to others you’ve worked on? Is there any part of this project that you’re not that familiar with or where you might need to rely on additional resources or subcontractors?
  • How comfortable are you with troubleshooting connectivity issues? How do you generally troubleshoot problems on your own?
  • Tell me about your remote project tracking experience. How do you tend to stay on top of your work and remain committed to your project milestones?
  • What are the go-to technical tools that you use on a daily basis? [Follow-ups] We use Skype/Hangouts/Slack, etc. How familiar are you with that? How do you typically use these tools to increase productivity and build relationships when working remotely?
  • How do you structure the pricing for your services, and what is generally included or excluded from your basic fees? [Alternative] Here’s how we set our fees and accounts-payable processes. [Describe.] Does that sound reasonable to you?


  • What percentage of your projects comes in on time and under budget?
  • How would you envision the finished product if you’re fully successful in this assignment?
  • Who will own the intellectual rights to the finished product? [Alternative] Our agreement would need to stipulate that we own the intellectual property for the work you create for us. Is that agreeable to you?
  • On a scale of one to ten, ten being the highest, how interested are you in pursuing this project timing-wise and in terms of building out your project portfolio?
  • How do you tie payment installments to interim project completion signposts? When is the remainder and full amount due? [Alternative] This is how we schedule installments and final payment. [Describe] Is that acceptable to you?

The gig economy is changing the corporate landscape in terms of just-in-time professional services that individuals can provide to companies as needed—providing freedom to portfolio workers and flexibility to employers but challenges in terms of workplace regulations, worker protections, and benefits portability. Likewise, remote employment is on the rise because of technological improvements that allow for distanced service delivery, bringing with it greater flexibility in corporate hiring practices and workers’ career-management goals, yet requiring a different set of interviewing, onboarding, and leadership skills.

Excerpted with permission from 96 Great Interview Questions to Ask Before You Hire by Paul Falcone, copyright Paul Falcone.

Bring It Home

Hiring a freelancer comes with an entirely different set of challenges. For example, I once hired a freelance designer to design a logo. Having been so excited to have found him, I failed to ask any questions other than to see his portfolio. Weeks went by without a word from him or an answer to my emails. Finally, three weeks after the project was due, I got an email from him with some sample logos. It was my first and worst experience in hiring a freelancer.

On the other hand, this past year, I had to hire a freelance illustrator for a client’s project. Though I was thrilled at the prospect of utilizing her talent at a rate that couldn’t be beaten, I didn’t rush into the partnership. I’d learned my lesson. Thankfully, she was disciplined, driven, and was able to complete the work on time without me looking over her shoulder. With the right questions asked at the start, it was a win-win for us both.

What has your experience been like when it comes to hiring freelancers? What kind of interview questions have you found that tell you the most about these potential independent contractors? Join the conversation below to share your insights!“~ HarperCollins Leadership Essentials

Paul Falcone

Paul Falcone is an HR executive who has held senior-level positions with Paramount Pictures, Nickelodeon, and City of Hope. A long-time contributor to HR Magazine, he is the author of many bestselling books, including 2600 Phrases for Effective Performance Reviews. He lives in Los Angeles.

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