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How to Answer Difficult Interview Questions

        posted by , February 11, 2013

What's the worst professional decision you've made?

Questions that specifically target negative subjects are commonly referred to as difficult interview questions. They're fairly common.

Difficult questions are easy to answer once you've established a technique. The following guidelines will help you to take a negative question and turn out an inspiring answer.

1. Be Optimistic & Positive

Once you start thinking of your career in negative terms, you're sunk.

Never be drawn into a negative answer — no matter how negative the question may be. Make your answers positive and professional.

Examples: Positive Answers To Difficult Questions

Q: I see on your resume you started a small business, why are you returning to the workforce? Wasn't your business successful?

A: My business generated some decent revenue and I consider it a success in every way. The business exposed me to a range of challenges that have helped me to grow. For example, the challenges of selling a new product pushed my sales abilities forward. I'm looking forward to using the sales techniques I've learned to sell established brands and products.

Q: Can you tell me about the worst boss you've had?

A: I've never had a bad boss. I got along with all of my bosses well. The toughest boss I've had was at YYY company. He pushed me to improve my sales proposals. He was a legendary salesperson who had high standards for proposals. He'd review my proposals and ask for revisions up to a dozen times. This process helped me to perfect my proposals. Thinking back, I think he helped my sales results as much as anyone I've worked with.

2. Be Candid

Difficult questions may be intended to discover how well you deal with stress, challenges and failure. If you pretend that you've never had any stress or failures — it's not believable.

For example, if a sales person says they've never lost a deal, interviewers are likely to roll their eyes.

Be candid, it's okay to discuss failure and stressful situations. By showing your positive, professional approach to difficulties you establish trust with your prospective employer.

Example: Candid Answers

Q: Can you tell me about a recent sales deal that you failed to close?

A: Yeah, we were in negotiations a few months ago with a big customer. The deal fell through because of politics on the customer side. The CFO rejected the deal due to infighting between his directors. It would have been better if I could have influenced the other directors to support the deal. The political dynamics of the situation didn't allow me to do this. I always seek to understand the politics that affect a customer's buying decisions. I seek to influence all decision makers. In this case, I wasn't able to reach all the decision makers.

3. Show What You've Learned From Difficult Situations

Difficult questions are an opportunity to show how you tackle difficult situations and turn them into positive results.

Example: Showing What You've Learned

Q: What's your biggest career regret?

A: I'm satisfied with my career. In terms of regrets, I don't have any. I've faced a number of challenges but I've always found that they helped me to improve. For example, I've been involved with new product development projects that were extremely demanding. For a number of months at a time, I didn't do anything but work. My personal life suffered. In the end, the sense of accomplishment at launching a successful new product was worth the sacrifices.

4. Answer the Question

Convention wisdom states that you should answer the question "what's your biggest weakness?" with a smart remark such as "I'm too dedicated to my job."

Being dedicated to your job isn't a weakness. This technique goes beyond being positive — it's avoiding the question.

By not answering the question, you'll annoy the interviewers. You'll also miss the opportunity that difficult questions represent — the chance to show that you're comfortable discussing the challenges you've faced.

Example: Answering The Question

1. If there's an elephant in the room (a big issue that no one has discussed) it's often a good idea to bring it up to clear the air.

Q: What's your biggest weakness?

A: For this role, I'll need to learn about the product. As you know, I have more than 10 years experience selling light executive aircraft. However, this role is selling heavy commercial aircraft. There's a big difference in the products. I plan to read as much as possible about the product. I'd also like to spend time with your sales engineers to learn the key specifications and selling points for your products.

2. It's also a good idea to show your perspective employer that you're committed to your professional development.

Q: What's your biggest weakness?

A: A few years ago my boss suggested my public speaking skills could use some work. So I joined Toastmasters to improve my skills. I've also read a few books on the topic of public speaking. I take every opportunity I can find to speak in front of people. This has helped me to improve tremendously. It's something I'm still working on. Recently I spoke at the YYY industry conference. My talk was a success and I got some positive feedback from customers.

This post is part of the ongoing series how to win your next job.

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