I didn’t plan to buy anything.
I walked into a timeshare sales room out of curiosity and accidentally got a masterclass in sales.
As someone who spends a lot of time thinking about how Small But Mighty agencies sell, I couldn’t stop analyzing what was happening.
And the biggest lesson had nothing to do with pressure selling.
I was staying at a beautiful resort recently when I was invited to a classic timeshare presentation.
You know the one: A 90-minute breakfast, a tour, and a very enthusiastic sales pitch.
I politely declined the breakfast but I was curious.
Not curious enough for pancakes and a slideshow… but curious enough to say:
“Sure, I’d hear what you have.”
So instead of the presentation, they fast-tracked me straight into the sales room.
What followed was one of the most fascinating sales experiences I’ve seen in a long time.
Not because I bought the timeshare.
(Although… I did end up buying something small at the very end.)
But because watching how the entire process unfolded was like watching a carefully choreographed dance.
The Sales Choreography Was Real
The first person we met was clearly the opener.
Friendly. Relaxed. Curious about us.
He asked questions about how we travel, what kinds of trips we like, and what we look for in a vacation.
Nothing pushy. Nothing aggressive.
Just conversation. Then came the closer.
This person was clearly the numbers guy. Calm, attentive, and an excellent listener. Every objection we raised was met with a thoughtful response.
One detail that caught my attention: they sent an Asian salesperson to close us.
I’m Asian.
Was that intentional? Possibly.
Was it manipulative? Maybe.
But it was also a reminder of how carefully these systems are designed. The closer immediately knew how to relate to us in subtle ways. He was incredibly good.
And honestly?
If the offer had fit our life stage, we might have bought.
But the first offer didn’t quite fit.
And that’s when the most interesting part began.
Then the Offers Started Changing
When we said no to the first package, they didn’t push harder.
Instead, they introduced a different version of the offer.
They introduced a different version of the offer.
Then another.
Then another.
By the end of the conversation we had seen four different packages.
At first glance they looked similar: access to properties, vacation flexibility, resort experiences.
But afterward I realized something important.
They weren’t just presenting different prices.
They were presenting different solutions for the same buyer in different situations.
Four Scenarios
All four packages were designed for the same type of person: someone who enjoys traveling and staying in resorts.
But they assumed that not every traveler is in the same situation.
One package clearly worked best for frequent travelers or larger families who could spread vacation weeks throughout the year.
Another suited smaller families who travel regularly, but don’t need a huge inventory of weeks.
A third felt designed for occasional travelers who take one or two bigger trips a year.
And the final offer was different altogether.
It was less about long-term commitment and more about the next vacation – a way to come back to the resort again.
That was the one that actually made sense for me.
Because at this stage in my life, I want flexibility. I want to explore different places. Locking into a fixed number of weeks every year isn’t appealing.
But returning to that resort someday?
That I could see. And that’s what struck me.
The offers weren’t random.
They were built around a very clear understanding of how people vacation.
The Real Insight
The assumption driving the entire sales process was simple:
If someone walks into the sales room, they probably want to buy something.
The question isn’t yes or no.
The question is:
What fits them?
And remember they were doing all of this in a condensed window of time.
That’s what impressed me the most.
Even as someone who works in marketing and sales, I found myself genuinely engaged by how well they used that limited time.
Where Agency Sales Often Break Down
Most agency owners understand their ICP (Ideal Client Profile) at a surface level.
You know the type of company you serve.
But where things often break down is that you think about the buyer from one perspective, usually the situation you see most often.
In reality, the same type of client can show up in very different situations.
For example:
The Fixer
- Something isn’t working. They need help diagnosing and correcting it quickly.
The Builder
- They’re growing and want to build something stronger before scaling further.
The Scaler
- Things are working, but the systems or strategy need to evolve to support growth.
The Explorer
- They’re thinking about what’s next and want guidance before committing to a big move.
Same buyer but different moment in their journey.
And that moment changes what they care about most.
The Lesson
The sales team didn’t just understand their customer.
They understood the different situations that buyer might be in.
And they designed their offers and messaging around those situations.
That’s why the conversations felt so well orchestrated.
Each offer aligned with a different version of the same customer.
And so for Small But Mighty agencies, the question becomes:
If your ideal client is consistent…
What are the different situations they might be in when they come to you?
And how does your messaging shift to meet them there?
Even if your core services stay the same, the way you talk about them may change depending on where the client is in their journey.
When you speak to the right situation, people start nodding their heads.
They recognize themselves in what you’re saying.
That’s exactly what this sales process did so well.
The Take Away
Sales isn’t about convincing someone to buy.
It’s about helping them find the right thing to buy.
When someone raises their hand for a conversation, they’re usually not asking:
“Should I buy something?”
They’re asking:
“Is there something here for me?”
A super power is to understand the situations your customer might be in. And designing your conversations accordingly.
For Small But Mighty agencies, that’s where the real advantage lives.
Because when you understand not just who your client is, but where they are, the right conversation becomes much easier to have.
One thing I’m curious about:
What’s the most unexpected place you’ve learned a lesson about sales or business?
Sometimes the best insights don’t come from a course or a book, they come from simply paying attention to how people solve problems in completely different industries.
P.S. This post is definitely not an endorsement of timeshares and I’m certainly not advocating for pushy sales tactics. Many people have had unpleasant experiences with those presentations.
What I genuinely enjoyed was observing the sales process from an analytical perspective. Watching how intentionally they structured the conversation, the offers, and the way they understood their buyer was fascinating. As someone who spends a lot of time thinking about how small but mighty agencies sell, it was honestly a masterclass in how deeply understanding your buyer shapes the entire sales experience.
