Meeting a new family is one of the most interesting parts of my consulting work. Often they are eager to meet me and tell me their story and, at the same time, are hesitant to open up that very story. There is usually some level of hope that I can help them manage the complex family dynamics that every family contends with—and families sharing a variety of assets have to manage such dynamics in exponential form. And there is usually some fear about how difficult and painful the process will be.

Often I get wisdom from these families. For example, in my September blog, the patriarch in a new family client shared solid wisdom about being a Mentor versus a Tormentor. There can be a fine line between these two roles in family business/wealth. He offered wisdom and wit, all at once.

It takes courage for a family to open themselves up to me. There are complicated family relationships with lots of history, and they share wealth in many forms—businesses, foundations, real estate, complicated trusts, investments—which interplay with relationships. Some families dive in. Others are slow and careful. And it is all normal and understandable as they consider letting in an outsider who they hope can help in a significant way.

Over the last two years, I have been in regular contact with a potential family client. First I spoke with one member of a group of siblings who reached out after reading one of my blogs, which had spoken to him on a personal level. We were part of the same organization, so it was a friendly call based on common interests. We stayed in touch, sharing personal experiences of being in our families’ businesses, and got to know one another. Over time, it seemed I might be helpful in a more formal consulting role, and we discussed how that might work. I then met another sibling out of the group of six in the second generation.

As we explored a first step, I hoped to meet the parents (wealth creators) and all six siblings, many of whom shared basic values with their parents and, as they married and started their own families, had developed values in a variety of directions specific to their new and developing families. As I worked to find common ground about an initial, in-person meeting, the siblings had different ideas about who should attend and what the focus would be. The mother and father had different levels of motivation for the meeting and any potential engagement with me. As we went back and forth, trying to help their family find common ground, my point of contact expressed his frustration with the following text:

Every family is different, and we all have our challenges. This experience can be one you will reference for decades as it breaks the flexible mold you have built over the years in starting an engagement with a new family.

I was struck by his belief that his family offered a higher level of challenge than others I’d encountered. This could not be further from the truth (which I hope to communicate clearly to him at some point). I completely agree that every family has challenges; this family is no different. And in every engagement I’m involved in, sooner or later, each family’s special dynamics—loving and formidable—appear. Ironically, I prefer to encounter resistance up front and early, as it tells me what is important to the family, what their fears are, and how they relate under pressure—all things that help me understand and help them.

Another accurate insight I greatly appreciated in his comment was his perception of the flexibility of my “mold” for starting family engagements (although I disagree with his assessment that his family will break it). My mold is tremendously flexible by design. Family is complex on its own, money is powerfully symbolic and engenders intense emotion, and when both are combined, it is a special kind of intricacy that demands flexibility—especially from a newcomer to the system seeking acceptance on a deep and meaningful level.

Wisdom for Enterprising/Wealth-Creating Families

Own your complexity and proudly show it when you engage with an outsider for help. This is a way you communicate your story and any professional you consider engaging should expect and appreciate your family’s way of showing who it is.

Expect flexibility. If a professional is rigid and balks at your attempts to find a way to work with your family, be skeptical. Family is not one-size-fits-all; something almost all of my most respected colleagues possess is collaborative adaptability.