Questions To Ask a Contractor Before Hiring Them

If you’re hiring a freelancer or contractor for your project, fit is everything. Get the right freelancer for the job with these thought-provoking questions.

Abby Wood


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Business Development

Abby Wood

Abby Wood

The Content Lab

Originally from Cambridge, England, Abby now lives in Ireland with her partner Nick and their border collie Bosco. A content strategist and copywriter for over 12 years, she's founder of The Content Lab (a white label content agency) and Content Goodies (providing white label content templates for agencies). She's also co-founder of Ireland Website Design (a full service eCommerce agency) and LearnRight (a white label LMS solution).

Questions To Ask
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There comes a time for many web designers and digital agencies when they need a little help on a certain project, or they have a bunch of work they just can’t fulfil in house. 

Enter The Contractor. 

Finding and hiring a contractor can be one of the most anxiety-inducing, stress-filled times a business owner can face. 

Seriously: you’ve either already got a project you need completed and you need it done right, on time, and on budget, or you need to hire a contract worker (or outsourced team) if your regular employees don’t have the skills or time to tackle certain tasks. 

But hiring a freelancer or contractor that doesn’t quite fit with your company, or doesn’t produce the quality of work you need, will only cause more stress, more problems, and more work for you – especially if you have a tight deadline.

Before I set up my content writing agency 4 years ago, I had an eCommerce agency with my partner – and got plenty of experience trying to find and hire reliable, talented contractors if we were in a pinch. 

Finding a contractor is best done in advance, before you need them (yeah I know, our world doesn’t really work that, does it?). To be sure your contractor or freelancer is a good fit for your company, you have to approach the hiring process as rigorously as you would for finding full-time employees. 

And, like any good hiring process, it all starts with a sound job description.

1. Write a (super precise) job description

Unlike a full-time employee job description, with a contractor job description you can’t cover unexpected scope creep with the usual “duties as required” line. Scope creep will cause your project to run over budget and past the deadline – which is something you definitely don’t want. 

To avoid scope creep you’ll have to be specific about the job your contractor is expected to perform and the results you expect at the end of the project.

Include the exact deliverables you want and the experience you’re looking for in a freelancer. Be as specific as you can about the project’s timeline and be ready with a clear budget when they ask you for it. If they don’t ask you for a budget – run away quickly. 

2. Do your stalking homework

After your job post is up and the candidates come rolling in, do a little online vetting aka professional stalking. This will help you get to know your contractors and help you find out if they’re the right fit for your company. 

Start with their website (they should definitely have a website) and check out their work samples. Do the designs interest you? Does the copywriting reflect a tone you’d like to see in your project? Is the development work flawless? 

Look for work samples that mirror the look and feel of your project. This will let you see if the contractor is up to the task of producing the quality you’re looking for. If you’re hiring a creative position, ask for the first draft and the final piece of work from their work examples, so you can see how much effort their previous employer had to put in to get the work completed. 

It’s also helpful to note whether the work samples reflect their ability to work on a variety of projects. If all of their work looks the same – that’s a bit of a red flag. You don’t want your project to be just another in a long line of samesy, bland templates. Look for work that showcases versatility and flexibility.

After exploring their website, investigate their social media presence. If you’re hiring a contractor for a social media or digital marketing strategy, their social presence will tell you if they’re capable of handling your project. But even if you’re not hiring them for their social media skills, it’s still a good idea to make sure they’re the real deal.

3. Ask them the right questions

Ok, so you’ve found a great candidate! Their experience fits the brief, their previous work looks impressive, and they check out on social media.

Now you’re on to the interview process! This is your chance to confirm if this freelancer/contractor:

  1. Has the right experience for your project
  2. Has the right personality for your team
  3. Is actually who they say they are

Below are some interview questions designed to get the information you need out of your interviewee. 

You’re not necessarily looking for the perfect or “right” answers to these questions. You’re looking for honest answers that reveal whether this person will suit your project and your team.

Experience questions

  • Do you specialise in particular industries or niches?
  • How do you deal with writing/designing/building things you’re not an expert in?
  • What kind of work do you do most often?
  • Do you incorporate SEO best practice into your work?
  • How long have you been doing this for?

Operational questions

  • How much do you charge? How do you charge (per design, per word, per hour?)
  • Are revisions/changes included in your pricing? If so, how many?
  • Do you have a minimum order amount?
  • Do you require a deposit?
  • How much lead time do you need?
  • What are your working hours?
  • What do you need from me/my time to complete the work?
  • Who owns the completed work?

Culture-fit questions

  • What’s your philosophy about what makes [insert their speciality here] great?
  • How do you react to/process feedback?
  • What kind of work do you love to do/what kind of projects are you not a fan of?
  • What can I do to make this job go smoothly and give it the best possible chance of success?

These questions, especially the cultural-fit ones, are intended to be thought-provoking for the freelancer and revealing for you. They help you interact with your contractor, see how they might react to not knowing an answer, and show you how dedicated they are to their work. 

Most importantly, they tell you whether their professional experience, attitude, approach and personality will be an asset to your project and your team.

4. Get an insight into their working style

Wrap up the interview by asking to speak to one of their clients or read some unfiltered testimonials (Google Business Profile is your friend on this one). Hearing glowing reviews from past clients is always a green flag when it comes to hiring a contractor, but knowing what it’s actually like to work with them will give you great insight into what your experience with them will most likely be. 

5. Give them a small (paid) trial run

You can ask all the questions in the world, but nothing can replace actually working with someone. 

If they’ve passed all your questions, try them out on a small task before hiring them for a full project. Set a trial piece with a limited, defined scope and clear turn-around time – it’ll give you confidence that you’re hiring a freelancer who can meet goals and deadlines with high quality work that’s ready to send on to clients.

Ultimately, fit really is everything

I keep mentioning that a contractor should fit in well with your team. That’s not fluff: it’s a reality of working together. 

Bad personality fits won’t result in a successful project. Work can grind to an unproductive halt thanks to miscommunication, misinterpreted deliverables, and missed deadlines – and a personality clash. 

I personally refuse to work with assholes, and you should, too. A good fit is essential to producing great work together. If you’re hiring a long-term contractor and you don’t enjoy chatting to them during the interview process, you won’t enjoy working with them. Keep looking – the right freelancer is out there, and your team and project deserve them.

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Abby Wood

Abby Wood

The Content Lab

Originally from Cambridge, England, Abby now lives in Ireland with her partner Nick and their border collie Bosco. A content strategist and copywriter for over 12 years, she's founder of The Content Lab (a white label content agency) and Content Goodies (providing white label content templates for agencies). She's also co-founder of Ireland Website Design (a full service eCommerce agency) and LearnRight (a white label LMS solution).

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