25 essential sales rep interview questions

Posted January 12, 2022

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By Serena Miller

Editor, Sales Best Practices at Outreach

Hiring a salesperson always feels a bit like a trust fall. Does this scenario sound familiar? You think you’ve found a great sales rep, spent time and money onboarding them, then weeks or months later, it turns out they aren’t quite the right fit.

Building a strong sales team is a crucial step forward for a growing business, but that task is easier said than done. A strong sales team is made up of reps who are motivated to create growth and surpass company goals. There are many things to look for when interviewing a sales candidate. While experience is one indicator of a good candidate, certain personality traits play an immense role in finding the best person for the job. Well-defined interview questions that help zero in on these traits will help you find a driven, ambitious, and goal-oriented candidate who will work well with a team and exceed sales goals.

This article provides a list of must-ask sales interview questions that help reveal candidates’ personalities so you can find the best person, or people, to join your team.

Rep Revenue Innovator Qualities graphic

Today's most successful sales reps are predictable producers that embrace hybrid methods and lean into collaboration.

1. How do you handle customer objections?

This question will give insight into the candidate’s process, or lack thereof, for addressing customer objections. Having processes in place shows strong preparation skills, which help maintain consistency and effective time management. 

Answers that describe exact processes in detail prove that the candidate can handle customer issues and has experience doing so. If a candidate does not have a process to explain or seems uneasy answering this question, consider passing on them.

2. When do you stop pursuing a prospect?

This question is effective because it will give the hiring manager insight into the candidate's persistence. The exact amount of attempts or touches will depend on the average deal size and industry.

A great answer to this question could be the candidate mentioning that it is appropriate to turn business away if the lead is not a good fit. This reveals conscientiousness and the ability to recognize qualified leads. A poor answer would be someone who says you should never stop pursuing a prospect or, on the flip-side, that you should only reach out once or twice.

3. What motivates you?

There’s no one-size-fits-all answer to this question. A good answer will depend on the company's unique values and culture. For example, if your company culture is very creative, a candidate who is motivated by thinking outside the box and taking risks could be a great fit.

4. Tell me about an opportunity you lost. What did you learn?

Humility is an important quality in a sales representative because clients and customers appreciate an honest, relatable salesperson. This question is great as it can help draw out humility in a candidate and give insight into how they handle rejection as well as challenges.

Look for answers that show optimism and grit most of all. Candidates who aren’t able to admit lost opportunities, or find lessons learned in lost opportunities, are probably not going to be the best fit.

5. Sell me something

Roleplaying should always be a part of your sales interviewing process. This strategy shows the hiring manager immediately how someone performs under pressure. It also gives insight into the amount of empathy they possess, which is an important trait for star sellers.

Good candidates will be able to jump right into the sales pitch, listen to your needs as a customer, and create a tailored response that is specific to those individual needs. Look for people who make easy conversation while remaining professional.

6. Walk me through your sales process

A strong candidate should have at least a basic understanding of the main steps in a sales process. This question will reveal their understanding of that process while also showing how the candidate is able to organize their thoughts and communicate complicated concepts.

Much like question #1, a good answer to this question will be one that details a clear process. Someone who scrambles to find an answer likely does not understand the sales process well.

7. What's more important: achieving quotas or keeping clients satisfied?

This can seem like a trick question, but a strong candidate will recognize that it is a balancing act between achieving quotas and keeping clients satisfied. Too much importance placed on achieving quotas, and the client relationship will suffer. Conversely, too much value on keeping clients satisfied, and quotas won’t be met.

Answers should show you that they are both goal-oriented and customer-centric, with equal importance on both achieving quotas and keeping clients satisfied.

8. Why did you choose a career in sales?

Drive is one of the top qualities of a successful sales rep. This question will show the hiring manager what drives the candidate and what they want from their career in the long run. It can also help hiring managers determine whether someone is in it for the right reasons based on what's important to the company.

Look for answers that align with your company’s values and culture. It is important for employee retention that employees get along with each other and feel comfortable with the company culture.

9. Describe a time when you collaborated with your team to close a deal

A strong sales team is exactly that–a team. This question can help determine whether the candidate is a team player. This is even more important if your organization prioritizes team-based goals. Plus, when a candidate values teamwork, it shows humility since they can recognize that two heads are better than one.

Candidates should be able to easily recall collaborative experiences and speak positively of their former team members.

10. If you asked your manager what your biggest strength and weakness is, what would they say?

This question will help determine how self-aware the candidate is. This quality is critical to selling to prospects and excelling at a company.

A good salesperson can read people well, including themselves. Perhaps more important than the candidate’s ability to recognize their strengths is their ability to recognize their weaknesses, and to make plans for improving those weaknesses.

11. How do you research prospects before a call?

A lack of research prior to a sales call is a bit like using the same cover letter for every job application (and forgetting to change the name of the company…oof). This question will show how diligent the candidate is in tailoring communication to their prospect. Someone who gives responses with actionable tailoring opportunities is a great candidate.

Bonus: dig even deeper by asking how they prepared for this interview!

12. How do you stay up to date on your target market?

The best sales reps are full of curiosity for their target market’s needs and pain points. This question can help the hiring manager gauge the candidate's levels of curiosity and drive. Are there conferences that are on their radar? A favorite social media account with daily sales tips or news? These are the types of answers to look for.

13. Teach me something

Asking the candidate to teach you something helps narrow down those with enthusiasm, clarity and passion for explaining and teaching. These are all valuable sales skills that will help build client trust. It isn’t so much important what they decide to teach you, rather the excitement and clarity with which they teach.

14. How do you establish trust with your prospects?

One of the unique skills necessary for a client or customer-facing sales role is empathy: the key to building a rapport. This question can help hiring managers determine the candidate’s emotional intelligence. How do they discover and stay tuned to their prospect's needs? Those who take a customer-centric approach are ideal for the job.

15. What career accomplishments are you most proud of?

This is another great question to see how driven and motivated candidates are.

For example, if a candidate tells a story of overcoming great odds to achieve a specific goal, it shows they are highly motivated. Hiring managers can build upon this question to help understand the work environment that helped them perform well. This can give clues into the company culture and management styles that work well for them.

16. How much time do you spend farming vs. hunting?

This question will give you a sense of a candidate’s goals. Ideally, you’ll want someone who understands that it's important to strike a balance between farming and hunting leads.

Look for answers that show the candidate understands that balance and doesn’t dismiss either the farming or hunting part of the role.

17. What's a new skill or concept you've taught yourself lately?

This question can help pick up on drive and curiosity. Like question #13, the skill they are learning isn’t necessarily important, just the desire to learn. Strong sales candidates will be hungry for new skills and eager to learn better selling strategies.

Answers to this question can also give you a glimpse into candidates’ hobbies and interests, which is a great way to gauge how they might get along with other team members.

18. Tell me about a time you received difficult feedback

Here is another great question to elicit humility in a candidate. This person should care about self-improvement and growth. They should be able to recall difficult feedback easily as it shows they can absorb constructive criticism and use it to fuel better results. Candidates with these qualities tend to be great team players as well.

19. Describe a time when you won over a challenging prospect.

This question can help hiring managers see how candidates approach difficult prospects and whether they can put aside their pride to move a deal forward for the greater good of the company. Particularly, listen for answers that mention any customer engagement strategies they used.

20. What's your favorite part of being in sales?

The candidate’s answer to this question will show how passionate they are. The best candidates will love what they do since that shows in the sales process. Passion is a highly-important quality to have as a seller as this natural drive creates interest and trust with the client or customer.

21. What's your least favorite part of being in sales?

This is a twist on the typical “what is your worst quality” interview question. The candidate’s answer will help the hiring manager gain insight into any areas that may be weak points and where candidates might need extra coaching.

It can also help alert you to any red flags, like if their least favorite part is a core function of the job. 

22. What core values do you think a salesperson should have?

Someone could give all the right technical answers in an interview but still be a bad cultural fit. This question will give insight into a candidate’s values and whether they align with the company’s values. If you're hiring someone with limited experience, consider these questions from Outreach SDR Leader Sam Nelson:

23. Tell me about a time you had to adjust your sales strategy to reach your target.

This question helps hiring managers see how driven and ambitious candidates are. It also gives the candidate an opportunity to provide insights into valuable lessons learned. Similar to question #18, this question helps determine whether the candidate has absorbed lessons and feedback. If they aren’t able to provide an answer to this question or think there is no room for improvement in their sales strategy, that’s not a great sign.

24. Have you used CRM software before? If so, tell me about your experience

Of course, the ability to sell is more important than past experience logging activities, and new hires can always be trained on preferred software. This question is more about gaining insight into the candidate’s sales experience, adaptability, and familiarity with industry tools. Furthermore, if CRM training is necessary, it should be planned for during the onboarding period.

25. In the past, how did you handle the situation when a customer was upset?

Finding out how the person handles an upset customer can show humility and sense of ownership. If they start to blame other departments or people for any failed sale or upset customer, it’s a major red flag. Team players take accountability instead of blaming others.

Finding the best sales rep starts with the right interview questions

The 25 questions in this article will help the hiring manager zero in on the top qualities of successful salespeople. These questions aim to make salesperson interviews more focused and purposeful, which will help you build a strong sales team and reduce unnecessary turnover. The goal is to find the best candidates and then make them want to stick around.

Once you’ve built the best sales team, you should shift your focus to supporting their productivity with the automation of manual, routine tasks and AI-driven insights.


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