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The World’s Longest List Of Sales Candidate Interview Questions

by Will Brooks 

The single biggest challenge in hiring salespeople is one that is both logical and emotional in nature. The logical part of the challenge is that having someone in place is better than having no one at all. This is a false position to take, however, when you take a look at what a bad sales hire can cost you:

  • Wasted leads and lost opportunities
  • Customer and prospect alienation
  • Loss of goodwill in the marketplace
  • Poor image and reputation
  • Morale problems caused for other salespeople
  • Post time and energy in hiring, training and retaining
  • Delivery and customer service problems
  • Picking up the pieces after the failed rep has left

The emotional side of the challenge lies in the danger of hiring someone you like regardless of their proven level of competency. Couple this with the often-used mirror test (the old method of being able to fog a mirror and you have the job!) and you can imagine the problems this causes.

Using thoughtful and thought-provoking sales interview questions is a way around this, though. That’s why I’ve come up with 30 sales interview questions you can use to determine if you’re next sales candidate is a fit for your organization, your product, your team and your culture.

Not all of these might be applicable to your specific open sales position, but I urge you to use them as inspiration to develop those that are. Enjoy!

Sales Interview Questions

  1. Give me an example of a time when a manager provided you feedback you didn't agree with. How did you handle it?
  2. How would you start developing a territory from scratch?
  3. Walk me through your process for developing a prospecting plan.
  4. What's more important: planning or action?
  5. Walk me through your sales process of choice.
  6. What was the last sales book you read?
  7. How do you evaluate the best way to invest your time in a typical day?
  8. What expectations do you have of your manager?
  9. Describe the ideal sales team you'd like to be a part of.
  10. Where specifically do you need to grow your sales skill set?
  11. Where do you see the world of sales prospecting going? What's the best place to find buyers in today's marketplace?
  12. How do you differentiate yourself personally?
  13. What separates a top sales performer from everyone else?
  14. Knowing what you know now about professional selling, what advice would you give yourself at the beginning of your career?
  15. What's more important to sales success: selling skills or interpersonal skills?
  16. Walk me through your process for preparing for a face-to-face call.
  17. Give me an example of a time that you completely mismanaged your first face-to-face meeting with a prospect. What did you learn from it?
  18. How do you go about crafting a recommendation for a prospect or customer?
  19. What role does sales team alignment with the rest of the organization play in the overall success of the team?
  20. What makes a world-class sales manager?
  21. What's more important: profitability or volume?
  22. What tools do you use to learn about a prospect before making contact?
  23. Describe your biggest success as a salesperson.
  24. Describe your biggest setback as a salesperson.
  25. What are your longer-term career aspirations?
  26. What have you found to be the most effective way to open a face-to-face sales meeting?
  27. What’s more important, being decisive or slowing down to pay attention to detail?
  28. Describe a time you lost a longer-term customer? What happened? How did you handle it?
  29. Describe a time you had to over-service an account that didn’t mean much commission to you personally. How did you handle it?
  30. How do you handle situations when a prospective buyer insists you cut your price?

Use these questions to determine if your sales candidate is a future superstar…or simply someone who will fill a seat. Finding a candidate that is a perfect fit for the position will benefit all parties involved, and will result in an employee who is highly interested, engaged, and motivated to do their job well.

Will Brooks is COO of The Brooks Group, a sales training, sales management training and sales assessment company based in North Carolina. Contact Will at 336-615-8835 or by email at This email address is being protected from spambots. You need JavaScript enabled to view it..