One Is Usually Better, But Not Always

This week we’ll be looking at an idea I’ve touched on in the past, but in a new light, thanks to an interesting exchange I had at a conference I recently attended.

When I crafted the title to this blog, I was convinced that I’d be able to link to a previous post that I’d written specifically on the “Responding Versus Reacting” concept I so often mention when speaking with people, but alas, that blog exists only in my imagination.

I will, however, still be revisiting the idea, because the conversation noted above forced me into a few different reflections: on the subject itself, how universally true I thought it was, and on how I share my thoughts on it.

So far this has been rather vague, I realize, so thanks for indulging my meandering style of setting up these weekly missives.


The Perfect Set-Up for Sharing a Favourite Idea

Allow me to set the context for you. 

It’s the evening before the first day of the conference, so I headed down to the hotel bar to see who else flew in early.

After chatting with some long-time friends and acquaintances at a table, I’m heading back up to my room to get some sleep when I happened to recognize a face from last year at the bar.

Next thing you know I’m offered a drink and I’m suddenly chatting with a small group of mostly strangers here for the same gathering.

One of the men begins relating a story about tension between a father and son, and we start talking about ways the son can learn to avoid similar situations with his own, teenage son.

Next thing I know I’m sharing one of many Zig Ziglar stories I have in my repertoire. 

(Curious readers are invited to type “Ziglar” in the search feature of my website).


Responding Versus Reacting

So I begin sharing the key differences between responding to a situation and reacting to it.

The simplest way to remember it, is to consider a medical situation and how we speak about the interventions that happen at the hospital.

“They gave him medication and he is responding” is always positive, whereas, “He had a reaction to the medicine” is negative.

When we take a step back and compose ourselves and respond to something that happens or what someone says, we have a better chance of things going well, versus immediately reacting without thought, which often escalates a situation.

When taken aback, I sometimes deliberately pause and even say, “I want to take a moment to think about this so I can respond, rather than simply reacting”.


I Thought It Was Clear, Until….

I felt like I’d made my point well and the conversation veered into a few different directions.

But imagine my dismay, when a while later one of the guys was relaying another story, where this time the problem was that someone had become way too complacent with a situation, and the protagonist was not responsive enough.

And as he concluded, he pointed to me and said, “Like you said, he should have reacted!”

Wait, what? 

I felt stumped and was thankful that the number of beverages consumed by all made this fade away as the subject once again got changed.

But I now had some reflecting to do, as my concept had been turned on its head.


Time to Revisit This

I think it was on the plane back home a few days later that it hit me that I needed to circle back and reconsider what happened and how I talk about this important subject.

Did I not explain myself well enough, was there a problem with my metaphor, or is it something else?

I believe I did explain it well enough, but there are limits to every metaphor, this one included.

It is still a good idea, in most cases, to pause and take a moment to provide a considered response to something, rather than simply quickly giving your gut reaction.

And, there are also times when pausing for way too long can be sub-optimal.


Flexibility Is an Asset

We need to recognize the limits of rigidity and the benefits of flexibility in many areas.

How long we take to reflect before we respond is probably one of those areas, but I will continue to err on the side of pausing.

All Happy Families Are the Same…

Most weeknights after having dinner and watching the news, my wife and I watch Jeopardy together.

A couple of months back while doing this, there was a clue that referred to a famous quote from Tolstoy’s Anna Karenina.

Because my wife was unfamiliar with it, I asked my friend Mr. Google to get me the exact line, which is actually the opening sentence of that classic book from the 1870’s.

It reads, “Happy families are all alike; every unhappy family is unhappy in its own way.”

Unfortunately, this highlights the fact that there are lots of ways for families to be unhappy.


99% Unhappy, 1% Happy?

The very next day we were driving somewhere together and for whatever reason, it came up again, and we talked about it.

She noted that there are way more unhappy families, suggesting the figure of 99%.

I chose not to argue with her, and we both agreed that I had the workings of a blog post about this, so here we are.

The title of this post is meant to highlight the fact that most families want to be perceived as “One Big Happy Family”, but that under the surface, very few of them actually are.

As someone who works with families on the important subjects relating to their future wealth transitions, helping move a family from “unhappy” to “happier” is part of what I’m usually going for.


Who Gets to Judge this Matter?

A constant challenge to this work is that the family is not one unit, it is a system of many interdependent human beings, who each have their own views, opinions, feelings, and behaviours.

Many of the professionals who handle the more technical aspects of this work can get away with thinking about the family as a unit, but those who work on the relationship angle between the family members are constantly confronted with individual differences in each person.

There are usually some people who think of their family as a happy one, where other members of that same family would disagree.

Who gets to decide if their family is happy? 

What if I think we’re happy but I’m the only one who thinks that?

Ideally, we can find a way for families to talk about this to find ways to make each person a bit happier, which should thereby make the family happier as a result.

Could it be that simple?


Looking Back at a Couple of Past Posts

Thinking about this subject conjured up a couple of posts I’ve written here that touch on this subject.

First, in On Wellness, Performance, and Relationships in Families, we looked at how those three subjects are a convenient way to consider how people are doing.

Are they feeling well? Can they do what they’re trying to get done? Do they get along with all the people they interact with?

I suggest that the more Yes’s you get to those questions, the happier you’ll be.

And if more members of a family can get 3 Yes’s, that family would likely be happier too.

Key Question: Are there ways for the family’s wealth to support and contribute to getting more Yes’s to those questions from more family members?


Should Happiness Be the Goal?

Unfortunately, many people put a bit too much focus on happiness as a goal, which can bring negative results.

Back in 2022, I shared Make Sure Happiness Is a By-Product, Not the Goal.

That post was inspired by a session at an FFI Conference where a person who specializes in addiction treatment and recovery was the one who stated the line I used as my title.

How many parents do we know who did everything to make their children happy, and then realized (and regretted) that their kids did not develop enough resilience and independence to launch into adulthood.


Maximizing Each Family Member’s Human Capital

As is so often the case, when I set out to write on this week’s topic, I didn’t know where it would lead.

Between you and me, that’s what keeps me coming back each week, but please keep that to yourself.

If you want a happy family, those “interdependent human beings” that compose the family should probably be your focus.

If you’re fortunate enough to have accumulated plenty of wealth, why not use a portion of it to try to enhance the “wellness, performance and relationships” of every family member?

Maybe that’ll help you have that One-Big-Happy-Family we all strive for.

What Happens When You Can’t See?

The virtual meeting world has certainly changed the way people meet, especially in the past half decade since the pandemic changed everything.

You’d think that after this many years, we’d have figured it all out, but alas, it seems like we have not.

Lest you think I’m getting tired of hearing “You’re on mute!” one time too many, that’s not where we’re going this week.

I’ve touched on some of the issues around virtual meetings in the past, notably in Who’s Zooming Who, and “I Can’t Hear” or “I Can’t Listen”?

But this week we’re going to look at what can happen when you purposely shut off a sense to good effect.


It Started with a Tech Glitch

A few months back I got on a call with a colleague and for whatever reason my camera did not work, so she couldn’t see me.

I was surprised to realize after a few minutes that the fact that I knew she couldn’t see me was affecting the way I spoke to her.

I you’ve ever been on a Zoom or Teams call with me, you know that I’m typically rather animated in my gestures and facial expressions.

Likewise, I prefer to be on calls where I see the others, because I also glean lots of information from non-verbal cues.

More recently, on another call with her, I mentioned this experience to her, it sparked her to mention the “hide self-view” feature in Zoom.

That’s where you can modify your settings on a Zoom call so that you still see everyone else who’s camera is on, but you don’t see yourself.


Try It, You’ll Like It

So we both immediately tried it for the rest of that call, and I’ve gotta admit, it was different, and maybe “more normal”?

Being somewhat slow to change habits, I haven’t incorporated this into my routine, yet!

Then a couple of weeks ago, on a call with my coach, she relayed an interesting experience she’d recently gone through as part of a leadership training exercise.

She and a group of people who’d been in the same cohort for a while were assembled in a group, and then blindfolds were handed out.

They were all instructed to put on the blindfolds, and then prompted to share something with the rest of the group.

Somehow, understandably, the quality of the sharing was deeper, because while blindfolded, there were fewer distractions that might otherwise have inhibited the person sharing.


Eliminating the Dominant Visual Cues

This story about the blindfolds prompted me to share what I just wrote above with her, and so she tried the hide self-view and liked it.

On our next call she told me she’d been using it ever since and loved it, so of course I mentioned that she had something stuck between her teeth and she believed me, for a second.

But this whole topic rang a bell about something she shared with me years ago, that difficult conversations sometimes go better while driving in a car, because the two people talking are not looking at each other.

When I reminded her of that, she mentioned that there’s research that proves that couples who go for walks together have longer relationships, quite possibly because they can have conversations where the dominant visual cues don’t actually harm the flow of ideas.


Tried and True Mediation Methods

Now that the ideas were flowing between the two of us, that roused in me the old mediation rule that you should try to avoid having opposing parties sit across from each other.

If you can get the people sitting beside one another, and put the “problem” on the table for both of them to look at from the same vantage point, your chances of success go up dramatically.

It seems looking at someone eye-to-eye may conjure up feelings of adversity that would be better off minimized.

This seems to be yet another case of “less is more”, where not having all the information or cues helps yield a better result.


Try Something Different for a Change

I’m hoping that this post might inspire readers to try to shake things up and try different ways of communicating, especially in relationships that may be getting stale.

Even that “hide self-view” feature on Zoom is something I think I may implement myself, because it probably feels more natural to talk to others without seeing myself on screen constantly!

The First Part of Is More Appealing than the Second

This week we’ll be looking at an aspect of the world of wealth transitions that I typically don’t put a lot of focus upon.

In some ways though, this is a subject that’s long overdue, and I finally have a good excuse to introduce it here now.

We’ll get into more details below, but I want to start with the words I put in my title this week, about how people in a wealthy family will eventually inherit wealth, but that wealth typically comes in some form of a “structure”, or more likely, “structures”, plural.

I recently heard someone put it that way, but the first person I heard it from years ago is a good friend who was recently my guest on a podcast I hosted, and because that episode just dropped, it’s fresh in my mind.


Stop Frankensteining It

The podcast was Family Enterprise Canada’s Let’s Talk Family Enterprise, episode 68, titled Stop Frankensteining It.

My guest was Cindy Radu, and she was the first one I ever heard say “people in families inherit wealth, AND structures”.

The Frankenstein part is all about how lots of different professionals are typically involved in the creation of said structures, and the result is often some abomination.

The take-away message for this part is that incoherent, overly complex and incompatible structures make it even worse.

I feel like I may be digressing too much so I want to just get back to what inheritors are actually going to inherit.

Suffice it to say that most are happy about the wealth part, and less enamored with the structures that invariably come along with the wealth.


Very Valid Reasons for Structure

There are of course a number of very good reasons why people create such structures, and so it’s important to acknowledge what they are.

The goal is typically one of wealth preservation over generations.

The cynical way to state this may be “I want my grandkids and great-grandkids to benefit from my hard work and good fortune, so I need to make sure my own kids don’t spend it all or allow it to fritter away”.

The most common reason espoused is to save taxes, wherein the government / tax man is the common enemy of the whole family.

It’s very easy for any wealth creator to be seduced by a plan that clearly shows, down to the last dollar and cent, that if you do nothing you’ll pay $XXX to the tax man, but, if you implement this great plan I’ve drawn up for you, that number shrinks or even disappears.

All too often, though, that “tax tail” ends up wagging the whole family dog.


Limiting Access and Maintaining Control

The structures that get put in place also usually limit access to the wealth to specific people at specific times and for specific reasons, all with the goal of maintaining the family wealth for posterity.

This is sometimes couched in reasoning like protection from creditors and former spouses too.

There’s usually some terms in place that allow for certain people to remain in control of the wealth, lest the heirs be allowed to use it at will.

You can imagine that those for whom all this is purportedly being done may look at these structures in a negative light, that somehow leaves them feeling less than perfectly trusted by their forebears.

And that’s why it’s important to take the time to discuss and explain everything to the stakeholders.


Preparing the Heirs for the Wealth

There’s an expression I like that says people spend lots of time preparing the wealth for the heirs (i.e. creating all these structures) and not nearly enough time preparing the heirs for the wealth.

Preparing those who will inherit is better than not preparing them of course, but what is sufficient preparation?

So many people immediately jump to “financial literacy”, and while important, it is rarely enough.

Regular readers know that I encourage regular meetings that include dialogue between generations, so that information can flow upwards as well as downwards.

This allows the family to learn how the wealth can and should be used and stewarded for future generations, and allows the structures to be understood and modified over the years to evolve as the family evolves.

The structures are necessary, as we noted, but they don’t need to become the bogeyman.

Throwing Another Analogy onto the Fire

If the quote in my title sounds familiar, you’re probably a boomer like me, who watched lots of American TV in the 70’s.

Peter Marshall, then host of the original Hollywood Squares TV show would utter that line several times an episode.

And that all has zero to do with my topic this week, i.e. circles and squares, and an analogy shared by a colleague recently, which I immediately embraced.

We’ll take a look at it together, as well as share an article I wrote a couple of years ago that deserves to be revived here too, because many readers probably haven’t seen it.

So we’re going to look at the Ten Domains of Wealth model from the UHNWI, bring in a piece I wrote a while back, and then layer in some circles and squares.

Let’s get started.


Ten Domains, and Ways to Look at Them

When the Ten Domains model came into being just a few short years ago, it resonated with me immediately.

It has evolved and been refined since then, and I like it even better now, because it clearly distinguishes between the four more technical domains across the top of the model and the five more relational domains along the bottom.

“Wealth Creation and Stewardship” is the label for the first four, while “Cultivation of Family Capital” is the moniker for the other five.

A couple of years ago I wrote a piece for CanadianFamilyOffices.com, which they titled “As Clients Demand More, Ten Domains Model Can Help Family Offices Deliver”.

That article was the first time I labeled the domains as “nine slices of a pie with a scoop of ice cream in the middle”.

The ice cream is the tenth domain, (or maybe it’s #1?) and it’s called “Family Advisory Relationships”.


So What About the Squares and Circles?

With that context now in place, we’ll move on to the squares and circles, and for that I need to thank a guy. That guy is actually named Guy, by the way.

As part of my participation in a local French-speaking group called Collectif Oria, I got to spend a whole day with my colleagues, discussing all matters relating to our work with families.

It’s a diverse group, and Guy noted that he considered himself and others who have a technical practice (he’s a financial planner) as “des carrés” (squares) while the relational experts (including me) are “des cercles” (circles).

He noted this early in the day, and as we progressed, I couldn’t help notice how many times it resurfaced in my head during a variety of discussions, and I shared those instances with the group at least a handful of times. 


Finding New Shapes, Squaring the Circle

Something that comes up in discussions with professionals who work with families who each arrive at this work from some “profession of origin”, is that many of us come in from one preferred “shape”, square or circle, in this instance.

But we quickly recognize that if we’re to be able to serve families well, we need to learn to appreciate the other shape, and understand them and their legitimate place at the table.

Many work very hard to learn to take on some hybrid shape, sort of a square with rounded corners, or perhaps a circle within a square or vice versa.

As a Canadian, the shape of a hockey rink comes to mind, which is not an ellipse but a “rectangle with rounded corners” as my friend Google just told me.

The article noted above talks about the fact that those who come from the professions who originate in the four domains of Wealth Creation and Stewardship typically know each other and are used to at least cooperating, and the same is true of those who work in the five Cultivation of Family Capital sections.

Can labeling them as squares and circles help make this more understandable?


Soft Versus Hard, Process Versus Content

There are many ways that I’ve written about this subject over the years, about soft skills versus hard, process or content specialists, and STEM versus liberal arts.

Getting back to Hollywood Squares, which is essentially Tic-Tac-Toe, at the end of every game there are both X’s and O’s all over the board, in different places.

In order to play a key role in Family Advisory Relationships, you need to be fluent and comfortable with all shapes.

Lots of Ways to Say It, and to Think About It

There are words in every language that are used in a wide variety of ways, and as someone who bangs out over 700 of them every week here, I’ve developed a certain appreciation for many.

This week, we’re going to hone in on the word “enough”, especially as it relates to the kinds of family clients that I deal with regularly, i.e. those who’ve created a business or amassed a certain level of wealth, and who are now concerned with transitioning those to their rising generation.

I had jotted down the idea of “enough” as a blog idea, and was wondering how to turn it into a longer title, and decided to go with translations into the languages with which I have some familiarity.

But rather than focusing on the concept in various forms used in different places around the world, I instead want to break my thinking down into its use with a few different verbs, to wit: Having, Being, and Doing.


Having Enough – How Much Does It Take?

The initial impetus for the idea behind this post came from something I saw online, probably on LinkedIn, that I clipped and emailed to myself.

It was a snippet from The Psychology of Money, by Morgan Housel, a book that’s chock full of wonderful anecdotes.

It describes a scene in which two guests at a party being hosted by a very wealthy man are discussing how much money their host had recently made in a single day.

One of them states to his friend, “Yes, but I have something he will never have: enough!”

And therein lies the obvious question when discussing the ultra rich: how much is enough?

I recall an interesting response to this that I once heard, which was “About 25% more than I have now”.

The man quoted in the story did have enough, while his much wealthier host seemingly did not, and the assumption is that no matter what, he never would.

And which of them is happier, I wonder?


I Am Enough – Not Always Easy

While the idea of having enough or not will often be a question we consider when thinking of those who created lots of wealth, let’s move now to something that will more typically affect their offspring, being enough.

Friend and colleague Dr. Jamie Weiner refers to this dilemma faced by many rising gens as the “Quest for Legitimacy”, and he wrote a book about it a few years ago. 

You can listen to The Quest for Legitimacy podcast I recorded with him.

His premise is that those who grow up in the shadow of very prominent parents so often suffer silently from the feeling that they’ll never be able to live up to the standards that those extraordinary parents have set for them.

This boils down to feeling like no matter what they accomplish, they will still never be enough.

Another friend and colleague, Danielle Saputo, wrote a book titled “I Am Enough” about her own version of this challenge.


I’ve Done Enough

My guess is that for many readers, the first two concepts above are ideas they’ve considered at some point, especially if they live or work in the family wealth and legacy space.

Let’s see if that continues to be true as we now pivot to the question of doing enough, or actually better stated as “having done enough”.

We are now in the world of “over-functioning” that some parents have a hard time letting go of.

We’re also back to the idea of having enough, so that we can now slow down and begin to thrive without having to strive as much.

See Striving Before Thriving in a Family Enterprise

The stages of life through which we progress are full of twists and turns, and how we occupy the majority of our time is naturally one that offers lots of opportunities for reflection.

What have I done, or accomplished, feeds into what should I do next.

Is there some “unfinished business” that needs to be tended to?


More of the Same, Or a New Direction

I began a fresh new decade of my life last year, which has me now asking such questions of myself.

It strikes me, though, as someone who works with multiple generations in families, that the questions around having enough, being enough, and doing enough are constantly sitting there.

I hope this framework helps you with your reflections.

Well, Hard Work Can Justify It!

A few weeks ago in The Elusive Perfect Cookie-Cutter Solution, I lamented the fact that the work that I do with families seldom allows for a formulaic approach.

Because each family is unique, every business is different, and the people who compose every family are one-of-a-kind individuals, much of this work involves starting fresh and doesn’t allow for a lot of “cut’n’paste” operations.

But there are naturally some aspects of the work that do repeat themselves in many cases, so this week we’re going to take a look at things from that angle.

And, as I’ve done a number of times in the past, I’m going to share a mnemonic way of remembering the sequence I’m sharing.

From my headline, which includes one word in ALL CAPS, you may have already guessed that MEDAL is what we’ll be working with.

(If you’re curious about past mnemonics, see: Start Cleaning Up your M.E.S.S., Is your Continuity PAL in Danger, and Seeking Resources to Get Back on Kilter).


Going for the Gold (Medal, That Is)

The first letter in Medal is M, and in my case, M is for Meet.

Everything starts with a meeting, and new phases of any work almost always necessitate a meeting as well.

A meeting, in many cases, involves me sitting in a room with a number of family members together, or it could be meeting virtually.

It could also be just me and one or two other people, and those situations, while more often virtual these days, can also be in person.

But important phases of most process work involve some sort of coming together to discuss things with others.


E Is for Exchange and Explore

Let’s not to minimize the meeting aspect of this, because for larger groups of people, simply getting everyone together at the same time and in the same place can be a huge obstacle.

Virtual meeting technology has made this easier in recent years, but even with Teams and Zoom, coordinating schedules with busy people is a huge lift in many cases.

Now that you are together, meeting, what are you going to do to maximize the fact that all this brain power is in one place for the next few hours?

This is where the E’s come in, and for me the two biggest ones are Exchange and Explore.

Exchanging is about both giving and receiving, which in the case of information involves talking and listening.

You brought everyone together, now let’s hear from them all.

If you accentuate the Exploration mode, to see what you can discover together, that’s even better.


D Is for Discern and Develop

So you had your Meeting where you Exchanged and Explored, and now you are each back in your own space, for the coming days, weeks, months, etc.

If each person then takes some time and makes some efforts to Discern what was learned and tries to figure out how to Develop something from what was discussed, that could be useful.

Integrating new learnings and reflecting on current realities allows the Explorations and Exchanges that you had at the Meeting take root.


A Is for Act and Advance

Now that something new has taken root as a result of the Meeting, the Exchanges and the Discernment, what’s next?

Well, hopefully you can find ways to Act and Advance ideas, projects, journeys, or whatever you are trying to accomplish together.

Too often there’s inertia that needs to be overcome, so this is a reminder to put things into motion with Action and Advancement.

New ideas were conceived and now new ways forward have emerged, which need to be Acted upon in order to Advance.

Some of these items can be done individually, others will involve additional folks who were part of the initial Meeting.


L Is for Loop Back and Meet Again

Eventually the progress that you have been making on your own or with a small group will come to a natural arc where it will become time to repeat the process again.

This is where you need to Loop back and Meet with the group again and enter into the next iteration of the process.

Coming together again in a Meeting, to once again Exchange and Explore, will begin the next cycle of the work that needs to be done.

After the next meeting, you will once again retreat into solitude or a smaller group, to Discern where you now stand, and Develop next steps.

You’ll figure out the next Acts and Advancements, and Loop back again.

Reminder to Occasionally Reflect on What’s Important

In this week’s missive I want to go to a place that I probably don’t venture to often enough, maybe because it’s a bit deep for many of us.

We’ll be looking at some very basic human needs here, as hinted at in the title. 

We all work towards getting what we want, but that changes as we go through life, and many of us have a tendency to keep making efforts in the same old direction, even when what we want has imperceptibly changed.

So if you’re game for something that may force you into reflection mode, let’s proceed. 

I know that writing this will push me into some areas of discomfort too, so we can do this together!


Dusting Off an Old, Odd Inspiration

Regular readers know that I use an email folder titled “Blog Ideas” to keep track of and store various inspirations that hit me from all over as I go through my days.

This week I’m dusting one off that’s been there a while, with “Baby Reindeer” in the subject line, of all things.

That’s a reference to a Netflix TV series from early 2024, that caught fire in the pop culture world back then.

I’ll spare you the gory details, but during the final episode, I actually paused the video to write down a verbatm quote from the main character:

   

                    “There’s nothing like getting everything you 

                          want in life to realize it’s not for you.”

 

Hmmm, there’s a lot to unpack there, and many of the people I deal with in enterprising families could stand to reflect on this too.


Back to Me Versus We Again

In the family enterprise context, this realization can be very striking, because as a family leader from the “NowGen” progresses through life, considerations about their “NextGen” invariably begin to rise into consciousness.

We’re back in the world of “Me vs. We” again. See: From “Me to We” and from “Mine to Ours”

That quote above can be looked at in many ways, of course. 

In the context of the TV series, it was the character’s realization that what he thought he wanted at the outset wasn’t actually resonating with him anymore now that he’d met that goal.

This happens to me all the time; I think of something I really want and then either work towards it or purchase it, and eventually realize that it isn’t giving me what I was hoping for.

In families this plays out in various ways too, so let’s look at some of those.


“I’m Doing All of This for You”

We’ve all seen some version of “I’m doing this for all of you”, whereby someone (who usually goes by the name “Dad”) exclaims that they’re working very hard for everyone else’s benefit.

This altruistic view of one’s efforts often fills a need for someone to be seen as unselfish, even though those who are ostensibly on the receiving end of those efforts may be shrugging their shoulders and thinking “I didn’t ask for this!”.

These situations are all about efforts that are being made for reasons that end up being less than well thought out.

If you don’t stop to reflect, and hopefully discuss things with other family members, you can end up wasting a lot of effort.


What Am I Even Doing Here?

Another common family enterprise scenario where efforts occur only to be called into question years later involves NextGen family members who take on roles with unrealistic expectations.

Often they hope for a quick path to the top, only to realize that the top spot is occupied by someone who isn’t in a hurry to give it up.

Other times, they come to realize that the parts they expected to be fun and glamourous end up being neither.

Those who begin to reflect on this sooner rather than later come out ahead in such cases.


Getting Out of your Own Head

While I set out in this post to try to encourage more self-reflection, it strikes me that in a family business context, actually getting outside of one’s own head is even more important.

Having conversations with other family members, whether they are directly affected or even only indirectly, seems like a no-brainer.

But too often, strong-willed people don’t trust anyone else more than themselves, and they continue to pursue paths that aren’t actually leading to a useful place.

Periodically stopping to reflect, and discuss, is always a good idea.

 

Providing Clarity Can Bring Change of All Kinds

One of the aspects that I love about my practice serving enterprising families is the variety of situations I get exposed to.

And sometimes the way things flow from one day to the next brings up interesting juxtapositions that kind of make me shake my head.

This happened again recently, and it made me realize that I wanted to share something about that here, but I needed a way to tie the cases together in a semi-coherent fashion.

So I landed on providing clarity, and we’ll see if I can turn this recent set of circumstances into something useful and entertaining.


Good and Ugly Versions (Also Sometimes Bad)

With apologies to Clint Eastwood and the movie title from back in the ‘60’s, we’re only looking at two scenarios I’m currently dealing with, so there is no “bad” version, just “good” and “ugly”.

Working with family members who own a business or assets together can bring me into situations with lots of promise for helping them achieve even greater things, and these are always fun to get involved with.

Other times, I get called in when things are going off the rails a bit (or a lot), which sometimes has me trying to help them avoid the worst outcomes. 

As you might imagine, these types of clients are not as much fun to work with.

As a self-confessed “life-long-learner”, I look at such cases as a learning laboratory for me, and a chance to work on different skills, like mediation.


The Swiss-Army Knife Approach

When I think about why some client situations seem attractive to me, part of what sometimes gets me interested is that chance to try to add value in cases where the outcome may not be rosy.

Such cases cause me to stretch and learn, and add more tools to my tool chest, or more prongs to the Swiss-Army knife that I sometimes like to think of myself as.

So let’s get into some of the details of my recent schedule, which saw me with the “Sanders” family on Thursday, followed by the “Fletcher” brothers case Friday.

The situations are about as far apart as they can be for people in my line of work, and I pride myself on being comfortable in either scenario.


Optimizing the Post-Liquidity Family Office

“Rob Sanders” contacted me last fall, after hearing about me from someone he trusted.  

Their family had begun some work on their “Family Office project” a while back, but the firm they used wasn’t able to continue to guide them on their journey.

After speaking with him and learning about the situation, I realized that this was a case where my partners at Blackwood Family Enterprise Services would be able to create a more detailed and durable solution in line with what the client was looking for.

We entered into a full “discovery project” with all family members, culminating in an all-day, in-person family meeting, which took place on a recent Thursday at an airport hotel of a large Canadian city.

By the end of the day, every family member had a great deal more clarity of what the family was trying to do, and how each family member could play a part.

We set the stage for some follow-on guidance that we can continue to provide the family going forward.

 


Keeping Things On the Rails a Bit Longer

After a fun and productive day with the Sanders family, I drove less than an hour and spent the night in another hotel, wondering how different the following day with members of the Fletcher family would be.

A month or so back in The “Plan A” FamBiz Transition Mirage, we looked at how so many families wrongly assume that passing down equal ownership and management responsibility to the next gen will work out well.

The Fletchers are a textbook case, and when two siblings can’t even speak to each other, it makes it difficult to run a company together.

When you layer in other complex family dynamics, things can go south in a hurry.

The clarity that I’m trying to help bring to them is that what they’ve attempted to do isn’t working.

I’m also trying to help them clarify what options they have ahead of them to minimize the damage that they may be doing to their family and their business.

Unfortunately, sometimes avoiding the ugly is about the best we can do.

My Annual Favourite Events Tour Begins Anew

Every year there are a series of events in the family enterprise space that I make every effort to attend, as a way of keeping up with the field and picking up topics to share about here in this weekly blog.

Regular readers will recognize that SG-FECC, the Schlesinger Global Family Enterprise Case Competition, is always the first one on my calendar each year, as it takes place during the second week of January.

I’ve been fortunate to be able to serve as a judge there almost every year for the past decade, and I typically share something about it here each time.

This year is no different, but I’m taking a bit of a different angle on what I’m sharing this time, as I had a bit of an A-Ha moment.

I always leave that event inspired for the future, and this year is no exception.


The Judges’ Preparation Sessions

The competition between teams from a couple of dozen Universities begins on Wednesday, and the best teams make it to the final round on Saturday.

There is a different family business case for each day, and while the teams are busy preparing to present their solution to the case, the judges all get together to prepare for what we expect to see during the students’ presentations.

While I’ve been involved in these sessions over the years, typically over two days of judging each year, this year resulted in a bit of an A-Ha moment for me.

The hour and a half or so we spend together with our judging panel, along with the panels assembled for the other divisions, is really an exercise in collective intelligence development.


Collective Wisdom + Intention & Effort = Collective Intelligence

I think most people are familiar with the term “collective wisdom”, and all of the assembled judges each arrive with their own life history related to family business in some way.

Among us are other consultants like myself, but also academics who study and work with family enterprises, as well as people who are part of business families.

So we begin each day’s discussion with a great deal of wisdom in the room, but then there’s an intentional effort to take all of that wisdom and turn in into collective intelligence through sharing.

A thoughtful discussion takes place, lead by experienced professors who are used to leading such discussions, where we talk about the case, as well as what we expect the students to present.

This is done first with the entire group of 25-30 people, all sharing our thoughts, perspectives, questions, and ideas.

After that we spend time with our individual judging panels, getting to know one another and planning some questions we expect we’ll want to ask during the Q & A section.


Now Let’s Share Again

Then to make sure we’ve gleaned as much as we can from the group, we go around the room and share some more.

Each lead judge shares some of the items that their panel unearthed, so that we can all learn from each other again.

My big take-away is that when you have a bunch of people in a room, all of whom are bringing their own experience and wisdom, it takes some effort and intention to really maximize what everyone can walk away with.

Time and a facilitated discussion are needed to make sure that we get the most out of each other.

As someone who works with groups of family members, there are some reminders and lessons there.


And It’s Never Sufficient!

Inevitably, though, at least one of the student teams will present something nobody expected or foresaw, despite the efforts made to get out ahead of them.

And herein lies another lesson for those who work with families.

We can prepare all we want, even discuss in advance with colleagues who have been working with families for decades, and we never know what might arise.

We always need to be ready for the unexpected, and be prepared to deal with whatever happens to show up that day.


And the Winners Are….

After Saturday’s finals, the winners of the Undergraduate League are from the University of Alabama, and the Graduate League champions are from Babes-Bolyai University (Romania).

Kudos as always to the awesome team of UVM volunteers who make it all happen without a hitch.

I look forward to returning again in 2026.