The Best Sales Interview Questions and Answers that You Want to Hear

Sales Interview Questions

Hiring salespeople is a challenge. It’s a task that requires finding the best communicators and relationship managers, made all the harder by the fact that salespeople are persuasive, and you must work past that to uncover their true personality—not just their memorized answers and sales techniques.

Despite the challenge of finding the perfect salesperson for your team, sales positions are the top hiring priority for talent acquisition leaders.

So, to help you find a sales professional who is right for the role—as well as optimistic, dedicated and a perfect match for your company culture—we’re taking you through the process of hiring salespeople, from the questions to ask in the interview to the traits to look for in the answers.

Table of Contents:

  1. The best sales interview questions and answers
  2. Curveball questions: the ones their not prepared for
  3. Role-specific questions for various sales positions
  4. Hiring sales team members
  5. The experts' favorite questions and answers
  6. How Pipedrive helped Railsware streamline their hiring process

The best sales interview questions and answers

So, how can you ensure you hire the sales representative with the ideal skillset, experience, knowledge and personality for the needs of your company.

sales candidate questions

No matter which sales role you’re interviewing for, make sure you include these eight must-have questions.

  1. How would you describe your perfect work environment in sales?

This question helps you uncover the expectations they have of their ongoing workload, their team, the office atmosphere and even the way tasks are planned and delegated.

While there’s no one-size-fits-all answer to this question, it should help you work out how open your candidate is to reflect on their work, upskill on an ongoing basis and lift other team members up as opposed to aiming for individual goals only.

    2. How did you land your most successful sale?

With this question, your potential sales rep should light up when thinking of this success and go into plenty of detail on their strengths.

A good answer is one that reveals their unique way of moving a sale forward. Make sure to ask follow-up questions to learn more about their mindset throughout that success, as well as the way they dealt with any hurdles and even the way they celebrated this sale.

    3. Walk me through your approach to the sales process in your most recent role.

A sales process question is a pure knowledge test. If your candidate keeps talking about all the sales they won in their last job, but can’t name the stages of the process or approximate how long they took, they are likely being dishonest with you.

You’re looking for an answer that clearly shows actions they’ve taken to move their prospect through the entire sales cycle.

   4. What is your least favorite part of the sales process?

Honesty is important, and sales is difficult. In their job, they are bound to deal with difficult people, roadblocks in the process, rejections and failed deals.

Even if they genuinely enjoy being part of that process, it’s unlikely they are always 100% motivated and content. When you get an initial answer, make sure to ask follow-up questions to uncover their approach when it comes to difficult moments.

   5. How would you describe our company based on what you’ve seen so far?

It’s not only important that the candidate is right for you, you have to be the right option for them, too. Asking this question will ensure that they know what they’re signing up for and the products, market and environment they will be surrounded with daily.

This answer should reveal if they’re a good fit for your company culture. If the company stands for working smart over working hard, but they believe you encourage working overtime and hustling 24/7, ask yourself whether this person will match with the rest of the team and the company.

    6. Why are you looking to leave your current job?

Another question that has no perfect answer, but it’s important for any industry and any type of role.

An answer should reveal their true intent for a job change. As long as it’s a positive reason, such as an opportunity to grow or even leaving an environment that wasn’t a fit for their personality or style of work, you’re looking at a great candidate. If they’re talking negatively about their current job or employer, beware.

Make sure to ask more questions if their reason to leave is something that might be the case in your company, too.

   7. How do you keep up to date on your target market?

The answer should show you the books, newsletters, courses, blogs and other resources that your candidate frequently consumes to stay on top of the industry. Follow up by asking them how much time they spend each week or month on learning.

   8. How do you organize your day?

With this question, you’re looking for the way your candidate structures their tasks, sales meetings, calls and their calendar and sales dashboard in general.

A poor answer is the one that reveals they deal with commitments as they come in, without any logic or a way to prioritize. A great answer will showcase their ability to start each day with a clear plan and reflect back on their tasks and performance at the end of the week.

Curveball questions:  the ones they’re probably not prepared for

Curveball questions

Salespeople are well-versed in giving answers they know you want to hear. Why not add these six questions to dig a little deeper into their motivations and experience—and potentially catch them off-guard?

  1. What core values should every salesperson possess?

The answer to this question will help you see how they truly feel about a career in sales, as well as how they think they fit into that.

   2. What is your ultimate career aspiration?

They won’t be in this role and your company forever. How does it play into their long-term plan? Do they believe it will make a difference in their career, or is it just a job to keep them busy and pay the bills until something better comes?

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

There’s no way to rehearse an answer to this question. It’s quite a personal question when you think about it; it has a lot to do with their personality and the internal drive to make the most of every situation.

   4. How would you explain our product or service in a single sentence?

This is a variation on the earlier question asking for a description of your company, but in a more condensed way, indicating how well what they’ve seen and heard so far has been understood.

   5. Tell me a team disagreement you’ve had. How did the team resolve the issue? What part did you play?

Another question that is almost impossible to fake an answer to. When you ask this, your candidate will have to recall their team experiences (negative ones!) and articulate them in a relatively short period of time. It will show their maturity and willingness to find solutions that work for everyone.

   6. Have you ever asked a prospect you lost why they chose not to buy? What did you take away from that experience?

This is another way of seeing how your candidate deals with rejection and failure. A great answer will reveal they’re always aiming to learn from unsuccessful deals.

Role-specific questions for various sales positions

One important part of building your list of interview questions is adding questions specific to the sales position you’re interviewing for.

Entry-level sales

Sales reps who are relatively new to the world of sales might be quicker to give up on prospects or get unmotivated after losing a sure deal.

They are also just getting comfortable with managing various pipeline stages, qualifying leads and figuring out the quirks of your industry and the typical hurdles in your market. An interviewer can ask these questions to make sure they are on the right track.

  • What made you want to get into sales?
  • A prospect you’ve been pursuing goes dark and then eventually tells you they chose a competitor. What do you do?
  • When do you give up on making a sale?
  • What are the most important qualifying questions you ask every prospect?
  • How do you make sure you keep your sales skills up-to-date? What do you want to get better at?

Courteney Cannon, Sales Operation Manager at Pipedrive, also uses these questions as core parts of interviewing for entry-level sales roles:

  • What was your favorite/least favorite thing about your previous role?
  • Give me specific details on your previous compensation scheme and success record
  • Tell me a story

“These questions will reveal their motivation to be in this role, as well as their ability to hold a conversation and engage the listener,” Cannon explains. “Details on their past commission structure and their track record are just hard to make up, so it’s an easy way to gauge their success in a similar role in the past.”

Call center sales

Call Center Sales

Call center staff often have to deal with a high volume of calls, notes and inquiries on a daily basis. This also makes them more exposed to frustrated prospects or customers, as well as uncomfortable phone conversations.

A friendly and highly detailed approach to this job is paramount. As the interviewer, you could ask:

  • Are you comfortable with cold calling with a script or without?
  • What are your favorite questions to ask prospects?
  • How do you deal with angry prospects on the phone?
  • How do you research prospects before a call or meeting? What information do you look for?
  • How do you make sure a task is completed before moving to another?

Account management

Account managers are problem-solvers who play a crucial role in the growth of a business. They do this by making sales, handling complaints, collecting and analyzing customer data and trying to improve the overall buyer experience.

Successful account managers are communicative, resourceful and highly organized.

  • Describe how you have built successful relationships with clients or coworkers in the past
  • What’s the best way to establish a relationship with a prospect?
  • How do you plan your day to make sure you can deal with multiple client accounts at the same time?
  • Tell me about a time when you retained a client who wanted to cancel a service or an order
  • Have you ever improved upon a company process? How?

Sales manager

Sales managers are in charge of hiring, coaching and motivating sales reps that can thrive in their team and grow both as individuals and in a group setting. That’s a lot of responsibilities to carry.

When interviewing for this role, make sure you assess the capabilities of your candidate to lead their team in the right direction, help them through rough times and missed targets, and stay composed in any situation. One way to do this is with situational sales interview questions:

  • If business priorities change, how would you help your team understand and carry out the shifted goals?
  • I’m a sales rep who has missed quota three months in a row. How would you handle this situation? What would you say to me?
  • What made you successful as a sales rep? How will your processes inform how you manage your team?
  • What skills and qualifications would you look for when hiring a sales rep?
  • What do you think makes for a successful sales rep coaching session?

Customer success manager

Your customer success manager makes sure that your product or service fills the gap between the customer and their success—literally.

It’s a proactive role that reduces customer churn and ensures customers are fully educated about the product and any potential frustrations are prevented before they turn into a customer service issue.

Customer success managers should be able to handle demonstrations and product walkthroughs based on the individual customer requirement.

  • What methods do you use to ensure the customer is successful with their purchase and happy with their experience?
  • How do you identify opportunities to upsell?
  • How do you handle multiple competing priorities? How do you determine the most pressing or critical priorities at a given time?
  • How do you communicate with customers the reasons why you can’t resolve a problem right away?
  • Have you written step-by-step procedures for customers? Could you share some examples?

You could also ask these sales interview questions when searching for a sales consultant.

Sales operations manager

Sales staff that work in operations management roles help teams reach their full potential by solving process-related problems, implementing tools and strategizing solutions that streamline everyone else’s jobs.

The interviewer wants to learn about their methodologies and past successes in sales operations.

  • How can a sales operations manager add the most value to their sales team?
  • As a sales operations manager, what is your management style?
  • Tell me about a specific way you’ve improved a process for a sales team.
  • How have you achieved personal development as a sales operations manager in the last 12 months?

Director/VP of sales

A VP of sales plays a critical role in building a resilient sales machine that carries the entire company forward.

Sales directors have to think about the big picture in everything they’re doing while being aware of the day-to-day progress.

  • What’s your view on sales tools and technology enabling sales? In which ones would you invest budget and time?
  • How do you drive change in the organization? What if the company pivoted in a direction and sales had to adapt? What would be your plan?
  • Given what you know about our company, how big of a sales team do you think we need?
  • Which functions are you going to build relationships with? How are you going to drive cross-functional support for sales?
  • How should sales and marketing/account management/customer success work together?

Hiring sales team members

Beyond asking the right sales interview questions and common interview techniques, what else do you need to keep in mind during the sales recruitment process?

Hiring managers shouldn’t just look for individuals who can confidently sell your product or service alone. They’ll be part of a sales team—a group of people that works towards big-picture, long-term goals for the benefit of the entire company.

An individual sales rep might come across as very skilled at their job: their past sales performance might be out of this world and they can sell literally anything to anyone.

But what happens when this sales rep doesn’t work well with others?

The rest of your sales team might become unmotivated around that team member or even frustrated about the lack of team spirit.

And if your team had been collaborative and productive up to this point, you will suddenly have a group of sales reps that can’t work well together any longer, jeopardizing the entire business.

The traits of a team player in sales

Patrick Lencioni, a bestselling author on sales leadership and team management, covered this exact problem in his book “The Ideal Team Player: How to Recognize and Cultivate The Three Essential Virtues.”

In his book, he lays out three traits that companies need to test for in order to hire team players. He even argues that these traits are more important than skills alone. They are:

  • Humility: team players don’t have big egos or concerns about status, they point out contributions of others and define success collectively and not individually
  • Hunger: team players are always looking for more—more to learn, more responsibility and they are always thinking about the next step
  • Smarts: team players have a great common sense of people, they ask good questions and deal effectively with others

The key approach is to always look for all three traits of a team player. If there’s even one missing, that sales rep might throw off the entire team balance, productivity and even trust.

For example, if a sales rep is missing the humility trait, he or she will know how to get what they want, but they won’t mind if it’s at someone else’s expense. On another hand, if they miss the hunger trait, they will easily slack at work—and potentially drag other reps down.

Filling the sales team gaps

High-performing team players can do a lot more for your sales team than simply collaborating well, they could fill the gaps in skills that your current team is lacking.

Let’s say that your current sales reps aren’t the strongest in following up. They close sales easily (and quickly!) with highly responsive prospects, which helps them hit their targets each time, but their less responsive leads go cold quickly.

A new sales team member who is on top of their follow-up game can improve the atmosphere because:

  • They will likely improve elements like pipeline velocity and deal conversion rate, thus making the team more successful
  • They can help other team members cultivate that skill and become better sales representatives

It’s important for you to take the time to assess your team’s strengths and weaknesses against their individual and team goals, as well as the mission of your company.

The best way to do this is by speaking with each of your sales people individually to gain a deep understanding of areas your candidate might be particularly valuable.

This will also be a great opportunity for you to encourage improvement and learning, and plan future sales training events. Most successful sales teams are those that are always growing, so take this as a chance to not only bring your sales people closer, but also continually help them develop their skills.

How to find a great fit for your sales team

Good Fit Sales Team

Here are some of the best ways to make sure your candidate has humility, hunger and smarts, and would quickly and easily get used to their new team.

Ensure you’re not interviewing in silos. An ideal interviewing situation is the one where multiple separate interviewers get to debrief before a final chat with the candidate. Another option is doing a panel interview. Both of these allow the interviewers to discuss personality traits they’ve noticed and analyze various answers and behaviors from the candidate.

Interview in a relaxed team setting. For candidates that make it to a later stage of the interview process, you can place them in a working environment with peers, superiors and subordinates on a problem-solving task. Those with good interpersonal and collaborative skills will thrive in this environment and build a relationship with others quickly.

Ask sales interview questions that show their personality, not just their skills. Their sales skills might get them far in a sales process, but make sure to test how they interact with others. Some of the behavioral questions you can ask are:

  • Can you be a good team player and disagree with your manager?
  • How do you approach a situation if you don’t agree with how your team wants to solve a certain problem?
  • What would you do if your sales results for the month are higher than anyone else’s, and you notice the team morale is down?

There are no perfect answers to these questions, but you can gauge the true intentions and the ability to empower others from your candidate’s response—both verbal and non-verbal.

What to look for in a sales rep

In the previous section, we talked about what are typically considered soft skills, and have a lot to do with drive and interpersonal skills. Now, let’s look into traits that are more often called hard skills, which are considered more specific, defined and measurable.

Even though sales roles can vary from entry-level positions through to account management and even executive positions, it’s crucial to look for these qualities in all potential salespeople, and identify their strengths and weaknesses.

A full understanding of a sales cycle. An ideal candidate will have a deep knowledge of the actions necessary at each stage of the sales cycle and identify ways to shorten parts of the cycle to help the organization grow. Look for this skill by getting your candidate to walk you through a sales cycle of a hypothetical, or even your own, organization.

Lead qualification. A sales team that gets lead qualification right is arguably the best team you can have. When lead qualification is well organized and managed, all your sales people will be more productive, follow up more successfully and win more revenue. Test this trait by getting your candidate to list questions they would use to qualify a lead for your company.

Product and service knowledge. Asking about their knowledge of what they’ll be selling indicates how enthusiastic they’ll be throughout their sales conversations. Try a role-play conversation in which you are a potential customer with a specific issue your product can solve.

High levels of organization. Taking a lead from early stages through to sales is a complex process. Look for this skill by asking how they manage their calendar on a weekly and daily basis, their emails, to-do lists, as well as which tools and techniques they use to keep track of their tasks.

The non-obvious traits of a top-performing sales rep

There are a few more things you should look for in your future sales staff that will make them an irreplaceable part of your sales machine.

Problem-solving abilities. Problems will inevitably arise in your candidate’s role. To see if your candidate has this skill, you can ask them to describe their most stressful work situations in the past and how they handled them, how they deal with lack of information when it comes to problem solving, or about situations when they were asked to solve a problem in half the time than usual.

Optimism. Failure and challenges are a regular part of sales. Ask them about the failures from their previous roles and the approach they used to deal with them.

Coachability. The best sales reps are those that see their growth as an ongoing process. Even when they’re at the top of their game, they’re able to see areas they can improve and excel. Ask your candidate about their favorite ways to upskill and how frequently they do it.

The sure-fire way to verify a successful sales background

Here’s the problem with all these questions and skills you’re looking for: salespeople are usually well-prepared for them.

It’s in a salesperson’s nature to be prepared for various scenarios, so it’s trickier to get honest responses from sales candidates than for almost any other role.

Beyond the common sales interview questions, you can dig deeper by asking them for answers that dive into their performance in previous sales positions, but keep in mind that this is also something that can be, and often is, rehearsed.

However, you can get beyond that by asking further questions to get your candidate to clarify specifics.

Four questions you could ask first are:

  1. Walk me through a time when you had a measurable impact on your sales team.
  2. Tell me about a time you exceeded your monthly or quarterly sales goals.
  3. What was your best month of sales in your previous role?
  4. Tell me about a sale you’ve almost lost, but managed to turn around and win.

The answer to any of these will almost always involve a number such as revenue, the number of sales, or a conversion rate.

Now take the time to unfold the story further. It’s easy to lay out figures, but it’s a lot harder to explain the process of achieving them.

Ask the following questions:

  1. How did you qualify leads during this period of exceeding your targets?
  2. What action do you think made the most impact when you achieved that?
  3. Were you able to reproduce similar results on another occasion?
  4. How did you identify the problem in the deal that you managed to turn around?

The deeper you go, the less prepared they’ll be, so you can be sure that they are describing their actual experiences and not reciting a rehearsed answer.

The experts favorite questions and answers

expert’s favorite questions answers

Jonathan Angelov

Co-founder and VP Sales, Aircall.

“Sell me Aircall like I am a guy you are cold calling.”

Why ask for this?

“As I am usually the last person they see in the interview process they usually feel quite confident about their knowledge about Aircall.

“They are mostly making the same mistake, unfortunately. They start their pitch without asking me any questions. They are just talking and talking. I call this the stress talk effect: you don’t listen, you talk.

“Selling is not about talking but it is about listening. They often get confused because they have learned what Aircall is doing, and then I ask them, ‘wait, do you know who you have on the phone? What is his business and how do you know it is relevant to him?’

“It is very important to me that candidates understand that selling is not just pushing the person to buy, but it is listening to them and making sure that you are selling the right product to the right person. I am usually quite tough on them when they fail, so they understand that they still have a lot to learn. The good news is that we are here to help them.”

Francis Brero 

Co-founder and CRO Madkudu.

1. “What was your biggest challenge in your previous role?”

2. “What would you need to close your first deal with MadKudu?”

Why ask these questions?

“The reason behind the first question is to look for what I call the ‘victim syndrome.’ If the candidate talks about everything they didn’t have to succeed, this raises a big red flag. We look for people who see opportunities rather than challenges.

“The second question helps us understand how the rep operates, how much support they look for and what they need to sell.”

Stan Massueras

Director, Sales EMEA, Intercom.

“Who are the companies that you truly admire and why?”

Why ask this question?

“I love to ask this question to understand how passionate a candidate is about technology and entrepreneurship. It doesn’t really matter which companies are mentioned by the candidate (there is no perfect answer to this question). I simply use this question to evaluate if the candidate can speak with passion, authenticity and energy about the values and the mission of the company she/he admires.

“Why? I can teach sales techniques to a sales rep but I can not teach them passion.”

Julia Pimsleur

Founder, Million Dollar Women.

“What about our organization aligns with your personal values?”

Why ask this question?

“You need to find a passionate, committed professional who wants to grow with your brand. This question also shows you how deeply the candidate has researched and analyzed the role in preparation for the interview.”

Allo Arro

Co-founder and CEO, Teamscope.

1. “Tell me about your past track record.”

2. “What’s the most challenging goal you have set for yourself recently?”

Why ask these questions?

“The principles of conducting a good interview are actually more straightforward than you might think.

“Ask specific questions about past performance or behavior, look for facts rather than opinions and assumptions and avoid ‘clever’ questions and brain teasers.

“In case of an experienced sales manager, simply ask ‘Tell me about your past track record’ and follow up with questions like ‘How did you set the sales targets? How did you perform against those targets? When your team missed your targets, what did you do differently the next month?’

“To dig deeper, you might ask, ‘Tell me about the most challenging deal that you have closed?’ or ‘Tell me about the deal that you are most proud of?’ and again, follow up with questions that help you understand the specific situation, action, and outcome.

“In case of candidates that don’t have a long track record in sales, look for behaviors that indicate they have the potential and drive to do the job. For sales, being self-motivated, tenacious, and organized is strongly correlated with performance, so ask questions like: 

  • What’s the most challenging goal you have set for yourself recently?
  • Why did you want to achieve that?
  • What did you do to reach your goal? 
  • How did you monitor your progress?

“Look for characteristics that are actually required in that specific sales process—if it’s not a direct door-to-door sales job, then being gregarious, cheerful and outgoing is actually not that relevant (so don’t judge based on the first impression or interview performance), but being organized and self-motivated definitely is.”

Alexander Theuma

Founder, SaaStock.

“If we spoke to your current/former bosses, how would they rate you on a scale of one to ten?”

Why ask this question?

“I’m looking for an answer of nine or ten—a salesperson needs to be confident in their abilities and themselves. If anyone gives below a nine, I question whether they really believe they are/can be exceptional and an A player.”

Jakob Thusgaard

Founder and CEO, Yoursales.

1. “What is your working method?”

2. “Name a few of the tools you work with.”

Why ask these questions?

“If they don’t name a method they’ll have challenges. If they can’t name any tools, I know they’ll have a problem—particularly in a sales environment.

“Successful sales is getting the right combination of people, processes and tools to fit with the way your offering is best sold. People with an understanding of processes and tools make this easier. They are the real professionals. The rest is just pretending.”

Patrik Juranek

Director, Prague, Startup Grind.

1. “What are your values?”

2. “What business case you will acquire within one month?”

3. “What is your biggest sales success story and why?”

Guillaume Moubeche

Ceo, Lemlist.

“When do you stop following up on a potential customer?”

Why ask this question?

“Depending on the answer, it can really help the person stand out. Someone who replies ‘I’ll never stop following up’ would be wrong in my opinion. Sales is much more complex than having someone super pushy that never gives up.

“On the other hand, answering ‘it would really depend on the company culture and the branding of the company’ would really show that this person cares about the marketing team and the company. And when you see how sales and marketing often struggle to work together this is definitely a good point! Another good answer could be: ‘it depends on the stage of the lead.’ This would show that the person already has some knowledge of the sales funnel.”

Marc Wayshak

Bestselling sales author.

1. “What do you know about our company?”

2. “What do you know about me?”

Why ask these questions?

“Any salesperson should have done extensive research before the job interview, just as you will want them to do before any prospect opportunity. This will let you know if they’ve done their homework or if they are just winging it. If they don’t know anything insightful about your company or you, then they are not someone you want to hire. Period. Ask this question at the very beginning of your first phone interview with the candidate.”

Andy Lambert

Co-founder, ContentCal.

“Name me one deal/situation where you failed/didn’t win and what did you learn from this?

Why ask this question?

“Objections and rejections in sales are one of the only certainties of the job. The best sales professionals plan to manage failure and develop strategies to bounce back fast after missing targets.”

Jaako Paalanen

Chief Revenue Officer, Leadfeeder.

“Explain the steps you would take in your sales process from the beginning to the end.”

Why ask for this?

“This question is great in so many different ways. First of all, it reveals how much of a numbers person they are. Do they know how many calls would they need to do to reach X, explaining how would they do it? What’s the tactic?

“The question is pretty open-ended so it leaves room for improvisation and really showing you can understand sales and have an idea of how to do it. This is especially important in our organization at Leadfeeder, being a remote team where employees need to be real self-starters.”

Paul Blair

MD, Spartan Retail Group.

“Tell me about a time when you helped a colleague achieve their objective. Explain what you did, how you did it, what was the outcome and why you did it.”

Why ask this question?

“I want to know if they believe a salesperson’s income is entirely within their own control. You want team players. I’d look to give them specific scenarios and ask them to explain what they would do in a position that demands teamwork or collaboration. Ask them how they would manage and why they would manage this situation in this way.”

Your Plan to Hire the Best Sales Professionals

As you hire for sales positions in your company, remember you’re not just hiring people that will help you sell more. Your new sales staff should become part of a group that’s productive, cohesive and complete thanks to the diverse range of skills, both soft and hard.

Ensure that they’re deeply knowledgeable about the responsibilities ahead of them in the role, the type of prospects they will be working with and the quirks of your specific market. More than that, you want them to be open to ongoing learning to help keep your company ahead of the competition.

Create a set of sales interview questions that will uncover their excitement, motivations and past experiences, and the way these will fit into the nature of their sales role.

We’ve created a customizable interview preparation guide you can download here and use it for your very next sales interview.

Happy hiring!