Failing to ask is failing to learn — and failing to give our best counsel

Someone wiser than me offered sage wisdom years ago, the precision and power of which still walk the corridors of my soul.


“The most difficult decisions in life,” my mentor observed, “are not between what is good and what is bad, but between what is good and what is best.”

As in so many places in the land of maturity, binary yes-and-no, good-and-bad answers may be easy, but not always accurate.

Each day, we weigh good, bad, and best issues. If we were fortunate to have been blessed with engaged and mature parents, teachers, clergy and friends, we learned right from wrong, truth from falsehood, and the ability to define what makes life meaningful.


The advisory business will test all of that and more, as clients sit with us to share their hopes, dreams, fears, values, and concerns. With regulatory standards in flux, this good-bad-best issue only rises to a higher level of visibility and importance. Even the fiduciary standard has limitations reminding us that the only lasting currency we have is our integrity.

Moving from the binary good and bad to what may be best begins when we invest ourselves in those we serve, hearing core words, and then moving to a conversation’s edge where gestures, emotion and tone-of-voice converge.

The easy decisions are those that pit “good” and “bad” against each other. But simply scoring a client’s risk tolerance from three or four answers to expected questions is only an initial foray into the longer journey of knowing that person’s greatest needs.

Yes, it may satisfy compliance requirements to have those boxes checked. Yet, somewhere in the back of your mind hangs the nagging, uncertain feeling when you know the client has more baggage to unpack, more stories to share.

Completed and approved forms are but the beginning of a longer, more salutary quest.


One of those treks may take you to a hospital room where you meet, for the first time, a friend’s adult child who lives halfway across the country. You knew her name and that of her husband and children, but you did not know she was estranged from her older brother until you walked in that room.

What if you had learned more from the parents months or years earlier? Neither good nor bad, it would have been best to ask, “Tell me how your children connect with each other as adults.”

Wouldn’t you agree that how those parents answered the question, the words they used, and the emotions they conveyed would have created a better, if not “best,” picture of this family?

When we fail to ask, we fail to learn – and in that deficit we fail to offer our best counsel.

The better choice, with the client sitting in the center of the relationship, presses past every default option to the most important question of all: What is best for this person or this couple or this family who have entrusted their very lives into my care?

To answer that question requires deeper discovery, perhaps a visit to the home or business, a conversation about their childhood and how money was discussed around their kitchen table when they were 10, and how spouses differ in their understanding of wealth, values, and financial security. That takes time and an investment of energy and uncommon transparency. Such ventures into the sacred spaces of our clients’ lives take courage. Most of all, this deeper, more caring quest to find what is best demands a commitment to ourselves and those we serve that transcends the easy answers.


Each day teems with all manner of casual and critical decisions. What if we framed the word “BEST” and hung it on a prominent wall in our minds? My guess is that given a passing binary “good or bad,” “yes or no” choice, we might ask another question or consider another option. Making that choice empowers both your life and work to function at a higher, more caring level. In doing so, you will move the relationship to a place binary answers rarely experience.


(The writer, who lives in Augusta, is a certified financial planner and author of Cadence of Care: Imagining a Transformed Advisor-Client Experience. He can be followed on his blog at www.



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