The challenge for managers in choosing sales interview questions is choosing questions that also challenge the candidate. Soft sales interview questions will not lead to the insights you want to make a hiring decision, and questions must be phrased carefully to direct the candidate into discussing what you want to know without telling the candidate the answer you want to hear. Following are five sales interview questions to use in your next round of sales interviews to find out more about what really drives your candidates.

1. What do you think will be this industry’s challenges in the next three, five, and ten years?

Standby sales interview questions usually include “What are the challenges facing this industry?” However, a well-informed candidate can discuss all time horizons in a way that demonstrates his or her industry knowledge, and providing further extended horizons will help you test how far out the sales person is thinking. A candidate who can not answer the issues at all might not be the best choice. Even if he or she is moving in from another industry, it is reasonable to expect the candidate to have done research into your industry before deciding to undertake a career change.

2. Tell me about some of your favorite methods for prospecting, and how those work for you?

Phrasing sales interview questions in this way prompts the candidate not just to discuss the mundane ways in which he or she prospects (e.g., “I usually set aside an hour each morning…”) but to explain why those methods work. A candidate who can answer sales interview questions like this cogently has given thought to the sales process, and is not just running through the motions. Furthermore, the self-reflection and awareness required to piece together why some prospecting methods work better than others may indicate that the candidate is more receptive to change and coaching.

3. Can you tell me about a time when you were sure that a deal would close but lost the sale?

Asking sales interview questions that probe a candidate’s disappointments as well as successes is an important part of the interview process. When asking this question, you are looking for self-reflection and a willingness to take on personal accountability; you want the ideal candidate to take the opportunity to discuss how he or she reflected on the situation and show that thought was given to how he or she could have done things differently to support a better outcome. Watch out for sales candidates who answer this question by placing all of the blame on the prospect or the circumstances.

4. What are you looking for in a new position that is different from what you have experienced in the past?

Experienced sales people know that when asked sales interview questions related to reasons for leaving their previous position, answers like “I did not get along with my sales manager” are to be avoided. However, because of the way this question is worded candidates are free to answer with what comes to mind first. Positive answers to this and similar sales interview questions include indications that the candidate is looking for:

• More / greater responsibility and / or a clearer route to advancement
• Larger territories, more challenging accounts to win
• Opportunities for personal development (training / coaching / experiential learning)

5. What do you think is the biggest challenge for sales people?

A good answer to this question should correlate to what your organization thinks the common challenges for sales people are and should include answers that incorporate the candidate’s personal point of view as well as an organizational point of view, showing the candidate has considered all of the angles. Note that candidates who answer solely in a personal context have not truly answered the question; this is one of the great sales interview questions that you can use to test future leadership capability.