The Best Interview Questions to Ask

It’s certainly an area that many senior sales executives and managers are focused on: finding the “right” rep. And, in many cases, it’s finding Challenger reps to fill an opening. While we’ve provided guidance on questions to ask candidates specific to Challenger behaviors, this Mashable article got me thinking: regardless of the role you’re trying to fill: what are your favorite interview questions to ask?

I like a few from the Mashable article to get us started:

What is your passion? I think we can all agree, if we don’t know what makes our people passionate (in life and in work), then it’s going to be tough to match the job to the right person.  The most successful people out there are passionate about what they do.


Who do you most admire and why? I really enjoy this one. First, it’s just really insightful to hear who people select and their answers for why. A variation that I’ve heard that I also like is “If you could have dinner with one person, deceased or living, who would it be and why?” It gives you a good sense of their perspective and you never know where this will take the conversation.  I think it provides a great deal of personal insight (and makes the candidate think hard).

Here’s a few I’ve heard or comes across and like:

What do you think is the most useful business knowledge to making great decisions, and when was a time that you used that knowledge? This has to be #1 on my personal list, mainly because of what it’s probing for – business acumen. We all know business acumen is a critical skill, but too long in sales, it’s been relatively ignored (or at least de-prioritized). This question gets to not only what the person knows, but what he or she uses to make decisions.


Describe a time you faced difficulty in completing an assignment/project/deal?  How did you go about overcoming it?  Certainly a behavioral question here; I enjoy this because it’s very action-oriented. You’re going to get a story. You get to see how resourceful this person is, how they process a challenge and come to a successful outcome. We know any role (especially sales) can be complex and relies heavily on others, so this type of question can get to the heart of uncovering their ability to deal with that complexity.

That’s just a few that I wanted to share.  Of course, if you’re hiring for Challengers, be sure that you utilize our hiring tools available (SLC members can access them here).

What questions would you add to this list that you find powerful?  We’d love to hear them!