5 tough sales interview questions and how to answer them

It's one of the hardest and most dreaded aspects of the hiring process—the job interview. It's your one shot to make a great impression and convince the interviewer you're the best salesperson for the job. One of the most difficult parts of the experience is coming up with intelligent answers to tricky sales interview questions on the spot. For sales jobs in particular, questions can vary from the direct to the abstract depending upon the interviewer and the company.

They may have loved your sales resume, but that was the easy(ish) part. No matter how many times you’ve sat in the hot seat, these questions can still catch you off guard. Take a moment to brush up on these five difficult sales job interview questions—and learn how to answer them with confidence at your next interview.

“Tell me about yourself.”

If you've ever interviewed for a job before, you've likely had to answer the keystone question: "Tell me about yourself." It's deceptively simple and a real stumbling block for many. What do you include? What do you leave out? How personal should you get?

Instead of giving a chronological history of your education and work experiences, focus on personal qualities such as strengths and skills that make you well-suited for the job. Include tangible examples whenever possible, but don't branch off too far into a lengthy story. Include interesting tidbits that the employer will want to ask you more about. This will help frame the rest of the interview and highlight why you’re qualified for the role.

“Why do you want to work in sales?”

The biggest mistake you can make when answering this question is to simply say, “Because I like it,” or worse, “Because the money is good.” This doesn't really tell the interviewer anything they couldn't have obviously guessed—and it certainly doesn't help to set you apart from other candidates.

Successfully answer this tough question by focusing on your sales history. Think back to when your passion first began. Was it because of a summer job? Or maybe it started as early as childhood. Briefly illustrate this passion with real-life examples and include a success story, if possible. Then tie it in to why you still want to work in sales. Employers will take note of this longstanding drive and remember your answer because of your personal story.

“Why did you leave your last job?”

This is among the trickiest sales interview questions. Thoughtfully explaining why you left your last job will tell the employer a lot about your personality. You've likely left, or are thinking about leaving, your last sales job because it wasn't a good fit or because you didn't like the work environment, the pay, or management. Though they may be truthful answers, all of these reasons carry a negative connotation and will pull down the mood of the interview.

First, state something positive about your last job. Maybe you learned a lot or enjoyed the people you worked with. Then, shift the focus of why you left by talking about what you're looking for in your next job that your past job didn't have. This might be more responsibility, relocation, or a different company culture. This will present your past work experience in a positive light and compliment the position for which you're interviewing.

“What's your greatest weakness?”

This question is a great opportunity to take a negative and turn it into a positive. It's among the most common interview questions and for that reason, it's also known for evoking some of the most cliché responses. Saying something like, “My biggest weakness is that I never give up on closing a sale,” won't come across genuine or honest.

To answer this question, think of a true weakness—you get stressed out easily, or your habit of multitasking can lead to distraction. Then, give specific examples as to how you're making an effort to strengthen these weaknesses. This will show the interviewer that you're honest—and when you recognize a weakness, you know how to take action to fix it.

“What motivates you to sell?”

This question sets the stage for highlighting your positive attributes as a sales rep. But when put on the spot, it can be hard to elaborate on exactly what motivates you. Don't give a generic or vague response. This is a personal question, so you'll want to dig deep and answer this.

Use this question as an opportunity to provide insight into your character. Are you motivated by goals, pleasing your employer, or being among the highest performing sales reps? This lets your interviewer know whether you'll be a good fit in the company and how to motivate you if you're offered the job.

“Do you hate to lose? Or do you love to win?”

Mark Phillips is the managing director of HireEducation Inc., an education industry recruiting firm that interviews thousands of salespeople a year. “The toughest interview questions are the behavioral ones and the best candidates are still able to push for the question behind the questions,” he says. Phillips says organizations that rely on high-volume sales are a better match for people who “love to win,” while those that rely on strategic deals that require a significant resource investment into the sales process are a better fit for “hate to lose” types.

"What’s your sales strategy?"

“Imagine you start this Monday. We define our target market and ideal customer, give you all the product or service knowledge you need, a laptop and a phone. If we give you no other direction, what specifically will you do to develop leads, appointments and sales in your first week? First month? First quarter?”

Jeff Goldberg, a sales consultant and trainer, says this question is a favorite. Sales reps must be able to outline how they’ll develop leads.

"What’s your sales process?"

“You get an appointment with a decision-maker. Define your sales process from start to finish.”

Goldberg says many sales reps like to talk about their excellent presentation skills, but that’s not what closes business. “I want to hear how they’ll establish rapport, what questions they’ll ask and so on,” he says.

"How do you learn from your failures?"

“Tell us about a deal you’ve lost and what you learned from that experience.”

Jordan Wan, founder and CEO of CloserIQ, favors challenging questions that are designed to make candidates uncomfortable, much like a tough sales pitch. “It's difficult because it asks a candidate to reflect on a failure they've had in the past. A great answer will include a sincere anecdote about a lost deal as well as a courageous reflection of the humble lessons learned from the experience.”

Put your most professional foot forward

Now that we've taken a closer look at these five tough sales interview questions, put them into practice by crafting your own answers and familiarizing yourself with how you want to present them. Want to learn more interview tips to keep you ahead of the pack? Join Monster for free today. As a member, you'll get interview insights, career advice, and job search tips sent directly to your inbox. From getting help composing your answers to knowing which questions to ask a hiring manager, Monster can help build your confidence in preparation for the real thing.