If you want to make it rain, connect with pain.
—Derrick Kinney
When I used to be a financial professional, one question came up frequently in social situations: “What do you do for a living?” I answered the same way most people in our industry do—“I’m a financial advisor.” And almost every time, I could feel the conversation stall. Eyes glazed over. Someone would joke about insurance. The moment passed—and so did any chance of going further.
After enough of those exchanges, I realized the problem wasn’t the people—it was the answer. Prospects don’t lean into job titles; they lean into problems they already recognize. As I like to say, “If you want to make it rain, connect with pain.” That insight led me to a better way to answer a simple question—and turn everyday conversations into real prospecting opportunities.
First, the “You Know How” Framework
Instead of leading with a job title, lead with something far more effective: a problem your listener already recognizes.
When someone asks me, “What do you do for a living?” my answer begins with three simple words:
“You Know How…”
Those words cue a familiar concern—“You know how people worry about running out of money in retirement?” Instead of leading with a title, I’m leading with a problem the listener already understands. You’re not introducing a new concern, you’re naming one people are already thinking about and understand.
To figure out which problem to lead with, look at two small groups:
1. Your five most recent clients
2. Your five favorite clients
Why did those people come to you? What were they worried about before working with you? When you review those conversations, patterns almost always emerge. Those patterns point to the problem you’re best positioned to solve.
Choosing one instantly recognizable worry for a specific client group doesn’t limit you—it focuses you. And, as I like to say, “When you own a problem, you own your success.”
For many, that problem might sound like one of these:
People who worry about running out of money in retirement
Corporate employees who are unsure about when they can actually retire
Teachers who spend so much time caring for their students that they put off their own financial planning
High‑earning professionals who feel stressed trying to enjoy the life they deserve Business owners who lose sleep worrying if their kids are ready to take over their business
People who make good money but still feel financially stuck
Doctors who are great with their patients but feel out of control with their finances
People navigating a major life transition—divorce, widowhood, or living solo—who suddenly need to rethink their financial plan
When I say, “You know how so many people worry about running out of money in retirement?” I don’t have to explain it. People recognize it immediately. They nod. They lean in.
That reaction is the point. When you lead with a problem people already understand, conversations stop feeling forced—and start opening the door to something more.
Once you’ve named a problem people recognize, the next step is explaining what you do—without overexplaining or turning the moment into a pitch.
Second, We Help Fix That
After you name the problem, keep your explanation simple. Saying “We help fix that.” signals confidence without forcing you to explain everything in the moment.
If the person says something like: “I understand that.” Or: “I can relate to that.” Then briefly add how you help—often with a simple three-step process—using plain language rather than details.
For example: “With our three-step (or five-step) planning process, we create a customized financial plan so people can feel confident they won’t run out of money.”
People like steps because they signal thoughtfulness and intentionality without forcing the listener to process details they’re not ready for yet. At this point in the conversation, less really is more.
I’ll often finish with a short statement about focus, such as:
“We specialize in retirement-income planning.”
Remember, people like to work with specialists.
What I don’t do is list products, credentials, or technical capabilities. In impromptu conversations, every extra detail forces people to think—and thinking slows things down. Simple language keeps the conversation moving.
When people recognize the problem you’re describing, they naturally want to hear more—to see if you might be able to help.
Next up is the final section—“Getting a Meeting”—where we show how to continue the conversation without pushing or turning interest into resistance.
