Boomers are planning their succession. Here’s the hardest question they face, according to a veteran generational wealth expert

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As my generation of baby boomers faces the inevitable, the vast majority of estate plans involve a fundamental question: Should each of the kids be treated equally–or should more assets be directed to those with less financial security?

We sit with folks, often in their late sixties, who tell us that their kids are all on track, with no special medical needs. The adult children have chosen diverse career paths and enjoy disparate levels of financial success.

Of course, there is no right answer. The nuances are important. But after decades of considering the issue, my default position is to treat all children equally.

I start with the obvious: “It’s your money. You are entitled to do as you wish, with no justification nor explanation.” However, the focus quickly shifts to what the parents are trying to achieve.

For most families, maintaining cordial relationships among future generations is a key goal. That becomes much harder when kids learn that their parents’ final wishes are not based on equal shares.

After a death in the family, even the sanest among us compare relationships. Who was the favorite? Was everyone loved equally? How obvious was the situation, both inside and outside of the family?

Feelings about love and money often merge or even collide.

Importantly, parents who note that their kids are all on track generally know that the next generation’s diverse financial status is a matter of career choice or lifestyle–not the kind of hardship that tugs at heart–or purse–strings.

For parents who want to even things up and give more to those who appear to need it, the wise choice is often to do so during their own lifetimes. There are many tax-savvy and well-recognized methods to achieve that goal.

Advisors disagree on whether and when to discuss these decisions with family members. Many favor open dialogue about who gets what, well in advance. My personal advice, echoing the late architect Mies van der Rohe, is that “less is more” in initiating such discussions. 

Family meetings of this sort are fraught with emotion, often invisible in the moment. People tend to hear and remember what they want. If you are thinking of convening a generation or two for such as discussion, rehearse being clear and direct, lest the curtain on the drama be raised unnecessarily.

A.G. Newmyer III founded U. S. Fiduciary Advisors, LLC, 25 years ago.

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The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.

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