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Confessions of a CRO: My Top 10 Favorite Sales Interview Questions

· interview,sales

With employment levels as high as they've been in the past forty years, recruiting is at an all-time high in terms of matching candidates with desired experience levels.

So, what do you do? You either keep searching, which has a massive opportunity cost. Or, you hire under your desired experience levels, invest in enablement, and cross your fingers.

When you have an experienced rep for the role, your focus is: what extrinsic things can we provide to keep this person motivated? Will they fit in and succeed here?

When you have an inexperienced rep for the role that you have to develop, your focus becomes: what intrinsic motivators can we tap to drive this person to maximize their learning, growth and success?

Below are the top interview questions I liked to ask, with "what I'm looking for" listed under each. Hopefully you can use this (a) as prep if you're interviewing for a role, or (b) as questions to ask if you're an interviewer to help illuminate what's inside the candidates you are interviewing.

Over the thousands of interviews I've done, I've found this collection allows me to get at the real drivers of engagement, passion, fit for the role, fit with the team, potential longevity and ultimately mutual success.

So here are my top no particular order (and, of course, they are not all asked in each some require that a rep has had more experience than others):

Question 1: Tell me your story

What I'm listening for: I know, I's not a question. But what I'm looking for is storytelling ability. How do you frame your career? Does this individual know how to communicate a clear, concise, compelling story? Are the overly verbose? How do they communicate? This one is a first impression maker.

Question 2: Walk me through the last X years of your resume. Why did you take the jobs you did? Why did you leave?

What I'm listening for: This one is a big one for me. "Job hopping" isn't necessarily a bad thing, but one issue I'm looking for is the possibility of poor "discovery" skills - an important quality of a successful sales professional. With this question, I'm trying to hear for (a) how you assessed whether an opportunity was worth committing to, (b) what you missed during that assessment, and (c) what you learned from each. Do you get happy ears? Do you blame others for your inability to have predicted your potential experience? Did you do your homework before committing? And when it didn't work out, how did that influence your assessment of the next role?

Question 3: If you were put in front of a room of 500 random people to give a talk, what subject would you know more about than anyone else in the room?

What I'm listening for: It doesn't matter what the subject of the answer is for this one...I'm simply assessing what a person is passionate about. The answer could be anything - one interviewee told me their answer was NASCAR, another told me it was their kids, another was an expert in the fine art of gathering travel points. Is this person capable of finding passion in something?

Question 4: What’s your most significant career achievement?

What I'm listening for: What are you proud of? Do you set goals? Was the achievement random, or something you focused on attaining? What kinds of things lift your spirits?

Question 5: From what you know about (our company) & this role, what excites you most about it?

What I'm listening for: Did you do your homework? How do you feel that the role, company focus, or anything else you found while doing your homework aligns to your passion? What about the role gets you excited that's specific to this role? Is your answer generic, or thought out?

Question 6: (Follow on to the last question) What’s going to stretch you? Meaning, what do you think will be the greatest challenge you will face here?

What I'm listening for: For starters (and I'm guessing you won't be surprised to hear this), but I'm looking for authenticity and transparency. I'm also looking to understand whether this person is looking to stretch themselves, or just looking for a wheelhouse position that aligns perfectly to their skills.

Question 7: In your career, who has been your favorite manager? Why?

What I'm listening for: This question provides an understanding of how someone derives engagement from their work. 70% of engagement is derived directly from an employee's relationship with their manager, so ensuring a culture match is a key element to diagnose prior to hire.

Question 8: Tell me about a deal you were responsible for that you’re particularly proud of? How did you develop it?

What I'm listening for: This is quite possibly the second most important question that I ask. Depending on the role I'm interviewing for, what about a deal do they take pride in? Is it the hunt? The farm? The build? The close? The entire process? Something lucky? Look for when they light up during the story. Are those types of opportunities even possible here?

Question 9: What is the value proposition of your current (or last) company? How would you describe what they do?

What I'm listening for: Do I understand it? Do I think I could take the candidate's answer and relay it to my wife so she could understand it? In a consensus sale, value propositions must be clear, memorable and easily passed along. Does this person truly understand what they've been selling, and are they able to articulate it in a way that makes sense to the layman?

Question 10: What kinds of things do you do to improve your selling skills?

What I'm listening for: I've literally had salespeople tell me answers like, (a) "I learn by doing" and (b) I took a Miller-Heiman course back with my first job, and that has served me well. You don't need me to tell you this...the world of sales is evolving at an accerating pace. The most successful people (in general) take pride in their profession, and are constantly looking for ways to extend their lead. They read, they listen to podcasts, they take classes, they participate in sales associations - they take pride in their career. Given my passion for learning, non-answers to this question typically result in a candidate pass.

Question 10b: What is the sales methodology/philosophy/approach that you most identify with and why?

What I'm listening for: This question often gives me a sense for the truth to question 10 above. Does this individual have a framework for their approach? Do they think about their profession like a pilot, ensuring they're always guiding the buyer along their journey without missing key steps? Or, are they just a dog chasing a car bumper down the road, not knowing where the car is going?

SIDE NOTE: Now, you may call me old-school, but you know what drives me crazy? Someone who shows up for an interview with nothing to take notes with. I know that an interview is like a date - it's a mutual assessment of fit. However, part of my assessment of your fit is your ability to listen and retain. Because, in front of a potential client, those are two important qualities. And, knowing how the human brain operates, if I'm sharing all sorts of goodness about the organization, team and role, I'm hoping that, like a sales call, you'll be able to show me that you've got it!

Hope that helps you with your interviews - on either side of the table.

Have any to add? Feel free to throw them in the comments.

As always, please feel free to reach out if you are looking for a speaker or workshop for your organization in 2020, or just want to nerd out on some of this stuff.

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