It’s a predictable part of the job interview, usually happening at the end of the interview process.

The wholesaler doing the hiring of a new sales rep asks their rote and standard questions (“Where do you see yourself in five years?” etc.). Then they ask you, the one trying to be hired as a wine sales rep, the question of common courtesy: “So, do you have any questions for me?”

Why yes, I do! (Shocking, I know.)

Here are some questions you can use:

Tell me the about the best decision this company has ever made. Now tell me about the worst.

Tell me about your meeting structure. How often are sales meetings, is the time frame guaranteed (start on time, end on time), is it always “all in” or do you do smaller groups, who leads the meeting, and do you think they are useful?

How are supplier ride withs organized and handled? Do you think they add value or distract from growing sales territories? Are you beholden to your suppliers for market visits, or can you say no when you want?

Without naming names, is there a truly weak link in the company staff? And how are you working toward changing that?

Who actually owns the company?

How many sales reps are on staff, and how many have been here more than 36 months? How about more than ten years?

Tell me about the last three people to leave their job here, and why did they?

Do you treat company paid wine travel as part of the job, and how much travel do your sales reps normally do? How do you handle vacation time if the vacation is to a wine destination on my own dime?

Is there a budget for wine education for your sales reps?

Are your sales reps guaranteed control over their customer base for all customers that increase in sales? In other words, can we make a written guarantee that if I grow a customer by 20% in one year I won’t have that customer removed from my territory?

What are the top three brands in your book by volume and what would happen if you lost all of those at once? Would my new job be the first to be cut, or are there resources to keep me around to help with the rebuilding?

What are the three things you seek in an ideal employee other than honesty since that should be a given. (This is a great zinger of a question, and listen to the answers carefully. Are their answers about control and consistency, or about growth and vision?)

What do you wish all of your current sales reps did better?

Here’s the kicker: you don’t need to wait for your next job interview to ask these questions. You should be able to ask them now. And if you feel like you can’t ask questions such as these now then you should think about why you feel you can’t, and then think about if there is a better company out there to work for.