Five tricky IT contractor interview questions for 2024

We’re all meant to be used to interviews, especially us contractors who undergo many more interrogations for work than full-time staff. And we’re all pretty used to handling the standard questions asked at conventional contractor interviews.

Even at contractor-friendly organisations, though, the questions will often be far more relevant to permanent job applicants rather than suited to the temporary role you’re going for or had in the past, writes Alan Watts, a service management consultant (retired), with more than 40 years’ experience as an IT contractor.

Sweaty palms, angst, and left field

This misalignment can bring on sweaty palms in even the most unflappable of contractor! But this level of concern is trumped by your nemesis -- the maverick interviewer who wants to catch you out, or even a standard interview but that’s for an unconventional, sought-after, or lucrative role. Then the angst can really set in!

So what are the hardest, trickiest, left field or just plain irritating IT contractor interview questions? I can only speak from experience, but these are mine and are worth being ready for in 2024.

1. Where do you see yourself in ten years?

Given you’re just probably supposed to be interviewing for only a three-month contract to deliver a specific solution, this common interview question is both irrelevant and dangerous.

You risk coming off as flippant – “Running my own consultancy” – or unambitious – “Doing what I’m doing now, most likely” – or clearly lying – “Still working for you”.

In fact, there is no answer that will be both honest and likely to impress the interviewer in equal measure. “Probably retired having made enough money” is likely an honest answer but it’s hardly constructive.

Rather than me suggest what’s best here, talk to a career coach or the agency in question if this ’10 years from now’ query worries you. Try to get a feel for what would be ‘acceptable;’ then even ‘good’ in terms of a response.

2. How would YOU do this?

This is trickier than it sounds.

Some interviewers delight in asking deeply technical or highly specialised questions that are nothing to do with the job in hand.

A classic example I remember:

Which Windows Registry settings would you change to achieve desirable result ‘x’?

Honest answer: ‘Don’t ask me, I’m only here to build a service desk, not manage the client environment.’

In practice; if you want the job, you cannot be that honest!

Instead, you must muster up some sort of an answer, even if it’s an initial ‘holding’ answer that gives you five valuable seconds to think a little longer about what you really want to say.

In my case, the answer given was: “I’d refer it to the relevant second line team to resolve.”

To some interviewers, that answer may have been acceptable but I suspect it was not what my interviewer was looking for.

A variation I recall: “Of course, this Service Desk flowchart is not ITIL compliant.”

The thing is, that’s a technically wrong thing for an ITIL specialist to say since ITIL is not a methodology, and you can’t be compliant with it! But then the interviewer and I had a reasonable debate about that very point. And thanks for asking but, no, I didn’t get the job!

3. Look at this. Where is the fault?

Another double-edge sword.

If you are presented with a piece of code that apparently contains an error, and then asked to correct it, are they looking for how you would diagnose the issue (which is fair enough), or are they looking for a free consultation to repair something they can’t?

I’ve seen technical interview tests that effectively require a couple of days coding to perform correctly.

I was once asked to bring a complete Service Design for the interview. Luckily, I had a framework of one in my personal files, representing several weeks’ work and several years’ experience, but I was very careful not to leave any copies behind. With client budgets under pressure right now, be on guard for these sneaky ‘questions.’

If you’re lucky enough to interview for Google, it’s known that you’ll get asked the following question (which I include here in this ‘top 5,’ as every end-user from your next corporate client to your local tech support SME where you’ll be working Sundays, can ask you it in relation to itself):

4. What is the next great, billion-pound idea for us here at Google?

A good question, but if you knew the answer to that, then you wouldn’t be sat there in the first place!

Thanks to Jarek Grzeskowiak for sharing this Google interview question on LinkedIn.

For reference, Grzeskowiak’s answer didn’t land him the ‘Don’t be Evil’ job, even though his response was far from terrible:

‘Create a global system that provides internet access to people everywhere in the world.’

5. How many one-pound coins could you fit into this room?

My answer would be “How much is four cubic yards of concrete?”, which I think would earn me a FAIL.

But with such ‘unanswerable’ interview questions, don’t fret because the point of these is not for you to give an accurate answer.

These unanswerable interview questions are more designed to see how you would go about solving the problem. They are off the wall because you cannot prepare for them, so you have to answer quickly. Annoying perhaps, but a good test of your mental agility.

And finally…

You can get unanswerable questions from the other side of the desk as well. I was interviewing a very strong candidate for a Change Manager role, and it all went really well.

At the end, I asked the usual, “Have you got any questions for me?” “Yes”, he says, “Have you heard anything in this interview that means you would not offer me the job?” Long pause on my part…In the end, I did offer him the role, and very good he was at that too!