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The Sales Power of Storytelling

No matter how young you are, there is a story you can tell that will connect you with your older clients.

By Charles R. Hale

It had become increasingly difficult to meet with Michael, my client. When I was finally able to get him on the phone, I told him I needed a few minutes to discuss an important idea. He agreed and we made plans to meet.

When I asked him how he was during the meeting, he said he was extremely busy and he had to meet someone soon. I had come to talk with him about charitable giving—Michael’s a very generous man of great wealth—and realized that I would have to get right to the point. I began by talking about setting up a plan of giving, but I soon noticed that he was preoccupied. It was clear my approach wasn’t working.

I’d known Michael for more than 15 years, and while our dealings were quite cordial, they rarely strayed far from business. Intuitively, I decided to take the conversation in a different direction and asked him about his youth.

“You grew up in New York City, right?” I said.

“Yes, I lived in East Harlem the first few years of my life and then we moved to Queens,” he said.

Since I also grew up in Queens, some of the stories we shared overlapped, creating a connection that previously hadn’t existed. Soon, Michael began to reminisce about his family, which led to fond memories of his youth. He stopped looking at his watch and asked, “You know what I would do on Sunday afternoons?” He didn’t wait for my response. “I would get on my bike and ride out to the wealthy sections of Long Island,” he said. “I’d cycle through the neighborhoods thinking, ‘This is where I want to live one day.’”

I asked him, “Can you relate any of this to why you’ve been so successful?” He responded: “I guess I’ve always had vision. That, combined with the fact that I’ve always believed in pursuing my visions with passion, has probably been my greatest strength.”


I thought of my client’s wealth and realized that his biggest asset wasn’t listed on his balance sheet. How do you place a value on vision and wisdom?

A few months earlier, I had become familiar with an organization called the Association of Personal Historians, whose goal is to help individuals and groups record and preserve their life stories, memoirs and histories. I mentioned this to Michael.

“You know, you’ve spent a great deal of time planning your financial legacy, Michael, but how much time have you spent articulating your visions, beliefs and values? Who will know your story?” I asked.

It was clear that he was captivated by the thought of a book or video about his life. “I’d never thought about that. That sounds like a wise idea,” he said.

As we walked to our cars, Michael told me he liked the idea about recording his life story and asked me to get some information for him. He also told me my charitable ideas were good and I should call his attorney.

Three weeks later, Michael, two of his attorneys, his accountant and I met in his office and we began devising a plan of giving. A few months later, my client purchased a $15 million insurance policy as part of the plan. After this, my eyes were opened to the value of listening to a client’s stories and sharing mine as well.

The power behind the story
What is it about a story that is so powerful? Why should you listen to your clients’ stories and share yours as well?

Within our stories lie the motivating forces of our life and our core beliefs. When we share our stories with our clients we connect deeply and discern quickly what truly matters to them and to us. An added benefit is we can learn if we are meant to work with each other, earlier, rather than later.

You may be wondering why a prospective client would want to hear your story. Well, has anyone ever said to you, “Tell me a little about yourself.” Sure they have. And if they haven’t, you can bet the question has crossed their mind.

Recently a client referred me to a friend of his. After our initial greeting the prospect said to me, “So, Charles, tell me a little about yourself.”

In the past I’d say something like this: “Mr. Prospect, thanks for taking the time to meet with me. My firm generates over $100 million of life insurance sales each year. Some of our clients are people you are probably familiar with. Most thought they’d taken care of their estate planning needs, but after spending some time we were able to show them things they weren’t aware of, which resulted in potentially enormous savings.”


I don’t think there is anything wrong with that approach, but I was never comfortable using it. I was taught that it worked and for years it did. But the words didn’t speak to what was genuine in me.

Now I start with: “Mr. Prospect, I do financial planning, but I’m really a storyteller ...” And I proceed to tell a story about who I am. I may talk about my values, my visions or family. Then I ask my prospect to tell me a story about his life.

Trust and storytelling
I believe that building trust in a relationship is a function of telling someone a story about who we are and why we are here. I tell the client what I am looking for in a relationship, and I ask him what he is looking for.

And guess what? My relationships are stronger than ever. After 25 years in the business, I’ve learned that the No. 1 attribute a client seeks is authenticity.

Often we’ll find that there is a deeper meaning to the stories we hear and tell. If we take the time to listen carefully, if we go to that deepest place, rich treasures in the form of unspoken values and visions can be unearthed.

Listening to a prospect’s or client’s story and sharing yours are important steps in the sales process. Stories help us understand who we are. They communicate how we see ourselves, the world and our place in it. Within our stories lie the motivating forces of our lives and core beliefs. When we share our stories with clients, we connect deeply and discern quickly what truly matters to them and to us. As an added benefit, we can learn if we are meant to work with each other sooner rather than later.

Bridging the age gap
I’m often asked by young newcomers to the industry, “What stories can I tell that will resonate with prospective clients who are 20 or 30 years my senior?”

That question reminds me of my first year or two in the business. Like many new agents, I was anxious to impress potential clients with my self-perceived brilliance. I’d attend a meeting, get a new financial idea or hear about a new product, and I was off to conquer the world.

When we share our stories with clients, we connect deeply and discern quickly what truly matters to them and to us.

Looking back, I can remember some of the looks on the world-wearied faces of the small-business owners who were my target market. I’m sure they were thinking, “Oh, man, nice kid. He really thinks he’s for real.” I cringe and then laugh when I think about those moments.

A story of storytelling
But unlike those of us who have been around long enough to have accumulated lots of stories--one of the advantages of age—the younger person doesn’t have that benefit. So what do I say to them? While I can’t suggest the exact story a younger person can share with an older person—I think the story has to be personal and come from the heart—I can lend some guidance. This is the story I tell them:

Not long ago, a bright, energetic young man came to interview me. (Now, at the age of 56, it seems the roles are reversed, and I’m that world-wearied business owner.) A few of the young man’s questions made me pause and think hard. Part of the conversation went something like this:

Q: Are you happy with where you are at this point in your life?

A: Well at this point in my life, I’m not sure that I think about the word “happiness” that much. I don’t know when or where it happened, but now I think more about how meaningful my life is. At some point I began to think, “What is my higher calling?”

Q: What are your goals?

A: I hate to keep changing your questions, but I think I’d ask that a little differently. How about, what will be your legacy? Working with older clients, I’ve discovered that planning a client’s financial legacy without honoring his emotional legacy is only doing part of the job. I also believe that speaking with others about their emotional legacy honors the dignity of their life. Many successful people reach a time in life when they wonder, “Is that all there is?” The singer Peggy Lee had a big hit with just that title. I call it the Peggy Lee story. When they get to that question, I suggest that the financial side isn’t all there is; there are road maps to create for those who will follow.

Speaking with others about their emotional legacy honors the dignity of their life.

After the interview, we walked through the house and toward the door. The young man, ever polite, mentioned that he was impressed with our house—we have an old Victorian—and our furnishings. Staying in character, I said to him, “You know, you’re right. We have collected some nice things over the years, but to be perfectly frank, nowadays I think less about my possessions and more about my experiences.”

The meaning of life
What’s the point of this story? I think a younger person needs to find a story that acknowledges where his elders are on life’s continuum. Personally, the stories that resonate within me are those that focus on life’s meaning, legacy and how we experience the world around us. I don’t claim to speak for everyone my age or older, but if my hunch is correct, my experience of my place in life is not unusual for someone my age.

I offer this story with hopes that it will provide some clues to the younger people in our industry who are looking for ways to connect with their elders.

Charles Hale is a contributor to

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