sales interview questions

18 Unique Interview Questions to Ask Sales Candidates

Reps are notorious for knowing what to say. And that makes it extra difficult to evaluate them during an interview.

As a hiring manager, one of your jobs is to ask the right questions so you can get a reliable assessment of the candidate’s potential.

We reached out to and hiring experts to share their favorite interview questions, and here are some of the best responses:

1) What is the most courageous thing you’ve done in your life?

After interviewing hundreds and hundreds of different people over the years I have refined my questions to only a handful. I want to find out more about the character of a person more than anything. This question tells me about 75% of what I need to know about a person.”

– Bryan Clayton, CEO, GreenPal

2) Talk about a time you had to put aside your ego, and do something that didn’t directly benefit you, but a co-worker or your company?

“Talk about a time you had to put aside your ego, and do something that didn’t directly benefit you, but a co-worker or your company? Most salespeople are great at selling themselves and communicating their successes. It’s more difficult for them to put that aside when necessary, but those are the kinds of people you want on your team.”

– Bob Clary, Director of Marketing, DevelopIntelligence

3) Please tell me about a time you gave a client bad news.

“A sales person’s values can be the most important thing to test in an interview. This question tests the candidate’s values and helps determine if they are customer centric or if they make excuses to protect themselves (or their commission).”

– J. Ryan Williams, Founder, SalesCollider

4) What hobbies do you invest time and money into?

“What hobbies do you invest time and money into?Explanation: This question not only helps to gauge the cultural fit of a potential sales candidate, it also opens up a discussion of values and time/money management. Keep a keen eye for employees (especially sales staff) that are mindful of their hobbies and understand the value of time. This will likely carry over into their professional work.”

– Jacob Dayan, CEO, Community Tax and Finance Pal

5) Would you show us, right now, how comfortable you are on the phone?

“Would you show us, right now, how comfortable you are on the phone? Then arrange for them to place a pitch call with someone in another office or even have them pitch a low-level prospect in front of you. If they embrace the request and execute the call well, they have demonstrated their ability to handle the unexpected by showing poise under pressure, which is critical for sales success.”

– Mike Scher, Co-Founder, FRONTLINE Selling

6) What do you want to know about our company, our product, our culture or this role?

“Question to ask: What do you want to know about our company, our product, our culture or this role? Reasoning: In my experience, people who are very interested in joining a company have done their homework. They typically have several detailed questions, and those questions reveal lot of things those people find important in their job. It also demonstrates their willingness to do their research and know their prospect — in this case, the hiring manager considering offering them a position.”

– Mikko Honkanen, co-founder, Vainu

7) If you started your own business tomorrow, what would it be?

“Many salespeople get into the profession because they are enthusiastic entrepreneurs by nature. By asking potential talents about a fictional business, you will learn more about their future goals and motivators. You will also get a taste of how they pitch business ideas.”

– Eva Wislow, Career Coach and HR executive at Careers Booster

8) If you could be a superhero, what would you want your superpowers to be?

“I really like this question because it usually catches the candidate off guard, but not in a way that will stress them out. This is a way to show the candidate that they can give a real human response without any fear of getting the answer wrong. It breaks the tension of an interview, and puts everyone at ease.”

– Scott Wesper, Hiring Manager, Arch Resources Group

9) Tell me about a deal you failed to close. What did you learn from that experience?

“A dedicated sales person will always take it hard when they don’t close an important sales, but a really good salesperson will reflect on that and learn from it and apply that wisdom to future sales.”

– Danielle Kunkle, Senior Executive, Boomer Benefits

10) What is a quarter of a half?

“It’s an intelligence question and it’s unacceptable for sales candidates to not know the answer since they are dealing with money. That being said, it’s incredibly surprising how many people get it wrong! Or, how many get it right, but aren’t quite sure they have it right. I want a salesperson who answers the question confidently and is almost offended that it was asked in the first place.”

– Bob Bentz, President, Advanced Telecom Services

11) Provide me an example of when you have prospected a lead creatively, and what are the steps you took to do so?

“When we are hiring sales, we want someone who is capable of thinking outside the box.”

– Ian McClarty, President, PhoenixNAP Global IT Services

12) What is the last self help book you read?

“To measure an potential sales persons dedication and desire for improvement, one of the questions I ask is what is the last self help book you read? Or podcast you listened to? Or seminar you attended? High performing sales people are always looking to get better, they study the best and look to pick up new techniques and tips.

– Mike Johnston, Business Manager, Schrole Group

13) What’s The Easiest Way To Get To Know A Potential Client On The Phone?

“This question gives me insight into a few aspects of a candidate’s typical attitude towards sales and what type of closer they are (if they dismiss the idea of getting to know someone versus a straight sale, for example) but it also lets me know how confident they are in their ability to progress in a phone call. If they think the journey in getting to know someone is an arduous path, I might question their ability to succeed in sales versus an individual who has a plan for client engagement.”

– Jake Tully, Head of Creative Department, TruckDrivingJobs

14) Who were you in High School?

“Really helps you understand both personality as well as organizational traits. E.g. Someone who was on debate team tells me that they are very prepared, take a lot of initiative and willing to do extra work. Debaters need to spend upwards of 30 hours a week prepping. If someone only talks of athletic achievements, they could be good salespeople but for other positions, I want to see if they rounded our their HS years with other activities.”

– Winston Lord, Cofounder and Chief Evangelist, Venga

15) Who else are you interviewing with? Have any offered a position? + If we did not select you what would you do next?

“As an interviewer you want to see if they are really looking into the industry or a job. On what are they basing the choice? You are looking to see if this is their real search. They should say they will go to your competitor because they want to be in the that business.”

– Mike Smith, Founder, SalesCoaching1

16) What does customer service look like to you and how do you demonstrate it?

This is more of a ideological question. Ideally, you want to see the sales candidate display the following skills throughout the interview:a) listening skills B)empathy towards the customer c)motivation/drive d)problem solving and these questions can help uncover whether the candidate will posses this in order to demonstrate they have the right sales skills.”

– Ken Kwan, Founder, Career Prophets

17) Tell me about a time you totally kicked ass

“The most successful salespeople are extremely competitive. They want to win and go to great lengths to do so. If their eyes light up and they launch right into their kicking ass story, you’ve found your candidate. If they take more than a few seconds to answer, keep looking for a kick ass sales person elsewhere.”

– Stephen Gibson, Founder,

18) Are you good at math?

Salespeople need to be able to crunch numbers quickly and think on their feet. When they answer “yes”, I ask a specific question like “what’s 18 + 14 – 6”. The purpose is twofold; to see if they can crunch simple numbers quickly and what happens when they’re put on the spot.

– Rhys Metler, Director, Sales Recruitment, SalesForce Search

Do you have any favorite sales interview questions we missed? Let us know in the comments below.

Featured image by WOCinTech Chat licensed under CC BY 2.0.    

James Meincke

James is the Head of Marketing @ Demodesk, the intelligent meeting platform for remote sales. Previously he was the Director of Marketing at CloserIQ.