10 common interview questions for IT contractor jobs

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You should always expect the unexpected in interviews, and IT contractor interviews are no exception!

It never surprises me to hear some of the random questions contractors are asked during interviews for temporary technology jobs. But there are common questions that do seem to put in regular appearances. You can plan for most of them, and use the answers in future interviews.

Over almost my three decades in the contract IT recruitment market, these are the 10 most common interview questions for IT contractor jobs, plus some tips from me on how to best answer them to stand out – for the right reasons, writes Matt Collingwood, managing director of Birmingham IT recruitment agency VIQU.

1. Do you have an example of…?

Many hiring managers/interviewers will receive structured training in the ‘black art’ of job interviewing. This training will likely cover the ‘STAR’ method, which is a way of asking questions to secure evidence of a candidate’s experience. The aim is to establish ‘What did you do’ instead of ‘What would you do.’

The STAR method is an interview technique that provides a straightforward format to craft compelling stories. So if you understand how to break down your experience into the four components that make up STAR, you will give the interviewer exactly what they are looking for.

STAR stands for -

  • Situation - Set the scene by offering the necessary details of your example. Paint a vivid picture to help your interviewer understand the context.

  • Task - Define your role and responsibilities in the given situation. Clearly outline what was expected of you.

  • Action - Detail the steps you took to address the challenge. How did you navigate the hurdles? What specific actions did you implement?

  • Result - Share the outcomes of your actions. What positive impact did your efforts have? This is the time to shine and showcase your achievements.

By structuring your answers using these four elements, you're not just responding; you're providing interviewers with a digestible but insightful example of what you did.

2. What insurance policies do you hold?

Not a conventional job interview question perhaps! But for contractors, Professional Indemnity Insurance (PI) isn't just a checkbox – it's of huge strategic importance. PI provides indispensable benefits for both contractors and their clients.

Therefore, it’s a question I am hearing clients ask more and more at freelancer interviews.

If you are asked questions on this subject, it’s important you have a PI policy in place; that you know the level of cover you have, and can specify that the scope of the assignment you’re interviewing for will be covered.

PI protects clients in the following ways:

  • Risk Mitigation - PI minimises the client's financial risk, ensuring they're not left shouldering the burden if things go awry.

  • Compliance – PI meets industry and regulatory requirements, meaning projects are kept in line with legal standards.

  • Project Security - Especially in complex IT projects, PI provides a safety net for both parties, setting expectations and minimising financial uncertainties.

In short, PI is your professional armour, and clients recognise it as a mark of reliability. In fact, we had a contractor rejected at interview because he said his PSC didn’t have PI.

The client’s response? ‘No cover, no contract.’

3. Can you provide references/case studies for your previous work?

My ‘go-to’ advice for any IT contractor not achieving their freelance tech career targets is this -- create a ‘brag folder’ of case studies and references from previous clients.

Maybe keep its name to yourself, but a brag folder is an undeniably powerful and risk-mitigating tool. It ensures that no matter how much time passes, you have evidence – ideally on a client company letterhead -- of the services you have provided to the company.

Building this folder of evidence means that you don’t need to rely on individuals responding to recruitment agencies/potential clients to confirm your claims – you already have it available for them to peruse at their leisure!

With a brag folder, you also circumvent any issues around managers who worked with you no longer working for the client; new people not knowing who you are/what you did, and references becoming uncontactable for whatever reason, such as retirement or travelling.

I know many clients who have made hiring decisions post-interview solely due to the candidate’s answer to this question being extremely strong. In fact, I’ve had clients tell me, “We’re going with candidate ‘A’ because they shared lots of references and many detailed case studies of doing this work beforehand.”

The brag folder is a must-have. It gives the client confidence in your abilities and experience.

4. What is your understanding of the project / opportunity?

In advance of the interview, ensure you thoroughly read the job spec/scope of work.

It sounds obvious, but some freelance techies don’t always take the time to comb through the detail in the original job advert or tender notice.

A good recruiter should coach you through the small print and check you have a solid understanding of the role you’re interviewing for. If you don’t have a job spec or feel you have not been provided with enough detail, ask the client/agent well before sitting down.

My recommendation to contractors? Prepare examples of when you have delivered similar projects/work. Make your answer even better by including metrics - budget saved, or delivered ahead of schedule by ‘X’ days, for example.

5. What do you know about us?

I remember my first interview for a proper job. I was 21, and the interviewer asked me, “What do you know about this company?” This was back in 1997, before company websites were easily accessible. So, sourcing this kind of info wasn’t as easy as it is today.

My response? I rattled off a few things the receptionist had told me before the interview. He spent the next ten minutes ripping me apart for not doing my research. I got the job, but I learnt my lesson.

It doesn’t matter if it’s a short-term contract or something more substantial. Read the company website, research their industry and the products/services they offer, and find out who the key figures in the business are. Consider looking up your interviewer on LinkedIn to see their background and any commonalities.

I’ve had clients reject contractors because they’ve not done their research. A good recruitment agent (if you’re using one) should help. But I think if you spend any less than 30 mins doing your background work, then you’ve not spent enough time on it.

6. How much is your day rate?

A word of caution here. In our experience, as many as 10% of contractors are asked about their day rate in interviews and simply aren’t prepared for it.

The unprofessional stumbling which follows, and the awkward silence, you want to avoid!

If you’re contracting via a recruitment agency, ask the client to pick this question up directly with the agent. Say that you don’t want there to be any miscommunications.

If direct-to-client, re-iterate the day rate you’ve quoted. Never say, “I’d like £500 per day”, as it implies that you’re flexible.

Say, “My rate is £500 per day”, and then be quiet. I’ve sat in interviews and heard contractors caveat, “But I can be flexible” after quoting their rate.

As we’re keen to impress and interviews are often stressful, some clients use this as the opening to negotiate. Be prepared for this question – and when it comes, don’t blink!

7. How do you handle deadlines?

This age-old timeline question is a favourite of integrators sat face-to-face with contractors.

Clients ask this question to gauge a contractor's capacity to perform under pressure and to understand the strategies they employ to manage various work assignments. Demonstrating effective communication, organisation, time management, and collaboration skills is crucial in your response.

A textbook answer for this textbook question:

“I prioritise tasks by evaluating their deadlines, importance, and impact on overall project timelines. I break down larger tasks into smaller manageable steps and use tools like to-do lists or project management software to stay organised and focused”.

Again, you should offer examples of when you have handled assignments and tight deadlines successfully.

8. How do you manage stakeholders?

Mastering stakeholder management is key to succeeding as an IT freelancer or tech contractor.

When faced with this question, have a process and a strategy to talk the interview through your approach. Here’s a classic three-way approach for contractors managing stakeholders:

  • Comprehensive Mapping - Begin by discussing stakeholder mapping, and how you visually outline relationships and interests. Mention the utilisation of tools like power-interest matrices that gauge influence and engagement levels.

  • SWOT Analysis – Then discuss the need to assess stakeholders' strengths, weaknesses, opportunities, and threats.

  • Categorisation Criteria – Finally, talk through how you categorise stakeholders based on influence, interest, and attitude towards the project. This categorisation informs personalised engagement strategies for maximum impact.

Let’s share a real-world textbook answer/example:

In a recent IT system implementation, I identified diverse stakeholders, from end-users to leadership. Through a strategic combination of mapping and SWOT analysis, I not only identified potential roadblocks but also uncovered key champions who significantly influenced project success.”

9. What are your strengths and weaknesses?

Even as a recruiter who’s expected to ask it, I hate this question!
It’s almost like everyone has been asked it at some point, so everyone feels the need to ask everyone else they encounter.

But it’s important to be prepared for it. I estimate the strengths-weaknesses question is fired in a significant 40% of our IT contractor interviews.

It is essential to understand the significance of this question.

Employers ask it to gauge your self-awareness, honesty, and willingness to improve. They seek insights into your actions to overcome weaknesses, and your perception of qualities that make you an ideal fit for the role.

Preparation is key. Even if the question isn't posed directly, having scripted responses allows you to confidently address various interviewers and fit your script to them, the circumstances, the nature of the conversation or the nature of the role you’re going forward for.

Use the question to create insightful stories of what you’ve brought to past teams and roles. Think about how you’ve overcome challenges, turning your weaknesses into positives.

Likewise, consider how your strengths make you the right contractor for this opportunity.

10. What happened the last time you and a client disagreed?

The trap! Almost needless to say contractors, be careful here.

The big picture to keep in mind is that many contractors choose temporary work because they enjoy escaping corporate politics, so they can just focus on the task at hand.

The other side of that picture is that in most cases, clients enjoy working with contractors who are subject matter experts in their respective fields. Clients like that such contractors can come in and challenge them and their best full-timers.

Clients invariably want to hire people on a contract basis who will be comfortable disagreeing with them, and I’d go further – they want that disagreement expressed directly. Clients cannot arrive at the best solutions unless people are willing to express alternative ideas.

Therefore, if you are asked this question, the hiring manager is not asking the question to find out whether you’re going to be a difficult personality to work with; they’re looking to understand your stakeholder management. The client wants to understand your problem-solving and negotiation skills.

My top tip when asked to share a contractor-client clash? Answer by going over situations where you’ve had to persevere with difficult stakeholders. Describe the tactics you used – whether that was finding commonalities, listening, attempting to build trust, or perhaps you suggested alternative solutions? Give an example of where you successfully negotiated with a resistant stakeholder to secure a good end result.

Final IT contractor interview tips for 2024...

The common thread that runs through my recommend answers to these 10 common interview questions for IT contractor jobs is hopefully clear. Preparation and plenty of examples! Use your time wisely while getting ready for your interview by listening and actioning my suggested responses and you won’t go too far wrong. Good luck!

Written by

Matt Collingwood

Managing Director of VIQU

Matt Collingwood is the Managing Director of VIQU Ltd. an IT recruitment and project-based consultancy company with offices in Birmingham and Southampton. Matt is also the co-founder of the Recruitment Canaries, a network of West Midlands based recruitment agencies who encourage collaboration, best practice and upholding the standards and ethics of the recruitment industry.

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