How to answer hard questions in a job interview (and what not to say)

How to master the hardest interview questions without sounding unprepared and avoiding giving generic answers.

Unlocking tech talent stories

May 17, 2023

If you’ve ever done a job interview, especially those early-stage ones where the company is assessing whether there’s a cultural fit or not, you know there are hard questions that are kind of universal but still manage to catch us off-guard. 

The worst that can happen is not knowing what to say to the interviewer and sounding unprepared. And let’s be honest, if someone asks me to recount a time when I failed in my previous job experiences, there’s a 99% chance of my mind going blank. I will not recall one single experience from my past and it’ll look like a dry desert inside my brain. That, or giving a terrible example that explains approximately none of the qualities that the interviewer is looking for. And not for lack of said qualities, but rather a lack of recall memory under pressure. 

So what should you do to avoid awkward situations and sounding unprepared? Prepare. And not just prepare the basic and simple answers to these questions that sound generic and like the dozens of other answers received from other candidates. Answers that actually show your qualities and are very personalised. 

Let’s look into some of the most commonly asked questions in cultural fit interviews and my suggestions for good answers. 

Before, let’s go over the basics: the STAR method 

The STAR method is a well-known format to answer interview questions. 

  • Situation: set the scene and give the necessary details of your example. 
  • Task: what was your responsibility in that situation? 
  • Action: what steps did you take to address it?
  • Result: what outcomes did your actions achieve?

This method is extremely useful to keep in mind because it helps you construct your thoughts and interview answers in a very structured and logical way. It not only helps you recount the specific examples you’re using but also helps the interviewer better understand the takeaways of those situations you’re recalling. 

It’s also one of the best ways to include all of the relevant information the interviewer expects to hear: your actions and the results, with the right context.

Now let’s get into the actual questions.

“Tell me about a time you failed”

This can be a tricky one if you don’t phrase things well enough to present your qualities. The interviewer doesn’t want to know about your failure per se, they’re looking to know how you dealt with it

They ask this question to understand your skills to overcome challenges. They know failure is part of anyone’s professional journey because no one is perfect and they are definitely not looking for someone who never fails at anything. What they’re looking for is someone who is capable of dealing with the feeling of defeat, knows how to relativise failure, finds a learning opportunity from it and picks themselves up. 

It’s what you do with failure that matters

So what should you answer? 

As there can be many possible good answers depending on your specific tech role, I can’t help you with a full-formed answer. But what I can suggest is for you to choose your failure example wisely. The severity of a mistake can vary depending on the context, project requirements, and the potential impact on end-users or stakeholders. You should go for an example that’s not too serious or where you can at least show a really positive comeback from it. 

Some things you should definitely consider when answering: 

  • Acknowledge your failure and take ownership of it. ​​Admitting your mistakes demonstrates integrity and a willingness to learn and grow.
  • Be transparent about the consequences of your failure, both for yourself and the team or project. 
  • Focus on lessons learned, highlighting how you handled the failure, including any troubleshooting, problem-solving, or collaboration efforts you undertook to mitigate the impact. Highlight your ability to stay composed, learn from mistakes, and persevere in challenging situations.
  • Always end with how the failure ultimately led to personal or professional growth.

Here’s a mock example, courtesy of ChatGPT :

In a previous front-end development project, I underestimated the complexity of implementing a new feature—a dynamic data visualization component. It resulted in performance issues, compatibility problems, and project delays.

However, I quickly took action by sharing the challenges with my team and the client, looking for input from colleagues, and researching potential solutions. I learned the importance of comprehensive planning, effective communication, and proactive problem-solving. I also strongly believe that by acknowledging my mistake and taking ownership of the situation, I was able to work closely with my team and the client to implement an optimised solution.

This experience showed me the importance planning, communication, and proactive problem-solving are crucial for the success of development projects.

“Tell me about a time you showed leadership” 

Basically, every time you have to recount a past experience, the STAR method will be useful and you should use it. This case included. 

  • Start by giving context; telling a story. Example: In a recent team project, we were struggling with coordination and communication, which was also impacting our ability to meet deadlines. I proposed implementing Scrum to mitigate these challenges and took on the role of Scrum Master, hosting daily stand-ups and introducing sprint planning sessions.
  • Describe the outcome. Example: This gave the team not only more transparency but better communication and more productivity. We were able to deliver features and bug fixes more efficiently, which reduced project delays and improved customer satisfaction.
  • End with how it felt for you. Example: Taking on a leadership role was both challenging and rewarding. At first, I felt a sense of responsibility and pressure to guarantee that was I’d suggested was successful. But seeing how positive an impact it had on the team and the project outcome, I felt fulfilment and accomplishment.

The most relevant things to consider when answering this question are: 

  • Relevance: make sure the example you choose shows your leadership skills in a context relevant to the position you are interviewing for. 
  • Impact: clearly communicate the positive outcomes or results of your leadership, highlighting the tangible benefits that came from your actions.
  • Growth: emphasise the lessons you learned from the experience and how it shaped your leadership approach. 

“What’s your salary expectation for this role?”

You have two options here: either you choose to be more evasive and invert the question back to the interviewer, or you choose to give a range instead of a specific number. 

Why should you avoid giving a specific number? Because by doing so you might be narrowing your chances of having negotiating flexibility and gathering more information about what the employer is willing to offer.

If you opt to invert the question back to the interviewer, it can give you insights into their expectations and help you align your future answer accordingly. It also shows that you’re knowledgeable about industry standards and market value. You could do this by saying: My salary range is flexible but of course I’d like to be compensated fairly. I’m open to discussing specific numbers after learning a little bit more about the job

If you’d prefer to be a bit more forthcoming, you can provide a range while still maintaining bargaining leverage. You could go about it like this: I’d love to learn a little bit more about the job before putting out a solid number. However, I understand positions similar to this range from X0-X0,000.

Remember that you should adapt these answers to your communication style and language, but always stick to a respectful approach. 

“What’s your biggest weakness?” 

First advice: please don’t choose generic weaknesses like “being a perfectionist” (it’s not a real weakness because perfectionism can never be attained and, honestly, lacks substance). 

Second advice: please don’t choose things that are absolutely crucial for the job role you’re applying for. 

The goal of this question is to give the interviewer a sense of your self-awareness and honesty. The best you can do is pick a weakness that won’t prevent you from succeeding in the role, that you can provide a specific example of, and that you can show you’re already trying to improve.

Choose a real weakness. For instance, in my case, I often struggle with spontaneous creativity. I’m not very good at cooking outside-the-box ideas on the spot and under pressure and usually work best with research, time and even team brainstormings. This isn’t a deal-breaker skill for my role as a content marketer, but it’s still relevant and I can give examples of the specific ways I’m trying to improve. 

This isn’t a weakness interviewers expect to hear and spikes their curiosity. It’s possible to choose something equally relevant and interesting for your tech role, you just need to spend a few minutes thinking about what you actually struggle with on your day-to-day. 

One of the best things you can do when answering this question is showing confidence, and if combined with the tips I mentioned above, you’ll definitely see a difference in how interviewers react.


I sometimes find it challenging to strike the perfect balance between creativity and adhering to strict design guidelines or brand standards. As a front-end developer, I tend to gear towards creative problem-solving and exploring innovative design solutions. But there are times when project requirements demand a stricter adherense to brand guidelines or a specific design language.

I’ve been actively working on refining my ability to balance creativity with adherence to established guidelines by working closely with designers and other stakeholders early in the project to get a clear understanding of their expectations and preferences, and to manage my own expectations from the onset.

I usually also seek feedback and guidance from the design team during the development process, making sure that I’m staying aligned with their vision while also infusing creative problem-solving when appropriate.

“Why do you want to work here?”

Make sure you don’t make this all about yourself because if they just wanted to know how capable you were, they would ask “why should we hire you?”. What they want to know is why you chose to apply for their company, what your motivations are and perhaps even why their company and not another one. Basically, you need to make them feel special.

Start by doing research on the company: their website, mission statement, values, products/services, recent news or achievements, social media, company culture, and any other relevant information. This’ll give you insights into what sets the company apart and why it appeals to you.

Then take some time to identify key aspects of the company that resonate with you

Try to structure your answer in the following way: 

  • Start by mentioning the key aspects you identified that resonate with you. Example: First, your company working culture and vision really resonate with me, and I truly believe you have a great product/solution. [insert short description of product]
  • Explain how your skills, experience, and aspirations align with what the company offers, and how the position and the company’s goals are an opportunity for you to contribute meaningfully and further develop your expertise. 

Try to have a very personal approach in your answer and avoid giving a generic-type answer. 

“Why should we hire you?”

Again, don’t make it all about you personally. Focus on what the company benefits from hiring you. It’s a subtle change in semantics but makes all the difference. 

Try this structure in your answer: 

  • Soft skills. Example: First of all, I have a good attitude. I’m a fast learner and hard worker, and I love to work with people.  
  • Hard skills. Example: Secondly, I’m flexible: I know how to create a solid [skill], I’m great at [skill X, Y, Z], and I have good experience managing [skill]. And these are 3 skills that I know are crucial to being successful in this role
  • Company flattery. Example: I’m a huge [company] fan. [Write something about them]

Tailor your answer to highlight your unique strengths and how they directly align with the needs of the role and the company. Focus on your value proposition, giving real and specific examples and achievements to back up your claims.

Final tip before you go 

Don’t overexplain: usually when you do, you go around and around the same thing and end up saying a lot but with little substance, sometimes even digging yourself a hole. Stick to short and relevant. You’d rather the interviewer ask follow-up questions to know more about you than give too much in one go. 

And remember, preparation is key. Sometimes winging it works out, but more often than not it just makes it easier to sound unprepared and opens the door for the unexpected. Besides, it’s really important to research the company to show how interested you are in the job role and how it aligns with your motivations and goals. 

If you’re searching for your next tech job role, check these out. And if you’re looking for more tips like this, why not subscribe to our weekly tech career newsletter?

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