62 Sales Interview Questions to Ask Sales Rep Candidates

Over my decade of B2B sales, I learned that to build a high-performing sales team, you have to hire high achievers. Here’s the key: have the right sales interview questions to ask.

Hiring top-tier salespeople is challenging at the best of times. Selecting and onboarding the wrong candidates can keep your company from meeting important business goals. You also have to consider the time and financial investments required to hire, train, and pay a sales rep who doesn’t work out — not to mention the impact on team morale.

Effective sales interviews can help you find consistent quota hitters, thick-skinned rejection handlers, and adept objection slayers to help grow your business.

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Interview Tips for Sales Hiring Managers

Are you new to conducting job interviews and need some sales interview questions to identify your next superstar? In this post, I’ve gathered some of the best questions I’ve been asked by sales managers — and some of the worst, which made me want to leave the building.

For example, I was once asked to tell the story of a time I lied to a customer to get a deal. The interviewer said he wouldn’t believe me if I said I never lied to close a deal. I didn’t get that job, which was probably for the best in retrospect.

Asking the right interview questions can help you find the best candidates for your organization who can hit the ground running towards hitting quota, or be coached to be a top performer in due time.

Technical Sales Interview Questions

I worked in technology sales for over a decade, so I appreciate how important it is for hiring managers to ensure the sales reps they hire:

Have strong technical acumen.
Can learn about your products and their benefits quickly.
Have a genuine interest in your industry beyond just earning a paycheck.
Possess the ability to cohesively explain complex concepts in context to a prospect or customer’s role in their company.

Use the following questions to distinguish the sales contenders from the pretenders.

1. How do you, or would you, keep up to date on the latest trends in [your industry] and what matters to your ideal customer profile?

Asking this question helps gauge the candidate’s levels of preparation and industry. It also shows whether the candidate knows who your industry’s thought leaders are and which publications and analysts they would listen to for guidance.

You might learn of new trends during this process, so don’t leap to judgment during the interview unless the trend seems made up or antiquated. I recommend you view this question as an opportunity to assess the candidate’s ability to research and prepare for customer meetings.

What to listen for: Does the industry and target market of the candidate’s last job differ from yours? If so, this process will show the candidate’s ability to find trade publications and data sources that the rep might use in customer-facing sales presentations.

Insight from my experience: When I interviewed for an IT security business development role, the hiring manager tasked me with creating a presentation about data security with statistics that could capture a prospect’s interest.

2. Explain a complex concept you understand well. You have five minutes to capture my interest.

This question helps you evaluate the candidate’s confidence and ability to think on their feet, much like the “Sell me this pen” exercise. It gives the candidate an opportunity to explain (or, in effect, sell) something they are passionate about or even something related to your industry or company.

What to listen for: While this technically isn’t a question, assessing whether the candidate can effectively demonstrate a concept or process is essential. Listen to hear how concisely they can explain the topic.

Insight from my experience: Like many candidates, I often struggled with keeping my nerves in check during sales interviews — especially when I was asked a classic “gotcha” question like, “What is your biggest flaw?” But, given the opportunity to speak on a topic I knew well, my nerves would ease, and my speaking cadence slowed and smoothed out.

3. In your last position, what percentage of your time did you dedicate to building customer relationships vs. hunting for new clients, and why?

Many large enterprises staff their sales teams with dedicated hunting, farming, and trapping specialists to maintain recurring revenue and land new accounts. Many sales teams in small- to medium-sized companies hire generalists who have essential sales skills across these categories.

What to listen for: This question can help you assess the candidate’s ability to prioritize and balance business development and relationship-building activities. It also helps to determine if the candidate is more of a sales hunter, farmer, or trapper.

Insight from my experience: I worked both with sales hunters who had a constant hunger for closing “big game” deals and farmers who preferred to help existing customers get the most from their technology investment. My sales mentor, Carl, had the best balance of account management and business development skills. We sold into government accounts, so fostering strong customer relationships was a great way to motivate clients to take mandatory reference calls from prospects.

4. What are your favorite questions to ask prospects during discovery calls?

Here, you can assess the candidate’s ability to ask open-ended questions when breaking the ice and building credibility with a prospect. It’s also important to gauge a candidate’s ability to ask probing questions to qualify for an opportunity and move it forward.

What to listen for: Good salespeople spend more time asking questions than pitching their company’s products and services. Seek out candidates who mention that they ensure and confirm they understand a prospect’s needs before asking questions.

Insight from my experience: I remember working with a non-profit organization prospect who was considering a competitor solution after thoroughly testing my company’s offering. The competitor’s product wasn’t interoperable with the content management system (CMS) they built their website on years before, while my company’s product was built for their website CMS.

I asked the prospect how his organization’s donors and volunteers would feel if they found out that he wasted an opportunity to leverage their existing technology and added weeks to the project timeline. That one question ended as a win for my company.

I have since used that scenario in sales interviews to successfully demonstrate my ability to ask tough questions that moved deals forward.

5. Tell me about a time when you overcame a customer objection. What was the objection, and how did you deal with it?

This question helps the interviewer to test the candidate’s problem-solving skills, resilience, and ability to think on their feet. Effective sales professionals need to address objections confidently and empathetically. You should prioritize hiring salespeople who can demonstrate how they can flip an objection into a value-based selling opportunity.

What to listen for: Look for a candidate who can demonstrate how they can flip an objection into a value-based selling opportunity. Preparing to deal with objections — instead of improvising — is critical. Listen for evidence of a process. For example, if you have a usage-based pricing model, the candidate should know how to position it if a pricing objection comes up.

6. What role does social media play in your sales process?

This question helps you find candidates who follow sales trends and align with what’s working, like social selling. Your marketing department may manage social content distribution, yet the 2024 HubSpot Sales Trends report found that 38% of sales reps are trappers who use social media as an integral part of their sales process, and 24% of those surveyed said social media was their favorite selling channel (only 3% less than selling over the phone).

What to look for: Social selling is becoming critical in all industries. If the candidate hasn’t used social media channels like LinkedIn for outreach, prospect research, or business development in the past, make sure they are willing to adopt it for their future on your team.

7. What role does content play in your selling process?

Candidates should understand the important role content plays in the buyer’s journey. Prioritize hiring candidates that have used (or are eager to use) content to:

Build trust and provide substantial evidence your products and services can address their pain points and business needs.
Move deals through the sales pipeline, such as using case studies and testimonials to help close a deal.
Nurture customer loyalty and engagement with existing customers, and inspire them with new ways to use your products and increase their return on investment.

What to look for: Look at the candidate’s social media posts to see if they helped distribute and amplify their former employer’s content before. Ask for any examples of where the candidate used content to generate leads or move a lead forward.

Insight from my experience: I once wrote a LinkedIn article about a Microsoft CRM portal solution I was selling. I shared the post in a LinkedIn group and used a trending hashtag for an upcoming Microsoft partner conference. By simply writing and sharing that post in targeted groups and tying it to discussions about a trending event, I generated several leads and booked a few meetings at the conference.

8. How do you research prospects before a call or meeting? What information do you look for?

This question shows candidates who can identify excellent icebreakers, create a positive atmosphere for prospects, and personalize communication. B2B prospects are more likely to spend time with (and buy from) those who invest the time to understand their business, and in understanding their unique challenges.

What to look for: Neglecting to use LinkedIn or a generative AI tool like HubSpot Breeze to research clients and enrich their account profiles is a recipe for failure in hyper-competitive sales marketplaces. Ensure candidates are searching for professional and personal customer intelligence that can open doors and spark productive sales conversations.

9. If I hired you today, describe your 30-60-90 day plan to be successful.

The best candidates to join your sales team are those who are self-motivated and have a heightened sense of ownership. They understand the importance of:

Meeting the coworkers that can help them succeed.
Ramping up on your products and services.
Learning your company’s policies and standard procedures.
Getting familiar with the prospects and customers in their assigned territory, industry, or product’s target market.
The short- and long-term goals of the position.

What to listen for: The candidate should be able to draw on experiences in other roles, projects, or internships to demonstrate initiative, confidence, and enthusiasm for contributing to your team’s success. Candidates who are prepared enough to describe realistic, viable plans for becoming a strong contributor to your organization are more likely to be able to plan their day-to-day sales activities than those who aren’t.

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

Here, you can see which candidates can find gaps in your organization and propose solutions. If you expect the candidate to help other businesses identify and solve business challenges, they should be able to call out areas of improvement for your own company as well.

This sales interview question serves two purposes:

You’ll learn how much research the candidate did before meeting with you.
You can assess their creative thinking and problem-solving capabilities.

Insight from my experience: I once found offensive material somehow published on the website of a company I was interviewing with. By pointing it out, I demonstrated that I was doing my research on the company, and I also helped them avoid embarrassing damage to their reputation.

11. How does [your company name] deliver customer value?

This question reveals the candidate’s understanding of your company’s unique selling proposition and their ability to communicate it to potential customers. Hopefully, they will have done their research on your company website or your social media channels and not try to make up something on the spot.

What to listen for: This is another question that shows how much research your candidate has done on your company. If they can’t even slightly articulate the benefits of your product/service, it might mean you need to move on.

12. What’s something you’ve taught yourself lately?

This question gives proactive, self-motivated candidates a chance to shine. You can see who has an excellent professional development ethic and who seeks ways to improve as a salesperson.

What to listen for: You want to hire salespeople who are hungry for new skills and eager to learn better selling strategies. This question helps you find those people. Listen to how thoroughly they describe what they’ve learned and ask which tools they used to learn it.

13. Can you describe your lead qualification process when you connect with new prospects?

This question reveals whether a candidate has strong critical thinking abilities and if they know how to identify important lead qualifiers — such as a prospect’s budget, authority, need, and timeframe (BANT).

What to listen for: The candidate’s response helps you gauge how effectively they qualified prospects in the past and what kind of training they would need to adopt your methodology. It also gives you a sense of their sales training and instincts. Candidates must be able to ask focused questions that decipher whether a prospect is a good fit.

Insight from my experience: When I worked with IBM, we added conditions of satisfaction to BANT (we called it BANTC), which reflected the outcomes that the customer wanted to achieve from their initiative.

Situational Sales Interview Questions

Situational questions let you assess each candidate’s skills and personality. By asking these questions, you can learn the mindset the candidate can bring to the team and your customers.

14. How do you approach short sales cycle transactions differently than deals with long sales cycles?

Candidates can show their understanding of the sales process, their sales experience, and how they would adapt to different situations.

What to listen for: Short cycles call for reps that can close quickly, and long sales cycles require a much more careful, tailored approach. They’re drastically different, and your candidate should recognize this.

Insight from my experience: When I was a team lead, I coached my colleagues to leverage low-value transactional sales conversations to uncover cross-selling opportunities. For example, for existing customers, we discussed the benefits of subscription-tier upgrades, checked to see if the client needed add-on user licenses, and discussed our consulting and training services.

15. When do you stop pursuing a prospect?

This question separates those who are rejection-tolerant from those who aren’t. Giving up on a non-responsive prospect and skillfully addressing objections are apples and oranges.

What to listen for: The right answer depends on your company’s process. However, the more persistent a rep is, the better.

Insight from my experience: I once had an interview with a sales executive who said, “I want someone who’s so driven to make a sale, they’d run through a brick wall if they had to.» He didn’t say a concrete wall, though, so even he knew there are limits.

I usually encouraged prospects to let me know if they had no interest in speaking with me around attempt five, but I always left the door open to re-engage in future. Trish Bertuzzi, the founder of The Bridge Group, recommends six to eight attempts before throwing in the towel.

16. How do you keep productive with a smile on your face during a hard day?

This question assesses the candidate’s resilience and positivity despite tough days. A career in B2C or B2B sales is not for the faint of heart, as working with people with a broad spectrum of personality quirks is challenging.

What to listen for: Assess the person’s attitude toward rejection. Do they need time to shake off an unpleasant conversation, or do they bounce back immediately? Discover the strategies they use to recover and move on. You may need to recommend some coping strategies if the candidate isn’t giving you the answers you are looking for on the other questions on this list.

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

This question shows the candidate understands your product and is keen on having a strong, qualified pipeline of potential customers.

What to listen for: Selling to everyone and anyone is a recipe for disaster. Make sure your candidate is comfortable turning business away if the potential customer isn’t a good match.

Pro tip: I learned through experience that in sales, chasing rainbows (aka, leads that will never become closed revenue deals) wastes time and resources. It diverts focus from realistic opportunities that have a higher potential for success. Outcomes are more important than effort in many circumstances.

18. Have you ever had a losing streak? If so, how did you turn it around?

This question uncovers highly motivated candidates who are driven to succeed and have a process for bouncing back from failure. As the saying goes, it’s not how many times you fall down but how many times you get up and get back up and get on another sales call that matters.

What to look for: Nearly everyone experiences a setback or misses a goal now and then. Beware of someone who claims they’ve never experienced a downturn. There’s nothing wrong with a temporary slump, provided the candidate learned from it.

19. Did you ever hold a win/loss review meeting after closing/losing a deal? What did you learn from that experience?

This question helps you determine whether the candidate can grow professionally based on customer feedback to improve their sales process. The salesperson and their team can learn what worked during the sales process, what didn’t, and how they can improve on future engagements.

What to listen for: Following up on deals to learn how to do better next time boosts the odds of winning in the future. A salesperson who takes the time to learn from both their successes and failures will be a valuable addition to your team.

Insight from my experience: I found these meetings to be crucial to my development. I once learned from a customer that another client we considered a reference was not happy with how their project was delivered. Although we lost the deal, we recovered the relationship with the reference customer.

20. Describe a time when you had a difficult prospect and how you handled that situation to win the sale.

Every salesperson encounters difficult prospects. Knowing how candidates deal with this prevents you from hiring people who’ll lose valuable leads in your sales pipeline.

What to listen for: The answer to this question shows how candidates approach tough prospects. If they can keep their emotions in check, swallow their pride, and move a deal forward for the company’s greater good, that’s a great sign. Listen for a logical explanation of the situation, the steps they took to fix it, and the results of their actions.

Pro tip: Give the candidate grace if it’s clear they didn’t have support from their previous manager to deal with a high-pressure situation. I once needed the support of my manager to navigate a tense relationship with the university where my company was “born” a decade before.

21. How would you exceed expectations in this role?

Hiring a candidate with ambition and drive is crucial. You want people who aspire to not just meet but exceed their quota and other KPI targets. Nobody has a magic crystal ball, but the candidate you hire should have concepts of a plan to ramp up, immerse themselves in your organization’s culture, and do what needs to be done to exceed their quota and other KPIs.

What to listen for: Asking this question helps you identify candidates who make their own luck with hard work, creative thinking, and dedication to delivering customer value.

22. If you started a company tomorrow what would it look like?

This question provides insights into a candidate’s motivation, interests, goals, and entrepreneurial spirit. Many companies embrace an “intrapreneurship” mentality, as it fosters innovation while providing a low-risk environment for curious, creative people to lead initiatives from within your company.

What to listen for: Many salespeople get into the profession because they’re aspiring entrepreneurs. You’ll learn about their future goals and motivators by asking candidates about a fictional company. You’ll also get a taste of how they pitch business ideas.

Insight from my experience: Many successful B2B salespeople have side hustles to earn additional income, provide an emergency safety net, and build skills for their sales roles. My freelance writing career began when I was in sales after volunteering as a communications lead for a non-profit that supported entrepreneurship across Canada.

23. How have you handled working with clients and colleagues from diverse cultural backgrounds?

By asking this question, you’ll determine whether a candidate is culturally competent, can adapt to different communication styles, and can work effectively with coworkers, partners, and clients with diverse backgrounds.

Even if the candidate can only speak in English, they should conduct themselves in a respectful and understanding way and work to foster strong, collaborative relationships with people of all races, cultures, genders, and beliefs.

What to listen for: Salespeople should be able to work with anyone, no matter their cultural background. By asking candidates how they’ve handled these scenarios, you’ll learn if they’re fit to work in a diverse and inclusive manner — and if they see the value of this skill.

Inside Sales Interview Questions

Finding candidates who understand the nature of inside sales is an advantage over reps without that type of experience. These questions are more complex and assess how the sales rep candidates have worked through adversity.

24. What’s the best way to establish a relationship with a prospect?

This question identifies candidates who can make meaningful, productive connections with prospects and customers.

What to listen for: Get insight into how they approach and maintain prospect relationships. Communicating over email or via the occasional voicemail is table stakes. But if a candidate claims to collect lead intelligence and build strong rapport over the phone, that’s a good sign.

Insight from my experience: Over my seven years as an inside sales rep, I developed foundational sales and marketing skills like:

Using data to back up my value-based selling approach.
Moving prospects down the sales pipeline and maintaining post-sales loyalty and engagement.
Picking up on cues from tone of voice, silence, and word choice when body language prompts are not visible.
Active listening and consultative selling.
Using channels like email, video meetings, instant messaging, and social media to move deals through the funnel.

These skills became especially important for me (and other inside sales pros) during the pandemic when remote selling and interviews became the norm worldwide.

25. Sell me something.

This question assesses the candidate’s ability to create innovative ways of pitching products instantly and addressing objections quickly.

What to listen for: Anything. It could be the classic “Sell me this pen” or “Sell me what you had for lunch today.” Letting them choose what they sell turns a tired question into a glimpse of how well your candidate thinks on the spot.

A great candidate will ask qualifying questions like these before selling the product:

“What problem are you trying to solve?”
“What are your success metrics for determining if you have effectively addressed this requirement?”
“What are you looking for in a solution that addresses your need?”

26. Explain the steps in your sales process from start to finish.

With this question you’ll get insight into a candidate’s understanding of the sales process, their level of experience, knowledge of sales methodologies, and their ability to manage the sales cycle from start to finish.

What to listen for: Determine how well the candidate understands and considers the sales process. They should also explain the tools they use to organize their thoughts and activities, communicate with key stakeholders, and keep the process moving forward. Do they explain their process clearly and cover the key steps: prospect, connect, research/evaluate, present, and close? These are two things you should look for in their answer.

27. Tell me about an objection you had trouble overcoming over the phone. How did you finally move the deal forward?

You’ll see how effectively candidates handle objections and their ability to treat tough conversations with potential clients effectively. The ability to listen and show empathy takes center stage here.

What to listen for: Every salesperson has at least one objection that plagues them. Did the candidate listen to the prospect’s concerns? Did they validate them? Did they help them reach a different conclusion? The answer to this question tells a lot about how your candidate solves problems and thinks strategically.

Insight from my experience: Once, I travelled across Canada to meet a customer who said they felt misinformed and neglected after they bought a solution from the recently acquired company I worked for. Fortunately, I rebuilt enough trust and loyalty with the client that they purchased enough software licensing to more than pay for my round trip.

28. Teach me something.

This question helps you assess a candidate’s ability to communicate, present product information clearly, and convince prospects to buy. It’s nearly impossible for a candidate to know what you would want to learn, so consider this a role-playing exercise, not a true learning opportunity.

What to listen for: Selling is about more than listing a product‘s or service’s benefits and features. This question lets your candidate show how well they can share knowledge and walk you through a new concept.

Can the candidate communicate a relatively complex concept effectively? Do they have a deep understanding of it? If they nail the description and are genuinely interested in explaining the concept, they should excel in explaining your product to prospects.

29. Share the steps you took to land your most successful sale.

This question highlights a candidate’s showcase win and demonstrates how they closed the customer. Be sure you look for a sparkle in the candidate’s eye and not a glazed-over expression. Every salesperson remembers their biggest deal fondly, so if the candidate seems to be making things up, they just might be.

What to listen for: Aim to understand the candidate’s thought process. Their answers should showcase their strengths using a real-life example. Successful salespeople are like accomplished fishermen. They love to tell stories of how they got a “bite” from a prospect and “reeled them in” to close a contract. They don’t have to embellish the experience.

30. Tell me about a time you lost a deal. What did you learn from that experience?

This question assesses a candidate’s ability to be self-aware and see loss as a learning experience.

What to listen for: Everyone loses deals, and there’s no shame in admitting and discussing it. The goal of this question is to explore the candidate’s lessons learned and how they have improved their sales techniques after losing to a competitor — or the dreaded project cancellation monster.

Insight from my experience: I once found out in a win/loss review meeting that I lost a deal because I responded to a proposal question about how many versions back we maintained support documentation. Our official and published policy was two versions back, so that was how I responded. Yet the company I worked for maintained documentation all the way back to the original version of our software. I should have asked for management help framing the response, but I was concerned about contradicting our published statements. Live and learn!

31. It’s halfway through the quarter, and you’re trending below where you need to be to meet your quota. What will you do during the second half of the quarter to ensure you reach your targets?

Whether you describe this scenario as a challenging quarter, month, or year, you’ll discover how effectively the candidate can course correct to ultimately beat their quota. Most of us get into a professional rut now and then. What separates the contenders from the pretenders is knowing how to rally and recover, be it independently or by asking for help.

What to listen for: Look for processes that showcase the candidate’s problem-solving ability. Maybe they found a way to replace a lost deal with a win they pulled like a rabbit out of a hat. Or maybe they learned a new skill or adopted a sales methodology that led to better outcomes.

32. How do you deal with a full day of rejections?

Escaping rejections entirely is impossible, and sometimes they appear in clusters in a single day. If this happens for an entire day, you need to know how they’ll deal with it. See if they practice healthy habits, like exercise, positive self-talk, or upskilling with a coach or colleague.

What to listen for: Rejections are going to happen in this job, and this question can help you get an idea of the candidate’s mindset and how they motivate themselves during slumps.

33. Pretend I’m a prospect who didn’t answer the phone. Leave me a voicemail.

This question helps you learn if candidates can leave a voicemail that a prospect will be compelled to respond to. Their voicemail should be brief and relevant while making it clear why you (in the role play) should call them back.

What to listen for: Prospects and even gatekeepers often use their voicemail to screen calls. Reps will encounter prospect voicemail inboxes many times during the day. This question can give you insight into how the candidate turns a missed connection into an opportunity.

Pro tip: The candidate may not follow your team’s voicemail script, but give them points for saying who is calling, why, and how to connect. Watch for how they pique interest and show value while setting expectations for the next touchpoint.

34. What’s your favorite question to gauge need and interest?

This question shows a candidate building rapport, establishing trust, and gathering vital sales information from prospects. The question, “What keeps you up at night?” is completely played out. A better sales interview question is, “What are your top business priorities for the coming year, and how do you see our services supporting those goals?”

This sales question helps build rapport with a prospect and helps them consider how your services could support them in meeting their goals.

What to listen for: While this question may be tough to answer on the fly without information about a company or product, the rep should still be able to provide an idea of how they’d qualify prospects.

Fit and Motivation Sales Interview Questions

These interview questions evaluate whether a candidate has the right motivation for the job. They help you learn what drives the candidate to work hard and better understand their ability to perform.

35. What’s worse: not meeting a quota every single month or not having happy customers?

This question shows a candidate’s values and priorities. Some will choose customer satisfaction over quota and vice versa.

What to listen for: Depending on your company’s goals, either answer could be right. But beware of reps who prioritize quotas over truly giving customers what they need — or withholding what they don’t. If you have a recurring revenue-focused business, focusing on maintaining your customer base and your reputation may be better for your business in the long run than missing your new customer acquisition goals.

36. What’s your least favorite part of the sales process?

This question helps you know if their weaknesses will be a problem. For instance, if cold calling or contract revenue recognition readiness are central to your sales processes, candidates who dislike those key responsibilities may not be a fit for your company.

What to listen for: If their least favorite part of the process is also the most important part at your company, that’s probably a red flag. Ask them how they make their least favorite responsibility tolerable or more enjoyable. This question can also alert you to areas that need coaching.

Insight from my experience: I found that my favorite and least favorite part of the sales process varied by company. At one company, I had a small territory to work with, and the cold call volume expectations were high. The company I worked for paid a telemarketing company to prospect into the same businesses I was, so I often heard I was the second or third person from my company they had heard from that week.

37. What motivates you?

This question helps you align and match (if possible) a candidate’s motivators with your reward system. Many salespeople are “coin-operated” and prefer a compensation plan that is based on their individual contribution to company growth, while others are content with an incentive plan that is based on team or company-wide performance.

What to listen for: Money, achievement, helping customers, being #1 — there are a lot of potential answers to this question. What makes an excellent answer versus a bad one will hinge on your company’s culture. Many salespeople are motivated to get out of bed in the morning to help their customers solve business problems. Make sure the candidate’s motivations align with your company culture.

38. What is your ultimate career goal?

By asking this question, you’ll find out if your company can provide the growth opportunities at a pace that matches what candidates aspire to. If the candidate shows promise, and your team can prepare them to meet their long-term goal (within your company or beyond) it could increase their engagement and commitment.

What to listen for: A lack of growth opportunities can cause salespeople to look for new jobs. If the candidate expresses a desire to pursue a career move your company can’t provide, you might need to hire again sooner than you’d like. That said, someone’s ultimate goal may be years off, and working on your team could be a means to an end. Asking the classic, “Where do you see yourself in X years?” question might be a better way to gauge the candidate’s near-term ambition.

39. What made you want to get into sales?

This question explores the candidate’s personal motivations and helps you determine whether the candidate has a real passion for sales. Maybe their career took an unexpected turn, or they may have been pressured into it. The candidate may really enjoy helping companies to solve business problems, or they may enjoy meeting new people or being in a competitive role.

What to listen for: Though likely part of the motivation, high commission earning potential is not the ideal answer to this question for most businesses. I was passionate about how digital transformation could help organizations better serve their customers, employees, students, and other stakeholders — though I admit commission payments were appreciated.

40. What’s your take on selling collaboratively vs. owning your sales from end-to-end?

This question identifies candidates who prefer to be “lone wolves” versus those who believe in teamwork.

What to listen for: Collaboration might be less important at some organizations than others, but candidates who aren’t willing to collaborate at all likely won’t make pleasant co-workers. Their independent-minded attitude may also be a detriment to knowledge sharing.

41. Describe a time when you had to collaborate with someone who had a different cultural or personal background than you are used to. How did you navigate their unique working habits or communication styles?

This question reveals candidates’ interpersonal skills, which are crucial for building and maintaining relationships with colleagues, partners, and clients.

What to listen for: As mentioned earlier, succeeding in a diverse sales team environment demands that candidates have EQ and social intuition to work with all types of people. You want a candidate who recognizes and respects these differences. Their response can tell you if they’re ready to join a winning team full of diverse individuals.

42. From a business role perspective, whom are you most comfortable selling to and why?

This question shows candidates who researched your company and know who you sell to. Some sales professionals have strong technical acumen and prefer to work with technology leaders, while others prefer to work with VP-level or C-Suite executives who “hold the purse strings” and control budgetary decisions.

What to listen for: Listen for responses that describe an ideal buyer versus a demographic with no tie-in to the buying process. Depending on your product or service, the second type of response might pose a problem.

43. What’s your opinion of the role of learning in sales?

This question identifies candidates with a growth and continuous improvement mindset. If your industry is in a constant state of change — like technology or life sciences — curiosity and a hunger for learning are real assets.

What to listen for: Being thrown for a loop by this question is a sign your candidate isn’t a lifelong learner — an increasingly important trait for salespeople. An ideal candidate should communicate their willingness to learn and grow in their role.

44. What are three adjectives former clients would use to describe your personality and selling style?

Asking this question can surface some of the personality traits of your potential hire that resonated with their clients. Some industries and customer profiles align with certain personality types. Many companies have candidates take personality assessment tests like the Myers Briggs Type Indicator® to identify their candidates’ true personality traits such as intuition and perception.

What to listen for: Look for characteristics like charisma, curiosity, responsiveness, helpfulness, and having a consultative sales approach — the latter of which is increasingly important in today’s B2B sales. It’s a plus if the candidate provides examples of when they exemplified each trait.

45. How would you describe the culture at your last company?

This question gives you an overview of a candidate’s last employer and the kind of working environment they are accustomed to. Asking a follow-up question about how they liked the culture could be key to seeing how they could “assimilate” into your organization.

What to listen for: You’ll learn a lot about what the candidate values, how they work with others, and what kind of leadership they thrive under. If they complain about long hours or rigid goals and your company thrives off the energy created by late nights and challenging numbers, it’s probably not the right fit.

You’d also want to know if their previous employer’s culture was inclusive or accepting of people from different backgrounds. You want to bring on staff who are compatible with your team’s culture. If the candidate was not in an inclusive environment, look for a constructive response on how the last company could have done better.

46. Describe your ideal sales manager.

This question helps you explore the candidate’s expectations of you as their manager and the leadership style they are most comfortable with. I had some great managers who were excellent sales coaches, and I had others with strengths in the HR realm.

What to listen for: Asking a candidate to describe their ideal manager shows you how autonomous they are, how they approach working relationships, and how they overcome challenges. Look for a candidate who can work independently and is comfortable taking direction from their higher-ups.

47. What core values should every salesperson possess?

This question shows whether the candidate’s values align with yours, your team’s, and those of your business.

What to listen for: To learn where their moral compass lies, listen for answers like “putting the prospect’s needs first,” “patience,” and “humility.” The candidate’s values should align with your company’s values to ensure a good fit.

48. Which of your life’s accomplishments are you most proud of?

This might seem like a tall order, but the answer illustrates your candidate’s values and motivations. I have answered this question with personal accomplishments and professional ones.

What to listen for: If the candidate tells a story of overcoming great odds to achieve a specific goal, that signals a driven and highly motivated salesperson. If a candidate’s most valuable accomplishment is finishing all seven seasons of Love is Blind, you should probably move on.

Sales Director Interview Questions

Sales directors must be capable of developing and implementing strong sales strategies for a team. Use these questions to gauge their understanding of the market, recent trends, and their confidence to deliver.

49. How would you describe your management style?

This question demonstrates which managers are hands-on in helping their reps meet their quotas, and which ones prefer to watch from the sidelines: coaching style vs. general manager style, if you’re a sports fan. I had both throughout my career.

What to listen for: An effective sales executive should be able to manage and inspire a team. As they share attributes about their management style, consider if these traits fit your company culture and the needs of your team.

50. Tell me about a time you had to motivate an underperforming team member.

With this question you can identify potential team mentors or even managers who can help transform underperforming reps into quota crushers.

What to listen for: Sales leaders are often responsible for inspiring and motivating reps. The answer to this question should provide some insight on how they would develop their team members who need a little extra help to reach their goals.

51. Can you describe a situation when you had to implement a new process or system? How did your team respond?

This question reveals a candidate’s ability to enact change and handle resistance from reps who want to stick to the old processes.

What to listen for: You can gain valuable insight into how they handle change management. You want to ensure your sales leaders can effectively manage the implementation of new systems and that they can address the concerns of your sales team during transitions.

Insight from my experience: I’ve been asked this question, and have a great learning opportunity that I used to answer it: I remember leading the adoption and upgrades of a corporate CRM system that was integrated with our deskphones. The system was less than user-friendly, and there were a number of delays that slowed the process down. Fortunately, my team was patient with the process despite many hiccups.

52. What is your leadership superpower?

This question highlights a candidate’s leadership strengths and lets them share what differentiates them from other sales leaders.

What to listen for: Listen for specifics. An excellent sales manager must have done many appraisals and identified their superpower over the years.

53. Tell me about a time you had to adjust your sales strategy to reach your targets.

This question allows the candidate to demonstrate how they can respond to changing circumstances and pivot as required.

What to listen for: Every successful sales professional has had to change tactics at some point. Listen closely for the unique lessons they share.

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

This question vets candidates to identify team builders and collaborators who every rep can count on. The sales teams I worked on had strong rules of engagement and territory definitions, so

What to listen for: As a leader, establishing trust with a new team is essential to the job description. The answer to this question will tell you how your candidate approaches building trust and how important teamwork is to them.

55. What’s one way [your company] could improve our sales strategy?

This is an example of a question that can be very challenging for a candidate to answer unless they have been a customer, or you gave them a comprehensive description of their sales strategy.

If you ask this question, give the candidate the flexibility to offer a unique strategy they’ve encountered, even if you are already using this strategy. If you are going to ask a question about a way to improve the way you do business, the candidate can’t be expected to have insider information unless you provide it.

What to listen for: You want to attract the best and the brightest salespeople to your sales team. Listen for thoughtful answers that show preparation and familiarity with your company’s current practices.

Insight from my experience: A VP of sales once asked me what characteristics or experiences I had that no one else he was interviewing had. I wasn’t standing outside the office checking out who he was interviewing, so I didn’t have the intel to answer that question. I said as much during my answer, but the interviewer wanted something specific. Maybe it was the look on my face while I answered the question, but he didn’t hire me then or since.

56. What is the most difficult piece of feedback you’ve ever received? How has that shaped your approach as a sales leader?

This question shows how the potential sales director uses feedback to iterate on their processes and drive results. Feedback from a colleague or leader can motivate you to be introspective and take steps to improve on something. Or you can ignore it, and risk improving the habits that others observe as a shortcoming.

What to listen for: Although difficult feedback can be challenging to give and receive, it can be necessary to grow in one’s career. Having the candidate share feedback they’ve taken to heart and acted upon lets you glimpse how they’ve grown over time.

57. Would you rather have a toxic overachiever or a supportive underperformer on your team? Why?

This question gives insight into how a candidate thinks about the problem and the steps they’d take to correct the toxicity, underperformance, or both.

What to listen for: In a management or executive role, the candidate will frequently face situations like this. On the one hand, you want your team to meet their targets. On the other hand, a toxic team member can bring negativity into an organization (even if they’re exceeding quotas). There’s no right answer to this question; it will depend on the candidate and the situation.

58. How do you know it’s time to let someone go?

This question reveals a potential manager who can make the tough call when necessary.

What to listen for: See how the candidate approaches team management as a leader, even when there are tough decisions to be made.

Software Sales Interview Questions

You need to bring on sales reps who will advocate for your product on a technical level. When asking software sales questions, assess the candidate for their experience, understanding of metrics, and their ability to create a strong narrative behind the software for a client.

59. Share the steps you take to learn about a new piece of technology.

This question helps understand which candidates can learn about products quickly. There are many learning styles, ranging from visual learners that can learn from reading and watching videos.

What to listen for: Technology is constantly changing. This question gives you a good idea of how your candidate would take steps to learn about new product offerings. Auditory learners can hear someone talk about a topic, and interactive learners (like me) learn best by jumping into an application, then clicking buttons and links to experiment with the tech. No answer is really negative in this case — unless someone says they ignore the tech, hoping it just goes away.

60. How would you explain the features of a complex piece of software to a prospect who is not as well-versed in technology?

This question assesses a candidate’s communication skills and ability to tailor their presentation to a specific audience. It can be easy for technically savvy salespeople to come across as condescending to a non-technical audience. Great salespeople will respectfully focus on the business benefits of the technology and give the prospect credit for what they specialize in.

What to listen for: The ability to explain complex concepts is an art for software sales reps. Have the candidate discuss a hypothetical situation where they explain a software offering to you in easy-to-understand terms.

61. What is one improvement [your company] can make to [featured piece of software]?

You’ll see which candidates can find gaps in software and propose solutions. This question requires the kind of preparation that doesn’t come from reading a company’s website. The candidate should go to review websites like Capterra, or social media sites like Reddit, to get inspiration from customers or industry analysts.

What to listen for: You want a team of creative problem-solvers and innovators. This question allows your candidate to share their ideas, which ideally translates to how they would share ideas as a member of your team.

62. What was the last book you read or podcast you listened to?

This question identifies candidates with a growth mindset who learn from the sales industry’s best. I often mentioned Jeffrey Gitomer’s Sell or Die podcast, or his Sales Bible when asked this question.

What to listen for: Individuals who are committed to continuous learning make inspiring team members. By asking this question, you get a glimpse into what kind of content the candidate consumes and how they continue to build their skills.

Bring On the Right Talent in Your Next Sales Interview

To hire a well-rounded sales rep, you have to ask the right questions to see how a candidate really thinks. This will help you improve your team’s performance and help you hit your business goals.

I hope you’ll use this guide in your next round of interviews — and find the candidates you’ve been looking for.

Editor’s note: This post was originally published in February 2020 and has been updated for comprehensiveness.