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4 of the most difficult interview questions to answer

May 20, 2024

At Recruiting from Scratch, we work with candidates every day on how to interview and what hiring managers are looking for.

We suggest preparing for these four common - yet difficult-to-answer - questions in advance. Before your interview, we suggest writing down bullet points on these questions and even rehearsing your answers.

Tell me about a time when you had to challenge a peer or a manager.

Hiring managers ask this question, or a variation of it, because they know that conflict and disagreements are part of every workplace. If everyone agreed all the time – there would never be any new ideas! However, respectful and healthy disagreement is the key here. If you can share a story where you calmly addressed your difference of opinion, offered solutions, and came up with a solution that both parties were happy with – hiring mangers see that as a win. Spend some time writing down two or three times when you’ve had to address conflict at work, and determine which story is the most relevant or impactful. Write down how you solved it, what the outcome was, and ultimately (if you can) how the disagreement actually turned into a success or something new. For more info on this question, check out our blog post.

Tell me about a time where you had to make a decision about something without all the relevant information.

This question is tricky because it forces you as the candidate to think back to a situation where you may have felt less confident or like you lacked experience. However, if we always waited for 100% certainty, work would move at a slow pace. Write down some notes about a difficult decision you had to make where you weren’t sure of the outcome. This could be a new product feature you wanted to test, or a particularly difficult coding problem that required lots of testing. How did you push through the unknown to keep the project moving? Be sure to share the result and what you learned - even if the project wasn't as successful as you would have liked.

Why are you interested in this company, specifically?

This question seems straightforward at first but needs a well-thought answer. Write down what specifically about the job or the company caught your eye in the first place. Is it in an exciting new industry, or fast-paced? Do you enjoy serving the customers you’d be working with? Do you have a personal story from childhood or another time in your life where a company like this had an impact on you? Giving a thoughtful answer that shows you’re invested in the company’s mission and vision, which will work in your favor.

It's really obvious when someone isn't prepared to answer this question, or worse - they give an extremely generic answer that shows they haven't done any research into what the company does, and just want a "job." This is a great question to help you stand out from the pack.

Why did you leave your last job, or why are you looking for a new job?

In some instances, the answer to this question was easy – perhaps you were part of a layoff or restructuring. In other instances, you may want to spend more time thinking about how you answer this question, especially if you were laid off due to a lack of performance.

Did you decide that a corporate environment wasn’t the right fit for you and that’s why you’re interested in a startup? Did you decide to take some time off or move to a new place? Give an answer that’s truthful, but make sure you’re staying cool and collected. And whatever you do - don't bad mouth your former employer (even if you feel like you were mistreated). We get it - we all have bad experiences at companies sometimes. But it's important to stay

Rehearse and practice these answers by yourself or with a friend. Over time, your responses will become second nature – and you’ll enjoy answering these questions!  

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