How to Hire Great Salespeople:
Interview Questions to Ask

Interviewing is an important (if not the MOST important) step in the employee selection process, and asking the right questions is detrimental to determining if an applicant's experience and personality meet the requirements of a sales role. 

P.S.) We’re a BIG fan of skills-based questioning as it's scientifically proven to provide better insight. In fact, all of the questions below have been pulled from Pillar’s library of hundreds of questions (you can even add your own).

1.) Communication

*Give an example of how you carefully considered your audience prior to communicating with them. What factors influenced your communication?

*How do you prioritize tasks and projects? How do you communicate this prioritization with those involved?

*Tell me about a time when you were communicating with someone and they did not understand you. What did you do?

2.) Motivation

*Tell me about a time when you lost your motivation or felt disengaged from your work. What happened? 

*What incentives or benefits would motivate you in this job?

*What motivates you to wake up and go to work every morning?

3.) Productivity

*How do you limit distraction at work? 

*What are your productivity hacks that you use in your day-to-day life?

*Describe the work environment or culture in which you are most productive and happy.

4.) Goal Oriented

*What project would you consider your most significant career accomplishment to date?

*Give an example of an important goal that you set in the past. Tell me about your success in reaching that goal. 

*What have you done professionally that you’ve succeeded at but isn’t an experience you’d want to repeat?

5.) Persistence

*How do you deal with rejection?

*Tell me about something that didn’t go according to plan at work. What did you do and what was the outcome? 

*Do you keep a positive attitude during difficult situations? How?

6.) Coachability

*What is one area, personally or professionally, where you see the need for improvement in your life?

*When was the last occasion you asked for direct feedback from a superior? Why? What was the feedback and what did you do with that feedback?

*What management style gets the best results out of you?

7.) Resilience

*How long are you willing to fail at this job before you succeed?

*Could you tell me about a time you were given a task that you had limited knowledge about?

*Describe a project that you had to work on for an extended period of time and how you stayed engaged?

8.) Empathy

*Are you helpful by nature? How so?

*What kind of things or people inspire you?

*If you were in my position, what skills do you think would be most important to the role you’ve applied for?

9.) Confidence

*Tell me about a time when you had to convince another team member or leader to buy into a new idea or project. How did you accomplish this?

*If you could claim to be an “expert” in anything (personal or professional), what would it be and why?

*Can you describe a time when you had a different opinion than your boss, and how you approached the situation?

10.) Curiosity

*What new skills have you learned over the past year?

*Describe two or three major trends in your profession today. 

*What’s the most recent topic you’ve Googled for work?


If the roles you’re hiring for are more senior in nature, here’s a few sales-specific questions to get a feel for the candidate’s previous selling experience.

*What is your best memory of a sale you won?

*What are 3 things you do to build rapport with a prospect?

*What is your approach to researching prospects prior to a call?

*How do you define a successful first meeting with a prospect? 

*How do you acquire leads? 

*At what point do you stop pursuing a prospect? 

*Tell me about a time you lost a sale. 

*What is your least favorite part of the sales process?