Interviewing Freelancers: 7 Questions for Finding the Right Fit

October 27, 2023 Summer Foote

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, engaging  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 independent talent 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.

The ultimate decision maker should conduct the initial screening and then loop in other stakeholders for the second interview—otherwise, you’ll waste a cycle. Seasoned talent often use interviews as pre-work sessions, so spend time considering the talent’s approach to the problem. Remember, these seasoned professionals are fully equipped to help you scope your project and craft the best solution. The proposal a candidate delivers in the interview can be used to inform the final project scope when it comes time for contracting.

As long as the right people were brought in for the second call, there shouldn’t be a need for a third. If you think there is, just remember that for every candidate you interview, they’ve got several other clients interviewing them, too.

Interviewing independents: Questions to screen for the right skills

Here are seven questions to help ensure a good 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 expert 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. When have you tackled a problem like this before?

Look for a story, not a general philosophy. Details about a time when the talent 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. Make sure to specifically note when they worked on it—and whether it’s a dated experience.

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 talent to articulate why and how that expertise is relevant to your project.

4. Given your prior experience, what challenges do you anticipate?

The natural follow-up to this is to also ask how they plan to overcome those challenges. Together, their answers should demonstrate both critical analysis and problem-solving skills.

5. When and where have you performed a similar role?

When you engage independent talent, 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?

6. How will you work with our team?

When you bring on an independent professional, 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 independents are used to collaborating with 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.

7. What do you hope to accomplish in your first two weeks in this role?

This question sets an expectation for immediate progress while offering insight into how well the candidate’s priorities align with yours. Though independent talent are ready to hit the ground running, look for answers that focus on specific goals and tasks, not end-project results that are unlikely to be realized so early on.

Making interviews more valuable

If your independent talent interviews are simply Q&A sessions, you won’t get the best sense of your candidate. Instead, utilize the time to discuss the project details, scope, goals, deadlines, and other details you established in the project scoping phase.

Here are some other best practices to help you get more out of each interview:

  • Have consistent interview questions for each candidate, so you can get a clear overview of your applicant pool and make comparisons.
  • Limit interviews to two or three stakeholders who will work directly with the candidate. This ensures that the people who know the project best are the ones making the decision.
  • Ensure that everybody’s expectations are established and vocalized. This will minimize the potential for miscommunication.
  • Discuss the project schedule, your time-of-day requirements, and any limitations on their availability, such as preexisting obligations that may affect the project start.
  • Ask yourself “Are their answers convoluted or straight to the point? Can they define success?” This can shed light on the way the candidate approaches work and how they will complete deliverables for the project at hand.
  • Don’t hesitate to ask for feedback from references.
  • Build in or allow for negotiation time during the interviewing process.

To save yourself additional time, as soon as you find a candidate that’s a good fit, it’s best to move forward and get the ball rolling vs. interviewing a dozen+ what-ifs and introducing unnecessary delays.


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 talent for each engagement. At BTG, 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.

Looking for more tips? Get our Guide to Working with On-Demand Talent

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