Interviewing Freelancers: 5 Questions For Finding the Right Fit

interviewing freelancers - job candidates

At Business Talent Group (BTG), we’ve seen the rise of high-end independent talent power a new path to organizational agility and performance, and the remote work revolution is only accelerating that trend. In fact, a recent Upwork study found that 3 in 4 hiring managers will maintain or increase their engagements with independent talent 3 in 4 hiring managers will maintain or increase their engagements with independent talent 3 in 4 hiring managers plan to maintain or increase their engagements with independent talent.

Whether you need a project manager to oversee a new initiative, an interim executive to lead through a critical time period, or niche expertise to capture a very specific opportunity, hiring independent talent is a fast, flexible, and low-risk way to access the skills you need precisely when you need them. Bringing on independent talent can be inspiring and rewarding for everyone involved, but you'll want to make sure they are a good fit in the interview process.

Interviewing freelancers is different from screening permanent hires. Why? For one, it’s more situation-driven. You’re not looking for long-term growth potential or executive ambition. You’re looking for someone who can fit into your company’s workflow and culture and perform a specific task.

To identify candidates who will contribute to the overall success of your initiative, you must first rigorously define each role and the expertise you need to fill it. Then, you can start to assess people based on those criteria.

interviewing freelancers: how to screen for the right skills

Here are five questions that will help you get the best fit.

  1. Why are you interested in this project?
    Just as you might ask a potential employee why they’re interested in a job, you’ll need to know what interests an independent consultant about your particular project. Try to steer the conversation toward specifics, which will help you assess whether the candidate’s vision aligns with your project goals.
  2. Have you tackled a problem like this before?
    Look for a story, not a general philosophy. Details about a time when the consultant helped past clients overcome a similar challenge are far more valuable than generic platitudes about the importance of making sure the whole team is on the same page.
  3. What is your level of expertise with regard to (a critical component of the project)?
    Many projects require specific expertise that you’ll need to be able to evaluate. You should also ask your consultants to articulate why and how that expertise is relevant to your project.
  4. When and where have you performed a similar role?
    When you engage independent consultants, you’ll need to understand how their leadership abilities align with your project goals. Be specific about what you need them to do. Is it detailed expertise you’re after, or do you need more abstract skills like the ability to synthesize information, inspire trust across multiple stakeholders, or develop a storyline? Will they be leading an internal team or working on their own?
  5. How will you fit into our team?
    When you bring on an independent consultant, it’s essential that they hit the ground running. Culture fit is a big part of this, as communication failures and incompatible personalities can exacerbate existing problems—or create new ones. Fortunately, many independent consultants are used to integrating into new teams and adapting to their work styles. But don’t be afraid to assess how well you communicate and get along with potential new resources.


According to Kelly Services, 64% of global talent managers are already using free agents, and consider them “the new normal.”

Yet misconceptions still exist—especially at the high end. Here are a few of the most pernicious.

  1. They’re too senior to get their hands dirty.
    Don’t judge independent consultants by their previous job titles or assume they’re too senior to want to join your team in the trenches. Often, independents chose that path because they enjoy a little hands-on analysis—and prefer doing work to talking about it.
  2. If they were that talented, they would be in a full-time role.
    Remember that 70% of independent workers are independent by choice—and even more at the high end. They value autonomy and flexibility, and they report greater job satisfaction than those in traditional roles.1
  3. They need to be persuasive to succeed.
    Some people are good at giving pitches; others aren’t. Give them the benefit of the doubt, rather than disqualifying them outright.


Overwhelmed by the prospect of interviewing an endless stream of candidates? Consider working with an on-demand talent partner that combines the selection of a marketplace with more personalized services that ensure you’re getting the best consultants for each engagement. At Business Talent Group, for instance, our dedicated in-house team curates and vets our talent to deliver the right resources for your project—all at the best market pricing available. We can even pre-build consulting teams to tackle larger projects. Contact us to learn more »

Working With Independent Consultants

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About the Author

Leah Hoffmann

Leah Hoffmann is BTG's Content Strategist. A former journalist, Leah worked for and The Economist before joining BTG. She is passionate about clear thinking, sharp writing, and strong points of view.

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