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What Does This Family Need, Now?

The Question That’s Always There

Each week here I discuss topics relevant to families who will be undergoing some sort of generational transition in the near future.

This work is complex and always needs to be done on a bespoke basis, because no two families are alike.

But that doesn’t mean that there aren’t some ideas that keep coming back, over and over again.

And sometimes those are the simple nuggets that help clarify things in a way that are more helpful than you could ever expect.

So this week I want to offer up one of the simplest ones out there, and that’s a question I always return to, time and time again.

And that’s why I used it as the title for this post: “What does this family need, now?”

THIS Family, Not That Other Family

It’s only a six-word question, and we’re going to spend the rest of this post looking at half of them in detail.

The first one is “this”, and that’s important for reasons already hinted at above.

Of course we can and will think about other families we’ve worked with before, but that can become a trap if we do it too often.

Every family is different, as already noted, but there’s also a time element to think about, but maybe I’m getting ahead of myself here.

We could also concentrate on the word “family”, to remind ourselves that we’re always considering the good of the whole family, and not any particular family member, which can often default to the one who’s paying us for these services.

What They NEED, Not Necessarily What They Want

The next word I want to highlight is “need”, and that’s because too often we end up paying attention to what the family wants, rather than what they need.

I realize I may be sounding a bit too much like a smarty-pants here, hinting that I know better than the family does, but I’m going there anyway.

Quite often what families come to us for when they hire us, based on what they say they want (because it’s really what they think they want) is not exactly what they really need.

Or at least the overlap of a Venn diagram of what they want and need is not a perfect circle, and usually far from it.

The Importance of Discernment

This work requires lots of discernment, and of course the tact to not point out what I just wrote above as overtly as I just did.

See On Discernment and Resourcefulness for Family Clients

My good buddy Mr. Google says that discernment is: 

         “the ability to see the big picture of what’s going on and 

           then to divine what needs to be done as a next step”

Fans of Patrick Lencioni, will recognize that his most recent book, The Six Types of Working Genius, includes discernment as one of the six.

It’s also one that lands in the top two of my own strengths, along with engagement.

NOW, Not Last Year, Not Next Month

As a family makes progress what they need from their advisors continues to evolve.

What they needed last year is different from what they need now, and if we get too far ahead of ourselves we may inadvertently be leading them into areas they aren’t yet ready for.

There’s a need to constantly try to assess and calibrate what we should be doing next.

Having other peers who also do this work can be helpful in getting some outside perspective on next steps too.

WHAT They Need, And Also WHO

I want to wrap up by looking at something that can be difficult to admit, and that’s the fact that sometimes what the family needs now is actually a new person to come and do this work with them.

It can be very gratifying to get a family to a better place and have them “graduate” from your services.

It’s also nice when you can see that moment before your client and exit before they fire you.

Sometimes a fresh person coming in to work with a family is just what they need, not unlike a sports team firing a coach who has “lost the room” and bringing in someone new with a different style and way of being.

In any event, the constant asking and re-asking of the question, what does this family need, now, is always a good place to return to when planning next steps.

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Where Everybody Knows your Name, and Job

Just Being with Others Who Get You

There are certain times and places where everything is just a little bit less of a hassle.

I’m currently in Boston, after spending the past few days at the Family Firm Institute’s annual conference here this week.

Such events offer an opportunity to catch up with lots of colleagues who do similar work, with similar client families.

Yesterday someone asked how I was enjoying the event and I replied that it was nice to be able to reply to the question “what do you do?” with a simple answer like “family governance and facilitation” and be met with an understanding nod, as opposed to a quizzical look.

Later on at dinner, a long time friend suggested tying in the title above, from the Cheers theme song, since we were in Boston (thanks AM!).

Knowing Others Facing Similar Challenges

All of those in attendance work with families in some way or another, and we all understand that every family is different, and that’s part of what makes this work interesting and challenging.

Nevertheless, despite the heterogeneity of families, we can all learn from one another, because in many ways, all families are the same.

See The Elusive One-Big-Happy-Family

When the work you do is so niche that most people you meet on a plane or at a party might require a detailed explanation, it can become tiresome to try to give more than a cursory response.

Spending time at a conference with others who face the same circumstances, with families as well as with curious acquaintances, offers a nice respite.

Let’s look at some examples from the past few days.

Mutual Apologies About a Tough Client

It was great to speak with another advisor who’d referred a client to me since the last time we were together.

But because that client situation did not work out great in the end for me or for the family, it was a bit awkward to talk about.

However, over the next day or so, as we interacted with others and shared minor details about the situation, it became funny because we realized that we were each apologizing to the other for what occurred.

He was sorry for the referral “gone wrong”, and I was sorry for the way it worked out too. Not every client is a good match for every advisor.

Imagine my surprise when I learned that the client was now starting to work with another long time friend and colleague.

I offered to share info with them, or not, should they choose to want my perspective on that family’s situation.

Parallels to the Family Business World

Having worked in the family business my Dad started for many years, I am also intimately familiar with the concept of everybody knowing my name, both inside and outside the company.

As I now coach those in similar circumstances, I sometimes refer to their name also doubling as their title, as in “you don’t really need a title, your name tells everyone almost everything they need to know”.

The fishbowl effect for such rising generation family members makes it important for them to have some coaching around this, as well as the opportunity to join peer groups so that they can commiserate with others who get them.

Everybody knowing your name has both advantages and disadvantages, of course.

The Latest Research and Books

The conference is also a good place to learn about the latest research and books available in the field.

I brought along a copy of a book I’d recently purchased because I knew that the authors would be there and I could get it signed by both of them.

I’ve had a grand total of one person do that for me (thanks PH!) and wanted to pay it forward.

Fewer Canadian Attendees

I also got to reprise my role as the unofficial, self-appointed, Canadian Ambassador to any international conference I attend, where I place Canadian flag stickers on the nametags of every fellow Canadian I meet.

For some reason I did not need nearly as many as I have in recent past years, but let’s not go there now.

I did get to use one of my favourite lines around smaller groups than expected, by saying we were going for quality instead of quantity.

Next year will be FFI’s 40th anniversary, and I’m looking forward to gathering with this group again in NYC.

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On Learning by Doing and Advising Others

If You Want to Learn Something, Teach It to Others

As I sit down to write this week’s post, I’m fresh off a couple of great experiences that I’m still processing.

Organising my thoughts to share here every seven days has helped me in more ways than I’ll ever realize, so if any readers also get something out of these posts that’s icing on the cake.

The first experience occurred last weekend, when I facilitated yet another family meeting with a client family, where we made progress for sure, but not in a straight line, and not without some emotions bubbling over.

The second was this week when I attended the final module of the most recent cohort of the FEA Program in Toronto, where all the teams shared their experiences and learnings from the family project they’d recently completed, including one by the team I’d been advising.

You Don’t Learn to Swim by Reading a Book

Let’s address the first part of my title, about learning by doing. 

The kind of work I specialize in is guiding families on their journey as they prepare to eventually transition their business or wealth to the next generation.

There are many technical and structural aspects to such work, all of which I recognize as important, but none of which I personally take care of.

Thankfully, the ecosystem of such professionals is finally learning to appreciate the value of those, like me, who have the knowledge and skills necessary to work with the human beings in these families, concentrating on the relationship and emotional aspects of this work.

These skills are learned by doing, usually first in training in areas like coaching, facilitation and mediation, and then honed in real life work, with real life people and their real life family realities.

You can’t learn to swim by reading books about swimming.

Doing, Teaching, Advising, Guiding

As occurs quite often in my blogs, a random combination of experiences in short order offers me a fresh perspective on things.

First there was an emotional outburst in a family I’m working with, then a presentation by people I’ve been working with in an advisory capacity, sharing a recent similar experience they had.

These experiences then coalesce in my head, and I process it all by writing this post.

Here’s a few notes I jotted down as I listened attentively to the team sharing their experience with the rest of their cohort:

  • When things get loud and then all of a sudden they get quiet, that’s OK.

 

  • Reframing by saying “I think you’re trying to say….” can work wonders when trying to help a family process their different views.
  • Being able to air difficult subjects is a strength of some families we work with.
  • Eruptions in a meeting are a sign that we’re doing good, important work

Sharing Is Caring, And Advancing the Cause

Whenever I work with a project team (I just started with my seventh) I always tell them that the final module, called “KIA”, for Knowledge Integration and Application, is the highlight of the program.

I’ve succeeded in inviting myself to parts of this module a few times and get so much out of it myself.

Participants sharing their experience and learnings, garnered from several months of working together as a multi-disciplinary team, with a real life family, is always enriching.

They’ve just learned by doing, and are all sharing that experience with others, who all just learned by doing as well.

Advising such teams on that journey is fun for me, and I learn so much from that experience.

And then I learn more again as I write about it, which also helps (I think) advance the entire cause.

Everybody into the Pool

I hinted at the swimming analogy above, which I often use when I talk about efforts to learn Bowen Family Systems Theory, so let’s jump back into the pool to wrap this up.

FEA Program participants are assembled into a team after having learned many concepts about family enterprises, what makes them tick, and the challenges they face.

They’re then forced to jump into the pool with a family, and they learn to swim by swimming.

The program provides structure and methodology, making sure the water isn’t too deep, and I guess as a project team advisor, I play the role of the lifeguard.

There’s no better way for all of us to learn together.

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Addressing Anxieties and Aspirations, Again and Again

Some Things Are Always on the Agenda

Working with families who want to transition their wealth or business from one generation to the next is fascinating and challenging.

Part of what makes it fun for me is that no two days are ever the same, because each family is different.

But some parts of the work are reliably predictable, and I always like to try to point those out when I come across an interesting way to do so.

So that’s where we’re going this week, with a hat tip to a long-time friend and colleague (B.E.) who unwittingly inspired this post.

She was hosting a webinar and innocently noted something about “…working with families on their anxieties and aspirations…”

I jotted that phrase down, loving the alliteration, which I later decided to add to in my title.

Alliteration Instead of a Mnemonic

Regular readers may recall that I self-confess to writing these weekly posts for myself, as a way to continue to refine my thinking about the career I’ve found myself in.

Sometimes I come up with a mnemonic way to remember something, which I’ve done as recently as a few weeks ago with Ideas on Dealing with the Family CRAP, or over eight years ago in Start Cleaning Up Your M.E.S.S.

While mnemonics have been a go-to for me over the years, I’m pretty sure this is the first time I’ve used alliteration.

Even though “anxieties and aspirations” barely qualifies, I decided to strategically add “again” for reasons I’ll expound upon.

Family Anxieties and Aspirations around Wealth Transitions

It’s completely normal for families to experience anxieties when thinking about how they’ll transition their business or wealth to the next generation.

My buddy Mr. Google says anxieties are “feelings of worry, fear, or dread”, and I know many family members have such feelings on a regular basis.

Aspirations, from the same source, are “strong desires or ambitions for things you hope to achieve”, and plenty of family members also have many such desires.

When a family is blessed with significant wealth, which some say is a great amplifier, both those categories, the anxieties and the aspirations, become way bigger than for the average family next door.

They Don’t Really Ever Go Away

Families have been dealing with these potential negatives and worries since the beginning of time, and the hopes of what they can achieve thanks to their privileged place are also always there.

For those of us to work with such families, part of our role is to normalize that these feelings are real, they exist, and that the best way to deal with them is to name them and talk about them regularly as a family.

The blog about Family CRAP mentioned above is all about Convening Regularly And Productively.

What I didn’t talk about in that piece was that anxieties and aspirations are always on the table, even when they aren’t labelled that way.

They’re just below the surface in almost every discussion.

The Family Is Comprised of Many Individuals

Things would be much simpler if there were such a single thing as “family anxiety”; of course each individual person has their own version.

The same is true of their aspirations.

This is why having a forum in which to discuss these, as a family, is so important.

When rising gen family members understand why their parents are concerned about things, conversations about that can assuage people.

When parents hear from their offspring about some of their aspirations, the family can come up with ways to support those.

Lather, Rinse, Repeat. Again and Again

These discussions are not a “one and done” occurrence. They need to continue to happen over and over.

When I’ve worked with a family for a few years, I feel like the Chief Repetition Officer, because we go over the same ground all the time, and that’s the way it should be.

There are always going to be anxieties, and the ones from 2015 or 2020 are not the same as the ones in 2025. 

And the ones in 2030 and 2035 will be different again.

The same goes for each person’s aspirations, they evolve and change all the time.

Addressing the anxieties and aspirations is never on the agenda, per se, but at the same time, they’re always on the agenda.

And they come up again and again, and that’s a good thing.

Families that make it a point to meet and discuss them will do better than those who don’t.

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Integrating the Wealth into the Family

Picking Up on Last Week’s Post

Last week, in On Family Wealth Integration, Revisited, we ran out of racetrack just as I was getting to something pretty relevant.

So I punted it forward a week and will now circle back to an idea I introduced, but then realized that I couldn’t do justice to in the space I had left.

I’ve become enamored with the idea that a big part of the role I play with some family clients is actually all about helping integrate the family’s wealth into their family.

I also understand that for many readers, maybe most readers, this is far from clear.

I’m used to the fact that the work I do is almost never clear, and I’ve been sharing ideas about it on a weekly basis here for well over a decade in an attempt to mitigate that fact.

I’ve also resigned myself to the fact that even if I continue for another decade, more work will need to be done.

But let’s see how much progress we can make on the idea of family wealth integration.

Let’s Check in with Mr. Google Again

My old friend Mr. Google is always very helpful so I’ll call on him once again here.

He now returns not just links, but also A.I. summaries, and you don’t even have to ask for them, they just show up, similar to ways A.I. keeps showing up unexpectedly and often unwantedly, all over our lives.

The A.I. overview of “integration” is “the process of combining multiple elements into a unified whole”.

For our purposes the two elements we’re combining are the family and their wealth.

While simply stated, this doesn’t mean much to most people, so let’s dig a bit deeper.

The family is comprised of several people, and since I typically work with families who intend to have their wealth last for multiple generations, I’m almost always dealing with parents and their offspring.

Talkin’ ‘Bout My Generation

The senior generation leaders have usually already integrated the wealth into their lives, so the challenge is around helping the rising generation(s) integrate the family’s wealth into their lives.

That leading generation, accustomed to the wealth as part of their lives, can sometimes underappreciate how the family wealth can be difficult for the rest of the family to fully integrate into their lives.

The Merrill report I linked to last week (download available at the bottom of that page) breaks down the journey that most rising gen family members go through during this lengthy process.

It begins with what they label as “Awakening”, which is all about when the young (or not so young) person becomes aware of the wealth that the family has, and that they’re now expected to integrate into their lives.

Let’s not forget that in almost every case, this wealth is not a simple drawer full of cash that everyone can access at any time, for any reason. 

See Inheriting Wealth AND Structures.

Confusion: The Most Difficult Part to Get Through

The stage that follows Awakening is “Confusion”, which has a sub-title that reads “I’m overwhelmed by what I don’t know”.

We’ll spend the rest of this post on this, but I need to share that the final three stages are Perspective, Learning, and Adaptive Integration.

Part of the difficulty in the Confusion stage is that it can be very frustrating, not just to the rising gen who need to work through it, but also to the leaders who can become impatient with the timeline.

And let’s not forget, we’re not talking about one monolithic generation of homogeneous people, we’re talking about individuals.

Each person has their own strengths and weaknesses, preferences and desires, learning styles and risk tolerances, and desire to do things together as a family (or not!).

When you then layer in a host of new relationships with advisors, it can quickly become a lot to take in, and it often intersects with a busy time in their lives, starting careers and families.

Why Does It Take So Long? Because It Does!

As I wrote years ago in There Is No Destination, this is all about each person’s life journey.

There’s no question that being part of a family with substantial wealth brings with it many advantages, but that doesn’t mean that it’s all rainbows and roses.

This stuff is very complicated by its very nature, and the family relationship aspect makes it very complex.

It takes time to integrate the wealth into the family, but doing things right usually does.

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On Family Wealth and Integration, Revisited

Is Integration the Newest Buzzword in Our Field?

Each week I share something that’s on my mind related to the world of families who own some sort of enterprise that’s expected to be passed down to subsequent generations.

I’ve immersed myself in this world for the past decade plus, and I’m fascinated at how it continues to evolve.

There’s always been a lot going on in this space, and it feels like it’s accelerating lately, which is generally a good thing.

And I’ve noticed that some advisors are using some new ways to describe the kind of work that I do and would love to see more of.

So this week we’re going to look at the word “integration” and see how it applies to this work.

You may be surprised that I’ve found three different ways to apply that concept to this work. Let’s go.

Integrating the Family Members into the Planning

I’m starting with this one because it’s been on my radar the longest, and some may consider it a favourite hobbyhorse of mine.

I first wrote about this idea back in 2018, in Stopping the Disintegration of Family Wealth.

That post came about when I suddenly realized that the word “disintegration” was actually just the opposite of “integration”, and I thought it was clever to suggest integrating family members into the planning to stop the wealth from disintegrating.

I believe in that concept even more strongly seven years later, although I’m less certain that my idea is as clever as I imagined at the time.

How About “Integrated Family Wealth Management”?

I’m a big fan of the work being done by the Ultra High Net Worth Institute and I have been since they introduced their Ten Domains of Family Wealth model a few years ago.

It’s too much to get into in a single blog post but if this is new to you, I suggest going to the UNHWI website or reading this piece I wrote about it for another website.

More recently, they release what they’re calling their “Wealthesaurus”, which is exactly what you would think it is, if you looked at the two words that it jams together (the first one being wealth).

If you scroll down their list of things they’ve made great efforts to define, you will find Integrated Family Wealth Management.

So let’s see what that is.

A Comprehensive Approach to Family Office Services

According to their definition, it’s a comprehensive approach to family office services that addresses all of the Ten Domains.

And, according to their definition, it also requires the involvement of at least one Integrated Family Wealth Advisor.

That person is “a family wealth advisor with the advanced interdisciplinary knowledge and skill to act as an integrator and team leader in the delivery of services to an UHNW client family”.

I love the fact that they’re naming it and defining it, because it incorporates so much of what I’ve been writing about here for years.

It truly is an idea whose time has (finally) come.

Here’s to more people who do this important integration work, fully understanding what it is and why it’s key.

What About Integrating the Wealth into the Family?

So now that we’ve looked at integrating the family members into the planning and having an integrated advisor who understands both the technical aspects and the relational ones, what’s left to integrate?

I’m glad you asked; it’s the wealth, which needs to be integrated into the family.

This concept leapt off the page for me recently as I’m working with a family that recently had a liquidity event, so instead of the family’s largest asset being a “wealth generating operating company”, it’s now a portfolio of stocks, bonds, ETFs, and other alternative assets, all being expertly managed by their MFO.

At our last quarterly meeting, I assigned some homework, namely the Inheritance Styles whitepaper from Merrill. (You’ll need to click to download the full report from that page)

The first half of that piece details three different ways inheritors act in families, and is quite enlightening in itself.

But the unexpected bonus is the second part of that article, which details the Five Stages of Wealth Integration.

To Be Revisited, Again!

This idea of integrating the family’s wealth into the family is one I will return to next week, because I’ve got a lot more to say about it and not much room left this week.

For families in a post-liquidity event scenario, it feels very compelling to me.

Much more to come next week.

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Ideas On Dealing with “The Family CRAP”

The Area Where So Many Things Break Down

Anyone who has any experience dealing with families in business together will recognize that such situations are rife with challenges.

Many experts say that situations involving the family relationships are more often the cause of business failures than problems that are “strictly business”.

Regular readers of mine will not be surprised to hear that I agree.

Yet so many professionals and experts who support business families concentrate their services in the business and ownership areas, and prefer not to get involved with all that “Family Crap”.

So this week we’re going to look at how some successful families actually deal with their “Family Crap”, and I’ll share some ideas that help families move forward.

All Families Need to Convene

The initial angle I was going for as I conceived this week’s post was around the verb “to convene”.

My good friend Mr. Google can help us out here, if I just enter the word “convene”, he returns with:

      Come or Bring Together for a Meeting or Activity, Assemble

I think that definition is helpful, because it puts a bit more formality around the idea of having a family meeting.

It speaks to the idea that someone has to initiate the “bringing together” and the fact that there will be some “activity” going on.

I’m often in a position to suggest that families get together more often to discuss important matters, and I’m starting to like the word “convene”.

They Need to Convene Regularly

So once we’ve agreed that convening family members is a worthwhile exercise, there are still a few other key elements we need to consider.

Quite often family elders and leaders will clearly understand that sharing information about how family assets are owned and organized is something that needs to be shared more broadly within the family group.

See Inheriting Wealth, AND Structures

And those folks also typically just want to get it all over with in one fell swoop. I get it, it probably won’t be fun, so let’s just rip the band-aid off and be done with it.

The problem with that approach is that it almost never works well, even if it feels good in the short term.

See The Dimmer Switch Vs. the On/Off

I always suggest that families get into the habit of convening regularly.

Letting the Clarity Evolve Over Time

When families establish a process of having regular meetings (quarterly or annually are popular intervals), information can be shared gradually, and family members who are usually not in the loop can absorb the information, and learn as they go.

The biggest problem with the “one big meeting” to get it over with, is that many family members end up drinking in the information through the proverbial fire hose, which is not the ideal way to satisfy one’s thirst.

So you want to get in the routine of convening the family regularly, and that’s still not enough.

You also want to ensure that the meetings are productive.

The meetings need to be set up so that when a meeting ends, things are more clear to everyone than when the meeting started.

CRAP: Convening Regularly And Productively

Apologies for waiting so long to get to the punch line, but the best way to finally deal with the “family crap” that so many families and their advisors try so hard to avoid, is to counter that crap with CRAP.

          Convene Regularly And Productively, i.e. CRAP!

You won’t be surprised to learn that I believe the key to “productively” is to have a neutral third party run these meetings.

Families all have their set ways of dealing with each other in the family group, or “family system”.

See Diving into a Family System Without Making a Splash

What I’m proposing in this “convening” is something special enough to warrant hiring an outsider to handle the facilitation of these meetings.

Yes, at first it seems like a luxury. In the long run, it is the biggest difference maker.

No, This Is NOT Easy. Most Families Don’t Do This, Either.

I’ve tried to simplify things here because simple is easier to understand. But simple doesn’t mean easy, and I’m not saying this work is easy to do.

Most families don’t do this. 

Most families don’t have as much at stake as families who own a business or assets together, that they are hoping to transition to the next generation.

That work takes planning, and making sure everyone is clear on what’s happening.

Start taking care of the Family CRAP.

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Let’s All Stop “Should’ing On People”

Say It Out Loud, Really Fast, for Effect

Writing this weekly blog is the main way I communicate my thinking, and it’s a wonderful medium to share my thoughts, for the most part.

Sometimes, it’s not quite as good as the spoken word, because the attempt at humour that I’m going for depends on the ability of the reader to pronounce a word in the exact right way to get a joke to work.

So I hope you’ll all been able to get it, and maybe the accompanying visuals will help.

If not, it’s OK, because the joke isn’t germane to the point, which is that we might do better in our attempts to advise people if we didn’t simply always tell them what they “should” do.

Yet Another “Combo Post”

So this sound-based double-entendre between should and “poop” is the initial inspiration, but on its own, it didn’t have the heft to carry a whole post.

As often happens, an idea sits in my Blog Ideas folder for a while, and then something else will come up and I combine ideas.

A while back, I had yet another exchange with a regular reader in which they relayed something about “changing ‘shoulds’ into ‘coulds’” being healthier when advising families. (Thanks JG!)

The point is that having a family come up with their own solutions is almost always better than having them simply follow the instructions of any advisor.

Let’s Stir In Some Self-Righteousness

Thus far you may be thinking that I’m directing these thoughts to advisors who work with families, and of course I am, but this also applies equally to members of families when dealing with each other.

The final part of the inspiration for this post was a missive from a few weeks ago, On Vulnerability and Self-Righteousness in Families.

Therein, we looked at how those who are self-righteous come from a position of assumed moral superiority over others.

When you add in that element to someone who’s constantly “should’ing on you”, I think you can imagine why such messages are sometimes not well received (even when they are acted upon).

When I say “I think you can imagine”, I do realize that while most people get this, those to whom this message is being directed are unfortunately least likely to recognize themselves.

From Know-It-Alls to “Just Trying to Help”

There are always people who just think that they’re so smart and are also very certain of themselves, no matter the situation.

Many people who grow up in successful families are blessed (cursed?) with such parents.

Most of these “know-it-all” types also convince themselves that they’re coming from a good place and “just trying to help”.

It can be difficult to escape their force field, especially when there’s ample evidence of their success, making their ideas seem like they should be correct.

We can have such people around us at work or within friend or community groups of course, but they’re often most dangerous within a family.

Insidious Within a Family

I’ve had the privilege to work with many family groups, where several people who are related by blood need to work together, in order to make decisions around assets that their family owns for the benefit of the group.

The propensity to “should” on others most often happens between generations, but also sometimes occurs in sibling or cousin groups.

It can actually be even more fascinating to observe in such situations, because it’s rather rare.

And when I say “between generations” you probably default to parents should’ing on their “children”, but in some families the script gets flipped as parents age. 

See My Favourite Oxy-Moron: Adult Children.

The attitude of moral superiority and certainty, which combine to define self-righteousness, is sometimes difficult to watch; imagine living under it!

Mel Robbins – The Let Them Theory

I probably shouldn’t mention a book that I have not read myself, but I will make an exception, based on the reviews it has received and some personal endorsements for it that I’ve heard from people I trust.

I can’t put it better than this, directly from the Amazon listing: “a simple mindset shift, to break free from others’ opinions, drama, and control”.

The book’s title suggests that it’s aimed at the “should’ers”, but that phrase implies that it’s also for the “should’ees”, which makes me want to read it.

It’s hard to get the “should’ers” to stop, so maybe equipping the “should’ees” is the way to go.

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Improving a Family’s Situation Vs. Solving their Problem

The Two Approaches Are SO Different

Enterprising families preparing to transition responsibilities and asset ownership to their next generation typically rely on various experts along the way.

Regular readers of mine know that I specialize in accompanying families on such journeys, trying to help them get things right.

You’ll also recognize that I’m sometimes frustrated that this “human relationship” work often plays second fiddle to that of the experts who support families with easier to understand services, like investment management, tax strategies and trust structures.

Each week here I try to illuminate some of the challenges in this work and this post is no exception.

I’m also a life-long learner, always working on finding new and better ways to support those who choose to work with me.

Family Systems Theory as a Base

It’s been over a decade since I first immersed myself into learning about Family Systems Theory, specifically the Bowen variety.

I even wrote a book about this effort, Interdependent Wealth, published in 2019.

More recently, I stumbled upon a course on Systems Thinking (i.e. general, not simply family systems) and decided it was worth taking.

I knew I’d learn a lot from it and I did, and this week I want to share one specific learning for the benefit of others involved in family continuity work like me.

The title of this piece gives a strong hint, yet I know that I need to put this all into proper context to make it make sense.

Let’s just start with what I think is obvious, that those who serve families with products and services like those noted above are problem solvers.

And families do have problems to be solved, so those problem solvers are very much needed.

Please Don’t Stop There. More Work Lies Ahead!

What so often occurs, however, is that once one of those “problem solutions” is put into place, the family believes that their work is done and that everything else will automatically take care of itself.

So many of those who serve families come from the “solution provider” angle, and not enough of us come from the “how can we improve your family situation?” side of things.

The Systems Thinking course I took gave me a fresh way to think about and talk about this challenge, as I had hoped it would.

The “problem solving” versus “improving a situation”, comes from two different kinds of systems thinking, unfortunately named “hard” and “soft”.

Hard Systems Thinking and Soft Systems Thinking

When I use the word “unfortunate” above, it’s because it just repeats a term that gets misconstrued in this work, which so often has the area in which I specialize categorized as “soft skills”.

I’m not sure why, but soft skills are frequently denigrated as less important.

I’ve written plenty on this, notably in Liberal Arts vs. STEM Skills to Serve Families, and Circle Gets the Square, Non-Hollywood Version.

In short, hard systems thinking is about solving a specific problem, while soft systems thinking is about improving a situation.

Here’s what Google’s A.I. summary shared when I asked it:

        Hard systems thinking applies quantitative, structured methods to solve well-defined technical problems with single, optimal solutions, focusing on objective criteria and predictable outcomes. 

         Soft systems thinking uses qualitative, human-centered approaches to address complex, ambiguous problems involving multiple, subjective perspectives, aiming for achievable and desirable changes rather than a single perfect solution. 

(Emphasis added in bold and italics)

More Metaphors and Analogies

It struck me that because I deal with families, I should share some analogies or metaphors related to families.

So here goes.

Having just celebrated my 33rd wedding anniversary, let’s go there. We had a wedding, during which we signed some documents to officialise our union.

That was a one-day event, and the following 33 years of our marriage have been all about learning to live with each other.

The priest who married us took care of solving our problem of not yet being married, but the work of a marriage and living together is much deeper.

Along Came the Children

Years l later, my wife delivered two great children to the household, assisted by some doctors and nurses along the way.

They helped solve the problem of getting the babies out of her womb, but the work of raising them was an everyday undertaking.

The soft stuff is always there, and it’s a lot of work.

Helping some families with the tasks of figuring out complex transitions goes better with the right support, hard and soft.

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Challenges Re-Engaging Families for Yet Another Journey

How Did Their Previous Ventures Together Go?

Each week here I share some of the realities that surround the kind of work I do with families.

Recognizing that my work is part of a “niche within a niche”, I know full well that most people have difficulty grasping just what it is that I’m trying to accomplish with my family clients.

As I crafted the title for this post, I stumbled upon a pretty apt word, “journey”.

Just about every family I’ve worked with has come to a point on their journey where they recognize the need to broaden the base of family members involved.

The current leading generation eventually accepts that there will be a point where they are no longer in charge, and preparation for what comes next must begin.

Bringing In Outside Support

Wise family leaders also realize that in order for this next phase of the journey to go well, they’d best bring in some outside support, because things can get complex pretty quickly.

I always applaud them for coming to this conclusion, even though sometimes it takes them more than one attempt to find the proper resources to assist them.

This week’s post is inspired by the fact that it recently dawned on me that I have three current family clients who initially embarked on some version of an expanded family journey with the rising generation a few years back.

And now, those past experiences are creating additional challenges for me as I try to help them navigate this next leg of trying to progress to a better place together.

Journeys Evolve Along with their Participants

My writing about journeys here goes back several years, my first post on this being There Is No Destination.

That post looked at how too many people consider so many aspects of life as “somewhere to get” as a goal, whereas I think it’s much healthier to focus on enjoying the journey along the way there.

I followed that up a few years later with Guiding a Family’s Interdependent Journey, which detailed how family members’ lives are probably more intertwined than they may realize.

Supporting families as they prepare for an eventual wealth transition is a very long process.

Ideally the work is spread out over years, although sometimes it happens in fits and starts.

The life stage of the participants is always an important factor to consider when assessing how much engagement you can get from everyone whose input and participation you’re seeking.

You’re Not the Boss of Me

Professionals who work with businesses are often surprised at how difficult it can be to get a large number of family members into a room together, or even on a virtual call.

In a “normal” (i.e., non-family) business, the boss calls a meeting and everyone shows up. If not, there are consequences.

Such rules are subject to different interpretation in many family situations, where offspring cannot simply be ordered to attend meetings.

So imagine families who’ve been on some kind of journey together, but it got “stalled” for some reason.

Trying to energize everyone to re-enroll in something again will probably come with major skepticism.

What a Difference a Few Years Makes – 3 Versions

Sanders:

Back around 2020, the “Sanders” family was fresh off a liquidity event. 

They all lived close together, and ideas of keeping the family fortune together had them assembled together with advisors from their accounting firm.

In 2025, now geographically scattered, their needs were now much different, and re-engaging them into a family project is more difficult.

Perry:

Around 2016-2018, the “Perry” family still had a large operating company run by 3 “G2” siblings, and they began working on gathering together as a large tribe to sketch a way forward to bring in G3.

After selling the OpCo, the work on the journey forward with one of the branches around the dining room table looks much different, and patience with “re-doing” some of this again is in short supply.

Taylor:

In 2019, “Mike Taylor” was looking for support to bring his teenage G3’s into a discussion about their wealth.

Now that most are in their 20’s and working, those shifts demand a new approach.

Facilitating Things from Where They Are NOW

When guiding them on these journeys and facilitating their meetings, I’m constantly re-assessing where they all are, and how the journey is progressing for each of them.

I’m meeting them “where they are” and that’s a moving target!

And I’m hoping they’re up for it.

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