I toyed with naming this piece “Holy Crap, We Bought a Timeshare” but since the transaction was reversed, I’m not sure that’s appropriate.

Have you ever been able to emotionally detach from a sales pitch? Not your own, of course. Have you ever been sitting there listening to a salesperson drone on about the most amazing product (that you don’t need), and floated up out of your body to study the situation?

When the concierge at our Maui hotel offered to sign us up for a “Vacation Opportunity Presentation” in exchange for $200 worth of activity credit, we knew what we were in for. My boyfriend and I had both sat through timeshare pitches before. We even joked about practicing “No!” several times before sitting down for the meeting. We were prepared to sacrifice a few hours of our vacation for a deeply discounted ATV trip. We were smart. We were strong. We were a united front.

We were wrong.

When we sat down with the real estate agent (let’s call him Bob), I was focused on viewing his sales process. I know, I was on vacation and shouldn’t have been focused on sales processes, but I know that timeshare salespeople are impeccably trained and I wanted to see how they handled the pitch.

So how did he do?

There were moments throughout the morning that I wanted to stand up and clap. Like seriously give him a round of applause for a job well done.

Instead, I found myself shaking my head when he’d left us to discuss, and saying something I’d never imagined I’d say. “This sounds crazy, but I can’t think of a reason why you shouldn’t do this.”

Wait… what?

Dang it, Sheryl! You’re better than this.

That’s how good the sales pitch was. He managed to sell us even while we knew we were being sold. I was supposed to be the voice of reason. Instead, I was lapping it up, imagining myself living large as we traveled to Japan and Scotland. Allow me to share some of the highlights:

We Were Made to Feel Comfortable and Special

The psychological consideration that went into this presentation truly rivals the Las Vegas casinos.

  1. We were offered pastries and coffee the moment we stepped into their world. I’m not going to lie, I’m fairly food motivated. If you offer me a Cinnamon Danish, I can’t be held responsible for my decisions.
  2. When we sat down in the room, our names were written on the board and he used them repeatedly throughout the morning.
  3. He took the time to get to know us: what we did for a living, what we liked, our hopes and dreams, etc.
  4. He talked about how very few people are given this opportunity and told us stories of “non-owners” who wanted to book a villa at this property and were turned away despite how much cash they flashed.
  5. He explained that the CEO of Costco owned 16 weeks with them. (I asked if he was single… he’s a woman. So, I offered my boyfriend up to date her. No reason not to take one for the team.)
  6. He showed us a sample villa and asked us how the room and the view compared to our current hotel… knowing full well that our hotel was under construction and the sound of the waves had been replaced by jack hammers.

He Put Us At Ease

“I’m not a salesperson,” he said while we were taking the visual “tour” of the different brands and properties under this umbrella. “You’re already a customer. This company will have your money whether you become an owner or continue staying at our hotels.”

Bob was just an “educator.” He explained that he was on our side and his job was to help us keep as much money as possible in our pockets.

Concerns and Objections were Addressed Up Front

One of the first questions he asked us was “What do you know about timeshares?”

We then proceeded to do exactly what Bob wanted… spew out our objections so he could counter them throughout his presentation.

My boyfriend’s father had owned one but found it difficult to book when he wanted…

My parent’s owned one and loved it, but the annual dues kept going up and up until they couldn’t afford them and had to give up the rights…

He swatted those reasons down like Mr. Miyagi taking down a drunken fly.

He Got Us to Agree Several Times

Bob asked us questions early on in the presentation that we couldn’t possibly say “no” to. Things like “Do you like to travel?” and “Do you want to continue traveling?” and “Do you want to keep more money in your pocket or put it in the hotel’s pocket?”

Umm… duh.

In asking us these obvious “yes” questions, he primed us for saying “yes” later on.

The First 3/4 of the Presentation was Entirely About Us

He wanted to know if we liked to travel. Had we traveled a lot on the past? What plans did we have for future travel? How many years would we be traveling before we stopped?

My boyfriend wants to go to Australia in the next few years. Had he researched it? Did he know how much it would cost?

Yep, he had and he did. He’d done Bob’s work for him.

The questions kept coming and he wrote down every single answer, referring back to each answer throughout the morning. Every point he touched on when he discussed the actual product, was customized to our responses. “When you take your lovely wife to Australia, do you want to have a bill at check out? Our owners don’t get bills.” (We didn’t bother to correct him on our marital status… we were too busy lapping up the attention.)

It wasn’t until at least an hour in that he even mentioned how the program worked. Even once he’d gone into the details, he only told us how much the fees were per year. The actual cost of the “property” didn’t come up until the very end.

He Stopped to Ask Who the Decision Maker Was

You know, if car salesmen did this, women wouldn’t hate them so much. When I went looking for my last used car, I brought a friend with mechanic experience so I didn’t buy anything that was likely to explode within the next 6 months.

The car salesman spoke directly to him until my friend said, “Stop talking to me. She’s the one buying the car. I’m just here to look under the hood.”

This didn’t happen here. About halfway through the process, Bob looked at both of us and said, “If you were to move forward with this opportunity, who would be making that decision?”

He didn’t assume (and piss me off in the process). He just asked.

He Brought in a “Closer”

Once we were sufficiently hooked and asking about cost, Bob assured us that someone would be in shortly to explain how the pricing worked. At this point, he just sat back and “oohed” and “aahed” as the new guy slashed the price for us, threw in extra points, and promised us dinner as a thank you.

Want to know how much I was questioning every tactic they threw at us?

When the 2nd guy walked in, I noticed that his name tag said my boyfriend’s name. I just finished reading Click by Ori and Ram Brafman. In the book, they mention that you are more likely to agree with something and connect with them if you have the same name. I may have been slightly paranoid…

Now, this is probably a good time to mention that everything Bob did right, this guy did wrong. We were just so far down the rabbit hole at this point, that it didn’t matter. He made assumptions about our careers and our roles in the relationship. He painted me out to be a 1950’s housewife who’s all dolled up and waiting for her husband to buy her something shiny. He threw numbers at us that made our heads spin and followed up every sentence with “sound good?”.

He epitomized the “”hard sell.” When I asked if my boyfriend changed his mind, was there a period during which he could cancel, he responded with, “Well, we only sell to people are really confident that they want to do this. Are you sure you want to buy?”

Truthfully, my skin is crawling a little bit as I mention him. When he left and we were alone with Bob, I repeated my question.

“I know that I already asked, and he really didn’t answer. Before we sign anything, is there a cancellation period?” I’m a serial returner and there was no way I was letting him sign anything without a potential out.

Bob put us back at ease.

I began this piece with a spoiler alert. While my boyfriend did sign on the dotted line, and while it may have been a good product, we both came to our senses and realized that this wasn’t the right time in his life and career to purchase a timeshare. Bob did his best to save the sale, but in the end, we stuck to our guns. We may not have property in Maui to our name, but I got a crash course in sales that I’ll never forget.

What’s the biggest sales lesson you’ve ever learned?

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About the Author

Sheryl Green is a New York native living and thawing in Las Vegas since 2008. After years of begging for money to support animal rescue, she discovered Cause Marketing and her life was forever changed. She now brings her knowledge of storytelling to non-fiction and content writing, working with businesses and individuals who want to position themselves as experts in their field and differentiate themselves from the competition. She is also the co-founder and president of the Cause Marketing Chamber of Commerce.

Sheryl is the author of 4 books and serves as the Director of Communications and Cuddling for Hearts Alive Village Las Vegas. Learn more at www.sherylgreenspeaks.com.