1) What’s your opinion of the role of learning in sales? Being thrown for a loop by this question is a sign that your candidate isn’t a life-long learner, which is becoming increasingly important in sales. 2) How do you keep up to date on your target market? Even if the target market of their last job is totally different than that of the one they’re interviewing for, this will show you their ability to find and keep up to date with relevant trade publications and blogs. 3) Explain something to me. While this technically isn’t a question, it’s important to assess whether the candidate has a helpful demeanor. 4) What’s worse: not making quota every single month or not having happy customers? Depending on your company’s goals, either answer could be the right one. But beware of reps who will prioritize quota over truly giving customers what they need -- or withholding from them what they don’t. 5) How would you approach a short sales cycle differently than a long sales cycle? Short cycles call for reps that can close quickly, and long sales cycles require a much more careful, tailored approach. They’re drastically different, and your candidate should recognize this. 6) When do you stop pursuing a client? The right answer here will depend on your company’s process, but in general, the more tenacious and persistent a rep is willing to be, the better. Trish Bertuzzi, founder of The Bridge Group, recommends six to eight attempts before throwing in the towel. 7) Who are you most comfortable selling to and why? Listen for whether they answer with a description of an ideal buyer, or a particular demographic with no tie-in to the buying process. Depending on your product or service, the second type of response might pose a problem. 8) What’s your least favorite part of the sales process? If their least favorite part is the most important part at your company, that’s probably a red flag. This question can also alert you to weak areas. 9) What motivates you? Money, achievement, helping customers, being #1 -- there are a lot of potential answers to this question. What makes a good answer vs. a bad one will hinge on your company culture. For instance, if teamwork is paramount within your sales team, a candidate who is driven by internal competition might not be a great fit. 10) What is your ultimate career aspiration? Lack of growth opportunities was one of the top three reasons that would cause a salesperson to look for a new job, according to a survey from Glassdoor. If the candidate expresses a desire to pursue a career move your company can’t provide, you might be interviewing again sooner than you’d like.