‘Why Should We Hire You?’ How to answer as an IT contractor

It’s right that ContractorUK readers know about the ‘hot’ IT contractor skills of 2025.

It’s also right that any potential New Year 2025 job search is carefully weighed up, in the shape of questions to ask yourself BEFORE you go looking – or not – for a new temporary IT role.

But let’s say you opt to make the jump and you get to the first stage, it’s got to be right, too, that you know how to answer the age-old, arguably most common tech interview question -- “Why Should We Hire You?”

Unimaginative, original, even IR35-ignorant

Granted, it’s not imaginative or original, writes Matt Collingwood of technology recruitment agency VIQU.

Worse still, “Why Should We Hire You?” irritates external IT contractors for being a question once confined to internal permies.

But with interviewers today not always knowing their freelancers from their full-timers, and since the IR35 off-payroll working rules forced many bonafide commercial contractors to work and suffer tax on a full-time employed basis, I’d estimate 90% of IT contractor interviews still pose “Why Should We Hire You?” or a close variant of it.

Here, exclusively for ContractorUK, I want to suggest how to answer “Why Should We Hire You?” in a way that won’t compromise your integrity as an independent contractor. And it’s a way of answering that also should both work in your favour at the same time as providing an honest and relevant account of who you are, and how you do it.

‘Engaged’ not ‘hired.’ Fair enough, but to the interviewer, it’s the same

To reiterate, you would be forgiven for thinking “Why Should We Hire You?” feels like a weird question to ask a freelance IT contractor. After all, IT contractors tend to be ‘engaged’, not ‘hired.’

But it’s still important for you -- the candidate -- to have an answer formulated that acts in your interests and catapults you towards a successful outcome.

So ‘Why Should We Engage You?’ is; for the purposes of this article and in the interviewer’s mind, the same question.

The point is that the decision-maker wants you to articulate why their organisation ought to take on YOU, not the next contractor they’ll interview or the previous candidate who arrived before you and aced the technical test.

Replies not to repeat to ‘Why Should We Hire/Engage You?’

These are some of my ‘favourite’ responses I’ve personally heard in interviews to this age-old ‘Why…’ question.

But I caution you -- these responses are not necessarily memorable for the right reasons!

Interviewer: “So finally, why should we hire you?”

Interviewee: “I haven’t said I’ll take the job yet; why should I work for you?”

Interviewer: Straight off the bat, we’d like to ask – why should we hire you?

Interviewee: “I think you need me more than I need you; can you tell me why I should even be interested in this role?”

Now, these answers might be brutally honest and valid (in some cases).

But both are invariably not going to win over the interviewer and secure the contract.  Most likely, any answers similar to the above italicised two will be taken badly and will give the interviewer the impression that you’re overconfident (even arrogant), and that you’ll be unlikely to fit in well or work in alignment with the existing team.

To form your own ‘Why Should We Hire You Answer,’ understand the engager’s distress

In many but not all cases, contractors in Computing/IT can be considered as a ‘distressed purchase -- one made by the organisation out of necessity rather than choice.

Maybe an urgent project has fallen behind.

Maybe some permanent staff have left unexpectedly.

Maybe there’s a skills gap that the organisation simply can’t plug internally.

Tied to this, decisions in business are often self-motivated; someone’s promotion, reputation, or even their job may be at stake.

A good recruitment agency should know the client’s ‘distress,’ or their reason for hiring.

Four steps to answer ‘Why Should We Hire You?’

Step One

Therefore, you -- the candidate -- should first identify the source of the organisation’s ‘distress’ as the first step to answering “Why Should We Hire You?”

Step Two

Next, address their distress and restate the problem.

For example: “I understand a key project has fallen two months behind, but you still need to deliver on the original go-live date.”

Step Three

Then, position yourself as the solution with your skills and experience.

For example: “Over the last decade, I have specialised in 14 assignments in helping companies get projects back on track, rapidly. A recent example with a client was…”

In the above ‘distress-fix-response,’ you’ve made it about the client, acknowledging their problem and explaining why you’re the right person to resolve it.

Step Four

When offering your example, give specific details of when and how you did it.

Include metrics, such as time and money saved, or percentage improvements.

How to head off being asked at all (potentially)...

Related, when you’re in an interview, don’t be afraid of the humble brag. And if you’re not afraid of it, you could head off “Why Should We Hire You?” from being asked in the first place.

Telling others how great we are doesn’t come naturally to most of us, however. Nor does it feel quite right. Contractors, as serial interviewees, are often better at the humble brag than most, but even then, they tell me it can feel awkward.

However, an interview is one of those rare occasions where you’re encouraged to brag, and it is acceptable.

So don’t be afraid to say: “I have extensive experience in ‘X’, making me an excellent match for this assignment.”

Or you could say: “I’ve been involved with many contracts like this, and client feedback has always been outstanding. I know I have the skills to deliver what you need...”

To some interviewers, either of those statements may be sufficient in answering ‘Why Should We Hire You?” resulting in them (hopefully) crossing this irksome question off their list.

Upon your exit from the interview, flip the script

At the end of the interview, if you feel confident, you can finish your answer to their “Why Should We Hire You” question by turning it back on the interviewer.

You could finish by asking: “Based on what we’ve discussed today and my answers, is there anything I’ve missed, or a reason you might not want to offer me the assignment?”

This isn’t to check if you’ve got the job or to feed your ego! Rather, it’s to address any objections the client might have, and to allow the interviewer to touch upon aspects of the role that you’ve not expanded on enough.

Not all interviewers will provide constructive feedback, but some will.

In summary, don’t be put off by this classic “Why…” question at interview, even if it doesn’t always feel like it has a place in the IT contracting space. Keep calm, and tailor your answer to what you hear before and during the interview to aid you in convincing the interviewer that you -- and you alone -- are the right individual for the opportunity.