How To Answer These 5 Tricky Interview Questions

02/01/21 - John Roccia

Interviews are happening again, and more than a few folks may be a little rusty. Time to shake the dust off of the interview technique and get prepared to answer these common foundational, but tricky interview questions. Each of these questions is one that I’ve asked in most of my recent interviews as a hiring manager, and my peers in the hiring world do the same. My job-seeker clients report getting asked these (or some variant) quite a bit as well, so I want you to be prepared for them!

Tricky Interview Questions

1. Tell me about a time you failed to meet a goal

Don’t: Try to avoid the spirit of the question with a clever dodge.

Do: Engage honestly and tell a story about your growth as a professional

Sounds like: “…and that failure taught me the importance of proactive communication, which is why I prioritize it today”

Hiring managers ask this tricky interview question to see if you have the capacity to admit failure (since every single person has had failures, trying to dodge just makes you seem dishonest) as well as the ability to learn from them. This is a chance to show off an “origin story” for your awesomeness.

2. Have you used [specific software/tool] before?

Don’t: Exaggerate your knowledge, or just say “no”.

Do: Respond with a question about their use of the tool, and connect it to something you have used.

Sounds like: “In my last role, we performed that function with a different tool. But it sounds like they’re very similar, so my proficiency with it should transfer over easily”

Specific tool questions are rarely deal breakers by themselves. More likely, they’re just trying to get a picture of how easily you could integrate. Most business solutions or tools have multiple similar or equivalent examples, and you’ve probably used one. And smart questions make you seem easy to teach!

3. Why did you leave your last role?

Don’t: Give a “safe” excuse (even COVID-19). Avoid fault isn’t selling yourself.

Do: Talk about your goals that couldn’t be met at your previous role, even if you had stayed. Talk about the ones you’re excited about meeting in your new job!

Sounds like: “Even though COVID-19 accelerated my timeline, I was outgrowing my role. I want to contribute more to a company that’s growing faster, which led to me apply here.

WAY too many people look to avoid blame when they hear this question. But your hiring manager isn’t looking to blame you – they’re looking to see why you might leave them in the future. You want to give them reasons why you’ll work out great together!  Talk about the positives of working for them, not the negatives of working at your last job.

4. Can you tell me about your remote work experience?

Don’t: Talk about how much you love “getting” to work from home.

Do: Talk about how you’re prepared to handle the unique challenges of that situation.

Sounds like: “I have a dedicated, quiet home office space that I’ve set up to be distraction-free and very conducive to high focus.”

Remote work has pros and cons for everyone, and secretly we might think that wearing sweatpants to a meeting is the greatest thing ever. But it’s not a “best foot forward” answer. There are negatives to working remotely, and many managers are still nervous about those negatives. Assure them that you’re an asset that won’t be difficult to motivate or keep focused.

5. Where do you see yourself in five years?

Don’t: Talk about using the role as a “stepping stone” to something totally different.

Do: Talk about the skills and experiences you want to get “vertically” in that role and more senior versions.

Sounds like: “I love public relations projects, so I hope to participate in increasingly more high-profile campaigns and eventually be trusted to run them.”

So many people botch this question by basically saying some version of “Well, after you’ve invested a bunch of resources into me and developed me professionally, I’ll jump ship because I don’t really want to be doing this, I just need to kill time until I’m qualified for what I do want to do.”  You don’t have to lie, and you don’t have to make up a cheesy “I hope I’m still doing exactly this” sort of line. But find the middle ground about gaining valuable experience and continuing to grow. After all, if you don’t want to grow here – why apply here?

A person holding a bulb

There you have it, our top 5 tricky interview questions and how to best respond. If you’re ready for these questions, you’re in great shape for a lot of interviews! But if you still have more questions or need interview help, book a free consult here to start your work with a coach!

Good luck on your next interview!

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