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Reflections on Some Recent “Yes or No” Decisions

Working with families trying to overcome the challenges of transitioning their business or wealth from one generation to the next can be fascinating.
As I move towards elder status in this field, making choices on which opportunities appear most interesting to me has changed a lot over the years.
Early on, what seemed attractive enough to pique my interest was much simpler.
With time and experience, the way I now think about whether something seems like a good fit for me has evolved quite a bit.
As I recently reflected on some sticky situations I’ve found myself in, I came up with a quick list of questions that I ask myself.
What Was Most Important Back Then
After having my calling to do this work with families on the human and relationship aspects of family wealth, I put up my proverbial shingle and got the word out that I was available.
During those early years, anyone who showed the slightest interest in hiring me to work with them was a hot prospect, and I was inclined to say yes to every opportunity.
“Will they actually hire me?” was the first question, followed quickly by “Can I get them to pay me for the work?”.
Now as I counsel younger entrants to the field, I sometimes have flashbacks to those days.
The criteria of someone new to the profession is necessarily different from that of a veteran.
Some More Recent Priority Questions
Let’s look at what is now the first question I ask myself when I’m introduced to a family.
“Can I help this family?” is my starting point.
This is not as simple as it seems at first blush.
It comprises elements of the family’s readiness to do the work I will be asking of them, along with my perceived expectation that I can get buy in from all family members that I’m there for them, and not just for the person who wants to bring me in initially.
There are a whole bunch of other nuanced versions of this question, not the least of which relates to whether they’re all working in good faith or not.
See My Good Faith Presumption When Working with Families
What Can I Learn from this Engagement?
A more recent addition to my list of questions looks at whether the new client or situation offers me an opportunity to learn something.
I’ve always loved the variety that this work brings with it, because I don’t want to get bored with more of the “same old same old”.
When a friend and colleague recently asked me to join them for a family mediation, I hesitated at first, because part of me keeps telling myself that I want to get away from high conflict families.
But then I thought about how this gig would offer me a chance to stretch into my discomfort and learn something along the way.
So, because I believed that I could help this family and that it would be a good learning opportunity, I said yes.

What About the “Getting Paid” Part?
We’re finally getting to the question that many would put at the top of the list.
I can attest that finding clients who are ready and willing to pay someone to support them through their challenges is not as easy as it might seem.
For over a decade I’ve been preaching that while there’s a huge need for people who do the kind of work I do, that need does not automatically create a huge demand for these services.
The question of how to charge and how much to charge is one that arises frequently when I am with peers.
It is not simple, all of us advisors are different, and the families are even more heterogenous.
When you add in the occasional “will I get paid?” on top of the already “can I get paid?” it’s even more precarious.
A Few More for Good Measure
After considering if I can actually help anyone and if I can learn something, getting paid for it is also nice.
I suppose some extra questions that come to mind is “Will this be fun?”, along with “Will I get to work with interesting people?”
As someone who shares about this work, there’s always a hint of “Will this work end up giving me some nice blog topics?” to consider.
Here’s to getting to ask these questions often for many more years.