8 Tough Questions To Ask In A Sales Interview

Going through the interview process can be uncomfortable. From the front line recruiters to hiring managers and beyond, job interviews are stressful. But just as much as job interviews are about the company interviewing and assessing your ability to provide value to the company, you should be evaluating the company and whether or not you'd enjoy working there.


One of the biggest challenges in the evaluation of your potential new employer is culture. How the heck are you supposed to get a feel for the culture in a few conversations? It's tough. I've failed at it several times. Here a few difficult questions you should ask in your next interview.


What is the CXO's leadership style?

You won't be reporting directly to the CEO, CRO, or CSO so why does this matter? Company culture starts from the top down. The leadership style in the C-suite will trickle down throughout the organization. Understanding what the CEO and the leader of your department value will give you the blueprint for being successful there.


What is the worst part about working here?


If you can ask someone in the same role as the position you are interviewing for, that's ideal but if not, even your potential manager will have insight into what the most challenging part of the job is. This is also a good way to gauge the honesty and authenticity of your new potential teammates. You may find that the worst part of the job is a total deal-breaker for you.


What is the culture really like on the sales team?


This is important to understand before walking into a new environment. Is this a cutthroat sales organization where reps are pit against each other or is it a collaborative environment where reps truly want to see their colleagues succeed. You could thrive in either but you should always get a baseline on what you're walking into.


What are the shortcomings of the product?


Let's be honest, no product is flawless. However, some flaws are more severe than others. If the shortcomings of the product are small bugs and short term issues, then you are in pretty good shape as long as your tech team is competent. Really you are trying to identify room for product growth and the product-market-fit.


Who are your competitors?


If you really want to understand where the company fits in the market place, you'll want to know who else is in the space. Do some research on the other companies and see where they fit in terms of reputation in the market. Even if the company produces disruptive new technology, there is always competition in the market.


What is the organization's perspective on the sales team?


Internally, what is the reputation of the sales team? Are you walking into a buzzsaw where all other departments think salespeople are mindless monkeys who smile and dial or is there respect for the work the sales team does? This is another question that can help get to the bottom of the culture of the organization.


What percentage of reps hit quota last quarter?


This question is important for 2 reasons. First, you want to know whether or not people in this role are set up for success. If reps are hitting their quota, great. If not, why? Secondly, and maybe more importantly, you want to know if the OTE (on-target earnings) that the recruiter pitched is realistic or not.


What happened to the person who used to be in this role?


If you are being interviewed for a brand new role, you won't be able to glean much from this question. Otherwise, you may find that the territory you are walking into is really great or really lousy. You could also find that the sales team is widely successful but for some reason, this particular role continues to turnover. Maybe the product is better suited for SMB than enterprise, or one industry rather than another.


It's important to ask a few people the same questions to see if the answers sync. If they do, then you can be fairly confident in the accuracy of that assessment. At that point, it then becomes a question of whether or not that culture is right for you. If they are different, then you need to do more digging to find out what the reality is and why you were getting mixed messages.


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