There’s a fine line between **upselling** and **being a walking sales
pitch** — and I used to trip over that line like it owed me money.
Early on, I thought suggesting meant listing the most expensive items
with a smile and praying they’d bite.
“The ribeye is *really* popular… it’s aged for 28 days…” *Crickets.
Side-eyes. Budget-conscious frowns.*
I felt like that annoying person at the mall kiosk trying to rub lotion on
strangers’ hands.
**That’s when I learned the magic word: context.**
—
A Lesson in Stealth Selling
The table was a family of four. Parents, two teenagers, and the
unmistakable “We go out to eat once a month, don’t screw this up”
vibe.
They were being polite but guarded. Budget was clearly on their mind.
No appetizers. Tap water. I didn’t see a single menu open past the
second page.
So I didn’t go in hard with the upsell. No pitchy energy.
Instead, I leaned into connection.
“First time here?” > “Yep.” > “Awesome. Let me make this easy — do
you like bold flavors or lighter dishes?”
The dad raised an eyebrow. “Bold.”
**Boom. Door cracked open.**
—
Suggest, Don’t Push
Instead of launching into a steak monologue, I said:
“Alright — bold flavor crew. If you want something fun but still in the
safe zone, the peppercorn burger’s a favorite. But if you’re feeling
brave, the jerk chicken pasta’s legit. Not everyone can handle it.”
Then I paused. Said nothing else.
**That’s key.** Silence is your friend.
People hate being sold to. But they *love* feeling like they discovered
something themselves.
—
What Happened?
They ordered the jerk chicken pasta.
And the garlic bread upgrade. And two sodas. And dessert.
The teenagers — who I swear were allergic to eye contact at first —
were cracking up by the end of the meal.
The parents looked relaxed. I looked like a genius.
Final Thought
Great servers don’t push products — they guide decisions. It’s like
being a food whisperer.
So next time you’re tempted to say, “Can I interest you in…” — stop.
Instead, try: > “If you’re in the mood for something fun…”
You’ll sell more. You’ll feel less like a salesperson. And your tips? They’ll
reflect it.
