Selling season is upon us! For most wineries, this season means higher traffic and sales, which sounds great, but when you peel back the layers and take a deeper look, you’ll find these perks often come with many hidden challenges. We’re addressing the top 3 challenges we hear about each busy season and offering suggestions to nip them in the bud and maximize the season.

The top 3 challenges we hear from our members and clients during selling season are:

  1. Staffing
  2. Higher Traffic (A double-edged sword)
  3. Remaining Consistent with the Guest Experience

Challenge #1 Staffing:

Why is it so challenging to find, hire, and retain talented tasting room staff???

  • Small Labor Pool 
    • With more Wineries Opening Every Day, the Labor Pool gets Their Pick!
    • Remote Locations​
    • Cost of Living in Wine Country​
  • Often Need Part-Time Only
    • (See above)
  • Winery Resources
    • Limited Time​
    • Limited Recruiting Experience​
  • Attract Wine Lovers, Not Necessarily Sales People

Who Do You Want in the Tasting Room?

The first thing you need to do before beginning your search for team, is identify who you want to attract. In the same way you want to attract quality tasters, you need to be focused on attracting quality team members. Remember your brand statement and refer to it each time you have a position to fill because it will help you identify people who will fit, and each person then, will become an extension of your brand. Just as tasters who feel the fit with your club will stay longer, employees who share your values and your brand vision will stay longer with your business. All things being equal, an employee who feels a connection with your winery, will not be tempted to leave for a dollar more per hour. 

Be Clear About Your Goals from the Get-Go

Next, consider what skills your tasting room team needs to have to help you achieve your goals. We NEED to sell wine clubs and wine! Often, we end up with team members who believe their job is to pour wine and talk about wine. They were hired because they have a good personality and they like wine, but not being told upfront that they’re expected to meet sales goals! We were recently called in to interview a prestigious winery who wasn’t meeting their sales goals. While interviewing the team we discovered that sales and club sign-ups were not discussed in the interview. Now the winery is in a sticky mess! How can we prevent this? By being upfront about our sales goals and brand position in the job description and interview. ​Communicate this, communicate this, and when you think you’ve communicated this, do it again!

Perception Vs. Reality

The root of most of our staffing challenge is that management and owners don’t see the value in investing in tasting room talent, training, and retention. We’ve talked with TR managers who say they rarely see the owner or winemaker… The TR team IS the face of your brand to your guests! If they are aren’t worthy of your time, attention, and resources, who is??? If you want proof of the TR team value, do the math! Tally your 2018 tasting room and wine club sales (bc all wc sales start in the TR) and see what your TR team salaries are as a percentage of that total. No other DTC channel produces as much as the TR for your winery. If you treat them like servers, that’s what they’ll become. If you value them as sales people and brand ambassadors, they’ll rise to the occasion.

Challenge #2 Increased Traffic:

Mystery Tasting results from our members have showed that increased traffic CAN have a negative effect on guest experience and customer satisfaction​. When we review metrics from July thru September​, we typically see the following:

  • Sales increase
  • Tasters increase
  • Wine Club increase
  • Sales per Taster decrease
  • Wine Club conversion decrease

Lead with Metrics

Does your team know their metrics? ​

  • Ask ​
  • Train ​
  • Review them in team meetings​
  • Start with why it’s important​
  • Give details​
  • Use visuals​
  • Have them calculate conversions​
  • Utilize Zoom or Skype calls to bring part timers in to be a part of the conversation. And pay them for their time!

Connecting with Guests When the Bar is Full

The number one bias we hear from tasting room team members during our trainings is “On a busy day I do not have time to connect with guests.” That is a BIAS! While you may have a shortened time with guests as compared to a slow weekday, you still have time with your guests. It is up to you how to best utilize that time. Ask yourself how you are spending the shortened time. Are you filling your time giving information, or are you asking open-ended questions about the guests so you can know how they relate to wine? If you must take a shortcut here, we recommend asking question about how the guest enjoys wine in their home life. Anytime we can get our guests thinking about our wine in their home setting is great! Here are some ways to ask:

  • How do you enjoy wine at home?​
  • What wines are you enjoying most at home right now?​
  • Who do you usually enjoy wine with at home?​
  • How could you see yourself enjoying this wine at home?​

Use the information to connect the guest interest to the wine club or buying wine.

Challenge #3 Staying Consistent:

When the season gets going, things can really start to feel chaotic! So how can you teach your team to consistently deliver a guest experience that showcases your brand?

Develop a Plan for your Guest Path

By creating a clear expectation of what you want your guest path to look like, it’s easier for your staff to stay consistent. Again, this should be clearly communicated from the get-go! As you create your guest path, always keep your 3 Key Messages of your brand in mind and make sure it aligns. Here is a sample guest path for when the bar is full:

Guest enters​

  • Welcome within (how many seconds?)​
  • Thank you for visiting/joining us​

Wine Club – plant the seed​:

  • Ask if they are wine club members – if they are members, take the opportunity to welcome them back and remind them of their benefits​
  • Mention club exclusive wines being poured​​


  • Ask a question – learn something about the guest​
  • Have you visited before?​
  • Are you a club member?​
  • What other wineries have you visited?​
  • Wines – describe tasting experience and what to expect​

1st Pour​

  • What is the first thing you’d like the guest to know about your winery?

Training Your Team

Once you have clearly communicated the expectation of what your guest path should look like, it’s important to train your team! We recommend training the whole team at once if possible. You can get creative with the timeframe, perhaps asking everyone to come in a couple of hours before the tasting room opens and providing breakfast. Training is necessary for consistency!

Start with metrics

Share your metrics with the team to allow them to see where your challenges and opportunities are, then ask the team to share their personal challenges around that. For example, if your wine club conversion is down and that is where you want to focus the training, then ask each team member to share their biggest challenge in asking guests to join the wine club.

Role Play

Allow each team member to role play through their challenge once as the TR associate and once as the guest. When they can role play through the guest path, it becomes more clear what they can do on the other side of the bar to give the guest a more positive experience. Allow the team to give positive and constructive feedback.

As you gear up for selling season, we are happy to help you with any of these challenges or other challenges you may be facing. We offer custom team trainings both onsite and virtually. Please reach out today to schedule a free consultation!

Need sales training for your staff? We created an online sales training specifically for tasting room hosts…all about how to sell more wine! CLICK HERE for more information!

Have questions, want more information, or want to chat about your specific challenges and goals for selling season? Call Lindsay at 512.308.2908 today!