25 Unique Sales Interview Questions to Ask Sales Rep Candidates

Can you imagine if Ethan Hunt, the 10-minute-breath-holding, the Burj Khalifa-climbing, the helicopter-piloting heartthrob, was not played by Tom Cruise? 

We can’t either. Some roles are one of a kind. SDR and account executive roles are, too. Because sales is a lot about the hardcore action sequences – persisting day in and out despite the endless rejections, learning, unlearning from every sales conversation and relearning in the next, redefining outreach strategies daily, and identifying objections even before they arise. And not everyone can play a Hunt.

But, if you are looking to hire a sales rep who’s the Tom Cruise of the genre, you’re in the right place. No, we’re not listing our substitutes to recast Hunt. Instead, we’re sharing powerful sales interview questions that you can ask to spot the best of the best salespeople within the industry.

What are the traits of a successful salesperson?

Off the top of your head, you may think that the traits of a successful salesperson are their ability to cold call, overcome objections, or negotiate. While all of these are true, Hubspot’s Mark Roberge, in his book, Sales Acceleration Formula, carried out significant research on the traits of the most successful salespeople and made a unique discovery. He found that coachability, curiosity, prior success, intelligence, and work ethic were the most commonly seen traits in sales high-flyers.  

But there’s a hitch. Such salespeople were successful in Hubspot’s context. Salespeople succeeding in a rapidly changing market, selling enterprise-level, high-value deals, showed these traits. 

So before you decide to interview the candidates, find out if you want salespeople who have to work with high volume or high value. If it’s high volume, they may not need some of these characteristics. In that case, you should begin collecting the employee data or testing the candidates on their work ethics, curiosity, coachability, and objection handling skills. 

Traits of successful people

So, we prepared 25 questions to test salespeople on these traits. 

To address the elephant in the room, ‘why did negotiation or objection handling skills not make the cut?’

“Statistics suggest salespeople who are intelligent and helpful, rather than aggressive and high-pressure, are most successful with today’s empowered buyer.” Roberge rightly adds in the book. As we mentioned earlier, it depends on what your sales strategy is. 

Broadly speaking, though, these questions will help you find the right candidate whether you sell to SMBs or Fortune 500 companies. 

20 Powerful Sales Interview Questions

1. Questions to test coachability

Test if the person is open to learning new things, and accepting mistakes. Coachability in this sense means, ‘can the salesperson be taught and trained to do something? Can they absorb that information and put it to practice?’ 

Today, we’re far from the times when the likes of Jordan Belfort and Glengarry Gloss win deals. Until recently, sales was about being alpha, or a lone warrior. Having bigger egos was more common. One of the biggest problems with having people like that on the team is that they’re difficult to give feedback to and be coached. While the lone wolf trope was once practical, empathetic salespeople are better poised to win more sales today owing to their ability to learn from others, and from their own mistakes.

Question 1: Can you share an example of when you made a mistake? 

Why this question? 

Admitting one’s fallbacks or mistakes isn’t easy, especially for a salesperson. You’ll be able to understand if the candidate is self-aware and introspects to find out what happened. This question is an excellent way to find out if they’re willing to accept that there’s a gap in their understanding and whether they’re open to learning or training. When they tell their story, notice if they blame others for a mistake or own up to them.

Question 2: If you’ve failed to hit the quota for the month, what will be your next steps? 

Why this question?

Good salespeople revisit their pipeline, activities, and outreach strategies to dissect and determine if the reasons were controllable or uncontrollable. Are they able to take a step back and get into the nitty-gritty of why the quota wasn’t hit – maybe due to poor qualification at any stage in the sales process or deals being stuck at stages for far too long? 

Instead, are they jumping on the opportunity to blame marketing or the engineering team for a ‘sub-par product?’

Successful salespeople would even go to the extent of constantly assessing if they’re targeting the right market or whether the market’s need for the product has dwindled. 

Question 3: What was the most challenging part of your previous job? 

Why this question?

Pay attention to how they answer this question. Do they see the challenges as something they overcame or ran away from? Are they trying to stay within what the role prescribed, or did they push themselves to solve new challenges and grow from the scope of their job? You may face challenges when exploring new horizons in your set-in-stone job role. So asking about roadblocks they faced would shed light on whether they tried to break out of their role to grow the team or the strategy or the plan. 

Question 4: Did you face a problem you couldn’t solve independently? What did you do?

Why this question?

Roger Federer didn’t become the number one tennis player in the world working alone. He had the support of his staff, coaches, physical trainers, therapists, and several people putting their noses to the grindstone behind the scenes. 

The infamous lone wolves will no longer be successful in today’s buying environment. Success in sales is being reclaimed by those who are good collaborators. They work with their managers and sales ops colleagues, and their marketing and product teams to close deals. This question is an excellent chance to determine if they sit on a problem until it sputters and boils over. Or if they let their guards down and ask for help. Did they exhaust all options to get the job done?

2. Questions to test curiosity

One of the most sought-after skills in sales today, curiosity, is what makes today’s salespeople book more meetings and win more deals. “Curious people are non-blaming, non-shaming, and supportive, working together, focused on exploring options to find the best solution, one that supports collaboration and leads to innovation,” Kathy Taberner, cofounder of the Institute of Curiosity, says.

In sales, all that and more is important. Curiosity means reps are asking questions as a journalist would. They are listening to prospects and taking notes.

Question 5. How do you open your sales conversations–in a cold call? 

Why ask this question?

The kind of language they use and their questions will give you an idea of how they approach the cold call. Do they use a cold calling strategy? Or are they winging it, and if they are, has it been successful? The ideal answer will show 1. if they are reiterating their approach based on trial and error to constantly improve themselves, 2. whether they care about the prospect or are just trying to meet their quota. 

The first few minutes are crucial in a cold call because you’re barging into the prospect’s day uninvited, so it’s important to note how they’d be buying the prospect’s time. Because a generic sales-first approach in the conversation won’t succeed. The rep has to be genuinely curious about the prospect and their problem. 

A key skill to note is whether they are listeners. 

Question 6: What are the top five questions you ask your prospects if you get on a discovery call? 

Why ask this question?

Similar to the previous question, the answer to this will show how seriously they take discovery calls and whether they follow a good qualification process. Ideally, they should be able to say one question. And admit that the rest of the questions would be natural follow-ups in the direction the conversation is heading. The rep should be able to direct their questions to find the root cause of the prospect’s problem. 

If you want to make this round a little more interesting, ask them: What do you ask a BANT-qualified lead?

Question 7: Which do you think is the most crucial stage of your sales process, and why?

Why ask this question?

This question seeks to understand whether the rep knows the different stages of a sales process and that the discovery process would be the most critical part. That’s when they can intently listen to the prospects and get vital details about the deal like the expansion potential, deal size, and use case. Ideally, the account executive can prioritize prospects or deals based on these details. 

Through the ‘why’ portion of the question, you’ll also know what kind of information they will find necessary. So if your sales candidate answers that they are curious about the prospect and their business, you’ve hit bingo!

Question 8: Have you learned anything new recently?

Why this question?

It’s a simple question. But a powerful one. The answer is a window into your candidates’ lives–how they view the world, their priorities, and their personalities. Salespeople are constantly learning new things or investing their time in new activities. It could be anything from sports to creative arts to music or anything under the sun. Whether they’re, in fact, a curious person, this answer will show.  

3. Questions to test past success

If you’re hiring a Tom Cruise, you should check if they have leaped out of helicopters. A “history of top performance or remarkable achievement,” according to Mark Roberge, shows if your candidate is an A-class performer and whether they’ll bring unique value to your team. This is also an opportunity to see how they perceive successes and failures. Do they quickly move on from rejections and failures? These questions will reveal.

Question 9: What was your monthly quota? What’s your average quota attainment rate?

Why ask this question?

The answer gives you a peek into what their previous successes looked like. It’s also about how they talk about their success. Do they talk about process changes or challenges they tried to overcome to get to success? How was the quota set? Was it progressive? Was it challenging? 

Question 10: What was your most satisfying sale?

Why ask this question?

Honestly, the size of the deal doesn’t matter. What matters is how the rep pushed the sale. Do they relish that they got no help, or own the fact that it was a collective success? Whatever the answer, you want to discover what about the sale they are proud of and whether they’re passionate about selling. 

Question 11: How do you define success in a sales role?

Why ask this question?

Booking meetings and closing deals both are standard success metrics. But knowing what kind of activities or processes to focus on to be successful as a salesperson also matters. Do they understand that the role’s success depends on the business objectives? Some companies would want to focus on a volume game, so success means doing as many outreach activities as possible or closing deals as soon as possible.

And if the company is focused on enterprise-level deals and the deal value matters, success would mean knowing their product strengths and weaknesses and knowing how to differentiate or which market would be the best to target. 

For example, it’s like – you’re building an MI phone, but you’re prospecting in Apple’s market. So yes, success is not only about reaching the pole-sitting atop the Burj Khalifa. It’s also about carrying a harness, using kit gloves, and knowing how to get there. People who eat success for breakfast don’t always go by the book. They double-check if they’re using the correct harness, suitable gloves, and the right map to get there. 

Question 12: What do you do when you’ve faced rejections the whole week?

Why ask this question?

How salespeople deal with rejections could say a lot about how successful they have been in the role. The ability to move past rejections is one of the fundamental soft skills of a salesperson. So, what do they do if they’ve been facing rejections the whole week?

Look for someone who can identify blockers and sets up feedback loops for iterations on their sales process. Rejections at a stretch mean something may be going wrong, and they should be able to point out the reason–whether it’s controllable or uncontrollable. A successful rep would move on rather than burn themselves out doing meaningless or ineffective activities. Because you can still win the world cup if you’ve won the key matches. 

4. Questions to test intelligence

The best salespeople are the ones who can ‘learn complex concepts quickly and simplify them to prospects. 

Can they sell technical concepts to non-technical users? Are they quick on their feet when facing difficult questions? 

Intelligence can be divided into four categories: Emotional intelligence (EQ), general intelligence, market intelligence, and analytics intelligence. 

First, sales reps need EQ—the ability to put themselves in their prospects’ shoes. General intel – they should be able to simplify complex statements and give context to the solution. Market intel – they should be aware of the strengths of the products and services they’re selling. They need to know where their product stands in the market and how they’re different from the competitors. 

Question 13: You have two leads, one who downloaded your ebook and one who signed up for a demo; what would your messaging to each look like?

This is to identify if they know how outreach differs with intent levels. Someone who downloaded an ebook would have little to no intent to buy, while the one who signed up is clearly looking to buy a product. 

So the ideal answer should be that there would be a difference in messaging and that the first lead would be put into an automated email sequence while the second lead would be treated as a priority lead; therefore, they should be given a call or an email. 

Question 14: If you could invite one prominent person from history to dinner tonight, who would it be and why?

Why ask this question?

The credit for this ingenious question goes to sales trainer Julie Hansen

How can you get a peek into their behavior in a 30-minute job interview and, maybe, a task or two? They are most likely in their best form, with the veneer of a different personality. This question will reveal their values and whether they can face an unexpected question.

Question 15: Pick a product/service in the market and explain it. 

Why ask this question?

This question will reveal whether the candidate is experienced and reads up on industry news. Test how clearly they’re explaining the concept. This will test their ability to simplify complex topics. 

Question 16: The prospect just asked for a feature that your product doesn’t have at the moment. What do you do?

Why ask this question?

Another one in the series of ‘unexpected questions’ is a common question AEs face during discovery sessions. How does the sales candidate answer this question? Do they say they don’t have it and kill the conversation? Or do they promise them the moon? Ideally, the answer depends on your sales strategy and the priority level of the prospect. If you’re a company that is still growing and want to 

Question 17: What should the ideal sales process look like?

Why ask this question?

A trick question because there is no ideal sales process. The sales process is dynamic. It changes according to your business’ priorities and goals. So, the correct answer is – ‘it depends.’

5. Questions to test work ethic

Work ethic is probably one of the most challenging things to find existing in tandem with the other skills. If they’re a successful lone rider, it may not fly with some businesses as team collaboration often brings out the best in everyone. They may be a great talker, intelligent, and curious. But, wait, do they care about your mission? Will they be your business partner in crime? Will they spend time and energy on achieving your company’s mission? You also need to check if the person is able to execute all the activities necessary to push the sales forward.

In between the actual selling, there’s a lot of prospecting, following up, CRM updating, and documentation, are they taking care of these activities meticulously? Such behind-the-scenes sales activities are just as crucial as their frontline counterpart.

Question 18: What does your day-to-day at work look like?

Why ask this question?

It will show how they prioritize their activities and how they plan for the day. It’s pretty basic, but whether they use any productivity strategies will give you insight into how much time and energy they invest in getting work done smartly.  

Question 19: A prospect just rejected you over the phone. What do you do after?

Why ask this question?

How do they deal with rejection on a day? You want to look for somebody who doesn’t take rejections personally. To find your all-star rep, find a salesperson who’s optimistic in their sales approach. These are people who are unfazed by rejection. They see them positively as an opportunity to introspect their own outreach approach, the market they’re targeting, or their sales strategy. 

Question 20: How did you handle a prospect who dropped you at the final stages of the sale?

Why ask this question?

If you ever see somebody in the sales team screaming into the void, they probably lost a deal in the final stages of the sale. From small to huge deals, the pain remains the same. The time and effort you poured into shaping the deal collapsed in a single, sad rejection email. It’s heartbreaking, so you need to find out how and what the candidate would do when they face such an incident. What would you want your ideal candidate to do in this situation? We’d want them to take a breather and revisit their conversation to check if the reasons could have been in their control or not. Then, simply learn from it, or move on if it was because of reasons out of their control. 

Question 21: If your sales manager could describe you in 3 words, what would they be?

Why ask this question?

Are your salespeople self-aware? Seriously. Do they know their own strengths and weaknesses? Being emotionally intelligent is very important if you’re trying to persuade people for a living. For example: if you know you sound off today, you’ll probably refrain from making many cold calls. Because the mood you have while talking to prospects affects your prospects, too. Think about it, how many meetings can you book with a gloomy pitch? Zilch! Most successful salespeople are reported to have high EI.

BONUS: 4 Sales interview questions for hiring fresh graduates

The following questions will help you understand whether they’re curious, go-getters, and can communicate well and simplify complex topics.  

  • Tell us something you did in college that you’re proud of?
  • Can you tell us about some non-academic work you did in college or outside of college?
  • Pick two of your favorite companies, and tell us why you chose them.
  • Pick your favorite smartphone, and explain why you chose that over the others.

Wrapping it up

Finding your people, whatever the size of your organization, is a herculean task. But finding top-performing salespeople, who will literally drive the revenue engine of your business, is significantly harder. In that case, you can’t cast anyone other than a Tom Cruise as the Ethan Hunt. So ask questions that dig deep into their personalities and past successes, almost like a journalist would. Ask powerful questions, and ask them for faux demos of products to get a complete picture of their selling ability.

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