Yes, we are in that time of year again. You know, the one that Hallmark celebrates 24 hours a day, filled with song and mirth and everyone celebrating together despite the inevitable travails, misunderstandings, and missteps. Somehow, by the end, it all works out perfectly. Sure, why not?

I don’t know for sure, but it is possible that Hallmark doesn’t accurately portray your family, or mine. Let’s face it, in reality, most families, even when they celebrate together, have challenges. Sometimes those challenges are simple differences in style or distance. Other times, competing life expectations are difficult or impossible to ignore. 

Many families use these holiday occasions for family meetings. For good reason. It may very well be the only time of the year when almost everyone is in the same place at the same time. If it is a family with shared financial responsibilities, the family meetings can be formal, and if the resources warrant, are often accompanied by non-family specialists such as attorneys or wealth advisors. Other times they are less formal, focused on the normal challenges of multi-generational families regarding senior citizen needs, property maintenance, and the like.

I am not a family systems expert, nor an attorney, nor a wealth advisor. But I do know something about family philanthropy [which requires that I also know at least a little something about family systems, law, and money]. It is often around the philanthropy meetings that the issues of expectations, values, life choices, intergenerational or sibling tensions get played out. The reasons are complex but, in general, it is because the philanthropy conversations can be an indirect proxy for all of the inherent issues of family dynamics. To take one of many possible examples: It may be overtly confrontational to accuse a sibling of being ego-driven and using family resources for personal social gain. It is a lot safer to allude to those things when that sibling insists on having his or her name prominently featured by a charitable entity and to address the implications for the rest of the family. Or for another: it may be awkward to accuse the founding generation of heavy-handed control when they are also the ones who have made your lifestyle possible. But it might be possible to get to that issue of control, circuitously, when that same founder insists that his or her charitable commitments must be endorsed by the grandchildren, even if reluctantly. It is a difficult discussion to be sure, but, when done well, that discussion can be about priorities rather than personality.

That these can be difficult meetings should not mean that they should be avoided. Rather it means that they often can benefit by being carefully planned or even facilitated by someone who understands the full picture. If structured well, with a full empowerment of all at the table, these can lead to a renewed family motivation, unity, and purpose. That does not mean unanimity of style, values, priorities; only that the process can be fulfilling in underscoring that this is a family choosing to honor its heritage, its possibilities, and its potential. There are proven methods to get there, and when done well, can leave a family much more gratified than when they start. 

For more than a quarter century, I have had the pleasure of teaching and advising literally several thousands of funders of all sorts. Most of them are family funders. Their starting point when they come to me, or to any of us who is in this sector, is often “giving money away is harder than we thought it would be.” 

There are times when deep underlying unresolved family issues are never far from the surface. I have seen late-in-life decisions by founders to create a family foundation in the hope that contentious offspring will find a way to resolve those hostilities with a common legacy and responsibility. Sadly, philanthropy can never magically resolve these kinds of long-simmering, never-resolved family issues – at least on its own. 

But for families with a more under-control set of issues, philanthropy can often enhance a family’s ability to appreciate one another and learn to make decisions together. They can lead to shared aspirations for successor generations and for a determination of how their noblesse oblige might be manifest in different places and in different ways.

Where might all of this play out? For many, at the annual family meeting. Since the decisions and feelings that will emanate from this meeting will last far beyond the aroma of even the most delicious holiday leftovers, it is worth putting time and resources into making it a productive and fulfilling experience for all.

Happy holidays.

Richard Marker is the founder of the Institute for Wise Philanthropy which educates and advises funders around the world. He is also faculty co-director of the University of Pennsylvania Center for High Impact Philanthropy’s Funder Education program.