How to Tackle Three of the Toughest Interview Questions

Interviewing is a skill that can be systematically improved. Here are three of the toughest interview questions. You'll see what most people say and how to improve your answers to land a top job.

Tell me about your work history

What most people say: "Oh, uhh...well, I started working at Acme Corp doing marketing work. Then I worked at A&B as a marketing manager, managing daily emails. Then I went to C&D, which is where I am now, and I've been in charge of PR and marcom."  

What you should say: "If you look at my work experience, there are 3 things that stand out. First, I have experience with many areas of marketing, including PR, advertising, and marcom. Second, I have a quantitative background in terms of what I studied, and my recent email-marketing experience. Finally, I've always wanted to take my skills to a larger stage, which is why I moved from A&B to C&D, and now I'm excited to be here talking with you.

Why this works: The hiring manager doesn't need you to walk him through your resume chronologically—he can read what's on the page, after all. It's far more valuable for you to highlight the key strengths of your background. If you've done your pre-interview homework, you'll know what aspects are most important (e.g., in the above example, the candidate noticed that this position would be quantitative, which is why he highlighted his quantitative background).

Tell me about one of your weaknesses

What most people say: "You know, I work too hard and sometimes have trouble with perfectionism."

What you should say: "I've spent the majority of my career working for one industry. In some ways, that can limit my perspective. Of course, I've worked in a variety of departments—and in fact I was promoted faster than anyone else to run project X—but I'm ready to take what I've learned to a di?erent culture and industry, and that's why I'm here."

Why this works: This question is a minefield that traps most candidates. If you answer too honestly—"I'm irritable in the morning and bad at time management"—you're an instant no-hire. But if you answer in a lie, it's transparently obvious. So be honest about your weakness, but be careful to explain what you've done to improve this weakness.

Tell me about a challenge you faced with a coworker

What most people say: "This one time, my coworker and I had a disagreement over something. It was pretty bad, but we worked things out in the end."

What you should say: "I once had a situation when I was presenting business ideas to the CEO of my company. He liked the ideas, but one of the VPs kept shooting them down—and I couldn't figure out why. Honestly, at first I was upset, but after digging into the issue, I realized it was because my plans would impact the VP's work in a negative way. I reached out to him directly, apologized for the oversight, and promised to keep him in the loop in the future. We haven't had an issue since."

Why this works: There are two main reasons the second answer is more effective: First, the longer answer shows how the candidate took control of the situation. Second, notice the difference in specificity. In a job interview, details sell, so the more specific you are, the more memorable you will be.

Interviewing isn't about being inauthentic or sleazy. It's about presenting your very best self to the interviewer and mutually deciding if this is a good fit for you.