Upselling Starts With the Bottle. Connecting Starts With the Guest.
A lot of tasting rooms think they have a hospitality problem when really they've just mixed up two different things.
Somewhere along the way, "upselling" and "connecting" started getting treated like the same skill. They're not even close. And I think that mix-up quietly costs wineries more than most people realize.
Upselling starts with the bottle. You're looking for the moment to bring up the reserve tier, the library wine, the bigger format. The wine leads, the guest reacts.
Connecting starts with the guest. You actually notice what they said. The anniversary. The trip they mentioned. The wine they lit up over versus the one they were just being polite about. The wine comes second, and only because it fits what you just heard, not because it's next on your list to mention.
Here's the part that gets me every time: guests can feel which one is happening to them.
Upselling feels like being sold to, even when you're being perfectly polite about it. Connecting feels like being understood, even if nothing gets sold in that exact moment.
And the funny thing is, connecting actually sells more. It just doesn't feel like selling while it's happening. It feels like a good conversation that happens to end with someone wanting to take a little of it home with them.
I've seen wineries lean hard into upselling training and end up with a team that's technically persuasive and completely forgettable. Great at hitting reserve tier numbers for a quarter. Not so great at creating the kind of guest who actually comes back, joins the club, tells a friend, remembers the visit years later.
The real cost isn't the sale you missed in the room. It's the guest who was handled perfectly and never once felt like someone was actually talking to them.
You can teach someone to upsell in an afternoon. Teaching someone to really connect takes longer, because it's not a script, it's attention. But it's the only kind of "sales" I've ever seen actually compound over time.
#WineIndustry #Hospitality #DTC
