Salespeople are particularly good interviewees and it’s no surprise why. They’re skilled at connecting with their audience, speaking to pain points, and overcoming objections. They can apply those same sales tactics to another goal: nailing their interview and getting the offer. And many sales job seekers are getting more interview experience than usual in the COVID-impacted job market. 

This isn’t a bad thing by any means. However, it does make it challenging for your team to narrow down candidates and understand who’s really the best fit for the role. 

We’re here to help. In this blog, we’ve curated a list of proven sales interview questions to evaluate applicants and put them to the test. We’ll also go over interviewing best practices to help your company shine, convert top talent, and improve employee retention.

25+ Sales Interview Questions and Exercises To Find The Best Talent

Sales interview questions and prompts run the gamut, from the classic “Sell me this pen” to some less helpful questions like “Which animal would you be and why?” Here are the ones to prioritize.

1. Walk Me Through Your Current Sales Process.

There will be plenty of time to talk through wins and losses. Most of all, you need insight into the candidate’s approach to selling, and that’s why this is one of the most common sales interview questions

Can they clearly explain their step-by-step process, from preparing their pitch and contacting leads to closing the deal and keeping relationships strong? How does it change based on customer segment, territory, etc?

2. How Do You Decide a Prospect Isn’t the Right Fit?

To achieve or exceed sales quotas, sales personnel need to be able to identify a worthwhile lead from a bottom-of-the-pile lead. What’s their criteria? What lead qualification skills and practices are they coming in with? How do they decide where to focus their energy?

3. Describe 2-3 Times When You Didn’t Meet a Goal or Lost an Opportunity. What Did You Learn? 

Everyone from a brand-new sales representative to an experienced VP of Sales should have a great answer to this question. 

Learning from failure is a huge part of being a strong salesperson and overall employee. Things won’t always go smoothly — mistakes happen, competitors get there first, and sales goals aren’t met. Listen for the lessons they learned, but more importantly, the concrete actions they took and the core values they’ve built from these experiences. 

4. When You Lose a Deal, How Do You Follow Up With That Prospect? 

The golden rule of sales is to follow up, and then follow up on your follow-ups. According to MarketingDonut, as little as one in 50 deals are made in the first meeting, and it can easily take anywhere from five to seven touchpoints to close a sale. 

Sales professionals have to expect and embrace the “no.” So, this question is great for digging into the specifics and understanding whether you’ve got a go-getter on your hands. 

5. Give an Example of a Time When You Received Constructive Feedback. How Did You Respond? 

A great sales professional is someone who’s able to take constructive feedback and use it to become a better version of themselves. After all, the most successful people in life aren’t born that way. They understand their areas of weakness and they dedicate themselves to improving in this area. 

You want to hear that the applicant remembers and absorbs the feedback they receive and that they use it to fuel better results in the future.

6. Teach Me Something. 

This sales interview question tests their ability to think on their feet and understand how to communicate with their audience in a short amount of time, just like with prospects. 

The topic doesn’t matter as much as how they explain the concept, engage with you, and keep your attention. They could teach you how to get on page one of Google, how to make a soufflé, or how a jet engine works. You’re looking for enthusiasm and clarity — candidates who are information-seekers and thinkers. 

Tip: To step it up a notch for experienced candidates, give them a time limit like 30 seconds or three minutes. 

7. What Did Your Last Product Do for Your Customers? 

Good salespeople won’t just talk about product features or their different SaaS plans. They’ll understand how their products served a particular need and solved pain points for different market segments. 

The candidate may turn this into a mini sales pitch to show off their skills or simply give you an overview. Either way, this shows how well they understood their company’s role in their customers’ lives, whether B2B or B2C. 

8. What Do You Know About Our Company and Our Product? 

This is often a make-or-break question. Each of your sales candidates should have done extensive research into your business before the job interview. And if they knew who on your team they’d be interviewing with, they should have combed through any info they could, just like with a sales prospect. 

Are they actually familiar with your product or did they send their resume out everywhere and hope for the best? This is also a shining opportunity for them to transition into pitching your product. But if they didn’t, follow up with our next prompt. 

9. Pitch Me Our Company’s Product./Pitch me Your Company’s Product. 

Roleplaying should always, always be a part of your sales interviewing process. It’s a prime chance for you to see each candidate in action and learn how they perform under pressure. But here’s the secret to getting the most out of this exercise: Don’t share your roleplay identity right away — see if they ask for it first. 

Some candidates will jump into their prepared pitch, launching into an attention-grabbing fact or anecdote. Unfortunately, they’ve made the mistake of selling without knowing who they’re selling to. 

Are you an enterprise company that’s used their software before? Are you a growing startup that’s wary of adding new costs? This info will shift their playbook in a major way. 

Note: Keep in mind that this tactic works best when you’re interviewing experienced salespeople. A lesser experienced or brand new sales candidate likely won’t know the ins and outs of pitching yet. 

10. Are You Ready To Jump on a Sales Call Right Now? 

Hopefully, the answer isn’t an immediate, “Yes, let’s do it!” 

At this stage, the candidate simply doesn’t know your product, customer objections, sales process, or tools. They probably haven’t shadowed any of your salespeople either. If they jumped on a cold call right that second, they’d be selling with the intent to sell when they should be looking for their ideal customer profile and fit. 

The answer you want to hear is, “I have a repeatable sales process that I can mold to your product right away. Once I learn enough to be a responsible salesperson, absolutely, I’ll be ready for a call.” 

11. Would You Rather Close a Guaranteed $10,000 Deal or Have a Shot at a $100,000 Deal?

(Adjust these dollar amounts based on your business model.) The answer can say a lot about the person you’re considering. Will they always go for the safe deal? Or, do their eyes light up at big, risky numbers? What’s their thought process, and does it align with your company’s sales strategy? 

Some sales leaders prefer their team members to go for the safe option — the guaranteed deal size — rather than taking risks. However, it really does depend on the nature of your business and the type of deals you’re working on.

The ideal answer here is that the candidate would be able to identify the opportunity for both, spend the appropriate amount of time on each deal, and shift their process accordingly. A great salesperson can flex their abilities to close the $10K and the $100K deal. 

In addition, they should explain that they want a healthy amount of mid-sized deals they can close while they work through the larger, more time-consuming “whales”. You want to see that they’re thinking about their entire book of business versus a single deal.

12. What’s More Important: Achieving Your Quota or Keeping Customers Happy? 

This question offers a window into your candidate’s sales philosophy. Ideally, you’re looking to see that candidates recognize it’s a balancing act. 

For instance, if you reach your quota but your clients are dissatisfied, you won’t be reaching your quota for much longer! However, if you aren’t reaching quota, it could be that customers aren’t happy or convinced they’ve made the right choice. There are many variables at play, so don’t be afraid to open it up to a conversation. 

13. What’s Your Proudest Sales Accomplishment? 

Help your applicants shine and talk themselves up. Did they exceed a sales target? Earn unprecedented customer satisfaction scores? Discover a sales enablement opportunity? Follow up with questions that help you understand their track record overall, and the work environment and actions that helped them perform well. 

14. Why Did You Choose a Career in Sales? 

The truth is there aren’t many kids who say they want to be a salesperson when they grow up. However, many eventually realize they’ve got exactly what it takes. Maybe they’ve always had the gift of gab, or enjoy making complex things (products/services) easy for anyone to understand, buy, and use. 

What is it about a sales career that drew them in? Understanding their motivation for getting started in sales can help you to learn about what drives them and what they want from their career in the long run. 

15. What’s Your Favorite Part of a Sales Job

We tend to perform our best when we’re happiest, so this is a good question to really get to know your candidate as an individual. What motivates them? What’s rewarding? What comes effortlessly? It clues you into the aspects of the job that will be easy for them and where you may need to coach or provide support.

16. What’s Your Least Favorite Part of a Sales Job

This isn’t a “Gotcha!” question. We’re human beings and we all have job responsibilities and requirements we like to move to the bottom of our to-do list. The ideal candidate is honest about what this aspect is, whether it’s paperwork, unenthusiastic clients, clunky software, or last-minute deal rejections. 

Tip: Be sure to follow up with questions to understand how they navigate these less-than-fun moments. 

17. How Do You Motivate Yourself?

Self-motivation is critical, especially when many salespeople have had to adapt to remote work due to the COVID-19 pandemic. While previous questions looked at why they started in sales and what they love about it, this question is more about their specific self-management tactics. 

Ideally, you want a team of exceptional self-motivators who can give themselves the boost they need to get results — and speak up when they need more resources (training, tools, team-building opportunities, etc).

18. How Do You Stay Knowledgeable About Your Target Audience? (Emerging Trends, News, Pain Points, Etc.)

The best professionals never stop learning, no matter what industry they work in. So, it’s critical to find out whether your sales candidate immerses themselves in the industry (past or present) and what they do to keep their knowledge up to date. 

Example answers include following thought leaders on LinkedIn, reading relevant blogs, attending industry events, and quarterly lunches with clients. 

This is a particularly important interview question for sales managers who will set the tone and coach their team to success. 

19. Tell Me About a Time When You Collaborated With Other Sales Team Members

Teamwork is at the core of outstanding sales teams. You need to know that your candidate is a good team player and can give and receive help while also keeping their eye on their own sales quota. This is even more important if your organization prioritizes team-based goals. 

20. Tell Me About a Time When You Collaborated With People Outside the Sales Team

The overlap and collaboration between sales, marketing, customer success, revenue operations, and other business departments is stronger than ever. Can candidates communicate effectively with others outside their team? Even more, have they leveraged those relationships to take their selling to the next level? 

Tip: Check out tactics for building trust between departments and our interview with Glassdoor Chief Sales Officer Kate Ahlering on how to unite different teams with common goals. 

21. If You Asked Your Manager and a Coworker What Your Biggest Strength and Weakness Is, What Would They Say? 

Being aware of how other people view you is critical to selling to prospects and excelling at a company. Without that self-awareness, your candidates won’t understand how they’re coming across in the eyes of the client, their team, or their manager, which means they can’t improve or self-coach. 

Does the candidate ask for feedback and make an effort to understand and apply it? Do they agree or disagree with the strengths and weaknesses they’ve heard? Of course, if they claim their managers or peers would say they have zero weaknesses, that’s a red flag!

22. Have You Used CRM Software Before? If So, Which and How?

Technology powers sales teams today, so find out which skills each candidate is bringing to the table. Are they comfortable with Salesforce, HubSpot, Gong, etc? You can always train new hires on your preferred software or workflow. This question is more about their sales experience, adaptability, and familiarity with industry tools. 

23. Which Sales Metrics Do You Pay Attention To, and Why? 

There are many “right answers” to this question depending on where they’ve worked and how they’ve been trained (or how they trained their team). From customer acquisition cost (CAC) to monthly recurring revenue (MRR), there are lots of different sales metrics that are worth paying attention to throughout the sales cycle. 

The hope is that, first, they can clearly explain why they chose certain key performance indicators (KPIs) and second, they aren’t focused on meaningless metrics like number of dials per day.

24. How Did You Change Your Sales Process To Adapt to the COVID-19 Pandemic? 

According to Salesforce, 61% of sellers are confident their jobs will never be the same after the COVID-19 pandemic. Sales reps, sales managers, and sales executives all faced challenges as the pandemic pushed sales to its tipping point.

You’ll get different answers based on whether they’re an exec, inside sales, outside sales, and so on, but the idea is to see how they strove to adapt and re-skill as the industry changed. Where did they succeed? What did they learn? How will they improve? 

25. How Did You Prepare for This Interview? 

Whether you ask this question upfront or toward the end, it’s another useful way to get insights into their researching, prospecting, and sales process. 

26. What Questions Do You Have for Me? 

The best salespeople — and strong candidates in general — have questions for the interviewer(s). After all, this is the company where they’ll invest their time and energy, possibly for years to come. Remember to allot time to open the floor for questions. 

It isn’t just about choosing the right person for the sales position in question. It’s equally important that they feel that your business is right for them. 

27. What Question Do You Wish I Had Asked (and Why)? 

After they’ve been in the hot seat for a while, this gives them a final opportunity to pitch themselves for the sales position. Your sales recruiters or hiring managers will get valuable feedback for future interviews, too.

Consider These Universal Job Interview Questions 

These tried-and-tried prompts can also help you understand each candidate’s experience, skills, and personality traits. 

  • Tell me about yourself. 
  • What’s your biggest strength? 
  • What’s your greatest weakness?
  • Why did you leave your last role? 
  • Where do you see yourself in five years? 
  • What do you like to do for fun? 
  • What did you like or dislike about your last company culture?

Sales Interviewing Best Practices To Keep in Mind 

  • Determine the most important competencies for the role early on. What characteristics are the most critical for the position you have available? Think about how you want them to strengthen the current team and learn whether their sales career path aligns with your succession planning. 
  • Get the most out of your hiring screens. Your hiring screen is a key ingredient in hiring top talent. Focus on the fundamentals. Share the responsibilities, pay, and team structure, and learn their goals and expectations. If they make the cut, move them along quickly.
  • Have multiple interviewers. It helps to have multiple voices and perspectives so that you can avoid bias and make the best possible decision. Give each interviewer a quality to focus on. 
  • Focus on skills, not just experience. There’s a middle ground in the talent vs. skills debate. Employees can and do grow into the role. If they’ve got a good track record and potential, don’t count them out. 
  • Put your candidates to the test. Actions speak louder than words. Use short but meaningful roleplays and exercises to see how they do with a real-world situation they’ll likely encounter.  
  • Be ready to address compensation. Transparency is paramount. Have your account executive compensation plans or leadership comp plans on hand and be prepared to talk through salary and benefits, especially remote work policies. 
  • Don’t worry about whether you’re the most unique and creative interview. Skip the fluff! Every question you ask should drive you and the candidate closer to determining whether they can do this job right now. 

Start With the Best Candidates, End With the Best Hires 

Sales Assembly makes scaling fast and easy. With our membership platform, you get access to a pool of vetted, qualified sales talent. Participate in virtual hiring events, use our onboarding and ramping programs, and level up your entire team with trainings and certifications. Chat with us to get started or learn more.

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