Working with enterprising families as they prepare to transition to the next generation, as I’ve been doing for the past decade, I’m continually amazed at the different challenges this work throws at me.

It’s been heartening to exchange with so many other colleagues who practice in this same space and to realize that this isn’t just something that affects me, but also everyone else who toils with family dynamics in their various manifestations.

It’s probably the biggest reason this work is so rewarding because you never know what you’ll discover when working in the “family circle”, and even what seems like it should be simple “discovery work” often requires lots of detective skills.

There’s Information in Everything

When starting with a new prospect, the mystery-solving begins, as the person who first reaches out presents their view of the issues and the presenting problem to be addressed.

At this point, it’s important to be a sponge and try to soak up any and all information, putting as many puzzle pieces on the table as possible.

As more people are heard, typically in one-on-one calls, more information is shared, and more puzzle pieces are added.

In addition to the facts that each person shares, there’s also information in how they share it, including who volunteers to step up for these calls quickly and who needs to be cajoled into participating.

Imagining the Entire Puzzle and Knowing You’re Wrong

When I first started this work, I’d get to a point where I’d heard from a few people and believed that I had a pretty good idea of what the challenge was, who the players were, and how I could go about working with them to make some important progress together.

Nowadays, I’m much more realistic in my expectations, and I understand that early on in any family engagement process, it’s next to impossible to get a good read on where things should go, can go, and will go. And that’s okay too. 

Well, it’s okay with me, but often harder to get clients to buy into the fact that whatever simple situation they initially believed needed to be addressed actually turns out to be much more complex and that a simple solution won’t likely suffice.

Subjectivity and Selective Sharing

Two of the major reasons underlying the difficulty in getting the full picture as an outsider to the family system come from the way we get our information.

On rare occasions, there are ways to read up on a family from third-party sources, but those can be fraught with misinformation in many cases, even where they do exist.

We get most of our info from the members of the family, each of whom has their own version of the truth.

Of course, knowing how each person in the family perceives the facts is very important to understand, but when the goal is to develop an objective, “outsider’s” picture of reality, skills of discernment always come into play.

There’s a deeper level to the subjectivity question too, and that’s the selective sharing that also happens, meaning that skeptical family members will hold back on sharing their full and true feelings until they believe that the person with whom they are sharing can be trusted.

Trusted with What, and for What, Exactly?

Of course, trust is a key concept in many areas of life, but when it comes to family businesses and the relationships of family members, everything seems heightened.

So when we look at developing trust as an outsider coming into the system, we need to do everything we can to make sure that each family member feels like they can trust us.

They need to trust us with their deepest feelings, many of which have not been shared with all their family members.

And they need to trust that we are there for them individually, as well as for the entire family as a whole.

To do so, we need to listen to them without judgement in order to gather all of the clues we’ll need to be able to properly serve them.

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