How to Answer the Most Difficult Interview Question Like a Boss

Disclaimer: The views expressed in this guest article are those of the guest author only and do not necessarily represent those of the blog owner.

Looking for a new job can be a dispiriting, and sometimes frightening, experience. Will I ever find another job that really suits me? It has to be at the right level, in the right location and be with a company that shares my values. And then, what if I do find that perfect job? Will I have the experience they’re looking for?

It’s a horrible process because it’s one in which we feel totally powerless, and it’s fraught with false hopes and crushing disappointments.

The world of software development seems to be particularly demanding when it comes to experience and even senior developers worry that their background isn’t rich and varied enough for many roles. Of course, this is partly because technology changes so rapidly, and keeping up-to-date goes with the territory, but there is a lining to this particular cloud and a couple of good reasons to not let a few holes in your CV get you down.

woman in blue suit jacket
So I started with C and that was too easy, skipped C+ and C++ and went straight to C+++.
Photo by Bruce Mars of Pexels

The first reason is, just because your prospective employer is listing hundreds of acronyms in the job description, it doesn’t mean they’re being realistic. Maybe nobody who would be interested in that particular role has exactly what they are asking for. It’s definitely worth applying, just in case.

The second, and far more important reason is that those gaps in your CV actually present a great opportunity to shine in one of the most difficult interview questions. If you haven’t already guessed, it is, of course…

“What is your biggest weakness?”

Not an easy question to look forward to, is it? In the mind of a nervous interviewee, it sounds incredibly belittling. It’s hard not to imagine a headmistress sort of figure, glaring over her half-moon glasses as she asks you what may as well be, “why are you such a failure?”

businesswoman interview meeting
You have no idea what you’re talking about,
do you?
Image courtesy of Tim Gouw

Horrible. The truth is, this question gets a really bad press, and in all honesty, if you understand why your interviewer is asking it, you’ll realise that it isn’t so bad. Also, it actually gives you the opportunity to sound a tiny bit awesome.

You are being asked this question because the hiring manager wants to know what support they might need to provide should they offer you the job. That’s all. Everyone needs some extra help when they first start a job, so the key here is to know what that would mean for you. You already know the answer, because it’s that thing you were stressing about when you read the job description. You don’t know any Python, remember? Sure, you could probably write something workable, if you could look everything up as you went, but you’ve never contributed to a project written in Python, so what can you do?

They’re cobras, not pythons but that’s the author’s fault;
don’t blame
Raul Cacho Oses at Unsplash

The answer, to those asleep at the back, is learn some Python. Go online, find a free course, get a tutor, buy a book… whatever, just learn some Python over a few days, a little bit each day. There are going to be bits that you find difficult but, guess what, that’s not a problem either! It can actually form part of an amazing interview answer. Here’s what I mean:

Q. What’s your biggest weakness?

A. Well, most of the job description totally suits my background and skills and I’m really excited about that, but I have never used Python in a professional project. I can see that it’s a very important part of this role so I’ve been studying the code in my spare time. Luckily, I’m learning pretty quickly, as it’s not that dissimilar to C++ and, from what I can see so far, it’s a great language and really fast to work with; I love that it’s dynamically typed. I am having a little difficulty understanding how to deal with the Global Interpreter Lock and, if we have time later, I’d love to ask you about that.

Can you see why this answer rocks? (If I do say so myself). It contains some very powerful ingredients. In this little snippet you have:

  • Reminded the interviewer that you are very well suited to the job (and really want it)
  • Answered the actual question about your biggest weakness
  • Shown that you have the initiative to identify a future problem and fix it before it happens (thereby also demonstrating how much you want the job)
  • Shown that you are making progress in learning Python
  • Demonstrated a little humility and opened the door for a slightly more informal chat in which the interviewer (or someone) explains how to deal with the GIL. Just remember to LISTEN if they do explain it to you. Sshhhh and listen. Take a couple of notes but keep it friendly and informal.

So, there you have it: how to ace the interview question that everyone hates.

Happy job hunting!

The good news is, I got the job. The bad news? I’m sitting on the floor of an empty warehouse. No, I don’t know why.
Thanks to Bruce Mars at Pexels
Matt Shewbridge

I’ve been Matt Shewbridge, your friendly, local interview coach.

If you have any more questions about this or other interview worries, you can find me on LinkedIn or check out my website at where you can read the rest of my blog.

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One thought on “How to Answer the Most Difficult Interview Question Like a Boss

  • January 17, 2020 at 12:39

    I’ve always thought that it’s better to focus on strengths than on weaknesses.

    Anyway, I would say that Matt’s advice makes a lot of sense, especially when he explains how to show the interviewer that you are very well suited to the job and you have the initiative to identify a future problem and fix it before it happens.

    As to the hiring managers who asked me that difficult interview question, though, I’m not sure all of them just wanted to know what support they might have needed to provide should they have offered me the job.
    In other words, I’m afraid sometimes sadism is still a thing… ?

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