How to Answer Common Difficult Interview Questions

In a practical sense, you should focus less on where you’ll be physically or practically in five years, and more on what you plan to learn between now and then, and how it might add to your set of skills.

Of bad interview questions, this is the gold standard. Most of the hiring professionals we spoke with said that this was a question they would never ask these days. Though it doesn’t mean other employers won’t, as you’ve probably already seen. That’s not to say it won’t appear in other forms. Questions like “Tell me about a time you failed and what you learned from it,” for example, offer an alternative to get the same information.

If you run into this question, your first reaction might be to answer the question by pointing out a weakness that’s actually a strength — “I work too hard” or “I’m a perfectionist.” Don’t do it. “Both of these come across as insincere,” Ms. Sailing said.

Instead, look for ways to pick an actual weakness, albeit a small one, and focus on the ways you’re trying to correct it. This isn’t an opportunity to point out that you’re chronically late or often absent. Instead, focus on smaller, more manageable weaknesses and what you’re doing to address them. “If you have to answer this question, you want to answer it in the framework of pursuing self-improvement and growth opportunities,” Ms. Sailing said. If I had to answer this question, I’d note that I am awful at estimating how long a project will take me to complete, and that leads me to take on more work than I can handle. To remedy the problem, I’m currently taking a class on Udemy, an online education platform, to learn ways to better manage my time and my work flow.

Mr. Edward agrees. He told us that he would be “looking for a candidate to show me how they might have leaned into their weaknesses and created solutions to find success in a previous role.” Microsoft calls this “learning agility,” and Mr. Edward said it’s an appealing trait for anyone he’s interviewing.

Alternatively, you could always point out flaws that aren’t related to the job. If you’re applying for a job as a software developer, for example, you could mention that you aren’t particularly good at, or fond of, public speaking. This wouldn’t often be a deal breaker, as public speaking skills aren’t commonly associated with software development.

Both Ms. Sailing and Mr. Edward stressed the importance of turning an interview into a dialogue. It shouldn’t feel like an interrogation, but a conversation. Look for ways to reciprocate interest, even asking your interviewer questions to learn more about the company or the role.

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