Sherpa CEO David Smith shares his four-step planning process for advancing senior living sales.

By David A. Smith, CEO of Sherpa, a Senior Housing Forum Partner

I first met Mary when she walked in with her daughter to inquire at one of our communities several months ago. A tall, elegant beauty of 83 years, Mary was hanging on to a lifestyle that was falling apart. She struggled to keep up her five-bedroom home, especially as she developed significant hearing loss and cognitive decline. She’d also had several frightening events, such as leaving her car running in the garage and taking the wrong medication. Her daughter wanted her to move into senior housing but, like the vast majority of her peers, Mary said she just wasn’t ready.

Last week, I saw Mary again. She was all moved in and had just settled down for dinner with friends. They were laughing and telling stories. I couldn’t help but smile when Mary told me that she wished she had moved sooner.

It is immensely challenging to guide qualified, higher-functioning prospects like Mary through the “readiness gap.” But it is also one of the most heroic and rewarding efforts I’ve ever experienced.

This is the story of how it happened for Mary.

Closing the Readiness Gap

When we first met, Mary should have been more than ready to move; her daughter clearly thought so. Despite our community’s obvious lifestyle benefits—and despite her daughter’s efforts to convince her otherwise—Mary said she wasn’t ready. She was struggling with the potential loss of her house and the change to her sense of security and identity. She had numerous internal questions and conflicts: Who will I be? I feel so vulnerable starting over. There are so many old people there.

We could have pivoted to a solution each time she presented an obstacle: Can’t cook? You’ll love our menu! Trouble with meds? Try our wellness program. But we didn’t, because that approach is counterproductive. I know this because I have tried it and watched a lot of others try. When we push too far too quickly, prospects disengage and go silent. That’s when the industry reclassifies them as “cold” leads and casts them aside—until a health crisis forces a move.

Mary didn’t need to hear our solutions. She needed a safe emotional space based on trust and a sounding board to work through her natural ambivalence. She needed time and guidance to process. She was not ready to move, much less to sign a lease.

So, what could we do next besides simply waiting for a crisis?

The solution to this apparent conflict between the need to “close” and the risk of losing the prospect altogether by asking too soon or too often is simple: Redefine “closing.”

Advancing the Sale

Last month, I published a Senior Housing Forum column titled “Advances: How to Measure Daily Success in Senior Living Sales.” In that post, I said sale success “doesn’t start when the contract is signed or the deposit is received. In senior living sales—where both cost and emotional resistance is high—success comes from helping prospects advance each day toward a buying decision. And that takes an investment of our time.”

An Advance occurs when something happens that helps the prospect “get ready,” including a new awareness or acceptance of problems in their current living situation that motivates them to take action. My sales teams meet every day to brainstorm and plan for advances for prospective residents like Mary. Here are the four stages of our planning process:

  1. Explore possibilities. Together, we discuss what Stage of Readiness we think Mary has reached and brainstorm ways to connect with her on an emotional level. Think about small and large steps, and don’t be afraid to look outside the box. In Mary’s case, we considered multiple options, including sending her flowers and asking to contact her daughter.
  2. Will it advance the sale? For each possibility considered, discuss as a group whether you think it will advance Mary’s readiness to buy. Since this is somewhat subjective, discussion and consensus can help. Collaboration will help teams clarify options and raise questions that need to be addressed as part of the plan.
  3. Easy or hard? Rank choices based on difficulty level. For example, it’s easier to send Mary flowers and a note than it is to request a home visit. How realistic are your proposed actions? What can you do now, and what will need time to achieve?
  4. Rank Choices. Finally, prioritize your options and record your next steps. For Mary, we decided to start by sending flowers and requesting a home visit. Here’s how we record these Stages on our Action Plan Worksheet, which is adapted from Neil Rackham’s The SPIN Selling Fieldbook: Practical Tools, Methods, Exercises, and Resources:

Request/Commitment Options

Will it advance the sale?

Easy or hard?

Rank choices

Invite for event




Request home visit



After flowers

Ask for the deposit




Contact daughter



Fall back

Send flowers & note





Why Advances Work

Advances are the key to bridging the gap between “I’m not ready” and “I wish I would have moved sooner.” Small steps. One after another.

Each Advance increases the probability of another. Each advance increases the prospect’s readiness to buy. Find a simple way to celebrate your advances. We ring a bell in the sales office, but you could also have an impromptu dance party or send a celebratory email.  

Multiple advances lead to a substantially increased likelihood of success—for you, for your community and most important, for prospects like Mary!

For more information on Sherpa’s Prospect-Centered Selling® Program, please visit the Sherpa website by clicking on the button below:

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