Become a better sales coach and sales manager today.

Even if you have years of experience interviewing salespeople, you’ll want to browse through this list of over 70 interview questions you can ask salespeople.

8-Steps to Creating a Coaching Culture by Keith Rosen
“I know how to interview. I’ve been doing it for years.” I hear this from practically every manager or HR executive I’ve ever had the privilege of coaching or training. And today, when speaking to one of my favorite clients, a VP of HR, this statement was echoed once again.

And it’s not like these managers or those responsible for making a hiring decision are doing it all wrong. Many are quite good at interviewing people, finding the right candidates and screening out the ones that just don’t fit. I’ve just observed over the years some key areas that many people are missing the mark on when conducting an interview and determining who the best candidate for the position truly is.

Especially when it comes to topgrading and rebuilding your sales team, getting the right candidate in the right position in the most expedient way possible is more critical than ever. The cost of not doing so can be severe. And this cost is compounded when companies onboard the wrong person. Just pick up any newspaper and read about another company closing their doors or missing their sales goals to exemplify how much of a priority this is today for any organization.

Below, I’ve listed some very key questions in order to reduce mis-hires and bring on the right people. If asked and asked correctly, these questions will reduce mis-hires by about 80% or more. Yes, that’s how powerful these questions can be. I would strongly suggest weaving these questions into your interviewing process. And keep in mind, most of these questions will apply to any position. Notice that I’ve also broken down these questions by category, as well as some additional categories that you can use to build out further interviewing questions.

Granted, you may already be using some of these questions during an interview. And keep in mind, this list can be built out even further. However, it’s the collective use of all the questions that are going to have the deeper, more positive impact when choosing the right hire.

Moving beyond simply the questions that you could ask, what other things are you doing to ensure you make the best hiring decision? Keep in mind, the interviewing process is multi-dimensional. To build off this, lets look at how you manage or facilitate a simulation or a role play. Many interviewers ask questions like, “How would you handle this if you were in this situation” or “Tell me what steps you would take before calling on a key account” or even “Walk me through a strategy you would use to build your pipeline.”

While these are all great questions, they are still falling short of one critical element. That is, the language this candidate would be using to facilitate the type of conversation described in these simulations. To go deeper in determining this person’s acumen or ability, it’s critical you’re able to evaluate how they communicate, as well as their overall communication strategy that would be embedded in each of these situations I’ve described in the prior questions.

The most successful salespeople realize that sales, just like leadership and coaching, is truly a language and a way of communicating. Therefore, it’s imperative you uncover not only how they think strategically and the processes they may use but how effective this person could be when you send them out to connect with your new and existing customers. Anyone can talk a good game regarding processes and approach from the hundred foot viewpoint. But how they deliver the message in a variety of different situations is something that can’t be faked during an interview.

When these questions and the simulation exercise are used correctly, you’ll find that the need to topgrade your sales team will diminish because you’ve fixed the breakdown in your overall hiring and retention strategy; the broken component that exists in your system and where it all starts, your interviewing process.

Work History

  1. What were your responsibilities in your last position?
  2. We all make mistakes. What would you say were a couple of the mistakes or failures you experienced in your last job?
  3. If you could go back in time and fix that, what would you do differently?
  4. What would you prior supervisor say if asked what your strengths and weaknesses were?
  5. What were some of the biggest challenges you faced and were able to overcome?
  6. What were your successes? What are you most proud of? How did you achieve that?
  7. What circumstances contributed to your leaving?
  8. What was your supervisors name and title? Where is that person now?
  9. Would your boss hire you back? Why?
  10. What were his or her strengths and weaker points from your perspective?
  11. Would you be willing to arrange for us to talk with him or her?

Next Position

  1. What criteria are most important to you in your next job?
  2. Describe your ideal position?
  3. How close does this opportunity fit your ideal position?

Excellence and Development

  1. How to you better your best?
  2. How do you raise the bar on yourself and others around you?
  3. How do you develop yourself and your skills?
  4. How important is it to you to be the best at what you do?
  5. How do you assure that happens?
  6. How do/did you keep your edge in such a competitive environment/marketplace?


  1. What does personal accountability mean to you?
  2. What areas in your life/career are you most accountable? Least?
  3. Give me an example of how becoming more accountable has contributed to your success?
  4. Where do you feel you need to become more accountable (in an area in your life or career)?

Decision Making and Problem Solving

  1. How do you solve problems?
  2. How do you go about making decisions?
  3. Give me one problem or challenge you had and walk me through how you solved it using that model.
  4. How do you go about making a career decision? What factors do you measure? Your approach?
  5. What were a couple of the most difficult or challenging decisions you’ve made recently?
  6. What are a couple of the best and worst decisions you’ve made over the last year or so?

Creativity and Solution Development

  1. How creative are you?
  2. How important is creativity in relation to your overall selling approach and strategy?
  3. Can you provide an example how you were creative in your last position that led to solving a problem or closing a sale?


  1. What are some of the values you have that you refuse to compromise?
  2. Describe a situation where you were pressured or challenged to compromise your integrity and what you felt was best and right? How did you handle it?

Self Discipline, Time Management and Organization

  1. How do you go about organizing your schedule and your day?
  2. Do you live by a set of best practices? How? What are they? (in selling, organization, etc.)
  3. When was the last time you missed a significant deadline? What happened?
  4. Everyone procrastinates at one point or another. Can you share the kind of things that you have a tendency to procrastinate?
  5. How much guidance and supervision do you feel you need?

Self Management/State/Stress

  1. What stresses you out?
  2. What do you when that happens?
  3. How do you eliminate it? How do you handle it?

Openness and Self Awareness

  1. What were the most difficult criticisms for you to hear and accept?


  1. What actions would you feel you would need to take during the first few weeks here in your new position if you were to join our organization?
  2. What obstacles did you face during your present/last position and how did you handle those?
  3. What would you be mindful of needing to do and the resources and training you would need to secure your success here?

Tactical Sales Oriented Questions to Recruit at a Deeper Level

  1. What was the average size of each sale? (Dollar amount, cost of goods/services sold.)
  2. What type of appointments were you scheduling when prospecting or cold calling? What was the goal here?
  3. Where the appointments on site/face to face with each prospect or via the phone?
  4. When actually closing a sale, did you actually sell over the phone or did you have to meet each prospect in person?
  5. Did you sell a product, a service or both? (Describe how you sold each product and why there was a different approach.)
  6. Did you handle the entire sales process from start to finish, including the deliverable? (Was there an account executive who you worked with, was it a team oriented approach to selling, were you only responsible for certain aspects of the sale?)
  7. Describe to me the products or services you’ve sold? (Complicated or simple?)
  8. Did you sell something that had an online component? Was it strictly a service? (Where they selling the tangible or the intangible?)
  9. Was your product/service a “nice to have,” a “want to have” (luxury, added benefit) or a need to have?” (Was it a necessity, i.e. gasoline, telecom, office supplies, utilities, mobile phones, insurance, etc.)
  10. What do you consider ‘prospecting’ and ‘cold calling’ to be? How do you feel about having to engage in this activity? (We’re looking to uncover how they think and feel about prospecting; their perception of it.)
  11. What type of prospecting and cold calling did you do? How much cold calling did you do each day/week? (Number of calls made.) How many calls did you have to make to (get an appointment, close a sale, uncover a new prospect, etc.)?
  12. Please share with me what your typical approach would be when cold calling. (Describe not only your process but exactly what you said when you were making a cold call.)
  13. Who was your target audience/prospect? (B2b, b2c, C level executives, business owners, sole practitioners, were you dealing with only one decision maker or did you have to coordinate with several decision makers, influencers, committees, board members, etc.)
  14. When were you calling on them? (Time, day, frequency of calls, etc.)
  15. What was the average size of the company you called on?
  16. What markets did you focus on? (Type of company, industry, vertical, etc.)
  17. How did you get your leads/uncover your prospects? Where the cold calls you made totally cold or were you getting them from another source and then following up with them? (These would be warmer leads from trade shows, web inquiries, referrals, call-ins, direct mail and marketing efforts, etc.)
  18. What were the concerns or objections that you typically encountered with your prospects? (What stalled your sales efforts?)
  19. How long was your average sales cycle? (From the time you connected with a qualified prospect up until the time when you converted that prospect into a client.)
  20. Were you selling based on a bidding process, RFP’s, etc.?

Simulations and Role Plays

  1. If you had to make a call to a prospect who you have never spoken to, what would be the steps you would take before making that call?
  2. What would that cold call sound like?
  3. If you were following up with a customer to explore and uncover additional selling opportunities, what would your approach sound like?
  4. Lets say you just delivered the final product/service to your new customer. They called you the next day with a major problem. They were frustrated and irate. Lets say I’m the customer in this situation. How would you facilitate that conversation? What would that dialogue sound like?
  5. There’s a prospect you’ve been calling on for months. They’re finally ready to make a decision to buy and you just found out that there are two more venders now involved in this bid for their business. What would be your strategy to position yourself as the vender of choice? (What would you say, questions asked, etc.)
  6. How many times do you call on a prospect before putting them on your do not call list? How do you determine that? What would your approach be? Why?
  7. You’re about to visit a new potential client for the first time. What preliminary work would you do? How would you craft your presentation and set the expectations of the meeting? (What would your presentation sound like?)
  8. You’ve been handed a client list of approximately 100 accounts to call on. You’ve noticed after several months, their monthly spending with you has slowly diminished. How would you handle this? What would you say?

Additional Topics That Require Further Questioning

  • Persuasion
  • Communication
  • Presentation
  • Assertiveness
  • Team player
  • Conflict management
  • Motivation and passion
  • Tenacity, commitment, perseverance
  • Education

Photo Credit: Axel Schwenke