Interviewing and Evaluating Freelancers: The New Frontier of Hiring Just-in-Time and Virtual Talent

By Paul Falcone July 18, 2018
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This is the first in a two-part series of excerpts from the newly published third edition of Paul Falcone's best-selling book, 96 Great Interview Questions to Ask Before You Hire (Amacom/HarperCollins, 2018).

The so-called "gig economy" is changing the corporate landscape. Individuals are performing just-in-time professional services for companies on an as-needed basis, freeing up to portfolio workers and giving employers flexibility. The trend in hiring freelancers and remote workers is growing significantly, and we hope the questions suggested here will help you make stronger selection decisions when evaluating talent for these types of roles. This is intended to be a starting point to help you formulate ideas for interviewing and reference-checking scenarios. The goal is to save you time and help you hire more effectively across this broad spectrum of workers.             

According to Charles M. Vance, professor of management and human resources at Loyola Marymount University in Los Angeles, "53 million Americans—one in three workers—derive some form of income outside of the traditional 9-5 setting and are considered contingent labor or freelancers. However you define it, freelancing is part of a huge global 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 that you may need to bring aboard temporarily to complete your project or at least particular aspects of it," Vance advised, "give ample thought to the vetting process to define and determine who might best meet your project-specific needs on a finite, short-term basis."

"Some of the critical areas you'll want to touch on include prequalifications, communication style and performance expectations, fee structure, and successful completion and follow up," said Angela Gardner, partner, media, entertainment and digital practice at executive search firm Heidrick & Struggles in Los Angeles. "It's critical that you address these key issues before any work is begun, and freelancers and consultants will respect your level of detail and diligence in ensuring a healthy and transparent onboarding, interim and follow-up structure." 

Consider some of the following queries as you review your prospective freelancers.  

Initial Considerations and Prequalification

  • How much time do you have to dedicate to the demands of this project? 
  • Do you anticipate having any competing projects or priorities while working with us? 
  • 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 to launching a project in terms of strategy, effectiveness and efficiency? 
  • What's the typical size of company that you support, and what niches (types of industries, nonprofit, international, startup, etc.) 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?  

Communication Style and Performance Expectations

  • How do you ensure that communication, collaboration, and accountability are part of the consultant-client relationship? 
  • If you win this project, how will you draft 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? 
  • What would you do if you think 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 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?  

Measurement, Accountability and Fee Structure 

  • Of all the projects you've worked on, which one mirrors this one most closely? What were the end results of that project, and what types of similar challenges could we expect? 
  • On a scale of 1-10, 10 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 stay on top of your work and remain committed to your project milestones?  
  • What are the go-to technical tools that you use daily?  
  • How do you structure the pricing for your services, and what is generally included or excluded from your basic fees?  

Successful Completion and Follow-Up

  • What percentage of your projects comes in on time and under deadline? 
  • 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? 
  • On a scale of 1-10, 10 being the highest, how interested are you in pursuing this project?
  • How are payment installments tied to interim project completions? When is the remainder and full amount due?  

Employee engagement, self-motivation and accountability are standards that strong interviewers set for those they evaluate at all levels—whether full-time or flexible and contingent. Look for no less among those that fulfill just-in-time roles. After all, depending on your organization's primary product line and service delivery model, such flexible workers and working arrangements can provide you with significant advantages and opportunities in the burgeoning virtual economy.

Paul Falcone is vice president of HR at the Motion Picture & Television Fund in Woodland Hills, Calif. This is the first in a two-part series of excerpts from the new, third edition of his best-selling book, 96 Great Interview Questions to Ask Before You Hire (Amacom/ HarperCollins, 2018). Part two will cover interviewing and evaluating remote employees.

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