Talking About and Selling Wine You Don’t Like

When I was in college, I worked part-time in a few tasting rooms in Walla Walla. One of the things that used to bother me was when customers would come in, taste the wines, and then, completely sh*t-talk the wines in front of me.  Normally when that happened, I would stand behind the bar with an idiotic grin on my face, while inside I secretly fumed and judged the men on their fanny packs, bad loafers with white socks and comb-overs, and the women on their cheap dye jobs, bejeweled t-shirts with phrases like “How Merlot Can You Go,” and pleated-front, high-waisted mom jeans (which, I’ll admit, were totally immature and sh*tty things to think about).

Wow, this wine is really...dry!

Wow, this wine is really…dry!

I saw that attitude again when I became a supplier rep and participated in retail shop tastings. I’d pour a dry red wine for someone, and she’d scrunch up her face, stick her tongue out and emphatically say, “I don’t like that one at ALL. NO. This one is…I really don’t like that wine!”  Eventually, I learned not to take it so personally, and also to explain to people that they should try to give the wine the benefit of the doubt—tasting it in a retail setting without any food or friends around to share it with probably made a huge difference in their perception; I encouraged them to acknowledge their own tastes, but be open-minded to the idea that it’s hard to taste in a “vaccum.” I always referenced the Pepsi Challenge, wherein most tasters preferred the taste of Pepsi because it tasted sweeter and the flavors were more “obvious” right away, but many people actually chose a less sweet beverage (Coke) over the course of an entire glass or can.

While I (mostly) got over my frustrations with consumers being rude about not liking wine during tastings, what I can’t get over is how rude some people INSIDE the industry are about their competitor’s wine. I hear people constantly bashing other people’s wines, quickly jumping on their perceived flaws. I think a lot of people on the sales side of the wine business treat selling their wine as a zero-sum game and refuse to recognize value in competitor’s products.  I recently got invited to a private tasting and was unable to go, so I gave up my spots to a couple other industry people. I then saw on Facebook that the person who’d taken my spot had a status update that totally trashed the wines, AND tagged the location where the tasting had been held.  WTF?shocked

Trust me—there are wines I’ve tried where I felt personally violated (in fact, just a few months ago at a trade tasting I tried a cult wine that basically raped my tongue with sugar, alcohol and oak). But it did get me thinking about how I would sell the wines that my friend found so “awful” in the Facebook status update. After all, I have had a few occasions where, because of the vintage, the style or whatever reason, a particular wine in my portfolio was not my favorite. Yet I still had to sell them anyway.

So what I want to talk about today is how to talk about and sell wines you don’t like. And a little etiquette…

1. One of the first things I try to remember is that, particularly if the winery is independent, a whole lot of work went into making that wine. At my last job, I became good friends with the cellar and vineyard crews, and I learned that each bottle of wine I opened meant countless hours of work and sweat and maybe some tears. To diminish that seems, to me, disrespectful and callous.

2. Just because YOU don’t like it doesn’t mean it’s not any good.  I went tasting with a dear friend of mine a few weeks ago, and we visited a well-known winery. We began tasting through their lineup, and as we tasted their merlot, she quickly said, privately to me, of course, that she didn’t care for it. I pointed out that for the price, the wine was well balanced, had moderate tannins (that many consumers shopping in that price-point would look for), pretty fruit, the wine was clean and correct, and that the label was beautiful. She nodded in assent and said, “Yup. Hadn’t thought of it that way.”  Here are some general things to consider when selling a wine you don’t like:

  • Is it a good value for the price?
  • Does it taste like it comes from somewhere? Bonus if it tastes like where it’s from.
  • Is the wine correctly made, or does it have some flaws like EA/VA or Brettanomyces (which some people love)?
  • What are the flavors like? Fruity? Tannic? Oaky? Think about what the account’s customers might like—will it fit in with their general taste profiles?
  • Is the label nice? Because hey, it can’t hurt to have a pretty label on the back bar…
  • Is the winery or the people who own it well known (which can help pull-through), or do they have any good stories relating to the wine?

3. Don’t talk sh*t about other people’s wines because you may one day be selling them. That kind of goes without saying—even if you are competing for a placement on a wine list or shelf, I find it’s often better to stress the positive attributes of your own wine (even if you don’t like it) than to stress the negatives of someone else’s. Plus, the winery personnel are probably really nice people–would you say those things to their face?

Dude! This wine is so oaky they might as well call it Chateau 2x4! And hellooooo powdered tannin. Malo anyone? Get out the movies, it's time to watch one with all this buttered popcorn!

Dude! This wine is so oaky they might as well call it Chateau 2×4! And hellooooo Malo anyone? Get out the DVDs: it’s time to watch one with all this buttered popcorn! [Cackles] We are so hilar! Wait, they just switched to our distributor? Oh, well, crap!

4. We’re all in this together (mostly). What I love about living in Oregon is that, by and large, people in the wine business are extremely supportive of one another. However, there are a couple big wineries in the Pacific Northwest that some folks love to bag-on because they’re placed everywhere, they have a massive sales force, a fairly corporate structure and produce thousands (if not millions) of cases of wine a year. While personally they’re not always my first choice to drink (even though I can appreciate that they are generally well made), I can see that those big wineries have made inroads for the little guys—training winemakers and sales people, buying fruit from many vineyards, nationally campaigning for the region—and for those things, I am thankful.

Yep--I am a bit of a Pollyanna about wine.

Ye, I am a bit of a Pollyanna about wine. She tried to see the good in every situation (she called it “the Glad Game”), which is what I try to do with the wines I taste and sell.

And just a quick shout-out to my favorite wine writer, Jon Bonne of the SF Chronicle—I think he’s a great example of someone who can taste wines from a huge range of regions and styles and come up with positive, interesting and extremely well-written things to say about wines of all stripes. Check out his writing if you need some inspiration!


Breaking Up is Hard to Do

I can remember the first time I ever had to “fire” a distributor—I was given the directive by my boss, and for a week, I sat and stewed about how I would do it. I finally wrote myself a little script, and with some resolve got my nerve to pick up the phone to call—my stomach was in my throat, my heart was beating rapidly and my mouth was dry. As the phone rang, I silently recited what I would say. The person on the end of the line answered so good-naturedly—I felt awful for what I was about to do. We exchanged some pleasantries and I awkwardly blurted out, “The reason I called is because I have some bad news. Unfortunately, we have decided we’d like to take the winery in another direction and we have decided to move to another distributor.” Of course, this is when the conversation veered off script. The person on the other end of the line started throwing out numbers and percentages about how our business had grown, and how this was a complete and total shock. As they talked, I realized that they were probably right—that they HAD done what they thought was, at the very least, a decent job, and that the winery had never approached them about the fact that we were unhappy with their performance and given a chance to try to change it.

I mostly just included this picture because it came up when I did a google image search for “awkward phone conversation.”

Even though I’m not working right now, I see my friends at wineries around the country wrapping up their fall travels, and begin looking towards the New Year, while taking stock of the progress and challenges of the previous one. This is a time where people start forecasting for their year-end meetings, and in some cases, start making plans to change distributors. The worst conversation you can possibly have in the wine business is the one where you tell a distributor you are planning to leave, and they have no idea that you were unhappy. I had a friend tell me once that when she left a distributor, it felt like a breakup—they weren’t even on speaking terms anymore.

So before you decide to make a move, please learn from my mistakes and consider the following:

Have you told them exactly what you expect?

  • No one can read minds—and even if it might be obvious to you, remember that distributors have hundreds or thousands of wines they represent so being pointedly honest and well prepared about what exactly it is that you expect is extremely important.

Have you asked them if they think your expectations are reasonable?

  • The sales you want to achieve might seem like a no-brainer to you, but distributors know their business and their market better than you do. They are your partners and so it’s important to remember that you need to listen to their side of the story and take into account their honest assessment of what can reasonably be done.

Have you visited the market regularly or supported them in any way?

  • If you haven’t been to their market, how can you even conceive of how much business they can do for you? San Francisco and Indianapolis have roughly the same population, but the markets are drastically different. Evaluating what one market might against one of a comparable size is like apples to oranges.

Do you have relationships with their Reps?

  • They can often offer valuable feedback about how your wines are received, or if they take them out regularly, if at all.

Have you gone over pricing? Have you offered any programs? Samples?

  • No one can sell your wine if no one knows what it tastes like.

Have you been consistent in your follow up?

  • People have a lot on their plates these days. Gentle reminders (maybe once every month, not daily as I have heard from some brand managers) can be effective—spreadsheets with information on depletions and shipments against expectations have proved helpful for me.

If ultimately you decide you need to make a change, I offer the following suggestions for a smooth transition:

  1. Make sure you are not breaking any franchise laws.
  2. Make sure that before you tell them you are moving, you have paid them for all bill-backs and that they do not have any outstanding invoices.
  3. You have a plan and the money to pay them for their existing inventory—will your new distributor buy it? Will you buy it back?
  4. Make sure IT IS NOT A SURPRISE. One of the people I admire greatly is a guy who has left any number of distributors over the years, but he has been able to do it with class, grace and a sense of dignity—each of the companies he has left has not been surprised—they’ve been a part of the conversation, have been given ample chance to correct or improve business, and ultimately both parties came to the table mutually agreeing that while it was sad, the winery was not a fit for them any more. In all cases, they have remained friendly years down the road. I think that’s something we should all aspire to. 

Saying Goodbye

A few months ago I rushed home from the airport after a long trip so that I could make it into Portland to have beers with a colleague of mine. He was in town on a supplier incentive trip—he and a few other people from his distributorship had been invited to Oregon by one of their wineries and he asked if I wanted to get together with him on his “free day.”

I met him at Hair of the Dog Brewery; it was one of those funny Portland days where the sun is shining, the sky is that classic Oregon bluish-white and it’s dappled with blotchy gray clouds. The temperature is hovering between 55-60 degrees and the wind is softly blowing every few moments, just enough to feel a little chill, but also to remind you that Summer is coming. It’s the kind of weather that I like to call “Goldilocks weather”—if you stand still or sit, you need a sweater, but if you move around, you start to sweat. You’re constantly putting your sunglasses on and then taking them off because the clouds keep moving and the sun flickers in and out. No matter what you do, it’s hard to feel “just right.”

So I came and sat down at one of the picnic benches outside with him and as the clouds passed over the sun, I removed my shades. He looked into my eyes, now uncovered, and told me, “You look tired, kid. How long are you going to keep doing this to yourself?” He surveyed me with genuine concern and I told him, “It’s true. I AM tired. But I also have too much to do to think about that right now. And besides, I love my job and my company.”

We talked for a while and he kept pressing me about what I was going to do with my life and what I wanted for myself in the future. I was adamant that everything was copacetic, and that at the moment I had no complaints. But something was nagging me and I knew that maybe I wasn’t being totally honest with myself.

Then, this fall, over the span of just 60 days, I traveled to Seattle, San Francisco, New Orleans, Dallas, Austin, Houston, Naples, Miami, Boston, Burlington, Portland (Maine), New Haven, New York, Chapel Hill, Raleigh-Durham, Charleston, Detroit, Phoenix, DC and Alexandria, and then I was really tired.

As my travels wrapped up, I sat down with my boss and we had a long discussion about me and my job; the ultimate conclusion was that it’s time for me to take a break. I have learned a tremendous amount in the last few years I’ve worked for him; I know so much more about the business of wine—how it’s made, how it’s sold, how to make a company run well, and how to keep your employees happy. I have worked with the most compassionate, intelligent and interesting people I could ask for, and I have had the luxury working under someone who is truly the most classy guy in the business (not to mention one of the best and most knowledgeable winemakers in the Northwest—where else can you learn about geology and classical philosophy in the same place?).  I am immensely grateful for the experience I’ve had here, and I will miss working with these folks very much. I can’t thank him enough for giving me the opportunity to work at such a fantastic place and I know we’ll be friends for many years to come. It’s only with gratitude and care that I take my leave.

So what do I do now? Well, for starters, I am going to take a little time for myself and re-charge. And then, who knows? I love to travel and I have a ton of great friends and colleagues around the country, but I don’t want to be on a plane every week. I definitely want to stay in the wine business, but beyond that, I’m wide open.

I still have a lot of thoughts and opinions about being a representative for an independent, family-owned winery, so I’ll continue to keep this blog updated. But in case I don’t see you for a little while (since I’ll be sleeping in my own bed instead of a hotel on the road), stay in touch and call me when you’re in Portland!

Staying Healthy on the Road

One time, I was on a sales call and was pouring wine for a chef who also buys wine for his restaurant. I started to pour the first wine and looked down at his hands. His fingernails were absolutely filthy. I mean, brown under each nail and his hands looked even worse. This was during the middle of the day and he had just come in; no cooking of any type had been done yet, so it’s not like his hands were covered in squid ink or something. There was no excuse for it.  And then? He offered to put together a few bites for me and the rep while we tasted. I shrugged and said I wasn’t hungry, but the rep was clearly oblivious and was all about the free noshes. The chef came back with a couple of lovely meat and cheese boards, some bread and some other small bites, but guess what? His fingernails? Even WORSE. I was dying inside. I choked down some prosciutto and tried not to think about what gross things came off his hands and onto my meat.

And then, shortly after my run in with the chef, I happened to be at an event where a well-known winemaker was pouring. He is someone I’d consider fairly well dressed, and yet, again, his fingernails? He might as well have rubbed coal under each nail. Long fingernails too.  And no, he did not have the excuse of working harvest.

These run-ins with folks in the business made me extra-cautious going into the traveling season and so I armed myself with a few things that I wanted to share with you to stay healthy. (If you’ve met me, you probably noticed I already have a fairly healthy dislike of germs. I am that weirdo that opens bathroom stalls with paper towels, uses my sleeve to push revolving doors, and I wash my hands about 100 times a day side note: did you know that men’s bathrooms, although smellier and more disgusting looking are actually cleaner? I am totally that person who will gladly go into the gent’s if the ladies is full. Oh and never put your purse on the floor. Ever. It is a foul and disgusting soup of microbial activity and poop.)

My borderline Hughes-ish behavior.

So without further ado, here are my tips for staying healthy during busy travel season:

1: Sleep.

When I was first starting out in the wine business (ok, actually until about 3 years ago) I was a complete dumbass and lived by the adage, “I can sleep when I’m dead.” I stayed up late, either hanging out with people or working, and ended up feeling exhausted the next day. Plus, it literally ages you. No bueno.

2: Work out.

I hate hotel gyms—the equipment is always broken, they’re dirty (that germ thing again), and I feel like a f*cking caged hamster on a ghetto, mirrored wheel. So instead I book my hotels near yoga studios and I try to go to at least 3 classes a week. For me, it’s a cool way to see a different side to the community I am visiting, and a way to add depth and knowledge to my practice.  Plus it really helps me after sitting on planes and in other people’s cars for hours. And, it’s the only thing I have ever found where for 60-90 minutes, I’m unable to think about anything else except what I am doing in the moment. Pretty much every scientific study shows that exercising relieves stress and helps keep you from getting sick. So get off your ass and go burn some of that Raveneau and foie off your lovehandles.

Yeah, basically this is me at a hotel gym.

3: Don’t drink so much the night before that you can’t get your lazy ass out of bed to work out.

This one sums itself up. JE, this one is for you. You know what I’m talking about.

4: Lysine/amino acids

They are the building blocks of life. And since recent studies have shown that taking fish oil (something I’d done for years) basically does jack-sh*t, and taking a daily multi-vitamin not only does nothing statistically appreciable for you, but they might actually give you cancer, I thought I’d add another potentially worthless pill to my morning cocktail (because it seems to work).

5: Elderberry extract

Ok, now I sound like I am getting all Portlandia on you, but this sh*t works. I heard about it from my hippy-wine friend, Eric, and whenver I feel a tickle in my throat or a little run down, I start taking this for a few days and feel tons better. Sometimes hippies DO know best!

6: Use a neti-pot

Another Portlandia suggestion, but again, scientifically proven to do a lot of good for your sinuses. And Dr. Oz recommends it, so it must be legit, right? Check out this creepy looking video of how to do it. I swear to you, I do this every night before I go to bed (so sexy!) and I have not had a sinus infection in years (I used to get them constantly).

7: Wash your hands, creep!

80% of all illness gets transmitted through our hands. And ditch the anti-bacterial everything. That crap is horrible for you and the environment. Just use good old soap and water!


Don’t eat sugar. It’s killing you. Don’t believe me? Check this out.

Don’t watch tv or flip the main light switch in your hotel room. Those remotes: nasty germ havens covered in fecal bacteria and sperm. Vom!

Sitting is literally taking years off your life. Get off your butt and stand. Or lie down.

What do you do to stay healthy during OND?

Dining Alone

I dine alone at least once a week. I have friends in most of the markets I visit, but invariably there’s at least one night during the week when either by choice or circumstance, I am at a restaurant, eating by myself. I’m fairly social, and I honestly don’t mind heading to a restaurant as my own plus one—I love sitting at the bar, ordering a couple of dishes and a glass of wine (or two), chatting with the other patrons and the bartender. I have had some of the best dishes of my life eating in my own company (the white asparagus at Daniel and the mini-birthday cake at Restaurant Eve are two of the singular dishes that stand out for me in recent memory…).

Hello tiny, personal non-birthday cake. You are delish.

On Saturday night, I had one of the weirdest experiences in my (nearly) ten years of solo-dining. Earlier in the day, I went to a fantastic yoga class and found that my teacher worked at a super-cool, mostly locals spot in the Garden District of New Orleans. I promised to visit her there later in the evening, which was a bright spot to look forward to in what would otherwise have been a lonely evening.

I only wish I was this stylish and chic while dining alone.

After spending a couple hours by the pool working on emails and spreadsheets, I headed back to my room, and by 6pm I was tired, bored and feeling totally unmotivated. A night in my hotel room with a movie on my iPad and a po-boy from down the street seemed to be singing me a siren-song, but I refused to let myself give into it. I forced myself to get ready and headed out to see my friend Molly, whom I’ve known since we both lived in Chicago, at an awesome new spot in the Quarter where she is the Somm.

I ended up having a great experience at Molly’s spot, R’Evolution—the bartender was hilarious and the service, food and wine list are unparalleled in New Orleans (seriously, if you are into food and wine and need a spot in the Big Easy, this is your joint). After a couple inventive and delicious cocktails I headed over to the Garden District restaurant Lillette and had 1) the most ridonk white crab legs with passionfruit butter (serious, serious foodgasm), and 2) the best fall cocktail of all time—I mean, honestly, this thing was like walking into your grandma’s kitchen full of apple pies and brown liquor (sorry—did I say your grandma? I meant mine—she loved her cocktails and she loved her baked goods).

This is my “hmpfh, I’m alone, with no one to talk to” face.

I finished up and had to check out Bouligny Tavern next door, which was as rad as everyone said it is. While enjoying my drink, a guy came and sat next to me, put an envelope in front of me at the bar and nervously asked, “you’re Jennifer, right?”

I smiled and shrugged, told him no, and took a sip of my drink. He slid the envelope a little closer and said, “It’s all there. Really!”

Thanks, but no thanks, MOFO!

At this point, I was feeling slightly confused and a little miffed that this random dude was interrupting my enjoyment of a delicious, handcrafted, artisanal cocktail.  “Sorry, wrong person…” I said, not with a little annoyance. He looked at me in desperation and proffered the envelope again. “If you want me to pay you more, I can! You are way classier and better looking in person than you were online anyway!!”

This exchange went on for a few more moments, while I insisted that I was not the Jennifer he was looking for, and he argued that he could pay me more. Finally, after slapping/pushing him away and getting some stern looks and words from other patrons and the bartender, he got the hint and took off.

Bitch, please. Let me enjoy my handcrafted artisanal cocktails in peace!

Luckily the bartender took pity on me (and of course recognized that I am not a woman of the night, but am in fact a classy, professional who happens to LOVE really good cocktails), and bought me a couple drinks. I randomly ended up talking to a bunch of MIT scientists in town for a Neurology conference, and later hit up both the phenomenal Spotted Cat for some jazz, and then Mimi’s in the Marigny for their 70s disco night (which was insane, and I HIGHLY recommend if you ever make it to town on a Saturday night).

So really, dining alone can result in both a great food and wine experience, and you just never know who you’ll meet. Have you had any weird solo-dining experiences, or have you met anyone “special” while eating out by yourself?

Getting People to Listen

I spent last night, a Friday, by myself in North Dallas. I ate dinner alone at 5pm so I could make it to a movie (Pitch Perfect, which was hilarious and awesome, so at least I had that). Afterwards, I went to bed at 9pm. The amount of travel I have been doing lately has really worn me out, and I’m just now past my half-way point. By the time Thanksgiving rolls around, I will have been in the car with at least 30 people and will have interacted with hundreds of customers and sales reps. I know it’s not an excuse (to the 5 people who actually read this), but I’ve been busy and tired and haven’t kept up with my blog (I also try not to write about people I currently work with, so even though I have had some whoppers in the last couple months, I have refrained from telling them out of respect to my colleagues).


Pretty much sums up my Friday night. All I need now is a bunch of cats.

SIDE NOTE: I actually hate when people constantly talk about how busy they are—you ask someone, “How’s it going?” and the canned response seems always to be, “SO BUSY!” To quote a recent article in the NYT, “Busyness serves as a kind of existential reassurance, a hedge against emptiness; obviously your life cannot possibly be silly or trivial or meaningless if you are so busy, completely booked, in demand every hour of the day.” (and for the record, when someone asks me how I am, my canned answer is “Living the dream…” which I probably should change up as well since the response is sounding a little tired).

In any case, traveling to tons of markets, interacting with so many people but telling the same stories about the same wines can get stale—not just for me, but for my colleagues. One of my biggest challenges has been to make the wines and the stories that go along with them interesting and fresh.

About a year ago, I was on a ride-with, at an account showing wines for the small, family winery I represent. During the pitch, I talked about a few of the wines as they were poured, including, at least to my mind, a wine of ours that has one of the greatest wine label stories in the business. We got to the next wine and the buyer suddenly had to get up to go help a customer. As he left, the rep turned to me and said, “So what’s the story with the crazy label?” I laughed at the joke—the one thing I hear about this label is that once you hear the story, you can’t forget it. The rep stared back at me blankly and confusedly said, “No, really! I want to know! What’s the story?”


Wow this wine is delish! What’s the story again? My eyes are glassy?

I couldn’t believe it. I had just sat there for a good 10 minutes talking about the lineup, and to my knowledge, even though the rep had been present, had been tasting wine with me and the buyer, had not heard a single word I had said, including the incredible story of that label.

I felt utterly deflated. I mean, I am guilty of the glassy-eyed nod and stare (listening to people talk about sports, or my husband’s recounting of his myriad crossfit routines come to mind as two instances I pretty much immediately stop paying attention), but I thought I was telling a great story (guess I was wrong!), and I had wasted at least 10 minutes of breath only to be asked to repeat the entire thing. To the same person.

So, to make sure that same situation never happens again,  there are three things I try to do whenever I make a sales call or ride around with a sales rep:

  1. Cut to the chasea buyer is in his or her position because, ostensibly, they understand what kind of wine will work for their place of business. When you pour wine for them, don’t bother telling them how it tastes. Give them relevant information and keep your point simple and compelling. The number one complaint I hear from distributor sales reps is about the supplier who drags on forever with boring stories. Here’s a great article from the Harvard Business review about creating a compelling, simple message.
  2. Listen and ask questionsWhen you truly listen to someone – when you offer them your undivided attention (you put down your phone, stop texting and looking at Facebook), ask them questions and show that you’re tracking what they’re saying,  shows that person respect and openness.  People who feel respected and listened to will automatically want to hear what you have to say.
  3. Stop talkingif people are distracted, looking at their phone, or getting that glazed look in their eyes, stop talking and ask them a question. Clearly your communication isn’t landing and it’s time to try a new tack.

I do not recommend this technique for getting people to listen to you.

How do you make sure you’re heard?

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.