person icon
Kyle Vamvouris
book icon
Min Read
clock icon
April 27, 2022

Hiring a single bad sales rep could cost your business $381,883.80. Use these 26 questions to find sales reps that will SUPERCHARGE your business.

BONUS: Here’s our CEO Kyle’s FAVORITE question to ask anyone he hires...

Here are 26 questions that will help you find your next sales superstar and avoid potentially bad hires.


1. How do you stay up to date with your target market?

Why it’s important: 

Do they keep up to date with industry news?  

It’s a lot easier to work with someone who’s already got their finger on the pulse of the industry than someone who doesn’t. 

As a follow up, you can ask them to tell you something they recently learned about their target market.

2. How much time do you spend cultivating customer relationships versus hunting for new clients? What‘s the philosophy behind the breakdown?

Why it’s important: 

Great candidates can do both.

Super candidates can do both and explain why they balance nurturing and prospecting the way they do.

3. What are your favorite questions to ask prospects that gauge their need and interest?

Why it’s important: 

The best sales people ask lots of questions. 

Keep an eye out for whether your candidate suggests open-ended questions or “Yes/No” questions. 

Open-ended questions are a sign that they’re already thinking conversationally, which is a great signal for future success. 

4. Tell me about an uncomfortable situation you experienced during a cold call. 

Why it’s important: 

Being able to navigate discomfort is an underrated skill. 

Someone who can tell an “uncomfortable situation” story effectively is a great sign that they’re a natural storyteller and can engage on a personal level.  

5. Tell me about a time in your sales career where you needed to start a territory from scratch. What did you do for the first 30 days? What would you have done differently? If I hire you, what will you do at this company?

Why it’s important: 

A challenge question like this will put the candidate on the spot and force them to:

  • Tell a story.
  • Think analytically + creatively.
  • Present a structured plan. 

6. What information do you look for when researching a prospect? 

Why it’s important: 

The best answers will give you insights into how they research and what traits they think are important in a prospect. 

7. What do you think our company/sales organization could do better?

Why it’s important: 

Their answer will show how much research they have done on your company and how creative they can be on their feet.

8. How have you handled customer objections in the past?

Why it’s important: 

You’ll find out if they have a process for preparing and handling objections. 

9. How does [your company name] bring value to the customer?

Why it’s important: 

This gives the candidate a chance to put your value into their own words. Good answers will reflect their research, creativity, and communication skills. 

10. Tell me about something interesting you have learned recently? 

Why it’s important: 

Can the candidate entertain you? Can they tell stories? Do they know how to be relevant and interesting at the same time, under pressure?

11. When do you know it is time to stop pursuing a potential client?

Why it’s important: 

You’re looking for a few key markers of a great salesperson:

  • Persistency. 
  • Knowing when to stop. 
  • Knowing how to manage their time and balance between pursuing potential clients and finding new prospects.

12. Have you ever turned a prospect away? If so, why?

Why it’s important: 

This tells you about their understanding of customer fit and their willingness to turn away bad fits. 

Having the wrong customers is more harmful to a company than fewer customers.

13. How do you keep a smile on your face during a hard day?

Why this is important: 

You’ll learn about how the candidate deals with rejection and maintains a positive attitude.

The ability to maintain a positive outlook is an essential skill in our field!

14. What do you know about our company?

Why it’s important: 

This gives the candidate a chance to show off their research and present it in a creative and structured manner.

15. Have you ever had a losing streak? How did you turn it around?

Why it’s important: 

Are they willing to get real with you?

Any good sales rep has had a losing streak - it’s what they did to turn it around that makes the difference.

16. What was a mistake you made? What did you learn from it?

Why it’s important: 

Here’s another chance to learn how honest the candidate is willing to be.

It’s also an opportunity for them to tell a comeback story and present their mistakes as learning opportunities instead of purely negative moments.  

17. Have you ever asked a prospect who didn't buy from you to explain why you lost the deal? What did they say, and what did you learn from that experience?

Why it’s important: 

Here’s a chance to see how committed the candidate is to improving their process. 

A rep who studies their losses has the potential to become a great salesperson.

18. Explain the steps you take, from the beginning of the sales process to the end.

Why this is important: 

See how logical and thoughtful they are. 

Do they just pick up the phone, or do they take the time to do their research and prep? 

It’s also a good chance to see how clear they are in communicating their thoughts and ideas.

19. How do you balance work and life?

Why this is important: 

Good sales reps work hard, but also have outside interests and will demonstrate a healthy work-life balance.

20. What motivates you?

Why it’s important: 

This question tends to trigger some “interesting” responses, both good and bad. You’ll want to look out for signals like:

  • Do you think they’re being honest?
  • Are they identifying internal or external motivations? Good candidates often balance both.

21. What do you do for fun?

Why this is important: 

Here’s a chance for the candidate to tell you about the rest of their life, outside of the office.

Their hobbies and interests can highlight a cultural fit (or misfit) with your team. 

Plus, it’s an opportunity for them to tell another interesting story. 

22. Tell me about a time you had to adjust your sales strategy to reach your quota?

Why it’s important: 

This question is a great way to figure out what valuable lessons the candidate has learned. 

But the most important aspect to look for is how they respond to feedback and incorporate it into their work. 

23. How do you establish trust with members of your team?

Why it’s important: 

This is a good question for a potential team leader.

It’s also important to know how a candidate goes about fitting into an existing team and a new environment.

24. Why did you choose a career in sales?

Why it’s important: 

Did they choose a sales career themselves or did they unintentionally stumble into sales? 

This will allow you to gauge their interest in sales and if they grab life by the horns to take control. 

25. What have you done that has beaten the odds?

Why it’s important: 

What does your candidate consider to be a challenge? 

How have they overcome adversity to get to where they are now?

26. Tell me how you’ve incorporated storytelling into your sales process.

Why it’s important: 

Storytelling is one of the best ways to captivate and persuade a prospect. 

It’s crucial to find candidates who can tell stories and incorporate them into their sales process.

Bonus Question


Our CEO Kyle’s favorite question measures the emotional intelligence of a candidate, by asking their opinion of how their previous interviews went:


Question: “You have spoken to person A and person B. I'm curious, from your perspective, what do you think they will be most excited about with you as a candidate, and what do you think their biggest concern will be?”


This question should be asked by the last person in the interview process.

Want to print off a sheet to have all these questions in one place read for your interview? Print off the next sheet for your next sales rep interview

  1. How do you stay up to date with your target market?
  2. How much time do you spend cultivating customer relationships versus hunting for new clients? What‘s the philosophy behind the breakdown?
  3. What are your favorite questions to ask prospects that gauge their need and interest?
  4. Tell me about an uncomfortable situation you experienced during a cold call. 
  5. Tell me about a time in your sales career where you needed to start a territory from scratch. What did you do for the first 30 days? What would you have done differently? If I hire you, what will you do at this company?
  6. What information do you look for when researching a prospect? 
  7. What do you think our company/sales organization could do better?
  8. How have you handled customer objection in the past?
  9. How does [your company name] bring value to the customer?
  10. Tell me about something interesting you have learned recently? 
  11. When do you know it is time to stop pursuing a potential client?
  12.  Have you ever turned a prospect away? If so, why?
  13. How do you keep a smile on your face during a hard day?
  14. What do you know about our company?
  15. Have you ever had a losing streak? How did you turn it around?
  16. What was a mistake you made? What did you learn from it?
  17. Have you ever asked a prospect who didn't buy from you to explain why you lost the deal? What did they say, and what did you learn from that experience?
  18. Explain the steps you take, from the beginning of the sales process to the end.
  19. How do you balance work and life?
  20. What motivates you?
  21. What do you do for fun?
  22. Tell me about a time you had to adjust your sales strategy to reach your quota?
  23. How do you establish trust with members of your team?
  24. Why did you choose a career in sales?
  25. What have you done that has beaten the odds?
  26. Tell me how you’ve incorporated storytelling into your sales process.
  27. You have spoken to person A and person B. I'm curious, from your perspective, what do you think they will be most excited about with you as a candidate, and what do you think their biggest concern will be?”


  • Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod