For years, I wrestled with finding a way to get to know my clients better so I could do a better job of being their advisor and advocate. Like most advisors, I face the challenge of getting clients to accept that the planning process is as important and valuable as investment management.

Most of my time was spent constructing financial and estate plans, but most of my income was generated through investment management. Sound familiar? Yet from personal experience, I knew there was nothing less important to the family of a deceased client than last month's investment performance. For them, it was the depth and precision of the planning that would ultimately matter most.

In an effort to help clients refocus on planning, I hit upon what I thought was a brilliant idea. I asked my married clients to pretend they only had a few days to live and to write letters to their spouses expressing their love, their cherished memories and what they had planned for the future. I also requested they write similar letters to their children. I wanted them to see what was truly important and envisioned these letters would become treasured family heirlooms, passed down and read by future generations.

It was a bust. Hardly any clients ever got around to writing the letters. I was disappointed that my idea had fallen flat until it struck me that I had delegated the responsibility instead of taking the lead.

So I tried again, but this time I told my clients that I wanted to record a conversation with them each year for three or four years. I wanted them to talk about themselves, their ancestors and roots, the important events in their lives, their plans and dreams for the future and for that of their spouses and children.

My plan here was to create a legacy for their future generations, and in so doing get to know my clients, their motivations and their financial perceptions better. In the process, I hoped to gain insights that would help me do a better job of planning for them and, in turn, help them better appreciate the importance and value of the planning process.

Interestingly, clients who could not find the motivation to write letters willingly submitted to the taped conversations. During these sessions, I try to remain merely a facilitator, asking a few questions to get the conversation rolling and then receding into the background.

The response has been truly heartwarming, not to mention productive. The conversations prompt people to recall events they haven't thought about in years. Many times, there is an emotional reaction to the recollection. People remember things they intended to say or do for their loved ones that were somehow forgotten. They frequently start to talk about something and it triggers a distant memory that had great importance but became lost in the recess of their minds. They open up and share all kinds of memories and dreams. They openly express their affection and hopes for their children. They explain their decisions in raising their offspring and how they tried to pass on their values. They talk about the meaningful events that formed their values, the choices they made early in life, the paths they took and those they didn't.

One woman I taped had previously said almost nothing during the numerous meetings I had with her and her husband, and I had regarded her as rather eccentric. But then during the taping she tearfully revealed her painful childhood. She described how her English mother was vanquished and sent to a Nazi concentration camp during World War II while her father, a native Italian, was conscripted into the war. The girls, ages 4 and 6 at the time, were to be sent to an orphanage in Germany, but instead, they hid in an abandoned farm with the family maid who refused to leave the girls and stayed on to raise them, despite living in a war zone hovel. When the Allies invaded, the three frequently fled into the woods as mortars and bombs flew overhead during exchanges with the Nazis.

Hearing her haunting childhood tales, I gained an understanding of why she had been reticent to talk and why home and security had a special meaning for her. Her disposition suddenly seemed quite understandable and not at all eccentric. We now have better conversations with a breadth of understanding I could not have had before. What a transformation!

Another client who had once been guarded about sharing information but who opened up during her taping was a native Alaskan. She recalled how her parents and eight siblings were huddled into a resettlement camp by the government during World War II. They endured a hardscrabble existence, subsisting on meager rations of lard and little more for several years. During this time, her mother became ill and died. She harbors some understandably bitter and unforgiving feelings about the experience.

Had I not learned about her experience during our conversation, I would never have understood the motivations behind her financial decisions and certainly been a far less effective advocate for her.

The conversations tend to take on their own life. They present an opportunity to pass on stories and events clients might otherwise have taken with them to the grave, and I get to know these people in a way I doubt I ever could have without the discussion. The difference in our relationship afterward is palpable; the level of trust much higher.

One man recalled an amazing story about how his life was almost destroyed a few years ago by political sniping. He had been a member of the Swift Boat Veterans for Truth, a group that questioned Democratic presidential candidate John Kerry's war record. The man was attacked in the press and opponents publicized details of his private life to discredit his testimony. Our conversation about those events was chilling. What an important piece of history to immortalize in his own words for his grandchildren and great-grandchildren.

His story also shows that sometimes people form biases that prove to be utterly incorrect. He is married to a Vietnamese woman who was largely detached during our financial meetings and rarely uttered a word. I assumed he met and married her while serving abroad, and I interpreted her reticence as compliance with his wishes.

But when she taped her first conversation, I discovered that almost nothing I had assumed about her was true. The couple did not meet in Vietnam. She was an interpreter brought over to the U.S. to help teach American troops the Vietnamese language. Her husband was among those soldiers. She had been living here and earning a good income for several years before they met. Her shyness soon gave way to some incredible insights about her wonderful new life in America. She provided eloquent and romantic descriptions of her new land and her new husband. She was positively electrifying!
Today, I have a new and better understanding of who she is and what's important to her. I am now a better coach and advisor to her and that is especially rewarding.

These conversations have a remarkable ability to take people to a place of safety where they can open doors to their history. They realize they are getting something beyond their expectations of an advisor, and they are appreciative. If all of this had never resulted in a dollar of additional income, it still would have been the best thing for my clients and my professional practice and for me personally. It has created a glow that I carry with me every day.

I understand my clients' motivations and thought process better. While we might not agree on a particular strategy or order of priority, this becomes relatively unimportant within the context of having this newly formed connection. We disagree, but still get along and make important planning progress because I know them so much better.

The recordings provide a legacy for the clients to pass on to their heirs.

I would love to be able to listen to my great-grandparents tell me about their amazing lives. I've gone back to their birthplace in Germany. I stared at the beautiful, lush green farmland they left to come to America and I have wondered why they settled on the barren, sagebrush-strewn farmland in Oregon. The two settings are so dramatically different; I am at a loss why they chose this place as their new home. How did they survive the first three brutally cold winters living in a tent while nearly all their neighbors either perished or abandoned farming? I want to know these things, but can't.

I do this for my clients and for their future generations and I know I am doing something worthwhile. I know because one my clients is a pastor and the best sermon on money I've ever heard was not delivered from a pulpit on a Sunday morning; it was given by this pastor, sitting alone with me, during his first conversation.

Wayne von Borstel, CLU, ChFC, CFP, MSFS, CAP, is founder and president of Oregon Trail Financial Services, a registered investment advisor company based in Portland, Ore. He is a registered principal with and offers securities through LPL Financial and can be reached at 541.296.6669 or [email protected].