Employer Resources

The Best Contractor Questions to Ask at an Interview

Pinterest LinkedIn Tumblr

This is it – you’re sitting down for a one-on-one interview with your short-listed freelance candidates and have limited time to make an important decision about whether they’re a good fit.

No pressure.

We’re all familiar with the standard interview questions, but which gives you the most valuable insight to make a quick judgment?

Here we’ll explain the best contractor questions to ask at an interview to understand the quality of your applicants.

“Tell Me About Your Freelance Career”

Start with something easy – but listen carefully to the answers.

Contractors almost exclusively work remotely, so if your project requires intensive collaboration with other team members, they’ll need to know how to manage those communications.

You can rephrase it any number of ways:

  • How long have you been working as a contractor?
  • What made you decide to be a freelancer?
  • Tell me about some of your biggest projects.
  • What do you enjoy about being an independent professional?

Now, you might want to juggle those suggestions around a bit depending on the nature of the role, but the question is always relevant.

If you want a contractor who can jump right in and hit the ground running, their experience is just as vital as the skills they bring to the table.

“What Do You Love About Your Work?”

Number two – look for the twinkle of excitement, the passion, the drive that tells you this contractor is going to blow you away.

Asking an interviewee what they love is an open market for them to expand on their knowledge.

If they struggle to answer, it’s likely a red flag that the work is out of convenience, and their heart isn’t really in it.

On the contrary, you’re probably looking for:

  • Freelancers who enjoy the challenge of working with different clients.
  • Independent professionals with a wide range of experience.
  • Or perhaps, new freelancers keen to showcase what they can achieve. 

There’s no right or wrong answer, but tapping into emotional responses is an excellent way to determine whether your candidates are cut out for the task.

“How Do You Measure Your Success?”

This is another open-ended question and a significant one.

Success is what drives our work, and we all measure that a bit differently. Answers will, of course, depend heavily on the job, but could be:

  • Hitting KPIs, measurable results, and performance targets.
  • Agreeing on success markers with the client (i.e., you, or the company you represent).
  • Producing work that meets the businesses’ satisfaction.

Like so many great interview questions, the trick is not to lead your candidate to the response they think you want to hear.

For example, let’s say you’re hiring an SEO expert. 

You’d expect their successes to be measured by search engine rankings, audience volumes, bounce rates, or something along those lines.

So, if you ask, ‘do you monitor audience volumes to determine whether your work is a success?’ – they’re going to say yes.

Making it open-ended allows a skilled freelancer to impress you and often highlights a weakness in a contractor who tends to hit and run; without really caring what the long-term outcomes might be.

“What Do You Do If You Miss a Deadline?”

Finally, initiate a conversation about deadlines.

We hear you; it seems counterintuitive to start even hinting that delays are possible – but even the best contractor is human, and you want to know how they deal with challenges.

Timescales and turnaround times are crucial in any contractual agreement, so they’re worth addressing right away.

Here’s a tip – always look for the contractor who confirms delays are sometimes unavoidable.

It’s tempting to go with the interviewee who says they’ve never been late, would never miss a deadline – but that’s not being honest.

The question isn’t about delays at all; it’s about communication skills.

A contractor, who can confidently chat about how they’d identify potential delays before they become a disaster, is a way better professional than someone who pretends it can’t happen.

Freelancers who ask for support, share difficulties, and keep in touch at every step of the way are usually the best hires out there.

Write A Comment