The TSB Success Attributes Interviewing Guide

Anthony Iannarino
Post by Anthony Iannarino
May 5, 2010

This isn’t your standard, run-of-the-mill interviewing guide. These are tough questions that help to enable you to determine whether the salesperson you are hiring is going to succeed. If you are a salesperson, this is your guide to discovering what areas you may want to improve.

Self Discipline

1. In what area of your life are you most driven to be disciplined and why? Give some examples.

2. In what are of your business life are you most disciplined? Give some examples?

3. What sales activities do you approach with a high level of self-discipline and why?

4. What is you believe about the areas in your life where you are disciplined that allow you maintain that discipline over a long period of time?

5. In what are of your life do you find it most difficult to exercise your personal willpower and self-control? What do you do to stay on track there?


6. Are you generally more of an optimist or more of a realist? Why?

7. When I ask your last two employers this same question, how do you believe they will answer and why?

8. What really has the power to discourage you or give you a little dose of pessimism?


9. Give me an example of time when you had to win against long odds.

10. Is it important to win, or is it more important to just play the game well?

11. Would you rather be the underdog in a contest, or would you rather be fairly assured that you would win in a contest?

12. Outside of work, what kind of competitions do you enjoy participating in?

13. How do you feel when you lose a contest? How do you handle loss?


14. What does it mean to take initiative? What does it mean to be proactive?

15. What do you do to act proactively for your clients and prospects?

16. Give me an example of a time when you took the initiative for your company or client and it made a difference?

17. Give me an example of a time when you took the initiative and it backfired.

18. Based on your personal experience, what are some of the best ways that salespeople can take the initiative and act proactively for their clients?


19. How do complete tasks and missions when you don’t have all the resources that you require?

20. Tell me about a time when you were encountered a seemingly impossible obstacle or situation and how you worked to achieve your goal anyway.

30. Have you ever had a time when your sales process didn’t work and you had to find a way to move a deal forward?

31. Who is responsible for ensuring that you have everything you need to achieve the goals that are set out for you?


32. When is it okay to quit?

33. How do you know when to give up on pursuing an all-but-impossible big client that you have little chance to win for a smaller, but easier to obtain, client?

34. Give me an example of a time when you were called upon to persevere against long odds and the result of that effort.

35. How many times should a prospect say no before you accept the no and try again at another time?

36. Tell me about a time where you weren’t able to deliver the result you promised a client and how you resolved that problem.


37. How have your past clients known that you cared about them and their outcomes?

38. What examples would one of your past client’s cite as proof that you cared about ensuring they achieved their objective when they bought from you?

39. What is the single best way to ensure that your clients know you care?

Empathy and EQ

40. How do you connect and build rapport with your clients and prospects?

41. How can you tell what a client or prospecting is thinking or feeling? What are some of the signs that you look for?

42. How does your client know that you understand them and you understand their issues and concerns?

43. What is the best way to get someone to open up about their beliefs and their feelings?


44. Is it better to be a great presenter or a great listener? Which is the best attribute for a salesperson who is presenting in a board room?

45. How do you know when someone is really listening to you and when they are just going through the motions?

46. How much time should you spend speaking and how much time should you spend listening on a sales call?

47. What makes someone a great communicator?


48. How do you influence or persuade others to your way of thinking?

49. What is the most important attribute a salesperson needs to possess to be influential?

50. What are some ways that you have influenced buyers who were stalled and refused to take action on your deal?


Interviewing salespeople is difficult. It is hard to unearth whether they really have the underlying attributes of a high performer, or whether they just talk a good game. The TSB Success Attributes Hiring Guide just may help you hire your next superstar, or avoid your next turnover statistic.

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Success 2010
Post by Anthony Iannarino on May 5, 2010
Anthony Iannarino
Anthony Iannarino is a writer, an author of four books on the modern sales approach, an international speaker, and an entrepreneur. Anthony posts here daily.