Smart Answers for Tough Interview Questions

Interviews can be daunting, and the questions you may get asked don’t help. While simple questions like “tell me about a time you worked in a group” can be a simple answer, there are plenty of questions that are common, yet still difficult if you don’t know how to go about answering them. 

“Tell Me About Yourself.”

This is often the first question you get asked and can set yourself in a strong or poor position for the rest of the interview. These questions in-particular takes a bit of thinking beforehand, but it’s okay because you know this question is coming so you have time to think about it before your next interview. 

The answer to this question is your elevator pitch. This answer should sum up who you are as a professional and as a person in just about a paragraph. You shouldn’t answer this as a bulleted list, but rather a short story, similar to how many of your answers will end up being. 

My Answer: Growing up, I lived in a creative household. I was a reader, a writer and always at the craft table. Thankfully, over the last few years especially, I’ve learned to turn that into the start of a career. I use my ability to tell stories to tell and shape the brands of companies in a wide variety of ways. It’s because I believe everyone has an important story to tell and for those that need help shaping that story, I want to be the one to do it. 

“What Is Your Greatest Achievement?”

What makes this answer more difficult to many is because of the fear of sounding arrogant. While you don’t want to sound like your boasting your accomplishments, there’s a difference between arrogance and pride in a job well done. 

Similar to the “tell me about yourself” question, you should answer this question as a story. You don’t have to answer this with a magical story about how you saved an orphanage of children from a fire, but just an experience you had that you feel proud of, no matter how small or what may seem insignificant. 

My Answer: One of the projects I’m most proud of comes from my first freelance client. It was an online video game that allows users to create marching band shows. It’s a unique website and in late 2015, I was asked to take over social media for them. It was a ground-up project where I got to completely start from scratch on Twitter and Instagram. Credit to them, they have a unique story, and I was trusted to share it. They allowed me to test out some ideas I had since I was relatively new to social media content creation. Within 6 months, they surpassed 10,000 likes on Facebook, over 1,500 followers on Instagram and Twitter, and had a monthly average of 80,000 organic impressions. I don’t work as often for them anymore because of my schedule, but I’m still very proud of that project.

“What Is Your Biggest Weakness?”

The key to this answer is honesty. An employer doesn’t want to hear “I work too hard” or “I’m a perfectionist,” a weakness that’s somehow also a strength. Everyone has their weaknesses, and it’s okay to mention one as long as you also answer what you’re doing to fix it. Don’t just say “I can be disorganized” without also answering “but over the last few months I have begun to use Google Calendar and Dropbox to organize all my work which has been helping a lot.”

My Answer: I tend to take on too many projects. I like being there to help my boss and coworkers, but I have a tendency to stretch myself too thin. Thankfully, now having some self-awareness, I’ve been able to think before I say yes. If it turns out I can’t, then at least I can try to recommend someone who can.”

“Do You Have Any Questions For Me?”

Yes, you have to ask a question! Don’t make the question “how much does the job pay,” but rather a question to learn something about the company or the person you’re interviewing. 

A lot of the time, you’ll come up with your question during your interview to ask at the end. That being said, you should still try and come up with a question beforehand, even if it’s simply like “tell me about the company culture here” or “what’s your day-to-day look like” if the person interviewing you has a similar job as you would. 

My Answer: [asked a hiring manager at Ogilvy] Before, you mentioned that you started from an associate position and worked your way up and have now been here seven years. Especially today, it seems younger professionals enjoying jumping from company to company after two years or so. So my question is what’s kept you at Ogilvy?”


Before you have your next interview, do your research and think of answers to these common questions you know you’ll be asked. Learn about the company culture as much you can or about your interviewer if you have that ability. 

Remember, an interview is just as much a learning experience for them you as it is for you about them. 

-Will Careri

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