9 Interview Questions to Find the Perfect Freelancer Online

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It’s usually pretty easy to spot someone who isn’t a good match for your business or project, but separating the good freelancers from the great—and ultimately selecting the best one for your project—takes careful consideration.

The interview stands as the single most important stage when considering an independent contractor. Their proposal should explain the basics: a brief introduction, how their experience fits your project, and an overview of how they’ll approach the work. But it’s the interview that brings that introduction to the next level. It’s a chance for both of you to speak candidly and see how well you’re able to communicate; you can learn as much from what someone says as how they say it.

From the project to the freelancer’s experience to their work habits, here are nine questions you may want to consider asking during your next interview.

THE PROJECT

1. QUESTION: ARE YOU ABLE TO MEET THIS TIMELINE?

If you have a tight timeline, you need to know right away whether the freelancer has a conflict. Most freelancers often manage multiple projects; this doesn’t mean they aren’t the right fit for your project, but it does mean that they need to be able to balance your project against the needs of their other clients.

  • Things to listen for: Project management skills. Are they confident about their ability to meet your milestones? What’s their approach to juggling multiple projects?
  • Follow-up question: “Is this timeline realistic?” An experienced freelancer should know whether you’ve allocated enough time, missed key steps, or aren’t leaving enough “buffer” for challenges that are likely to arise.

2. Question: In your opinion, what are the three core skills needed for this project?

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?”

EXPERIENCE

3. QUESTION: CAN I SEE YOUR PORTFOLIO OR SAMPLES OF YOUR WORK?

An experienced professional should be able to share samples of their work or tell you about projects they’ve worked on. Use your best judgement about this based on how they’ve represented themselves: Some types of work aren’t always public or easily shared, for example, and someone with years of experience may not have a big portfolio if they’ve recently made the move to self employment.

  • Things to listen for: Quality. Does their work represent the skill level and attention to detail you’re looking for?
  • Follow-up question: “What was your approach to this project?” This question will help give you more insight into how they collaborated with others, addressed the client’s needs, met challenges, or exceeded expectations.

4. Question: Tell me about a recent freelance project you’ve worked on that you’re proud of. What particularly brought out the best in you?

Different people thrive in different situations. What elements of this recent project helped them excel, and what can you do to replicate them?

  • Things to listen for: Work style. Are they able to work independently? Are they good at prioritizing? Consider how their preferred work habits fit your project.
  • Follow-up question: “Considering that same project, what do you feel could have been improved?” As above, listen for clues that indicate their work habits.

5. Question: What feedback have you received from previous clients?

Many freelancers, like those who work on the Upwork platform, have testimonials and client feedback they can share with you.

  • Things to listen or watch for: Highlighted qualities. Does the freelancer deliver quality work? Do they communicate effectively? Are any problems identified? Working relationships aren’t always flawless, but you should feel comfortable that any issues were isolated or have otherwise been addressed.
  • Follow-up question: “What are your top strengths and weaknesses?” or “What worked well and what did not work well in past projects?” This classic interview question gives freelancers an open-ended opportunity to be genuine while also positioning themselves as a great fit for your work. You could also ask for references.

WORK LOGISTICS

6. QUESTION: DO YOU HAVE TIME TO TAKE ON ADDITIONAL WORK?

Not all freelancers are available on a full-time basis, and if this hasn’t already been discussed, it’s important for you to know their availability. Many people have successful freelance businesses in addition to other employment, and you should feel comfortable that your expectations will still be met.

  • Things to listen for: Time management. Confirm that they can meet your deadlines and communicate in a timely manner.
  • Follow-up question: “What time zone are you in?” There are benefits to working across time zones, and often the impact is minimal. However, this will help set expectations; it’s also helpful to identify hours that overlap so you know when you’re both available to connect live.

7. Question: If I contract you for this project, what will you do on the first day?

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?”

8. Question: What do you feel are the keys to success when working remotely with a client?

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

9. Question: What additional questions do you have about the project or our organization?

This is a standard way to close an interview, giving the contractor the opportunity to ask any questions you haven’t covered.

  • Things to listen for: If you’ve communicated your needs well, or if the project isn’t very complex, they may not have any follow-up questions. Even so, questions about your organization or your next steps in the selection process show an active interest in your project.

One last tip: Try to conduct your interviews via video conference, using a tool like Google Hangouts. While these nine questions can help move the conversation beyond surface details, seeing each other face-to-face will make it easier to connect with the candidate and see what it might be like to work with them.


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