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Sales Tip of the Month: Drilling Down – Asking Questions for Deeper Understanding

Back in March’s blog, “Asking the Hard Questions,” we talked about asking a prospect questions that may feel too personal or uncomfortable, but are necessary to ask in order to learn why they are considering a move to senior living. Even though the questions may feel pushy or uncomfortable, they help to build the relationship with the prospect, move them along in the sales cycle, and uncover their needs.

Uncovering their needs takes some effort. Asking single, unrelated questions won’t gain you a deeper understanding of what prompted them to pick up the phone or walk in to see the community. You need to ask a series of related questions – drill down – to really understand their motivation. 

Asking Open-Ended Questions

Open-ended questions are paths to drilling down for greater understanding. Closed-ended questions – questions that typically result in a yes or no answer – usually offer very limited opportunities to drill down further. Let’s look at two similar questions that ask basically the same thing, but one is closed-ended and the other is open-ended:

Closed-ended: “Does moving to a senior living community sound like something you’d like to do?”

  1. If the answer was “yes”: Congratulations, you’ve found a unicorn, an older adult who is motivated and eager to make the move, and has no objections to downsizing, selling their home, and moving to an unknown community filled with strangers. Probability of a yes answer? Very low.

  2. If the answer was “no”: They’ve expressed to you that this is something they would not like to do, so you’ve effectively ended that line of questioning. If you tried to build value on a “no”, you would be only guessing at their wants and needs, and probably be presenting them with services and amenities that may not be of value to them. Probability of a no answer? Very high.

Open-ended: How do you feel about moving to a senior living community?

No matter what their answer to this question is, you still have opportunities to drill deeper with follow-up questions. For example:

  1. “I don’t want to.”: You could drill deeper with: “I completely understand. Many people feel that way. What concerns you most?”

  2. “I’m not ready right now.”: You could drill deeper with: “I completely understand. When do you think you will be ready?”

  3. “I don’t want to leave my home.”: You could drill deeper with: “I completely understand, you must have a lot of fond memories of your home. What things about owning a home would you not want to deal with any more though?” 

  4. “I don’t want to live with old people.”: You could drill deeper with: “I completely understand, a lot of people think senior living is like that. You might be surprised to find that a lot of our residents are young at heart like you! What are some things you enjoy doing?”

  5. “I don’t want to move to a nursing home.”: You could drill deeper with: “I completely understand, a lot of people think that senior living is like a nursing home where the residents stay in bed or in their rooms all day, but I think you’ll be surprised to see how busy our residents are throughout the day with activities! What kinds of things do you enjoy doing?” 

As you can see, open-ended questions, unlike closed-ended questions, create opportunities for dialogue with the prospect, and give you more avenues of additional inquiries and options.  

Drilling Down as a Reason for a Follow-Up Call

Don’t feel like you need to exhaust a line of questioning in one call or visit when you drill down. Saving some drill down questions for the future is an excellent reason to make a follow-up call to the prospect. As you finish the call, set a next step in your senior living CRM to make a follow up call to the prospect with the specific purpose of asking some additional open-ended questions to drill down further on your previous inquiry questions. They will be glad to know that you remembered some important details from the last call and are interested in them.


Drilling down is an essential tool for the sales person to use to learn more about the prospect, uncover their needs and wants, dispel misperceptions, and set next steps in the sales cycle. Be prepared by having your drill-down questions ready before the call, and practice regularly with your sales manager. The benefits of drilling down will be seen in increased activity in the senior living sales sales cycle, increased activity conversions (lead-to-prospect, inquiry-to-tour, and tour-to-depost), and increased occupancy!


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