The Experts’ Favorite Sales Interview Questions and Answers

We’ve asked some leading influencers for the best sales interview questions they think you should always ask prospective new salespeople during the recruitment process—as well as the answers you want to (or don’t want to) hear.

Jonathan Anguelov 

Role: Co-founder and VP Sales, Aircall.


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

Why ask this question?

“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 do 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

Role: 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 this question?

“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 

Role: 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

Role: Founder, Million Dollar Women and Little Pim.


“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.”

Alo Arro

Role: 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 this question?

“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

Role: Founder, SaaStock and host of The SaaS Revolution Show Podcast.


“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

Role: Founder and CEO, Yoursales.


1. “What is your working method?”

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

Why ask this question?

“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 Juránek

Role: 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 

Role: 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

Role: Bestselling author of “Game Plan Selling” and “Breaking All Barriers”.


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

2. “What do you know about me?”

Why ask this question?

“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

Role: 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.”

Jaakko Paalanen 

Role: Chief Revenue Officer at Leadfeeder.


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

Why ask this question?

“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 

Role: 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.”

Prepare a question list to ask in sales candidate interviews 

Think about the things you want any potential new salesperson to bring to the company, whether that’s experience, passion, personality, talent or potential. 

You also want to find out if they’re the right fit for your team, so if you’re coming up with sales manager interview questions, or interview questions for sales reps, think about the company culture that you already have.

The other thing to find out is how quickly they’ll adapt to your sales process. 

Are they familiar with the tools you use? Have they got experience working with a CRM like Pipedrive?

Make sure you have a prepared list of sales interviews questions and a checklist of desired responses or insights you want to cover off. This preparation will allow you to maintain control of the interview and confidently select the right candidate for the role. Don’t underestimate the importance of hiring the right salespeople. These decisions will have a direct impact on your ability to scale up quickly.

The Experts’ Favorite Sales Interview Questions and Answers | Pipedrive
The Experts’ Favorite Sales Interview Questions and Answers