6 Lessons from the Vacation Sales Boiler Room

Vacation Sales Boiler Room

There we were, lazily stretched out on a beach bed, aimlessly gazing out at the aquamarine water of the Caribbean. It was the third day of our five day vacation. My wife and I hadn’t done much, which I suppose is the whole point of a vacation. But as my traveling companion for the past 12 years, my wife knows me all too well. I wasn’t going to be content just laying around on the beach for another day.

She turned to me and begrudgingly asked, “Is today going to be the day?” I replied, “Well, I suppose today is as good as any.” With her implied permission, I quickly rose from the bed, threw my baseball cap on, and made my way to the “hospitality lounge” to see Walter.

For the past decade, I’ve deliberately subjected myself to just about every timeshare and vacation club sales pitch imaginable. They’ve become an integral part of my vacation, providing me with a delightfully perverse form of entertainment. To-date, I haven’t purchased anything, but I do come away with tremendous lessons in communication, interpersonal relationships, sales, and regular ole’ tomfoolery.

Back on the first day of our vacation, we were welcomed to the resort by Walter. Walter asked us a few questions and invited us to breakfast the next morning at 8am. He told us that breakfast was his treat and that we needed to join him to learn more about the property and to ensure that our transportation back to the airport was properly scheduled.

A few things jumped out at me during that exchange. For one, I’m on vacation―our first day, mind you―and the first thing you’re asking me to do is to be somewhere at 8am? That’s a counterintuitive way to get me to show up. Second, he told us that breakfast was his treat. Did Walter not know that this was an all-inclusive resort? All our meals―as many as we wanted to eat―were already included! Lastly, he said he wanted to ensure we got back to the airport without any issues. That one really got me. It was an obvious play on an unsuspecting visitor’s fear of missing their flight home―or worse, being abducted by some criminal gang and held for ransom. C’mon Walter. If you want to invite me to a sales pitch, just tell me.

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For two days, we took the calculated risk of not meeting Walter, leaving our transportation, and our lives, in our own hands. But on day three, I was finally ready to immerse myself in the sales pitch obstacle course. I made my way towards the “hospitality lounge” – a classy name for the waiting area before one enters the sales boiler room. I told Walter I was ready to learn more about the property – and, more importantly, how to get to the airport alive and with both of my kidneys.

Once again, he offered me a meal – his treat of course. I smiled, thanked him for his amazing generosity, and we made our way to lunch. He insisted, well, down-right demanded that my wife join us as well. He wanted to make sure she was included and shown the same hospitality I was. Once again, Walter stretched the truth as to the real reason he wanted my wife to join us. You guessed it, he needed all decision makers present! By now, my wife knows the routine: show up, smile, and let me do the talking.

Towards the end of lunch, Walter asked us a few questions regarding our travel and vacation habits, and said he would show us how much more enjoyable and affordable future vacations could be – with his help, of course. Walter escorted us to the sales boiler room. Inside, there were a dozen rounded tables, each with four chairs. About half were occupied by sweaty, sunburned, and visibly uncomfortable couples.

Walter cut right to the chase. Based on the questions he’d asked over lunch, he selected several vacation club packages that he knew would be absolutely perfect for us. I grimaced, took a deep breath, and told him they were just too expensive. Walter half-heartedly expressed his disappointment and apologized for not being able to propose a deal that made sense for us.

I tell you what,” Walter said. “You guys are in luck. My boss is here today and he’s able to do things that I’m not able to. So sit tight, let me get my boss over here and we’ll see what we can work out.” After a brief sideline conversation, Walter and his boss, Eduardo, returned to our table where he introduced himself. Eduardo was…memorable. His gelled-back hair, golden cuff-links, and putrid smell that is best described as an even-part mixture of cologne, sweat, and cigarette smoke stood out.

Eduardo had three things: a pen, a pad of paper, and a calculator. Two minutes into the pitch, I started having frightful flashbacks to college calculus. In between his fast talking explanations, Eduardo was feverishly punching keys on his calculator and scribbling numbers on his paper―none of which made any sense. Once he was done, he paused, circled a number at the bottom of the paper, and said, “This is how much you will pay to have everything that Walter showed you.” As he extended his hand across the table, he said, “Do we have a deal?

As with Walter, I grimaced, took a deep breath, and told him that it was still too expensive. And just as Walter had done, Eduardo expressed his disappointment and said, “I tell you what. Being that it’s the end of the month, my boss is here to help us meet our goals. I can’t tell you how lucky you are because he makes deals that none of us can. Sit right here and let’s see what we can work out.”

Needless to say, the next sales pitch looked and sounded just like the ones before. When I told the growing group of salesmen that we weren’t going to be able to make a deal, they jumped up from the table, shook our hands, and finally shuffled their way to the next couple at another table.

But we weren’t out of the woods yet! When we returned to the hospitality lounge, the gentleman working the room asked why we were unable to reach a deal. I told him it was just too expensive considering our current financial obligations. “I tell you what,” the nice dressed gentleman said. “As the [insert made-up title here], I can make deals that no one else can.” “Well how about that,” I said.  “You’re the third person that’s told me that!” I politely ended the conversation and made my way back to our room.

So here’s what I learned from our latest adventure to the boiler room:

  1. Respect the time of your client. Propose a time that works best for them, not you.
  2. Be absolutely transparent and direct as to why you’re requesting a meeting.
  3. You can’t fake genuineness and empathy.
  4. Ensure your appearance is professional and non-offensive to your client.
  5. Speak clearly, at a moderate pace, and frequently pause to ensure your client is following along.
  6. If you’re using a sales script, chances are your client has heard it before. Use your own words.

Will Adams

Will Adams is the GM for Small Business Services for GoSmallBiz.com. Will leads the company’s efforts in serving small business owners and their employees through consulting, software, education, employee training, and advocacy. Will is also the co-founder of a successful Software as a Service (SaaS) business that currently serves small museums and family offices throughout North America. In addition to his business interests, Will serves on the board of Atlanta Children’s Foundation, connecting individuals, organizations, and resources to meet the needs of children in foster care.