Asking the Right Interview Questions

I went through a huge breakup when I was in my early 20s (HA! I can say that now, because I’m officially in my 30s as of a couple weeks ago) and so I decided I needed to leave Seattle and start somewhere fresh. Somehow, almost immediately, I was interviewing with a quickly growing, ultra-trendy importer for a Midwest regional manager position, and before I knew it I was meeting with the new national sales director, who told me as I sat down that the job was “mine to lose.”

In retrospect, I can hardly believe I got the job. I had never tried any of the wines I was looking to sell (mostly because the region didn’t produce wines that I was particularly interested in or fond of), I didn’t really do much research on the company except for a peremptory glance at the website, and in all honesty, I was totally under-qualified for the job. The truth was that I thought I might actually get back together with aforementioned ex-boyfriend, so I was kind of trying to self-sabotage.

…I’ll tell you now, I keep it on and on

On the day of the interview, we met at a hipster coffee bar in Seattle and right away I could tell that the interview was going to be weird. Among the cool, bespectacled coffee drinkers sat my future boss, who was crammed into a vintage wooden chair, red-faced and sweating profusely underneath his too-tight Brooks Brother’s collar. He wore pleated khakis and tasseled loafers and looked so unbelievably out of place I started to feel uncomfortable for him. We went through a few pleasantries, and eventually got into the interview questions. He started with some of the most basic questions, like, “What wines of ours have you tried?” And when I answered that I had tried none, he almost spit his coffee out on me. A couple more questions and awkward answers followed, and then, the classic: “Are you good at sales?”

Am I good at sales? Do I look like I’m good at sales? I’m GREAT at sales.

I responded in the affirmative (obviously). And then he asked me something I will never forget. He glanced around our table, which seemed dwarfed by his large, overstuffed appearance, and grabbed a couple sugar packets. “Sell me these.” I was taken aback, “What, now? I thought we were talking about selling wine?” He smirked and said, “Well, if you’re good at sales, you should be able to sell anything!” I quickly got my mental sh*t together and BS’ed my way through a really random, totally lackluster sales pitch on the pros of purchasing raw sugar. I have no clue why, but he thought my presentation was hilarious, and a few days later I was shocked to receive an offer from the company.

What’s it gonna take for me to get you into this packet of sugar?

Looking back on it now, I see a few mistakes that he made (and tons more that I made myself), that, if I were in his position, I probably wouldn’t have hired me.

The first and most glaring is that he came into the interview with a huge confirmation bias. He had obviously heard glowing things about me from my acquaintances (who naturally had told him those things because they wanted to help me out) and he let those positive statements inform his opinion of me without rationally and critically analyzing my interview responses. When I appeared not to know an answer, or didn’t give an answer that seemed sufficient for him, he helped me along by offering threads for me to pick up on so that I would give him what he wanted to hear.

Secondly I think he asked some very softball-type questions that really didn’t tell him much about who I was or what I wanted to do with the company: the “where do you see yourself in five years” type questions. Many people will have canned or made-up answers for these kinds of questions and you won’t get the full story.

So what questions should you ask?

When interviewing someone for a potential sales job, try to ask situational questions, and if possible, bring in another person who has not looked at the candidate’s resume to get a second opinion (studies have consistently shown that when people are provided information about a potential job candidate, they will find that whatever information they were given was “true” after the interview—hence a confirmation bias). Besides the basic questions to establish whether or not a candidate is worth interviewing in the first place, throw in a couple more interesting questions that can show a candidate’s ability to think critically. Finally, if it’s at all possible, get a writing sample; so much of the communication that we do in the wine business is via email and I think the ability to write well can be crucial to success in sales.

 Here are some examples of good interview questions. The answers are often surprising.

First, the basic questions:

  • Which wines of ours have you tried and what were your impressions? (You would be shocked to hear how many people show up for an interview and can’t answer this question. If someone can’t take the time to go out and try a couple of your wines before the interview, what is the point of hiring them? Seriously, this one blows me away.)
  • What kinds of wine do you like to drink? What are some of your favorite restaurants and wineries? (Hint: if they mention that they’re picky or are not really into fine dining, they probably would not be a good fit. Eating in restaurants is a huge part of what we do. I once heard Richard Betts say that he considers wine “a condiment,” a statement I loved—wine is best consumed with food. If the candidate says his favorite restaurant is the Outback Steakhouse, he probably isn’t someone who should be working at a small, independent winery.)
  •  Make a pitch: describe us, explaining why the wines must be on the wine list of cutting edge, farm to table restaurant, then adjust the pitch for a conservative chain steak house. (this is a good question to potentially get as a writing sample; but if you ask it in person, it shows whether a candidate has done his/her research, and also shows a basic ability to think on one’s feet.)

 And then the hard questions:

  • Have you ever been given a project with very little direction on how to complete it? What did you do? (I think this question pretty much sums up what being a wine sales rep is all about. Anyone worth their salt should be able to easily answer this question.)
  •  When you are given 10 things to do, and you only have time to do 3, how do you choose the 3? (pretty much the story of my life in the wine business.)
  •  Tell me about the last time you broke the rules.
  • Describe the most difficult person you ever worked with. How did you deal with them? How would you deal with a customer that is consistenly difficult and tough to manage?

And once you narrow the field, here are some questions I think are good to get in writing, to see if the candidate is a good culture fit:

Name five chefs and five wineries you admire and why?

Name one or two wine writers you admire and why?

Describe your most memorable wine experience and, if they are exclusive, your most memorable food experience.

How about if you’re the one BEING interviewed?

Finally, if you are interviewing for a position at a winery, do your research! Read as much as you can about the winery, and for god’s sake, try the wines! It’s worth going out and spending $50-$100 on a couple of bottles so you can speak proficiently about their wines at the interview. Finally, remember that you are interviewing (most likely) with people who have built their business from blood, sweat and tears, and their success was probably hard earned. You should try to show your excitement about the prospect of working with them (hopefully you are, but for some reason many people don’t show it). Show them that you know your stuff, and make it clear that you’re willing to roll up your sleeves and get some hard work done. Lastly, show up early. I shouldn’t have to explain that one.


2 thoughts on “Asking the Right Interview Questions

  1. My favorite interview question: “what book is on your night stand?” It is a good indicator of their taste level, if they are literate, and ability to think on their feet.

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