How To Sell Things People Aren’t Comfortable Talking About

How To Sell Things People Aren’t Comfortable Talking About

Marketing | Posted by - August 28, 2018 at 12:30 am

When you’re building a new product or company, one of the best places to start is with a void. Sometimes the void exists because it’s a new market sector that hasn’t had time to get crowded. Other times, it’s because the sector just isn’t cool, and the product isn’t an easy sell. Afterall, not all products are sexy or cool. However, these uncool products can often be the perfect place to start.
For Jennifer Xia, Co-Founder and Chief Product Officer at FreeWill, the very uncool ‘nut’ her co-founders and her needed to crack was about as tough as they come — death.
56% of Americans don’t have a will and, in Canada, nearly one-third of citizens between 45 and 64 don’t have a will. In both countries, hundreds of thousands of people each year are dying without a legal document that states their wishes, which can be an emotional and even financial burden for their families. Despite this, people aren’t writing wills because the act of drawing up end-of-life plans has long been seen as cumbersome and uncomfortable. The process, Xia says, is “usually perceived as scary and complicated and expensive.” Basically, the definition of uncool.
The positive side of this, however, is that its ick-factor is what makes the business of will-writing and end-of-life planning ripe for disruption.

The first challenge Xia faced was how to get rid of that ick-factor. After multiple iterations and countless tweaks, the FreeWill team found that the best way to sell people on planning for their own deaths was by warming up the process.
“We discovered,” Xia shared, “that of all the angles you might use to persuade someone to do something, the one message that we found resonated the most was generosity.” After all, making a will is a profoundly selfless act. The maker will never be able to reap any reward from it, so there is a thread of joy and thankfulness woven through the FreeWill process.

Today, generosity is at the center of the FreeWill system. The language FreeWill uses throughout their product is designed to emphasize the generosity towards family, loved-ones, and the causes the will-writer cares about. This is all part of an experience that Xia describes as “warm.” Expanding on what ‘warm’ means when your product is all online, Xia clarifies that “the language that we use is very simple and straightforward as if a friend was telling it to you. Not a lawyer. Not an academic. A friend. And that is what has made the product successful so far.”

Xia says that another secret to their success, and something that can be applied to uncool businesses across all sectors, is the simple act of listening to customers and iterating rapidly in response to their feedback. Unlike businesses with more naturally popular products, businesses that are facing a tough sell can’t operate under the ‘build it and they will come’ mentality. Instead of deciding what your prospective customers need, how to talk to them, and how to frame your product, and then pushing out a final version without knowing what would resonate best, Xia recommends following the Lean Startup method.
While most stereotypically applied to high-tech startup companies in Silicon Valley, Xia advocates for the Lean Startup method because it forces you to operate on the assumption that you don’t have all of the answers. Instead, you start with a market, perhaps with a proposition or a proposed solution, and with a huge stack of questions that need to be answered.

“At the core,” she says that if your product is “something that is providing value to people, your job as an entrepreneur is to help someone understand that value.” That can often mean testing different angles before dialing down on the perfect one. For FreeWill, the recipe is generosity and warmth, but every company, and every product, has its own tonal sweet spot – especially when products aren’t easy sells.
Part of the value that FreeWill offers is that the will creation service is free. Instead of charging their customers, FreeWill generates revenue from partnerships. By taking the financial transaction out of their relationship with the writer of the will, they are able to immediately remove some of the discomfort associated with the process. This isn’t a solution that works for most products, but, for Xia and the rest of the FreeWill team, it’s never been about ‘most products’. It’s about their totally awesome uncool project and getting it into the hands of the people who need it most. 

Tags: brand awareness, branding, business advice, communication, entrepreneur, marketing, selling, startup

Pippa Biddle

Pippa Biddle is a New York-based writer. Her work has been published by MTV, Matador Network, The FBomb, Antillean Media Group, and more. Visit her at

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