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Article • ~ 20 Mins

Pre-gaming tough Interview questions

Get ahead of tough questions by drafting answers to tricky interview questions.
Interview Skills

In this article, we outline three types of questions that can might trip you up during an interview, explain what makes them tricky, and suggested strategies on how to answer them with confidence.


We all have interview questions that make us nervous, but the thing that differentiates great interviewers from the rest is how they prepare for those questions.

Theme 1 | Questions about your past experiences

You'll of course need to share some details about what you've accomplished in your past experiences, but be mindful to not overshare details about what wasn't so great about your past roles. It's never a good idea to use an interviews as a forum to vent or air frustrations.

Our advice: Keep your answers brief, with an eye to the future. You want to express yourself as someone who doesn't dwell on hard moments of the past.

Here's an example, and an answer that would work well:

  • "Why did you leave your last company?" 
    "For me, it really was less about leaving a company and more about exploring new opportunities. While there was a lot of good at my last company, I was really ready to find something new where I could continue to learn, grow, and develop new relationships. And while I know there's always risk in leaving a job before having a new one locked, but I wanted to be able to focus on my search fully."

Theme 2 | Questions that might have "loaded" answers

Sometimes, interviewers look for specific key words or phrases in your answers as a way to determine if you're right for a role. We won't get into why this is a deeply flawed approach, but we do want to make sure you don't take the bait.

Our advice: Avoid making a single declaration in your answer, and instead explain the process you'd use to find the right answer.

Here's an example: 

  • "How would you contribute to our team?" 
    "First and foremost, I'd want to make sure that we're super aligned on the job description and the immediate tasks at hand. I'd want to get clear on your expectations for this role in the first few months, and hear from you if there's any roadblocks I should avoid along the way. Longer term, I want to meaningfully contribute to the culture of team and help bring out the best in us all. That will of course take time as I'd really get to know how you all work and get things done together. I'd never want to make any assumptions about the team or how they work before bringing solutions to the table."

Theme 3 | Questions you don't have answers to

We've all been there: someone asks a question that you don't yet have a clear answer for. You might think you can either throw together some answer that sounds okay or dodge the question entirely. But in reality, there's a third option.

Our advice: Talk about yourself as an explorer, not someone who is lost.

Here's an example: 

  • "Where do you want to be in 10-15 years?" 
    "I have been asked that question a lot in my life, and for me, it's I'm realizing that it's less about a specific endgame and more about making the most of each part of my journey. There's more learning and experience in this industry than any one person can accomplish in their lifetime, so as long as I'm continuing to do meaningful work and stretch myself along the way, I'm going to feel good about the career I've built." 

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