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Sales Consulting
December 8, 2020

26 Sales Interview Questions, (And The Greatest Hire Of My Career)

Kyle Vamvouris
CEO, Vouris

It’s no secret that the growth of your business is up to the sales team. 

So making sure that you have the absolute best candidates for all of your sales positions is crucial.

Here’s the ugly truth: hiring a single bad sales rep can cost your business $381,883.80, this does not even include the bad hire’s effect on the rest of the team!

To avoid burning this much money, only hire high performing sales reps. The most effective way to sort out the good from the bad is to ask the best sales interview questions to learn all you can about each candidate. 

After hundreds of interviews, I have learned that the best reps have many things in common.

What Kinds Of Sales Interview Questions Should You Be Asking?

First thing is first, the exact answer that they give you is not what’s important here. It is how they answer your question that is important.

Do they give you some cookie-cutter response? Or do they give you a specific answer that involves an experience of theirs and how they overcame their problem? 

Another important aspect to pay attention to is how many questions the candidate asks you, and about what? This will allow you to gauge their interest and how much they really care about your company and this position. 

There are two primary topics that every hiring manager should learn about the candidate. 

  1. You Should Be Trying To Learn Their Experience

Reading their resume is a great first step in sorting out your candidates. But you can only take so much away from reading their resume. 

The goal here is to figure out what they have done in the past, and how they did it. This will give you insight into whether they are a good fit or not. 

But on the flip side, if a candidate comes in and they have 30 years of SDR experience with one company...

They are most likely stuck in their own ways and cannot learn your process and align with the company culture. 

Regardless of what position you are hiring for, knowing how much experience they have will be crucial. 

  1. You Should Be Trying To Learn Who They Are As A Person

Get to know them. Figure out what they do in their off time. 

Can you really spend 40 hours a week working right next to them? Knowing if they spend their time doing interesting things or not will give you insights into who they are. 

So now that we have covered what you should be learning about your candidate, it’s time to dive into which questions to ask your candidates in order to learn this. 

List Of 26 Sales Interview Questions And The Kind Of Response You Are Looking For 

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

This will demonstrate their ability to find and keep up with changes. Find out something that they recently learned about their target market. You can dig deeper to see what blogs they follow. 

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

Make sure the candidate can do both, not every salesperson is great at hunting and farming. Also, find out how they split up their time. 

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

The best salespeople spend most of their time asking questions, rather than pitching. Some of the best questions that reps should be asking prospects are open-ended questions. This allows for a more in-depth understanding of the prospect’s problems. 

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

Their answer should show how they navigate through difficult situations, and if they are comfortable with cold calling. 

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?

Understand what their process for starting from scratch looks like. Figure out if their previous methods will work in your company. If you’re a start-up, this is crucial.

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

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

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

This can show you two things, how much research the candidate did of your company, and their creative thinking abilities. 

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

Find out if they have a process for preparing and handling objections. 

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

Watch and enjoy as they sell their current company to you. This will allow you to understand how the candidate talks about his/her company.

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

This is to figure out if the candidate can captivate and entertain you. Listen to see if they use storytelling to explain this. 

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

Every company has their different sales process, but the more tenacious and persistent a rep is, the better. 

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

Figure out if the candidate can identify what customers are a fit or not. Having the wrong customers is more harmful to a company that fewer customers.

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

Learn how quickly the candidate can bounce back and have a positive attitude. Is the candidate comfortable with rejection?

14. What do you know about our company?

Listen to find out if the candidate did some research about your company. 

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

Don’t believe a candidate who says they have never had a losing streak, we all have our up and downtimes. Listen to figure out what they learned from their losing streak.

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

This question will allow you to know if the candidate is aware of themselves and if they are proactive at fixing their mistakes. 

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?

With this question, you can find out if a candidate wants to learn all they can to better their sales process. Someone who studies their wins and losses will become a great salesperson (or they are great already). 

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

This question will show you how well the candidate understands their sales process. Also, you can learn how the candidate organizes their thoughts and if they can communicate clearly. 

19. How do you balance work and life?

Listen carefully to find out how dedicated to work they are, and if they are an interesting person. An answer that demonstrates a healthy balance of hard work and good life experiences is ideal. 

20. What motivates you?

A good candidate has the ability to motivate themselves. This is even more important than ever because our world is becoming more and more remote. 

21. What do you do for fun?

The odds are you are looking for a happy and interesting person to work with. See what kind of hobbies they enjoy and if they are a motivated individual.

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

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 thoroughly they take feedback and incorporate it into their work. 

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

Although more important of a question when hiring a leader role, learning how a candidate builds trust with others is important. 

24. Why did you choose a career in sales?

Did they choose it themselves, or did they unintentionally fall into sales? This will allow you to gauge their interest in sales, and if they grab life “by the reins” to take control. 

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

Is the candidate someone who takes healthy risks and stands-out from the crowd? These are good attributes to look for in a candidate. 

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

Storytelling is one of the best ways to captivate and persuade a prospect, so learning if your candidate can tell stories and incorporate them into their sales process is crucial.

My Favorite Interview Question Of All Time (And The Greatest Hire Of My Career)

I still remember it like it was yesterday. 

A man walked in the door confidently and curiously. Soon after he arrived, our CMO interviewed him.

Before I had a chance to ask the CMO how the candidate did, our Account Executive interviewed him.

Between the two executives, there was some disagreement as to whether or not he was the right fit...

So it was settled, I needed to determine this candidate’s ability to make the final say on whether or not he was going to be hired. 

I went through my usual list of questions (listed above) to start out fresh with this candidate and learn as much as I could about his experience -- and who he really is as a person. 

I’ll be honest, at first I liked him, all of his responses were witty and demonstrated his previous industry experience.

But as the interview progressed, there was still the elephant in the room, why did one executive like him and not the other?

And then it came to me, I will ask this candidate his perspective on what the first two interviewers thought of him. So then I asked him, 

“You have spoken to the CMO and the Account Executive. 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?”

His eyes lit up with shock, it was obvious that he had never heard of such a question!

Then there came the pause………..

30 seconds of silence later (a lifetime in an interview), the candidate told me the exact concerns and excitements that the previous interviewers had of him. He even went as far as explaining in detail how he did not mention to one interviewer the specific size of the deals he had made before, and how the other interviewer was excited about his experience in the industry. 

I was amazed by his response!

He hit the nail so hard on the head I looked at his belt to see if he brought a hammer to the interview. To my astonishment, there was no hammer in sight!

Well ok, maybe I didn’t look for a hammer. 

Anyway, this candidate’s answer demonstrated that he knew the concerns and excitements each interviewer had of him and overcame the concerns. 

This is how I made the greatest hiring decision of my career and came up with the most powerful question to ask when interviewing someone for a sales position. 

The reason why it is so effective is that it allows me to gauge any candidate’s emotional intelligence and self-awareness, some of the most important attributes of a human. (especially a sales rep) 

As for the other potential candidates? Even though a few had more experience, they didn’t demonstrate as much emotional intelligence as this fine gentleman did. One other candidate only answered half of this question, a response that raised a red flag. 

The moral of the story is if you want to determine who will be the highest performing sales rep, you need to ask the best sales interview questions.

In other words, 

To Gauge An Interviewee’s Emotional Intelligence, You Should: 

Have the last person of the interview process ask the candidate:

“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?”

I wish you the best of luck with filling your sales position! It’s no easy task, and it can seriously hurt your business if you hire a bad sales rep -- or take too long to find the right one. 

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