Sales Lessons From the Queen of Mean

Leona Helmsley practically invented what we know today as content marketing. What she taught me still guides the way I practice real estate today.

Once upon a time, a queen created the concept of “content marketing.” It wasn’t any of the Elizabeths or some character from a children’s fairy tale. It was none other than the controversial trailblazer Leona Helmsley, “Queen of the Palace Hotel” and empress of a vast real estate empire in New York. In the 1980s, long before digital companies wrapped your thoughts in a hashtag, Helmsley was using techniques that would be practiced in the new millennium, and I was there to learn from the best.

I worked directly for the infamous Mrs. Helmsley in the corporate leasing program at The Palace Hotel. Corporate leasing in hotels was at the time a hybrid of what is now done by companies through condominium ownership. A company would “purchase” a suite in the hotel and management, clients, and friends were booked into the suite as if it was a corporate apartment. It was appointed with company details, and depending on who was visiting, the amenities could be targeted to the desires of those staying there. The refrigerator might be filled daily with particular foods requested by your client visiting for a three-day sales meeting with your team. Banks, ad agencies, Fortune 100 companies—they all used this easy, luxury approach to housing their visitors. 

Also, our program brought in consistent occupancy guarantees for The Palace. It was a success for the hotel and the guests because our corporate guest experience was customized based on the company’s demands and the guest’s personal needs. The Palace was one of the great training grounds for a young man to learn about real estate sales from an icon in the industry. Indeed, Helmsley was so talented you never even realized she was selling real estate. 

So what did she do so differently? Looking back, I see Leona Helmsley as the originator of content marketing. I spend a lot of time now encouraging my sales teams to stop using the hard sell with clients. We talk about the agent’s role as someone assisting their client in finding a home. My associates have to understand their clients’ needs and maintain a friendly but professional relationship. The client should feel comfortable knowing that their agent is working hard on their behalf.

In that same way, Helmsley never “sold” the suite. She connected with the person and in that connection made it easy to “provide” them the suite through a shared understanding of what they needed. Whether it was the expectations of a suite for a multimillion-dollar client or someone who needed the utmost discretion and privacy, she made it clear that she understood their expectations and that those needs would be met.

And she did her research. Helmsley knew everything there was to know about clients before they arrived at her all-pink executive quarters. One time, she learned that a potential client happened to be in the market for a Learjet. She sent me to get a magazine with an ad for one, and left it open on the coffee table so they would see it when they sat down. Sure enough, the CEO said, “Are you in the market for a jet? We’re looking at them as well.” She went on to give him some information she’d gathered, they chatted and commiserated, and he was hers. That was content marketing in the 1980s: It was not just the luxury suite, but also knowing about the client she was addressing and suggesting to that person that our team was in sync with the needs of his team. 

What this further underscores is Helmsley’s steadfast belief that your brand is everything. “Where The Queen Stands Guard” was the proclamation made in the print campaign for the Helmsley Hotel chain. The ads, written from her perspective, promised that everything down to the towels would be of the same quality that she would demand for herself. In her case, her brand was the company’s brand. Today I preach to my sales teams that you cannot rely on your employer to ensure the success of your image. Only you can truly create and manage your brand.

Today, it is a common occurrence to find comment cards in your hotel room. In the 1980s, it was very unusual. Helmsley would answer every single comment card herself. Whether it was in response to a compliment or a criticism, each answer went out on her personal stationary. We’re talking dozens every week. And she took great pleasure and pride in the task. She understood that success is in the details.

Alas, the tides changed and boards of directors weren’t comfortable with the line item cost of corporate hotel accommodations. They started buying condos and furnishing the units themselves. I still believe that it’s much more costly and less efficient to have an internal staffer take care of a corporate condo when services are already built into a luxury hotel environment. But an avoidance of impropriety, which was really more about client entertainment, had its way and the corporate leasing programs in luxury hotels dried up.

Leona Helmsley taught me the value of enthusiastically researching clients (both the buyer and the seller) to provide them a level of comfort that would allow us to easily navigate the deal to its inevitable conclusion. And to this day, I think it’s that level of detail prior to meeting with a potential client that will separate the best brokers from the rest.