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50 Questions to Upgrade Your Sales Lifestyle

1. According to a recent survey of C-Level executives, what is the most important trait that you want from the salesperson that you are working with?
a. Empathy
b. Enthusiasm
c. Product Knowledge

2. Your sales pitch will usually be better when it is…
a. Off the dome
b. Rushed
c. Rehearsed

3. Successful salespeople begin each week by starting with the opportunities that are…
a. Closest to the end of the sales process
b. Farthest away from the end of the sales process
c. Not in the pipeline at all

4. Productive salespeople organize their to-do list for sales opportunities based on…
a. Whether they took their vitamins that morning
b. Where each opportunity is in the sales process
c. Where they were born

5. Good salespeople start each week by working first on the opportunities that are…
a. Far from closing
b. About to blow up
c. About to close

6. Great salespeople work last on the sales opportunities that are…
a. Close to signing
b. Somewhat interested in signing
c. Far from signing

7. Scenario: You’re at a job interview and you get asked- “Are you comfortable making cold calls?” A prepared salesperson is likely to give the following response:
a. No way, Jose!
b. Yes, I enjoy sharing new ideas with new people
c. What? What? Am I even in the right job interview?

8. Scenario: You’re at a job interview and you get asked- “Can you make cold calls?” A prepared salesperson is likely to give the following response:
a. I absolutely can, I welcome the challenge of introducing a solution to new people.
b. I definitely can’t. Where is the closest exit?
c. Maybe I can’t, maybe I can; how much are you paying me?

9. Scenario: You’re at a job interview and you get asked- “Would you be willing to make cold calls?” A prepared salesperson is likely to give the following response:
a. No I would not be willing to make anything besides making money
b. Who do you think I am, a sucker?
c. Yes, but I prefer to start the sales process with a prospect who has shown some interest.

10. Scenario: You’re at a job interview and you get asked- “Would you make cold calls?” A great salesperson is likely to give the following response:
a. Yes, some of my most interesting deals have been the result of a cold call
b. No, the only thing I make is time for the ladies
c. I don’t know

11. Scenario: You’re at a job interview and you get asked- “Have you consistently met your sales goals?” A high-performing salesperson is likely to give the following response:
a. Why are you asking me that? I didn’t see that question in the job application.
b. Not consistently since I broke up with my ex 10 years ago.
c. I have not just met but have exceeded my sales goals consistently and I’d like to share some examples with you.

12. Scenario: You’re at a job interview and you get asked- “Have you consistently met your goals?” A thoughtful salesperson is likely to give the following response:
a. Yes, both personal and professional goals
b. Is that a trick question?
c. I don’t even know, man.

13. Scenario: You’re at a job interview and you get asked- “Do you consistently meet your sales targets?” A thoughtful salesperson is likely to give the following response:
a. Targets are for shooters, man.
b. Yes, I can share some examples of how I plan my sales activities based on the target for a given sales period.
c. Yes and no. Yes, when my boss is treating me well; and no when my boss is on vacation.

14. Scenario: You’re at a job interview and you get asked- “Are you consistent in hitting your sales goal?” A great salesperson is likely to give the following response:
a. Rules are meant to be broken, and goals are meant to be flexible
b. How are you going to ask me that when you can just look at my resume?
c. Yes, I have hit my annual sales goals 4 out of 5 times in the last five years

15. Scenario: In a job interview, you get asked- “How consistent are you at hitting your sales quota?” A hard-working and funny salesperson is likely to give the following response:
a. Well, that’s why I want this job…duh!
b. The only time that I didn’t try my hardest to hit quota was when I was in the womb
c. Quitting a goal is better for me than hitting it

16. Scenario: In a job interview, you are asked- “Do you prefer a long or short sales cycle?” A successful salesperson is likely to give the following response:
a. Both have advantages. I prefer a longer sales cycle as it allows more time to learn the customer’s needs.
b. Honestly, I really hate selling… shopping is more my thing.
c. Neither. Buyers are liars and sellers are beggars.

17. Scenario: In a job interview, you get asked- “Do you prefer a long or short sales cycle?” A thoughtful salesperson is likely to give the following response:
a. A longer sales cycle can go on for months and months and my dreams can’t wait forever.
b. A longer sales cycle gives me more time to educate the prospect on the product so I prefer it.
c. A shorter sales cycle is just like a longer sales cycle so that’s a dumb question.


18. Scenario: In a job interview, you are asked- “Do you prefer a long or short sales cycle?” A high-performing salesperson is likely to give the following response:
a. I enjoy the quicker pace of a short sales cycle because I am very results-oriented
b. I enjoy the fast turnaround of a short sales cycle because I don’t like working that hard
c. This interview is not going to turn out well for me, is it?

19. Scenario: In a job interview, you are asked- “Do you prefer a long or short sales cycle?” A great salesperson is likely to give the following response:
a. I don’t have a preference, I just do what the prospect wants
b. I enjoy both because I believe the cycle can be adjusted based on the individual client’s needs and timeline.
c. I don’t have any opinion on that because I don’t work for you.

20. Scenario: You’re in a job interview and you get asked – “Do you prefer a long or short sales cycle?” A great salesperson is likely to give the following response:
a. I prefer a short sales cycle because I like to get right to the point about the benefits of the product
b. I prefer a short sales cycle because I like to make fun of the prospect’s indecision
c. Who cares?! I got fired last week and I need this job.

21. Scenario: You’re in a job interview and you get asked – “How did you land your most successful sale?” A thoughtful salesperson is likely to do which of the following:
a. Say “I’ve never landed any successful sales, woman! I only land on airplanes.”
b. Describe the situation e.g. a customer invited me to a networking event and I was able to demo my product to multiple prospects at the same time…
c. Describe the way to ask a girl out and make sure she says “Yes”.

22. Scenario: You’re in a job interview and you get asked – “Do you have a sale that you would rate as your most successful sale?” A thoughtful salesperson is likely to do which of the following:
a. Shake head and then nod and then shake head again.
b. Hand over an old business card with a funny name and title.
c. Say “In my experience, successful sales are first and foremost measured by the client’s overall experience…”

23. Scenario: You’re in a job interview and you get asked – “Do you have a sale that you would rate as your most successful sale?” A thoughtful salesperson is likely to do which of the following:
a. Say “My most successful sale happened when I had to take over from a colleague who had not invested the time to learn the client’s true needs…”
b. Say “My most successful sale happened when I tricked your HR department into giving me this job interview…ha…”
c. Show a YouTube clip of a cat kissing a dog.

24. Scenario: You’re in a job interview and you get asked – “How did you score your most successful sale?” A thoughtful salesperson is likely to do which of the following:
a. Laugh out loud and say “Goal!”
b. Give an example that matches up with your work experience
c. Repeat a story that you heard a CEO tell on CNBC.

25. Scenario: You’re in a job interview and you get asked – “How did you score your most successful sale?” A thoughtful salesperson is likely to do which of the following:
a. Say “My most successful sale happened over email after several failed attempts to get the prospect on the phone…”
b. Say “My most successful sale happened when I was in a conference room alone with my boss’s wife… oh boy…”
c. Wink at the interviewer

26. Scenario: You’re in a job interview and you are asked – “How would your colleagues describe you?” A successful salesperson is likely to do which of the following:
a. Walk out right then and there.
b. Lift the table up and say, “Muscle memory!”
c. Say “As a reliable team player.”

27. Scenario: You’re in a job interview and you get asked – “How would your colleagues describe you?” A successful salesperson is likely to do which of the following:
a. Ask for some cold water
b. Respond with positive character traits such as “diligent and disciplined”.
c. Smile at the interview and say “Enough said”.

28. Scenario: You’re in a job interview and you are asked – “How would your colleagues describe you?” A great salesperson is likely to do which of the following:
a. Say “My colleagues compliment me for being so organized which they say helps me with the volume of accounts that I manage.”
b. Start rapping, “Can’t nobody take my pride, can’t nobody hold me down…”
c. Make air quotes without saying anything

29. Scenario: You’re in a job interview and you get asked – “How would your colleagues describe you?” A good salesperson is likely to do which of the following:
a. Pull out a whiskey bottle and take a sip
b. Sigh deeply and look at the clock on the wall
c. Say “My colleagues compliment me for being a people-person which they say helps me exceed customer service expectations.”

30. Scenario: You’re in a job interview and you are asked – “How would your colleagues describe you?” A high-performing salesperson is likely to do which of the following:
a. Say “They would not describe me because they are all scared of this fist.”
b. Reply in a way that highlights strong character traits
c. Giggle and then try to tickle the interviewer

31. Scenario: You’re in a job interview and you are asked – “How would your manager describe you?” A high-performing salesperson is likely to do which of the following:
a. Say “Did my manager put you up to this?”
b. Say “I recently got a Thank-you email from my manager about my attention to detail”.
c. Cough and try to avoid eye contact with the interviewer

32. Scenario: You’re in a job interview and you get asked – “How would your manager describe you?” A high-performing salesperson is likely to do which of the following:
a. Say “She would highlight my work ethic especially in resolving customer service issues”.
b. Lay down across the table
c. Ask to take a smoke break

33. Scenario: You’re in a job interview and you get asked – “How would your manager describe you?” A successful salesperson is likely to do which of the following:
a. Do cartwheels in the conference room
b. Ask the interviewer to switch chairs
c. Say “My manager really appreciates my ability to work with different teams to get a task completed.”

34. Scenario: You’re in a job interview and you get asked – “How would your manager describe you?” A successful salesperson is likely to do which of the following:
a. Say “My manager recently got drunk with me… case closed.”
b. Say “My manager recently commended me for being a self-starter.”
c. Ask the interviewer to wrap up the interview early

35. Scenario: You’re in a job interview and you are asked – “How would your manager describe you?” A successful salesperson is likely to do which of the following:
a. Say “My manager doesn’t appreciate anything I do.”
b. Pull out a soccer ball and ask the interviewer to kick it
c. Say “My manager appreciates my willingness to solve problems first before I bring it to management attention”

36. Scenario: You’re in a job interview and you get asked – “What are your long-term career goals?” A thoughtful salesperson is likely to do which of the following:
a. Say “I don’t’ have any right now, I just need to pay my bills this week.”
b. Say “To manage a large successful sales team and leverage that into a consulting career”
c. Say “I don’t know, man”.

37. Scenario: You’re in a job interview and you get asked – “What are your long-term career goals?” A thoughtful salesperson is likely to do which of the following:
a. Paint a vision for where you want your career to be 10 years from now
b. Paint a vision for who in the office is way hotter than your ex
c. Shy away from the question while fake-sneezing

38. Scenario: You’re in a job interview and you get asked – “What are your long-term career goals?” A thoughtful salesperson is likely to do which of the following:
a. Share with the interviewer where you see the industry headed and how you plan to use your position as a salesperson to drive change.
b. Share with the interviewer what you ate for breakfast that morning
c. Share with the interviewer where you see yourself eating lunch if they hire you

39. Scenario: You’re in a job interview and you are asked – “What are your long-term career goals?” A thoughtful salesperson is likely to do which of the following:
a. Give a fist bump to yourself
b. Give up any hope of getting the job
c. Give a specific job title (VP, Sales) that you hope to secure in a specific amount of time (seven years).


40. Scenario: You’re in a job interview and you are asked – “What are your long-term career goals?” A thoughtful salesperson is likely to do which of the following:
a. Describe a passion project (e.g. microfinance in Sub-Saharan Africa) and how you plan to leverage your sales experience to drive the project forward.
b. Describe all the times you went out to party in your college days
c. Describe how cool it was to skip class in high school

41. Scenario: You’re in a job interview and you are asked – “Do you have any weaknesses?” A thoughtful salesperson is likely to do which of the following:
a. Relate a weakness (e.g. impatient) to your strength (e.g. results-oriented).
b. React childishly and start crying out loud
c. Change the topic of conversation to basketball

42. Scenario: You’re in a job interview and you get asked – “What are your strengths and weaknesses?” A confident salesperson is likely to do which of the following:
a. Say, “I only have one weakness and that was coming to this interview today”.
b. Say, “One of my strengths is that I am persistent, and one of my weaknesses is that I can come off aggressive especially when I know I can really help a client.”
c. Party like a Rock-Star

43. Scenario: You’re in a job interview and you are asked – “Do you have any weaknesses?” A thoughtful salesperson is likely to do which of the following:
a. Bow out
b. Relate a weakness (e.g. somewhat inflexible when plans start to change) to your strength (e.g. discipline to stick to a plan).
c. Compliment your interviewer’s voice and say “I love your yummy voice”.

44. Scenario: You’re in a job interview and you get asked – “What are your strengths and weaknesses?” A confident salesperson is likely to do which of the following:
a. Describe a weakness and strength, and then briefly explain how you manage the weakness to ensure productivity.
b. Say, “I am a legend”
c. Say, I don’t appreciate rhetorical questions in a professional setting”.

45. Scenario: You’re in a job interview and you are asked – “Do you have any weaknesses?” A thoughtful salesperson is likely to do which of the following:
a. Say “No, I’m way too talented”.
b. Laugh nervously and say, “Is this being recorded?”
c. Relate a weakness (e.g. fear of failure) to your strength (e.g. ability to learn from others).

46. Scenario: You’re in a job interview and you are asked – “What do you find rewarding about being in sales?” A thoughtful salesperson is likely to do which of the following:
a. Say “Young Mullah, baby!”
b. Say “The most rewarding part of being in sales is the time spent with customers, helping them make the right decision about a product.”
c. Rap “Cash rules everything around me…”

47. Scenario: You’re in a job interview and you are asked – “What do you find rewarding about being in sales?” A high-performing salesperson is likely to do which of the following:
a. Describe how you helped an important client solve a critical problem
b. Describe how you hate sales so much but your mom made you do it
c. Describe how you find joy in lying to customers

48. Scenario: You’re in a job interview and you get asked – “What do you find rewarding about being in sales?” A good salesperson is likely to do which of the following:
a. Get even or get mad at the interviewer
b. Give an example of how sales has taken everything away from you… even your smile
c. Give an example of how sales has allowed you to be a better communicator

49. Scenario: You’re in a job interview and you get asked – “What do you find rewarding about being in sales?” A great salesperson is likely to do which of the following:
a. Say, “I enjoy meeting new people and my sales career has allowed me to establish relationships.”
b. Say, “This sucks. I would rather be a garbage collector but they’re not hiring right now.”
c. Storm out of the interview and make sure you slam the door for dramatic effect

50. Scenario: You’re in a job interview and you get asked – “What do you find rewarding about being in sales?” A great salesperson is likely to do which of the following:
a. Remain quiet
b. Say, “In sales, I can earn more by working harder and smarter which is different than a number of other jobs.”
c. Suggest to the interviewer that they play hide-and-go seek around the office.