How To Answer Tough Interview Questions?

Most of us feel pretty comfortable during a technical interview, since questions are usually based on things we do routinely, or at least heard of at some point. But what happens when asked something like “Tell me about your weaknesses”. The question is easy; answering is the problem, right? 🙂

Personal questions such as that one are daunting and misleading, since there is no right or wrong choice. Having interviewed several applicants (and also being interviewed) throughout my career, there is a handful of questions I usually see candidates sliding off the cliff. Hopefully, this article provides you with a few tactics to optimize your job hunting experience and land a good job.

What I present hereinafter is basically a philosophy I practice in my life, which should be applied every time an action is required (meaning, ALWAYS). I call it the P3 strategy: PLANNING, PREPARING, and PRACTICING.

In this case in special, that’s how it works:

PLANNING: First and foremost, search for job openings for which you have AT LEAST 80% of the requirements. This might sound a bit radical, but nowadays it’s unlikely a company will hire someone that need extensive training to start bringing some value (unless you’re a graduate). Moreover, chances of you being unsuccessful at the technical interview are considerably higher, costing you lots of time and loss of morale with every failed interview. Another card to always have up on your sleeve is a professionally written resume (I will talk about it in a future article). You resume is the instrument used to lure recruiter’s attention, and you can’t dare to fail at this point.

Once recruiters see you’re a good match to the job, your chances of proceeding are much higher, and you should receive the awaited call. Time to get ready for the interview!

PREPARING: Interview time, at last! You know everything about Information Security, Risk Management, Compliance (or whatever your specialty is). However, usually the first round of interview is performed by an HR professional, pre-selecting candidates he deems fit for the COMPANY as a whole (have you thought of it before?). That’s the tricky part: he won’t analyze you only as a high skilled professional for a given position, but also testify whether you’ll get adapted to the company’s culture, your future boss, and so on. This is the stage where you should be already prepared to answer the tough questions to come.  At this point, thinking like a recruiter is the way to go.

PRACTICING: There are many ways to practice for an interview. But my personal favorites are pen & paper and enactment. Pen & pPaper technique is to write the tough questions down and put all the relevant points that come to your mind. It doesn’t matter if it might sound tacky; just put it down on paper. Once you have gone through everything that crosses your mind, start elaborating your answers based on our recommendations we provide below. That way, you’ll eliminate the surprise element that hinders your performance during the interview. Another technique to strengthen your position is enactment: just ask a close friend to interview you with the very same questions. 5 out of 10 people might stammer or get nervous while doing this practice session. Enactment enables you to talk smoothly, without gaps. However, you shouldn’t sound as if you were reciting a story. Once you have answered those questions ask your friend how your body language was, how you sounded while answering, whether you were enthusiastic, whether he/she was able to understand the points put across, etc.

After knowing how to be prepared for the first stage of job hunting, let’s go into some tricky questions and what they really mean:

– Tell me about yourself

It might sound obvious, but they’re not asking if you’re into sports, dance, whatsoever. What they really want to know is how you perceive your career, and steps you made to be where you are. The job post will usually give you some clues about the position (how much of staff management or technical work is to be done, technologies/tools and standards), so capitalize on it. Depending on the case, briefly talk about the teams you led before and your satisfaction of doing it, or how you’ve build your technical knowledge. Remember to stay focused and just share what’s relevant for the interview.

– Why do you want to work for our company?

The interviewer wants to make sure you have got acquainted with the company’s business, values and perhaps connections you might have inside. He doesn’t want to hear that the salary is attractive or that you’re fed up of your previous job. Make yourself sound interested about what they do, and looking forward to drive the company to its objectives. In case you have been referred by a friend, mention that he/she always tells you about the company’s pleasant working environment and challenging posture that could further develop your skills.

– Where do you see yourself in 5 years time?

Show them you have a solid plan established for your life, and how this new position will aggregate to your plan. No need to say you want to be sitting in your boss’ chair in 5 years; Let them know whether you want to lean toward decision making or technically specialist areas, and become the company’s reference in your subject matter.

-Why should I choose you?

Sounds tough, but actually an easy one: Plain and simple, because you are the best candidate they will find! Obviously it shouldn’t be put this way, but pick 3 requirements for the job and show them how your skills have helped previous companies to achieve their goals (the more examples you can think of, the better)!

– Tell me about your weaknesses.

Uh… the dreadful question. My mother used to tell me that knowing you have a problem is already part of the solution. Do not try to transform a potential strength into something negative, such as:  – I work too much. I am passionate about my job but I just overdo it. That definitely sounds lame and cliché.

Instead, pick a real weakness and elaborate on how you’re working to improve it. Ex: – I dislike speaking on the phone (my case, by the way). I rather go to someone’s desk and solve the issue on the spot, but I also understand that a phone call is the way to go sometimes, thus I’m changing my mindset and opening myself up for it.

– Do you prefer working for smaller or bigger companies?

This question is all about your personal preference. Smaller companies require you to wear several hats due to the reduced number of employees and the urgency of profiting in the short term, whereas bigger organizations already achieved a higher process maturity, and your job scope can be very specific. The key point is: Get informed about the company before going to the interview, its size and mission. This way, you avoid getting caught in a contradictory position during the interview, which usually increases your tension level leading to a loss of concentration. That’s not what you want, right?

– Tell me about your last accomplishments.

Focus on tangible facts and numbers. State the main accomplishments along with the situation involving it. Describe the problem presented, the conditions it was brought to you (overdue/a disaster recovery situation/a long term plan, etc). Demonstrate how you grasped the full picture, managed resources and time to achieve a satisfactory solution. Highlight the outcome and appraisals you might have received, and also lessons learned. Be concise, and above all, straightforward.

– What salary do you expect for this position?

Ok, the whole interview was a success so far (or so you feel)… Now you’re struck by the uncertainty of asking too much, and being refused for the job, or asking too low, and missing the opportunity to get the ideal salary you’re looking for.

One more time, preparation phase will pay off: The internet is crowded with salary surveys and researches (free and paid ones. A thorough survey for Australia can be found here). Try to search for average salary earned by professionals in your country (region, etc), and don’t stray far from it, either above or below. Remember to ask about the benefits and taxes, especially if applying for a position abroad. Some countries have income taxes as high as 50% of your salary, so watch out for such cases! Another way to stand out in today’s competitive job market is to acquire a technology degree

To finalize, once I’ve read somewhere that if you were invited for an interview, it means you already gave the company a good impression. I heartily hope the steps above will help you to be better prepared for your first meeting with your potential employers!

Good luck!

PS: Share your interview experience with us! Tell us about your your success or failure, and what you have done to overcome it. The comments section is all yours!

Filed Under: ArticlesFrom me to youJob MarketMy career


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  1. Pavel Kutina says:

    One thing I disagree a bit is requirement of match between requirements and knowledge. 70 – 80% of interview is your ability to sell yourself. It is tough telling such a thing to IT people, but it is true. I’ve seen that a few times crowned by situation when I was hired for a job I had NO match with formal criteria at all. I don’t advice random picking, but don’t be afraid if you match is lower. Just take it as oportunity to sell yourself and expect nothing. By that your fear and anxiety are significantly lowered and you will look much better than many knowedgable candidates blocked by anxiety. Of course such approach is also a commitment that you will actively gather knowledge required for the job in your private space. Maybe you will have to study long hours at home, maybe you will have to pay yourself a training… But definitely try it.

    And there are 2 more advices:
    1)Always start with positions you consider less atractive. If you are successful your wories get lower and your mindset will improve. And even if you fail you have an opportunity to reflect.
    2) In case you fail after interview, ask HR person a question: “Could you please teel me one thing I could improve to become better candidate for you in a future?” Most of them are willing to give you some feedback. And remember!!! It is not important your opinion on that area, it is also not important opinion of your friends. Important opinion is from a person who is going to hire you or not.

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  6. Raghu says:

    Amazing job Buddy! I feel the only web page which talk on Info Sec completely!

    Keep up the good work!

  7. […] I’ve said it before, but it’s worth repeating: The first step to solve a problem is to acknowledge its existence. […]

  8. gerray says:

    You have to add a print button function…

  9. Fábio Dias says:

    The best thing in a job interview is that you can practice your skills for the next one.

    See the podcast with a lot of ideas for your next job interview:


    • Definitely a good point, Fábio. Practice makes perfect, and so is the case with interviews!
      Usually the first couple of interviews are the scariest ones, since you might not have applied for a job in a while.
      But after some time you’ll build confidence and answers will flow naturally.

      The key point is: ALWAYS think positive!