Answering 10 Tough Interview Questions


—Bite-sized advice for better business writing—

Answering 10 Tough Interview Questions

“An interview is like a minefield.”

— Michelle Williams

A job interview can feel like a blind date—full of potential but also brimming with disaster. You want to make a good impression.

But, like a blind date, an interview is a two-way street. While the company interviews you, you interview them.

And then, there are those tricky questions. It’s good to anticipate them and know how to respond. Here’s a list of tough questions and successful answers.

1. How would you describe yourself?

Ouch! No time for small talk. We’ll jump right to big talk.

That’s okay. This is an invitation for you to tell the story of you—to connect to the person. Be yourself, but also come across as personable, talented, hard working, and committed. Evoke not just admiration but also empathy.

Example Response

I’ve worked for the last ten years developing motherboards and circuit boards for a great company, but I’ve risen as far as I can in the ranks. Designers can’t become managers, which is a position held by MBAs. That’s not the case here at Rankin Technologies. In fact, your president is a former hardware designer. I’ve admired your products—I have them in my home-built gaming tower—and I like to join the creative team that makes these products.

2. Why should we hire you?

This fastball is actually a blessing. The interviewer is inviting you to highlight your best qualities. Swing at this fastball and hit it out of the park.

Companies want four main traits in employees:

  • Skill, talent, experience: Let them know the suite of abilities you offer.
  • Hard work and dedication: Show them how you get the job done.
  • Grace under pressure: Demonstrate that you can solve problems.
  • Team orientation: Show that you can work with others.

Example Response

For the past ten years, I’ve worked for your direct competitor, developing the same type of microprocessor systems that you create. I’ve long admired the products you create and have felt I could contribute to the team that makes them. I’ve innovated some new network systems, and would love to add them to your product line. I have a passion for creating hardware solutions, and it’s obvious that Rankin Technologies shares the same passion.

3. What did you like and dislike about your last job?

This is a tricky one. You should highlight positive features of the last job that are present also in the new company, and should complain only about features not present in the current position.

Also, recognize that this question is a character test. If you will rat out your last company, you might not be loyal to the new company. Be diplomatic, and avoid offense.

Example Response

Big Tech is an entrepreneurial environment, which means that employees can plot out their own courses. I would propose new products and present them to upper management. If they were greenlighted, then I would assemble my team and create them. That’s exciting and free-wheeling. But there is a downside. Since everyone is constantly competing for company time and resources, the groups become a bit tribal. One set of creatives is pitted against another. The competition is healthy, but some people get a little nasty about it. I prefer a more collaborative environment.

4. What do you consider to be your weaknesses?

Ah, yes, the old weaknesses question. You can’t duck it: “I honestly have no weaknesses.” Nor should you provide ammunition: “I’ve been fired twice for working too slowly.”

Instead, you need to select something that is in fact a weakness, but that can also be a strength. Our greatest strengths can often also be our greatest weaknesses. Work that fact into your response.

Example Response

I have a lot of ideas. Too many, some people say. And I am excited by more of them than can be practically realized. So part of my process has to be about paring ideas down from the hundred things we could do to the two or three things we should do. The enthusiasm I bring to idea generation then can be channeled into creating the one or two products that will best meet the market need.

5. What was your biggest mistake at your last job?

That’s a question that brings the sweat. Remember that everyone makes mistakes. What matters is how you correct them and how you learn from them. So your response is a chance to tell a story that gets the interviewer on your side.

Talk about a real mistake that you made—preferably an understandable one—and what you did about it. Show that you’ve learned and won’t make that mistake again.

Example Response

My boss—who is a great person—and I have different communication styles. I like face-to-face communication, hashing things out in real time, but my boss prefers written communication, so he has time to think things through. It took me a little while to realize this. I’d knock on his door and try to talk things through, and I could see him just kind of shutting down. So I learned to use email. And that really helped us both. It caused me to be more deliberate in the ideas I presented, and it gave him the space he needed to think. So, now, I always pay attention to the communication styles of the people on my team.

6. Why is there a gap in your employment?

If you have a gap in your employment history, a future employer will want to understand what happened. The gap can reflect badly on you (“I just didn’t have any motivation to find a job since I had a bed in my parents' basement”) or well (“I took a year off to create a start-up. I used my hardware-designing skills to create a set of interactive toys that teach language to toddlers. A friend and I are still producing these toys, but I need a steady gig as well.”)

Give a true response that reflects well on you.

Example Response

My mother was having some health issues, and we had debated whether to hire in-home care for her or have me do the work. We’ve always been close, and I hated the idea that I was just working to pay for a stranger to take care of her. So I took a year off. She’s finally back to her old self, so I figured it was time to relaunch my career.

7. How do you deal with pressure or stressful situations?

This is another balancing act. On the one hand, you want to seem incredibly able to handle pressure, like some sort of ER doctor. On the other hand, you don’t want to take a job that will have constant pressure for no good reason.

Answer in a way that shows both sides of your position.

Example Response

I love pressure when it relates to successful completion of a project. We need to get X done by Y, and so we have to do Z. Yes, bring it on! There’s nothing like the sense of accomplishment that comes from delivering great work on time and on budget. However, I’m not as patient with needless pressure. If someone is trying to derail a project or distract the people working on it, I will usually either ignore the person or tell the person to stop. A team needs to have a common goal, and if someone on the team is working against everyone else, for me that’s a problem.

8. How do you like to be managed?

This question is problematic because there are many different management styles. Some managers are hands-off, which is freeing but can leave you to flounder. Other micromanage, preventing you from actually making the decisions you need to do your job.

You need to give a safe answer, but you also need to feel out the interviewer to understand the management culture of the business.

Example Response

I think fundamentally it’s about respect. I respect the manager, and the manager respects me. I trust the person to help me do my job to the best of my ability, and the person trusts me to do so. Some folks are hands-on or hands-off, and all of that is fine as long as there is respect and trust. What would you say is the management style in the department that I would be part of?

9. What are your salary requirements?

In a negotiation about money, the person who first names a number is at a disadvantage. So find out what the salary range is before you go in to interview. Compare it to your previous salary and what you need to make monthly expenses. Then be ready with a figure.

Also, be ready with reasons to justify the figure. Reasons that relate to facts are more powerful than those that relate to emotion.

Example Response

You are advertising a range of $60,000 to $80,000 for this job. Given my ten years of experience and my proven track record for technological innovation, I am looking for something in the upper end of that range. Of course, the total benefits package–including insurance and vacation days—will impact the decision.

10. Can you sell me this pen?

Are you kidding me? Seriously!

You may get this question if you are applying for a sales or marketing position, but you also might get it just to challenge your thinking. Remember that success in the workplace involves convincing other people to do what needs to be done.

So, make a sales pitch. Be genuine, and focus on the needs of the interviewer.

Example Response

Throughout this interview, you’ve been taking copious notes, which I think is a terrific practice. Of course, this is the pen you have been using. Now that you don’t have it, you won’t be able to write down anything about my current response. You need this pen. It’s critical to a successful interview. And here’s the good news: I got this pen for free from a new friend of mine. I can’t let it go at cost. That would not be a smart business decision. It’s a nice pen. But since I don’t need it, and you do–this new friend of mine–I’ll let you have it for a penny. A penny for a pen. A penny for your thoughts, written by this pen on that pad next to all of your other thoughts. Surely, your thoughts are worth a penny!


Try It Out!

Imagine that you are interviewing for a new job and you get this question. Write your response. Then scroll down to see one possible response.

When have you shown leadership skills?


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Editor's Recommendation

When have you shown leadership skills?

Example Response

I took charge of a project that had been getting nowhere for about six months. It was a new motherboard that needed to be half the size of the last one but have twice the speed. The team was smart, but they couldn’t decide on a single direction, so they were competing against each other. I got them all to present their different design ideas and recognized the strengths and weaknesses of each. Then I challenged them to find a way to join their approaches to solve the motherboard problem. Within the course of two hours, we had a plan, and everyone had tasks to complete it. That’s how we innovated the next-generation motherboard that has been powering Big Tech computers for the last three years.