Hiring a contractor of any discipline is not without its risks, but then that’s not so different to hiring a permanent member of staff, is it? The difference with a contractor is that you’re paying more over the short term and expecting a higher standard of result.

After all, no hiring manager wants to handhold when they’re spending hundreds of pounds a day for an expert, do they? But, if you get it right, you can reap short- and long-term benefits from your freelancer hire. A project completed on time and to spec, plus a lot of expert knowledge transfer to your team with some fresh thoughts about how to handle future work.


To help make sure your next contractor hire gives you all this, we have put together a list of the best questions to ask before you hire.

Why Hire a Freelance Developer?

Before we launch into our questions, we want to answer one that might have popped into your head already. Why hire a freelancer in the first place?

Well, no one is hiring the contractors on wellpaid.io without a very good reason. Top talent does not come cheap, but an experienced contractor is a worthy investment in many circumstances.

Critical project stalled

Businesses are constantly pushing the boundaries with the projects they are trying to deliver internally and to clients. Business-critical is rapidly becoming business-as-usual, and any delay could spell disaster. Bringing in an experienced contractor who can steady the ship in any storm will go a long way towards keeping projects on track and keeping stress levels amongst you and your team at a (relatively) safe level!

Need for Flexibility

Imagine a client wants you to deliver a huge piece of work for them, but they need the new application to work with their archaic, proprietary, or highly niche systems? To avoid having to choose between hiring a whole new member of staff specifically for that part of the work, or turning down the entire project, you could hire someone with the right skill set for a week and be able to deliver a turnkey project while keeping your costs manageable!

Added Value

Yes, it might sound like a cliché, but adding value is something that experienced contractors can do, and it can be a godsend for less experienced teams and start-ups. The best contractors will leave a lasting impression by sharing their wealth of knowledge with your staff and guiding you on best practices that will help increase your success on future projects.

These are just a few of the many examples of why you might want to hire a freelance developer. If you're already looking for one, you are probably already acutely aware of why you need them!

If any of these sound familiar, read on to discover the 10 freelance developer interview questions you should ask before hiring a tech contractor to make sure you don’t “just” hire someone good, you hire the best!

10 Developer Interview Questions to Ask Before You Hire a Tech Contractor

Without further ado, we present the wellpaid.io list of 10 questions you should ask before hiring a freelance developer. Not all of these are technical questions or are specific to freelancers, but they’re all very relevant and useful, so consider them as potential additions to your interviewing arsenal!

What’s Your Rate?


Let’s get the awkward one out the way first, shall we? The rate conversation can be a minefield, especially if you’re dealing with a third-party recruiter (often they’ll try and ban the conversation between you and the contractor altogether) or hiring remotely.

But this should be one of the simplest questions of all. After all, you know your budget, and the contractor knows their rates! When hiring with wellpaid.io you can search and filter results based on your budget, making this step an absolute breeze.

What are Your Impressions of Our Company?

This is a twist on the classic “what do you know about our company” that invites your candidate to share their thoughts on what they know about you.

This should give you some insight into the level of research your contractor has done about your company as well as what they might be able to bring to your project over and above their expertise in coding, design, or development.

What Languages/Products Do You Prefer & Why?

We all play favourites, it’s a universal thing whether you’re in design, engineering, DevOps, management or any other tech-related niche. So, your contractor will almost certainly have their preferred set of tools.

Knowing what they are most comfortable with helps you to identify how good a fit they could be for your team. It may also clue you in about other areas they could help, be it on the current project or something you have in the pipeline.

What’s The Most Important Thing to You When Deciding Whether to Take on a Contract?

This is a useful question to help you identify what motivates your contractor. Two big reasons why this is an important question to ask before hiring:

  1. You learn how risky it is to hire them – if they are motivated purely by money then what’s stopping them from jumping ship when a juicier contract comes their way?
  2. You find out the right levers to pull if you find yourself in a bidding war for this person’s time and effort – especially useful if you know the person sitting opposite you is the absolute best you will find!

How did Your Last Contract Go?


A nice, open-ended question here, the answer to which should give you some insight into how good your potential contractor is at reviewing their own performance and being honest about areas they may need to work on.

Contractors must be self-aware enough to review their own performance honestly. To a degree, they are their own managers, so getting a sense of how they managed themselves on their last contract is helpful.

If you don’t get quite enough info from their response, try this follow-up question…

Would You Have Done Anything Differently on Your Last Project?

Having a project run completely smoothly from start to finish is a rare, almost mythical occurrence. There is almost always room for improvement and lessons to be learned.

Asking this question should fill in any gaps you might have about your contractor’s ability to critique their own efforts.

How do You Keep Your Skills up to Date?

Again, this goes back to the need for contractors to be their own managers. Part of a manager’s job is to keep their team well trained and widely literate in their area of expertise.

Contractors are not short of options when it comes to keeping their developer skills sharp. Many attend seminars, either in person or online, while others prefer online courses and other types of e-learning. Some tech contractors like to work on personal projects in between contracts to ensure they stay at the top of their game.

There’s no right or wrong answer here, but if this question draws a blank look and no response then you could consider that a bit of a red flag!

Give me an Example of a Time You Disagreed with a Co-Worker and How You Resolved the Situation

You should take the time to ensure your contractor has the soft skills needed to work effectively within a team as well as the technical know-how. Dispute resolution is one of the most useful of these soft skills to have on a project team, especially for a contractor whose entry onto the project could ruffle some feathers amongst your permanent employees.

What Open-Source Projects have You Worked on?

Open Source

There are many reasons why developers might choose to contribute to open-source projects:

Builds their portfolio

Gives them the chance to learn and share their own knowledge

Enables them to connect with like-minded people

Why would you as a hirer be interested in this though? Well, for one thing, involvement in open-source projects is a good indicator of a contractor’s commitment to their craft, and a good indicator of the quality of their work. For another, there is a chance you could have come across some of their work already and don’t know it yet!

If a contractor has not worked on any open-source projects then that’s not necessarily a red flag, but open-source experience is certainly a nice-to-have and could give you an idea of other ways they could help you and your team.

Are You Happy Working Outside IR35?

The introduction of the updated IR35 rules meant more complexities to the hiring process. If you already know you are looking for outside-IR35 contractors (which is usually the least expensive option), it is important to ensure the tech contractor has the same preference as you. Like the question of rate, this is another potentially awkward conversation if left to the later stages of your process. Again, it’s best to cover this off as early as possible.

Luckily, with wellpaid.io, you can avoid this potentially awkward conversation altogether, since you can be sure all contractors prefer working outside IR35. Our platform is focused entirely on outside-IR35 contracts, which ensures you and your tech contractor candidates are on the same page in this matter – right from the start, before any other project discussions.

How to Find the Best Freelance Developers

A great contract engineer

Cultivating your talent pool is essential if you want to consistently find the best contractors in any discipline, and tech is no different.

With wellpaid.io you get access to a selection of premium contractors that you can message freely. Our job postings ensure that your contract roles are shared with the best candidates, plus you get access to our extensive network and database of thousands of engineers, designers, developers, architects, testers and much more.

If you want to de-risk your contract hiring process and save time and money, sign up for a hirer package and benchmark us against your other talent resources. If you want any more info about how wellpaid.io can help make your job as a hirer easier, please contact us on LinkedIn or via the website!