Some of the best business lessons I’ve ever learned didn’t come from a conference, a sales seminar or an industry meeting. They came while traveling for leisure.

In 2019, it was “All about the Yapa,” a sales lesson from Cusco, Peru. In 2025, it was “Endurance: Defining the operator’s experience with one word,” a business lesson from Antarctica.

Last month, my wife Peg and I spent a few days in Sonoma County, one of our favorite destinations. We love the area because of its exceptional Chardonnay and Pinot Noir, its relaxed atmosphere and charming towns like Healdsburg. It also reminds us that great businesses, regardless of the industry, often succeed for the same customer-centric reasons.

A curated experience

Today’s premium tasting experience is carefully curated. Reservations are required. Tastings often last two hours, include thoughtfully paired food and personal service, and typically cost well over $100 per couple. Because of that, we’ve changed our approach. Instead of racing through three or four wineries in a day, we now choose one exceptional experience and enjoy it.

This trip took us to two outstanding wineries: McRostie and Flowers. Both produce excellent wines. Both have beautiful facilities. Both employ polished and knowledgeable professionals.

Yet, I walked away from one thinking, “That was one of the best customer experiences I’ve had in years.” The other? Very good. Very professional. Very forgettable.

One asked questions. One delivered a presentation.

At McRostie, we were welcomed with a glass of sparkling wine as we walked in and received an explanation of what we were drinking. Our host sat down and immediately began asking questions. What wines do you typically enjoy? Which McRostie wines have you best enjoyed before? What styles appeal to you most?

Our wine-tasting host had already reviewed our wine club purchase history before we arrived. Within minutes, she completely abandoned the scheduled tasting menu. Instead, she selected wines that she believed matched our personal preferences. Every pour became part of a conversation. There was no pressure. No sales pitch. She disappeared when we wanted to enjoy the scenery and our charcuterie board, then reappeared at exactly the right moments with another story or another recommendation.

At the end of the tasting, she surprised us with a couple of additional glasses of wine simply to thank us for being club members. It felt personal. It felt customized. Most importantly, it felt like she cared more about creating the perfect experience than completing the program she had been assigned. We ordered a case of wines that we tasted to have shipped to our home.

Expectations were...

The following day we visited Flowers Winery. Beautiful property. Wonderful, higher-end wines. An extremely polished wine educator. But the experience couldn’t have been more different.

We were welcomed with a glass of sparkling wine, but no one explained what it was. When our tasting began, our presenter flawlessly delivered each wine exactly as outlined in the tasting program. He knew the wines inside and out. When I asked questions, he answered them expertly. Then he immediately returned to his presentation.

What did not happen was the most interesting part.

• He never asked us what wines we liked.
• He never asked what brought us there.
• He did not check our order history in advance.
• He simply delivered the presentation exactly as designed.

We enjoyed the wine tasting. We purchased a couple of bottles of wine, but we never felt as though the experience had been created specifically for us.

As we prepared to leave, I asked whether they had bubble wrap so we could safely transport our purchases. The initial answer was “No.” Only after I reminded them that they ship wine every day did someone remember there might be some in the back. Nothing disastrous, but just another example of following the script instead of listening to the customer.

How to win in the service business

Driving away that afternoon, I couldn’t stop thinking about how closely these two experiences mirror what happens every day in the office coffee and convenience services business:

• Some salespeople arrive carrying a presentation.
• Others arrive carrying questions.

The difference is enormous.

Too often, operators walk into a prospect’s office determined to show the coffee plan they’ve chosen, the pantry program they’ve designed or the micro market they want to install. Meanwhile, the customer may have completely different priorities.

You’ll never know unless you ask.

Over the years, I’ve shared what I believe may be the most effective opening question in our industry:

What would you need to see today to make my company your new supplier?

Instead of guessing what matters, you discover it. The customer might say:

• “I need better coffee.”
• “I need better service.”
• “I need equipment that actually works.”
• “I want a break room that our employees will actually enjoy.”

Now you’re solving their problem instead of presenting your solution. That’s exactly what McRostie did. They learned who we were before deciding what to serve us.

Flowers assumed the tasting menu was the right answer. One experience felt customized. The other felt standardized. The irony is that both winery representatives were excellent communicators. The difference wasn’t product knowledge, professionalism or personality.

It was curiosity. One salesperson was determined to learn about us. The other was determined to tell us about the wine.

The next time you prepare for a sales call, ask yourself a simple question:

Am I walking in with a presentation, or am I walking in with a conversation?

Customers rarely remember every feature you showed them. They almost always remember how well you understood them.

Sometimes the best sales lesson isn’t learned in a conference room. Sometimes it’s learned overlooking a vineyard in Sonoma, with a glass of Pinot Noir in your hand.