Discover the top 26 sales interview questions, both for beginners and experienced sales professionals. Learn the key insights behind each question, what the interviewer is looking for, and how to answer confidently and successfully. Get one step closer to landing your dream sales role with this comprehensive guide and advanced tips.
If you’ve been searching for a list of the most critical sales interview questions to prepare for, look no further.
When it comes time to interview, most sales professionals show up to the meeting under-prepared. Regarding how much preparation you should do, we would ask, “How badly do you want the position?”
With over 20 years of experience placing sales professionals, we’ve heard almost every question possible. However, a short list of questions comes up in most sales interviews. Along with your company research, preparing your brag book, and other crucial steps, having a solid idea of the questions your interviewer will ask and how you will answer is essential.
This article is a compilation of the most important interview questions for beginner and experienced sales professionals, the meaning behind each question, what your interviewer is searching for, and how you should answer. To further help you, we’ve sprinkled some advanced tips into some of our example answers below that can be applied to any questions (such as check-ins, which is explained in Question 5 below). A thorough review of the questions and answers below should prepare you for almost anything an interviewer might throw your way and move you one step closer to landing your dream sales position.
Before we get to the questions, keep the following tip in mind. A successful interview will feel more like a conversation (relaxed and back and forth) rather than a series of answering questions put before you. Feel free to clarify questions, ask for permission to share examples, and ask questions of your own. It’s important to note that there are multiple ways to answer each question. And how you say your answers is just as important as what you say (body language, confidence, etc.).
Without further ado, here are our 26 sales interview questions that we’ve broken into basic and advanced questions.
Basic Sales Interview Questions
While our first fifteen questions fall under the “basic” questions category, they appear in most sales interviews. Because these questions are the basics, there’s a high chance your interviewer will ask them. Take the time to think through and practice your answer to each. A strong answer can be the difference between receiving an offer for your dream job and coming in second place.
1. Tell me about yourself.
When hiring managers say, “tell me about yourself,” they don’t actually mean, “tell me about yourself.”
They mean, “Tell me about your professional self as it relates to this position you’re interviewing for.”
Your ability to answer this question confidently will speak to your ability to engage a listener and build customer relationships by selling yourself. It is also the interviewer’s first impression of you. Do you come across as focused and confident? Or do you ramble and give a long-winded answer that leaves the interviewee less than impressed?
Can you briefly articulate why you are qualified for this role and set the stage for why you’re the best candidate for the job? Take the time to practice this question, as almost every interview you go on will start with it. Given that this question forms the interviewer’s first impression of you, we’ll spend more time explaining how to handle it. A great answer starts with your 3-Point Story, which you can cover in 60-90 seconds.
First, start with your current professional experience by briefly summarizing your current work. Short and sweet.
Second, summarize why you’re qualified for this specific role. What are your selling points? How have you been successful in your role? Highlight a few of your skill sets relevant to the position you’re interviewing for, and give succinct examples of your accomplishments. Be yourself, but be your BEST professional self.
Don’t give generic examples. Use specific examples of your successes; ideally, they should be measurable–exceeded goals, grew revenue, or ranked compared to peers.
Third, share why you’re interviewing for the role. This is simple. Do your homework and have 2-3 authentic reasons why you’re interested in the company. Share your enthusiasm and how your background and strengths apply to this role.
Let’s look at an example that includes all three points.
- “I’ve been an account executive in software sales for the last five years. I focus on winning new accounts and then managing and growing those relationships.
- My strength is my ability to get in the door with new prospects and quickly earn their trust. That’s one of the reasons I’ve been so successful in my role. Last year I was #2 on my team of 20 reps, and this year I’m on track to be #1.
My manager has told me I’m great at asking the right questions and listening to understand my clients’ needs. My clients trust me because I’m genuinely interested in solving their problems. That’s what enabled me to bring on two of our largest customers last year, and winning those higher revenue deals is where my true passion lies–I like working on larger, more complex accounts.
- This brings me to why I am very excited to be interviewing for this position! From my research, I was impressed with the new products you’ve recently launched. I can see that you work with some pretty big-name clients, and this role entails hunting for larger accounts. That’s why I jumped at this opportunity.”
2. Why are you interested in a sales position, or why did you get into sales?
This question is most applicable for entry level sales roles up to about 2 years of sales experience. Given the level of rejection faced in sales, it’s important that your reasons for interest in sales align with the realities of the job. To that end, this question allows interviewers to gauge what motivates you and learn whether sales in general and the position you’re interviewing for fits based on those motivations.
Your answer will help them to understand your personality, level of commitment to (and fit with) a career in sales, and whether your motivations align with their company values.
Advanced tip: Think about the sales position you’re interviewing for. If this is an aggressive, cold-calling position, don’t say you’re interested in sales because you like building long-term relationships. Of course, you shouldn’t be interviewing for an aggressive transactional position if relationship-building is your true motivator.
This is your opportunity to showcase how you discovered your affinity for sales and how your motivations align with the company. The more aggressive the position, the more critical it is to be motivated by money. We don’t suggest making that the sole focus of your answer, but don’t be afraid to share it.
Many potential sales professionals point towards their love of people and the attractiveness of getting paid to connect. Although this is true, sales positions come with much rejection. After all, more potential customers will say “no” to you than “yes”… If you don’t have a solid and convincing answer as to why you’re interested in a career in sales, stop reading this blog and figure that out. Examples we like to hear are the desire to compete, be paid what you’re worth, and be challenged… If you have personal examples from your past where you enjoyed and excelled in competition, weave them in.
“My love for sales started when I opened my childhood lemonade stand. I ran that stand for three summers, had a lot of fun running my own business, and made good money. That experience taught me that my hard work and hustle translates into success and I’ve held several retail sales jobs since. I also have family members who are in corporate sales and have done very well for themselves. Beyond that, I miss the level of competition that I had playing basketball in high school. I loved the pressure and want to work in a career where it’s on me to perform and I’m rewarded when I do.”
3. What do you know about our company and our product?
This question immediately exposes if the candidate spent time preparing for the interview while revealing what draws them to the company.
A tight answer demonstrates your preparedness and alignment with the company’s mission, while a poor response serves as a telling red flag. A significant factor in a sales professional’s success is their preparation before client calls. If you don’t take the time to prepare for something as important as a job interview, it suggests you won’t prepare for sales calls.
This is your first opportunity to demonstrate your research before the interview, your knowledge of the company, the product they sell, and how seriously you take your career. Learn everything you can about the company through its website, customers’ websites, reviews, and Youtube product explanations. Practice your answer to ensure you can distill what you learned into a succinct 30-45 second overview.
(Bonus points if you take the time to connect with and speak to a sales rep (or two) on their team. You can find them and connect via LinkedIn.)
“I learned a lot about your company culture after talking to a sales rep from your company through LinkedIn. They specifically shared how your product solves customers’ problems better than your competitors. I also learned that your product is the most expensive, and I love the idea of selling on value. Beyond your product, your company values also stood out to me. As I mentioned earlier, I miss the teamwork of being on a basketball team. Your emphasis on collaboration is something I’m looking for.”
4. What interests you most about this sales position?
This is another question that will reveal the level of pre-interview research you invested while also demonstrating your ability to sell the company and yourself by explaining how your skills, interests, and abilities align with the available position.
This question can reveal much about you and your level of interest in the company. Similar to question 3, It’s an opportunity for the interviewer to see how much time you invest into something you want and how well you can take what you know about the company and pitch the product enthusiastically.
This is your opportunity to give the interviewer an elevator pitch about the company. When done correctly, an elevator pitch can demonstrate your sales skills, understanding of the company, and how your interest in the position makes you the best candidate. You can also use it to explain why you’re potentially leaving your current job artfully.
“What interests me most about this position is the quality of your product. When I can sell a product I genuinely believe in, I’m confident in my ability to perform. The fact that your product provides benefits 1, 2, and 3 to help customers accomplish X, Y, and Z at this price point is outstanding. I’m also interested in your comp plan. From what I understand, it’s uncapped. My current role has a cap on earnings. I was 176% of quota last quarter, but my commissions max out at 150%. Many reps on our team sandbag and push sales into the next quarter, which goes against my personality. I love to push as hard as I can.”
5. Walk me through your current sales process.
This is a critical question. Along with highlighting your understanding of a structured sales process and your unique creative approaches, this question gives the interviewer a better understanding of your ability to remain organized in a self-directed role.
It’s essential to focus on your ability to explain your sales process. Do you describe your process with good depth or give a straightforward summary? The level of detail provided in answer to this question demonstrates your understanding of the role of the interviewer and your ability to explain complex concepts. All other things being equal, hiring managers will choose candidates who can explain their sales processes and why they’re successful.
When responding to this question, be sure to demonstrate a thorough understanding of the core principles of a sales process: prospecting, initial outreach, researching, pitching, and closing new clients. Additionally, include any unique steps you take that have proven successful in the past and the tools you use to remain organized throughout the process. It’s a bonus if you’ve uncovered a difficult aspect of the company’s sales processes and can explain how you excel at that.
“My sales process begins with building a list of potential clients in x-software, which I’ve found helpful when tracking my progress with each client. When I reach out to a potential customer, I focus on connecting with them personally (seeking common interests, displaying empathy, etc.). Throughout the conversation, I ask questions designed to uncover opportunities for our products to solve problems. From my conversations with a few of your reps, it came up that getting in the door with your customers is the most difficult part of the job. I’ve won several prospecting contests and used creative ways to get in the door. Would you like to hear some examples of how I’ve done this?”
Advanced tip: It’s easy to give answers that are too short OR too long. The remedy to this is checking in with the interviewer. Check-ins keep the interviewer engaged and keep you from droning on or tangentially into the material the interviewer isn’t interested in. You can provide a succinct answer to their question and check in with them to see if they want to hear more (as we just demonstrated in the example answer above). If they’re good, move on. If not, find out what they would like to hear more about.
6. What’s your proudest sales accomplishment?
This question allows you to share your home run accomplishments. It also demonstrates your motivations, ambition, and work ethic. Be prepared to go into how you “won” and why your achievement moved the needle for your company.
How you answer this question can be very telling regarding your motivations, your level of success, and the impact you’ve made. For example, if you give answers with financial figures, this indicates a financial incentive. If you answer with a customer service success, this may suggest to the interviewer that you are motivated by human connection or even reveal a lack of significant financial success.
When sharing your most significant sales accomplishment, explain why that experience was a success in your eyes, the specific steps you took to reach the outcome, and how that benefited your employer. When considering your answer, make sure that it aligns with the culture and demands of the position. The more specific you can be with your example (customer’s name, challenges, and obstacles to success), the more specific you can be with tangible benefits, the better.
“If I had to single out my proudest sales accomplishment, I’d have to go with the time I was finally able to close XYZ prospect that our company had been pursuing for quite some time. After several failed attempts by other account executives, I was able to close the deal by establishing a genuine connection with the customer and helping him see some of the weaknesses in their current vendor’s offering. Despite that, Bob, the company’s decision-maker, told me that despite these weaknesses, he was loyal to his current vendor, and the cost of switching vendors was high. I stuck with the sale because I saw a huge opportunity, and I focused on learning more about the challenges he faced and tried to stay top of mind with him.
Eventually, their existing provider failed to fulfill an order, and Bob called me in a panic. He shared that he couldn’t switch all of his business to me, but he was hoping I could help… That was all the window I needed to show him what our company and I could do. Within six months, I had gained all of their business which took me from 101% of the quota for the year to 212%
(Check-in) Would you like to hear more about how I was able to build on that initial sale to gain all of his business?” [No]
7. If you asked your manager and a coworker what your biggest strengths and weaknesses are, what would they say?
On the surface, this question informs the interviewer about the candidate’s strengths and weaknesses. However, it also allows you to demonstrate your self-awareness and capacity to internalize constructive feedback.
While the strengths and weaknesses you share will give them a better understanding of how you will fit into the organization, how you respond is often more important to the interviewer. Did your answer come across as sincere and candid? Did you come across with a positive and open tone, or were you defensive? Did you agree or disagree with the feedback (especially regarding your weaknesses)? Did you take action after receiving the feedback?
Honesty, vulnerability, and discretion are the key to answering this question correctly. While it’s easy to talk about our strengths, very few people enjoy discussing their weaknesses, especially in interviews. Note that you aren’t trying to hit a home run with this answer. You are trying to display self-awareness and openness to feedback.
With this in mind, the best examples of weaknesses to share are ones from the past that you’ve remedied or negatives that don’t apply to the position you are interviewing for. Give a short but open answer, look the interviewer straight in the eyes and wait for the next question.
“In my previous role, my manager and coworkers all made comments about the level of passion I brought to the workplace. I learned that, while my passion is one of my greatest strengths in selling, I received feedback from my managers a few years ago that my passion can also cause others stress. Sometimes I push the internal team to deliver excellence to our customers. I never want to compromise on my commitment to my customers, so I took that as a sign that I needed to strengthen my relationships with our internal team.
Once a month, I made it a point to connect with each member of the internal team personally. It helped them to understand me better, especially my desire to give excellent service to our clients. They have a hard job, so I now go out of my way to thank them when they deliver for our clients. I appreciate receiving this feedback about my “passion,” as I now have deep internal relationships. These relationships have helped me win accounts that I wouldn’t have otherwise.
(Check-in) Would you like me to give a specific example of a client I won because of this?” [Yes]
“In 2020, we had supply chain delivery issues of our products that cost our company more than a few sales. I sat down with Jenna, our liaison with our largest supplier, to strategize what we could do about this. After our meeting, she worked on building her relationship with their internal team, just like I had with her. A few weeks later, Jenna called to tell me that she had secured an additional shipment of product which I already had a prospect in mind for. Because of this, I made a sizeable sale, and I also took the time to recognize her and make her the hero during the next department meeting.”
8. How did you prepare for this interview?
Preparing for a job interview is similar to the preparation required when approaching a potential client. You can read our post, How to Prepare for a Sales Interview, to learn more on the topic. Here are a few steps to help you understand the company:
- Read the company’s Glassdoor reviews and focus on posts similar to your position.
- Review their website.
- On Linkedin, read their company page, and review the hiring manager(s) and a few of your potential peers’ backgrounds.
- Reach out to a few peers on Linkedin before your interview to learn more about the position.
- Watch videos on Youtube or other platforms to better understand the company’s offerings.
Here are a few steps to prepare yourself to answer the hiring manager’s questions:
- Review your annual sales performance for each of the last five years. Most hiring managers will ask you about your sales performance. Be ready with your exact % to quota and rankings.
- Your big 3. What are your big 3? Your top 3 sales successes. Be ready to share a succinct story about the obstacles you encountered, the skills you used to win the deal, and the specific numbers involved in the win. Ideally, you will have different stories for each skill you have mastered. For example, have a sales success story that displays your prospecting skills, account management skills, and most significant win.
- Advanced tip: prepare your brag book. If you’re a top performer and can prove it, we share how to put one together in our blog – The Sales Brag Book. You can attach an electronic copy of this book when you email the hiring manager a thank you email post the interview.
The level to which you prepare for their interview is the only indicator that they have as to your willingness or ability to prepare for a sales call. It is also a good indicator of how badly you want the job. A common mistake we see is candidates being underprepared for an interview because they aren’t sure if they want the job. After meeting their potential boss, they realized they wanted the position badly… but it was too late. The hiring manager chose the candidate that came to the interview fully prepared.
Here are a few questions to ask yourself to determine if you’re ready for this question:
- Can you give a high-level explanation of who they are and what they do?
- Do you have three strong reasons why you’re interested in working at this company?
- Do you have three strong reasons why you’re interested in selling their product/service?
- Have you connected with 1-2 peers on the team to learn more about the company, its offering, and what it’s like to sell it?
- Are you ready and able to share your exact sales performance?
- Are you ready to go with your big three sales success stories? Ideally, they’ll be tailored to the job’s demands, which you learned about when you spoke with one of your potential peers via Linkedin.
“I did several things to prepare for the interview. I started on your company website, watched Youtube videos, and reviewed LinkedIn to ensure I was interested in your company and understood what you do and what I would be selling. Then I reached out to one of your reps (give their name) on Linkedin to learn more about your company, what it’s like to work for you and what it takes to be successful here. My conversation with her was extremely helpful and cemented my desire to work here. Finally, I reviewed my sales performance over the past several years to prepare me for your questions when they arise.”
9. Why did you leave your last role (or are you considering leaving)?
Leaving a sales job and starting over in a new position and territory represents a lot of hard work. Without question, you need to be prepared to give a solid answer to this question. A lack of a great response is a red flag.
The interviewer’s objective is to learn whether you left for desirable reasons (such as seeking greater opportunities) or less desirable reasons (such as missing sales quotas) and use that information to evaluate how they would fit with your company.
This is another question requiring a tight, honest answer… Give enough to explain why you would leave but refrain from listing every reason. You want to get a head nod from the interviewer and move on to questions that show your performance. To put it another way, you aren’t going to win a job based on your answer to this question, but you can lose it.
A few more thoughts. Start positive about your experience with the employer and give a solid reason why you left without ever disparaging your previous employer or boss.
“I genuinely enjoyed my time at XYZ. After two years, I’ve accomplished all of my goals. My boss, Cheryl, allowed me to move into a senior role and championed me the whole way. My next promotion would be her job, and she’s not going anywhere. Sadly this means that I have to move on, but now I’m ready for the next challenge, and I’m super excited about this opportunity.”
10. What is your most recent quota? How did you do vs. your quota YTD? And the previous year?
It goes without saying that your answer to this question is critical to getting hired. This question helps interviewers to evaluate how well you have performed, how big of a quota you have carried, and how well your performance aligns with the expectations of the new position.
Quotas are often hard to compare from one company to the next. For example, your quota might be easy to hit or extremely hard to reach, and the interviewer would like to understand what your numbers mean. Ideally, your response will give the interviewer a black-and-white answer as to how well you’ve performed, how much revenue you are responsible for, and how your company measures your success.
Be ready to share the numbers as to how you are performing and how your quota works. The more precisely you answer, the more believable your answer will be. In the best-case scenario, you can share employee reviews or other documentation that proves that you’re a top performer. This information gets compiled into what is known as a brag book that you can email to the hiring manager after the interview (read The Sales Brag Book for more). It’s also helpful to give the interviewer context. For example, you might be 97% of quota, but #1 on the team and the second best rep sitting at 81% of quota.
If possible, determine the company’s performance expectations before the interviewer asks this question. If your quota is currently much lower than their expectations, find out the deal size, prospect size, and who the decision maker is. More important than how much your product costs is the difficulty of their sale relative to yours. All other things being equal, hiring managers like to see that you’ve carried similar responsibility levels and sold to a similar clientele.
“For 2023, my sales quota is $1M. Last year my quota was $850k, and I finished the year at 127% of quota. This placed me in the top 10% of the national salesforce, and I earned our President’s Club award. To give you some perspective, my average deal size was $86k, and all this revenue was from brand-new accounts. I’m happy to explain more about any of our sales metrics and/or how I exceeded quota.”
11. What are some common hurdles you face in this position? How do you handle them?
In addition to further understanding your strengths and weaknesses, this question allows the interviewer to evaluate your problem-solving ability and compensate for areas of weakness.
This question can reveal precisely what you’re not good at and what you don’t like doing. For example, you might share that your company lacks marketing support and provides very few inbound leads. If the interviewer is looking for resourceful sales reps who know how to find prospects independently, you will be out of the running. In addition to this, interviewers look to see how you respond to challenges and hurdles. After all, every company has shortcomings. Do you rise to meet them or use them as an excuse to explain poor performance?
This is another situation where it’s hugely beneficial to connect with a current rep so you can learn the pluses and minuses of the job before interviewing. All sales workers experience unique hurdles while on the job, and good employers will be willing to help you overcome them. The key to answering this question is clearly identifying the hurdles you face, then choosing one with a successful outcome that shows your ability to be flexible and creative in addressing those challenges.
“Every company has its challenges, and ours center around supply-side shortages. Last quarter I received orders for $1.1M in product, but we could only deliver $770k of it. I knew this was going to be a problem, so I worked on a strategy for each customer to ensure we didn’t lose the business. Fortunately, most of the business we didn’t deliver last quarter will happen this quarter. (Check-in: Is this a challenge right now with your company?).”
12. What accomplishments in your life are you most proud of?
Similar to the “proudest sales accomplishment” question, this gives the interviewer a deeper understanding of your motivations. In addition, the personal nature of the question highlights your values and personal interests.
Your answer to this question will give the interviewer a better idea of who you are and what drives you personally. Perhaps it’s not fair, but it can also let the interviewer know how much you value your career. That said, a personal answer can be impactful, especially if it shows how you’ve overcome significant adversity.
Give a genuine answer that can be related to your career. We face many setbacks and challenges in sales, so your answer can be personal or professional. If you’re new to sales, personal examples might be all you have to share.
“One of my proudest accomplishments was graduating from college. It might not sound like the most impressive accomplishment, but I came from a poor family that didn’t value education. Early on, I knew I wanted to go to college, so I got a job at 14 and started saving. Because it was all on me, I had to work full-time to pay for school and support myself. It took me five years, but I’m the first person in my family to get a degree, and I graduated with a 3.2 GPA.”
13. Describe your ideal sales manager.
This question is vital for understanding your expectations of your potential boss, how those expectations align with the personalities of the management team, and the type of culture you best fit with.
It has been said that people join a company and leave a manager. The personal fit between yourself and the interviewer is, well, personal to the interviewer. They will most likely keep looking if they can’t see themselves spending long hours with you.
Before answering this question, it can be helpful to write down examples of bosses that have inspired you and those that demotivated you. This question comes up often during interviews, so be prepared with three things you look for in a boss and keep your answer authentic and as positive as possible.
(Bonus points if you did your research, connected with a potential peer, and learned more about what it’s like to work for them.)
“I’ve worked for three different sales managers at this point in my career, and I’ve learned a lot from each of them, including the style that works best for me. There are three things that I’ve realized that I need. 1. I want to work for a boss that I respect and who has my best interests at heart. 2. My best managers have challenged me and inspired me to perform at my best. I’m internally motivated, but it’s a lot more fun for me when my boss demands that last bit more from me. 3. I appreciate feedback. I might not always enjoy hearing about my shortcomings during the moment, but I’ve realized that it’s the only way that I’m going to get better. My favorite boss, Kim, gave me two things to improve on each quarter and her feedback and that push is the reason why I hit President’s Club last year.
This obviously works both ways. What are you looking for in a working relationship with a sales rep, aside from exceeding quota?”
14. What are your long-term career goals? Where do you see yourself in five years?
Asking about your long-term goals over the next five years will allow the interviewer to gauge your level of ambition and the potential long-term fit between yourself and the company.
Does your career vision match what’s available at their company? Do you have goals and a game plan to execute those goals? Do you even know what you want for yourself past today? Can the interviewer see and feel that you are driven? The sales profession is challenging; they are looking for your drivers and the “why” you’re willing to work hard.
What are your career goals? The answer might be flexible, but it’s essential to understand what doesn’t work for you. This is another question where having some insight into what’s possible at the company can be helpful. As an interviewer will usually ask this question towards the end of an interview, you should be able to learn about the long-term potential with the company, and feel free to ask what’s possible before answering.
If you have a clear vision, share it but tailor it to the opportunity (assuming it’s authentic). Sharing dreams over three years out can often get you into trouble, especially if it doesn’t fit with what’s available with this employer.
(Bonus points if you can connect your vision to the company and tie in concrete drivers such as your dreams for your family.)
“I’m a bit flexible as to how my career might play out. What I know for sure is that I love sales, and I need to feel challenged. My research on your company showed me that there are several levels of sales reps, such as major and national account reps. That is super inspiring to me. More important to me than a title is being able to provide for my family. I didn’t grow up with much so being able to provide is a big driver for me.”
15. What questions do you have for me?
We all know that first impressions are crucial but so are last impressions. Almost every interviewer will leave a little time at the end of the interview to allow you to ask them questions. Leaving the interviewer with a great last impression is so important that we’ve written a separate blog, Smart Questions to Ask at the End of the Interview. Below you’ll find a succinct example of how to handle this question.
This is another and the last opportunity to see if you did your homework, and it tells the interviewer how badly you want to work for them (vs. just needing to get a job). It also shows the interviewer the quality of questions you ask, and a huge part of success in sales is asking prospective clients intelligent and revealing questions. If the candidate doesn’t ask any questions, it’s a red flag.
Before the interview and throughout your conversation, write down any questions that come to mind. Quick tip – don’t get carried away with writing during an interview, and do ask the interviewer at the beginning of the interview if it’s OK if you take a few notes. If this is a first interview, refrain from asking detailed compensation or benefits questions, as that is getting ahead of yourself. There can be an exception if it’s clear that you did well during the interview and are juggling multiple great opportunities (we’ll show you how in the example below).
“I do have a few questions:
- I noticed on Linkedin that many of the reps on the team hadn’t been there very long. Can you speak to that?
- I’d like to understand the sale a little better. What’s the most challenging part of the job, and what do your competitors do better than you? What do you do better than your competitors? Basically, if I come to work for you, I want to win, and I’d like to know what I’m going to face in the field and what it takes to be successful.
- My interest in the position is a 10/10, but I’m currently deep into several interview processes. I don’t know if you’re just as impressed with me, but I’d like to ensure that the position’s compensation level matches my needs and where I’m at in my career.”
Advanced Sales Interview Questions
The following twelve questions are advanced and will be encountered more often for upmarket sales positions. Each of these is more in-depth than the previous questions and plays on your experience throughout the years. Consider them carefully and come up with potential answers even if you don’t have direct experience with the situation given.
From experience, we see that experienced sales professionals often do poorly during interviews because it’s been years since their last interview. Performing a few mock interviews and asking for feedback can be helpful if that’s the case for you.
1. How do you acquire leads?
While generating leads is a fundamental component of the sales process, not all sales professionals are proficient. This question allows the interviewer to evaluate your ability to create and fill a sales pipeline.
There’s an unspoken truth about most sales professionals. Many hate to prospect, are unorganized, and shoot from the hip. The interviewer will be keen to understand if you fall into that category. As you describe your process, the interviewer will also listen to see if your story lines up. We have interviewed sales reps claiming that they make 50 cold calls daily. As we went into their daily activities, it quickly became apparent that they didn’t even have the hours to make that many calls.
Before answering, clarify if they want to hear about your entire lead generation process or if they want to know where you get your leads, such as inbound or self-generated. If they are looking for the former, avoiding ambiguous answers and giving a detailed description of your lead generation process, including metrics and goals, is crucial. Make sure to check in to see if the interviewer wants more or less detail as you describe your process.
“Are you asking where my leads come from or do you want to hear about how I find opportunities and keep my pipeline full?
(If the interviewer wants to hear the latter). I take great pride in prospecting, and my boss has me train new reps on how to fill their pipeline. About half of the clients I’ve closed in my current position started via cold outreach, and the other half came via referral. Aside from regular cold outreach, I ask each of my existing customers for referrals at least once per quarter and use several tips I learned to ask for referrals when prime opportunities arise, which I can explain if you’re interested in hearing more. Beyond referrals, cold outreach is the part of my job where I have the most control, so I take it seriously. Would you like me to take you into my approach?
(If yes). I block half of Monday, Tuesday, and Thursday to identify, research and contact potential clients. My employer wants to see us connect with five new prospects each week, which is a lot, given how difficult it is to get the level of prospect I’m chasing on the phone. My own experience tells me that I need to find about 25 new prospects each week. I follow a series of 5 touches for each prospect in addition to quarterly follow-ups with prospects that didn’t respond to me previously. If I see a trigger event or a creative way into an account I might take a different approach to that lead. Would you like to hear more about these touches?…”
2. Describe 2-3 times when you didn’t meet a goal or lost an opportunity. What did you learn?
This question allows the interviewer to evaluate your ability to learn from your mistakes and use those lessons to improve in the future.
This can be a backdoor question to uncover weaknesses that could limit your success with your company. It also reveals to the interviewer if you have self-awareness and can learn from your mistakes.
We’ve all made severe mistakes or experienced significant failures that left an indelible impression and taught us a lifelong lesson. However, choose your answers wisely. For example, avoid sharing recent mistakes or weaknesses in areas critical to this role’s success. Give examples that occurred long enough ago and can clearly show you’ve overcome. Be sure to explain the lesson learned and actions taken clearly. While it’s best to keep your answers focused on your career, personal experiences with lessons that translate to the workplace might also be appropriate.
“Four or five years ago, a potential customer I had been trying to close for a year called me with a large, last-minute order they needed to be filled on a Friday afternoon. In my excitement, I promised them I’d get right on it and we would have no problem filling the order. Unfortunately, when I went to complete the order in our system, we had just sold out of our stock. I couldn’t reach the customer until after the weekend, and they were understandably upset when I got a hold of them.
They never gave me another shot. I’ve never forgotten that lesson, and I never promise a customer anything I’m not confident we can deliver. Fortunately, that lesson has paid dividends as I’ve won several customers who have shared that they 100% believe I will provide what I promise.”
3. Pitch me our product. Pitch me your current company’s product.
This is an updated version of the old sales interview question, “can you sell me this pen?” The purpose of this question is to evaluate your ability to ask insightful questions, uncover a prospect’s needs and sell under pressure. A twist on this is the “demo” used by most software companies in their interview process. During the “demo,” you will be asked to run a mock demonstration of their product or the product you are currently selling.
Do you follow a formal, questions-based approach to selling, or do you share the features and benefits of the product you are selling? The alternative approach is described as “show up and throw up” in many circles. If you take a questions-based approach, you will have cleared the first hurdle. The second hurdle is how you come across during the roleplay. Do you listen, take in the answers, and confidently tailor your approach to the prospect’s needs?
Preparing for a “pitch,” whether it is a pen or a company product, starts with curiosity. What questions would you ask to uncover your prospect’s needs and buying motivators? Write them down. The next step is to roleplay with a colleague or friend and ask for feedback. How do they rate your listening skills and sincere interest in helping them find the right solution? What are your motivators? Did you approach the “pitch” with curiosity and a desire to help them find the right solution, or were you focused on selling them what you have?
“I’d like to ask you a few questions about what you’re looking for in a pen to understand what will best fit your needs. Tell me about your favorite pen. Who are you buying the pen for? Is this for a special occasion or use? Are there any frustrations you have with your current pen? What’s your budget?”
The answers to the questions above will guide the direction of the conversation. For example, you might find that the person wants a special pen to use when they sign important documents. By listening and asking clarifying questions after each answer, you discover the prospect only signs these documents after a lot of hard work. After hearing their own motivators, your prospect wants an exceptional pen to sign these important documents. There isn’t a limit to their budget, and they want to feel a rush of accomplishment every time they take out their special pen to sign.
With this knowledge in hand, it should be clear which pen(s) to show the prospect. In summary, the right questions, good listening skills, and curiosity to explore the answers received are the ingredients for an excellent sales pitch.
4. How did you land your most successful sale?
This question lets you speak to your greatest sales success and the steps you took to close the deal. Interviewers also use it to glean insight into how you have achieved your accomplishments.
Aside from understanding the upper limits of your success thus far in your career, this is another opportunity to evaluate your self-awareness and sales processes. When they dig in, will they find that your success involved luck, or was it a result of a structured and repeatable process?
This is an opportunity to demonstrate your most significant career success to date. There are two types of “most successful sales” experiences to consider when answering these questions. One is the most financially rewarding, and the other is the sale that proved to be the biggest challenge to close. When sharing your story, give specific details, including the company and buyer’s names, the obstacles faced, and the exact results.
“In November, I closed a $552k deal with XYZ company. I have closed a larger deal during my time with my current employer, but I’m sharing this example as it’s the most challenging one I’ve ever closed and the one I’m most proud of. I first started calling on XYZ during my 2nd month on the job.
Early on, I realized that our offering was a great fit for them, but they were acquired right after that, and all new purchases were frozen. I stayed on top of this account only to see the entire management team turnover, and I had to start from zero. The new management team had completely different priorities, and I had to rethink how our solution could help them achieve their goals.
(Check-in) Would you like me to go into detail as to how I did that? [No.] There are only so many customers with the potential of buying more than $250k in my territory. Balancing the tenacious pursuit of these large accounts while winning the smaller deals can be a real challenge, but it’s been the secret to my success here and why I’ve hit President’s Club the past two years.”
5. How do you research prospects before a call or meeting? What information do you look for?
Similar to the “interview preparation” question, this provides the interviewer insight into your preparation and dedication to your career.
Interviewers are looking for a “Goldilocks” answer to this question. Do you follow a structured approach and demonstrate that you know what information to look for? It’s easy to research both too much and too little. Thus the interviewer wants to hear the “just right” answer. The more complex a sale, the more research the interviewer will typically seek.
Similar to the research you completed regarding the interview, you should be able to explain your process for researching prospects, including each resource you explore and the information you’re looking for along the way (personal commonalities, apparent problems, company trigger events, etc.)
(Bonus points if you give a specific example of an account you won due to information gleaned during the research phase.)
“I use Fridays to research the prospects that I will be calling the following week. If you want, I can give you the specific approach I took with XYZ, which I closed for $356k last month, or I can speak about my process in general terms. (check-in) Which would be more helpful to you? [You can keep your answer generic.]
With XYZ (or any account, really), I research their business from a high level to help me understand how our service might help them. Then I look for challenges they may face or trigger events that increase their need for our services. In the case of XYZ, Crunchbase revealed that they had just received significant funding. Using Linkedin, I saw that they were dramatically ramping up their hiring, which our product can indirectly help with.
From there, I used Linkedin to find the appropriate contacts. Finally, I knew that we had won similar accounts, and I connected with the sales reps on our team that had won them. They were very helpful in helping me craft my messaging and understanding what challenges those companies had faced and why they ultimately chose to go with our solution.”
6. Can you define consultative sales for me?
Google “What is consultative selling?” and you will get hundreds of answers ranging from simple approaches to sophisticated 8-step processes. If you don’t have a firm handle on the question, you might want to brush up on a few of the more popular models and tailor them to your approach.
Interviewers are looking to see if you have a structured sales process, and one of the more popular approaches is consultative selling. In fact, about half of our clients specifically ask us to find sales professionals that understand consultative sales. Most experienced sales professionals take a consultative approach to selling, but many can’t succinctly explain what consultative sales is. When it comes down to you or another equally qualified candidate, the one that can explain their approach and process is the one most hiring managers will choose.
During an interview, it won’t matter that you’re terrific at penetrating a sales territory if you can’t articulate your sales process. To put it bluntly, the hiring manager isn’t evaluating how well you’ll do in their territory. They are assessing how well they think you’ll do. A significant component is your sales methods when you’re in front of one of their customers. The better you can articulate that, the more confident they’ll be in your abilities.
“Consultative sales is a questions-based approach designed to uncover customer needs and business challenges that prospects face. Customers today have access to much more information, usually have ideas about what they need, and are often suspicious of many sales reps’ claims. By using targeted questions to better understand my customers’ problems, especially those they might not be aware of, I’ve successfully used a consultative sales approach to separate myself from my competitors and win a lot more business.”
7. Tell me about a time in your sales career when you needed to start a territory from scratch. What did you do during the first 30 days? What would you have done differently?
If the interviewer is asking you this question, there’s a pretty good chance that you are interviewing for a new or underdeveloped territory. In situations where that isn’t the case, the position is usually heavily focused on acquiring new accounts. Keep this in mind when answering this and any other prospecting-focused question you receive.
Your answer will reveal if you have experience starting a territory from scratch and, perhaps as importantly, your comfort with beginning from scratch. Can you articulate the steps you would take to fill your sales funnel? Does your body language and tone of voice convey confidence that you can and will take on the challenge of starting from scratch?
Before answering, clarify the condition of the territory that you would potentially be taking over. Use this information to inform how you’ll answer the question. Be prepared to discuss the territory prospecting plan you used when you started with your current position or a position you have held that was the closest to starting from scratch.
Be ready with specifics, including metrics and results. Finally, prospecting is tough. When answering a question like this, it’s not just what you say but how you say it— project confidence and willingness to work smart and hard.
“I haven’t started a territory from zero, but I have turned around an underperforming territory that required heavy new account generation. With my first position at XYZ, I inherited a territory that finished at 57% of quota the prior year. When I started in this territory, the first few weeks were a bit of a shock for me. I quickly realized that I had to do significant damage control as the previous rep had turned off many of the more prominent prospects in the territory.
(Check-in) How much detail would you like to hear about how I turned that territory around?
In addition to these challenges, the prospect info in salesforce needed to be updated, and I had to start over. Fortunately, I like building out my territory strategy. For the first 30 days, I focused on identifying low-hanging fruit and uncovering the top 200 potential prospects in the territory. I further segmented the 200 into three categories broken up by revenue potential and my best guess as to how well that prospect fit our solution so I could focus more on my best prospects.
I’m happy I took the time to map this out, as the selling cycle is close to 9 months in most cases. Because I had identified some easier wins, I was able to get to quota that first year while I built out a pipeline that got me to 157% of quota and President’s Club my second year.”
8. If a client told you that they liked our product, but it’s too expensive, how would you turn them around?
This could be a crucial question depending on where this company’s pricing is relative to the marketplace. In our experience, this question only comes up with companies that sell more expensive offerings.
Do you sell on price or know how to demonstrate value to the customer through an ROI or similar approach? Along these lines, do you understand how to uncover the various influencers involved in the sales and how to get their buy-in and sign-off?
Where do you fit into the sales world? Do you like selling a more expensive solution that usually requires more persistence, patience, and a strategic approach? Can you tailor your offering to the customer’s specific (and often unknown) needs?
“First off, at almost every company I’ve worked at, we were the most expensive solution in our industry. I take a consultative approach to find significant pain points we can solve. If I can identify a specific pain point(s), I do my homework to uncover the ROI of our solution vs. our competitors. For example, the customer might be focused on decreasing costs across the board but tasked with increasing market share. With that knowledge, I can easily get around the cost of my product.
The main point is my willingness to do my homework before closing the customer. Part of that homework is looking internally for similar customers that I can use as a reference to speak to our ability to help this prospect achieve their goals.”
9. How would you approach a short sales cycle differently than a long sales cycle?
There are usually significant differences between short and long-cycle sales beyond timing. For example, some solutions take longer to sell because the offering impacts multiple departments, which increases the complexity of the sale by involving more buyers in the sales process.
Do you have experience selling larger deals with longer selling cycles? Have you received formal complex sales training such as Miller Heiman? Do you take a one size fits all approach, or do you develop a strategy for each account? Once again, do you have a process for longer sales cycles, and once again, do you project confidence when discussing your abilities to sell more complex deals?
If you aren’t presently selling a longer sales cycle offering, we suggest you reach out to a current rep with this company and pick their brain. Why does it take longer to get to yes? What increases the complexity of the sale? What are the most challenging obstacles to overcome?
If you do have experience with longer sales cycles, how do you approach them differently? What factors cause the cycle length to increase? How do you keep the sales process on track and progressing toward a close? Are there key markers or steps, such as identifying the primary decision maker and all the influencers, that help you advance the process?
“I have three different offerings that I sell with dramatically different pricing, and they each have different challenges with selling them. Our most expensive offering is our most profitable, but it’s also the most difficult to sell with a sales process that averages about a year which is twice as long as the other two.
Because this offering is over $500k a year, the customer’s CFO often gets involved in the deal. They often don’t understand the challenge their production teams face and grasp how our offering can save them substantial time and save the company significant money. I had to figure out that getting enough time with the CFO almost always starts with finding someone within the company with strong ties to the CFO who also wants our solution. There really aren’t shortcuts in this process; it requires a lot of diligence and time spent learning the company’s team and building a strategy to navigate the sale.
(Check-in) I can give you a specific example with a large account I just sold to XYZ after 14 months. Would that be helpful to hear?” [No.]
10. What are your favorite questions to ask prospects?
It has been said that most people like to buy, but very few like to be sold. This applies to the people interviewing you. The difference is helping customers get what they need and want vs. being pitched and closed. Understanding a prospect’s needs starts with questions. The better the questions, the better you’ll understand your prospects.
Do you take a consultative and questions-based approach to sales or fall back on pitching and aggressive sales tactics to try and advance the sale? Do you ask open-ended, next-level probing questions? Aside from your answer to this question, have you demonstrated curiosity and an ability to listen throughout the interview?
Through your experience, you should have a handful of questions you have found successful when speaking with prospects. Take the time to compile your favorites and include real-life examples where you won or advanced a sale based on great questioning. An excellent reference book for this is SPIN Selling, a questions-based sales approach.
“I am always curious about my prospects’ businesses and take the time to prepare several questions that I think will be helpful based on the homework I’ve done in advance of the meeting.
I can give you an example of a prospect I just closed last month if that’s OK?
One of my prospects, XYZ, was interested in replacing some of their production machinery, and they were comparing our offering with one of our competitors. While researching them, I noticed on Linkedin that they had dozens of open positions for which they were hiring. Out of curiosity, I started asking them about this and discovered they were launching a new line of products. The more I asked and learned, the more I could see that the machinery they were considering buying would need to be replaced in a few short years if this new line of products sold as they were projecting.
Of course, they had never been through an expansion like this and didn’t realize that upgrading now could save them hundreds of thousands of dollars in the long run. I really didn’t need to sell that hard. I just asked question after question about their direction, and their answers kept pointing them toward the best long-term solution. Ultimately, they purchased our most advanced machine, which became my biggest sale of the year so far.”
11. How do you define a successful first meeting with a prospect?
Sales leaders like to hire sales professionals that follow a clear sales process. With that in mind, do you start with clear goals for each sales meeting? An example of a clear goal for a first meeting might be booking a product demo with the prospect.
Do you follow a clear sales process? Do you know where you’re at in the process? Are there explicit goals for each meeting? Are the objectives measurable? How do you get sales back on track if you cannot achieve your goal(s) for the call? In short, sales leaders want to know if you have a process to advance each prospect toward a sale systematically.
Thousands of interviews have shown us that many sales professionals sell by feel and don’t have concrete goals for every meeting. Even if you have followed this approach with a high degree of success, sales leaders will almost always choose candidates who can define exactly how they move towards a sale. Mindful of this, how do you navigate each sale? Are there clear and measurable outcomes that you are trying to achieve during the first meeting.? “Establishing a relationship with the prospect” isn’t measurable, and it’s tough to define. “Introducing myself and my solution to the prospect,” although clear, doesn’t necessarily advance the sales toward a close. Every deal is different but pinpoint clear indicators showing that the meeting helped advance the sale. Examples can be uncovering the prospect’s needs, booking a 2nd appointment, discovering if other decision makers are involved in the sale, and learning the customer’s buying cycle.
“My goal for the first meeting is usually dictated by what I uncover during my research of the company. Can I give you a specific example? After nine months of effort, I just closed XYZ textile last month and knew their situation was unique after my first meeting with them. Before I met with them, I learned that a private equity group had recently acquired them. During our first meeting, I set a specific goal to uncover how the acquisition would impact their production department and what that would mean for my prospect.
Through questioning, I learned that the production manager, Jim, whom I was calling on, was under a lot of pressure. He had been tasked with increasing production while decreasing costs, and the idea of spending more money on production equipment was the furthest thing from his mind. I left that meeting with more questions than answers, but I knew one thing, my usual approach to selling to Jim wasn’t going to work. I promised him I wouldn’t waste his time pitching him our services and would only reach back out to him if I had a solution to address both his goals.
(Check-in) Would you like to hear how I did that?” [No.]
Sales Interview Questions in Review
Although preparing for a sales interview can seem daunting, a few basics apply to every question. For example, an OK answer delivered brilliantly will almost always impress more than a technically excellent answer given unconvincingly. Your body language, confidence, and energy are vital ingredients in how you come across. The best way to perfect this is to roleplay a few of the questions above with people you trust.
(Bonus points for leveraging the power of zoom by recording the roleplay so you can see your performance with your own eyes. You can find more zoom specific tips in our blog, 4 Zoom Interview Tips. Our second tip is to answer questions with specific examples. The more detail you can provide, the more that interviewer can tune into your story and, more importantly, you.)
Finally, the best advice that we can give is to be yourself. Center yourself on the knowledge that you have a lot to offer and that you’ve done your homework. Best of luck to you, and we hope this guide helps you land your dream job.