Very Subtle Difference, But It’s Actually Huge

Working in a family business can be a fantastic experience, and it can also sometimes be pretty dreadful too.

For some people, it’s actually possible to live both versions at different times, and it can even toggle between the two.

One of the biggest contributors to whether the experience is positive or negative, comes down to how the person actually feels while they are there.

The lucky ones feel like they truly belong, while the others are always making an effort just trying to fit in.

This week, we’re going to look at the differences and see if we can learn something. I’ll also share a personal perspective around how my own life and career have evolved.


Belonging to the Family – Hopefully a Given!

The idea for a post on this topic came to me a few weeks ago, during a meditation session using the Calm app.

While contemplating what I’d write about this week, I decided it was time to take this one up, and lo and behold, this morning during my meditation, it came up again, so now I have no choice.

Writing about business families and the challenges they face, especially around their generational transitions, there’s almost always an opportunity to contrast between how things affect the family versus how they impact the business.

When I think about a family, I like to believe that all members feel like they really belong, and that hopefully every family member feels that way.

And of course I know it isn’t always the case.


Fitting in, In the Business

When it comes to a family member who joins the family business, my bias is that it’s much more likely that there will be some period where the newcomer needs to make a bit of an effort to fit in.

Eventually, the hope is, they will feel like they actually belong there.

It can take a while, and then it’s great when you gradually get there. 

But some people never do, and end up staying anyway, which I’ve seen far too often.

And what usually ends up happening then is that the longer they stay, the harder it is to even consider leaving.

I wish there were an easy solution to this frequent dilemma, but there isn’t. 

The simple answer is that they should leave and find someplace where they’ll be happier, somewhere they can feel like they belong.

But as I always say, simple and easy are not the same thing.


A Huge Case of FOMO

In some cases, one of the major factors is FOMO, a.k.a. Fear of Missing Out.

When there are a number of family members who are working for the family business, it can be difficult to be the only one who opts to do something else.

To willingly exclude yourself, you need to have the courage to take a stand and not be lulled into the morass of “one big happy family”.

But please realize that the “one big happy family at work” is not as common as it might seem. 

If you’re working with your family members and it feels like it takes a lot of effort just to fit in, that’s probably a big clue right there.

You might ask yourself what else it is that you are missing out on in your life, that you might find if you left.


Mustering Up One’s Courage

It can take a whole lot of courage to make such a bold move, but others have done it and lived to tell the tale.

Some coaching or therapy may also be a huge catalyst to make such a change, because courage often comes more easily when bolstered by an independent outsider.


This Is My Life

I hinted that I’d share something personal, so here goes.

I joined the business my Dad had started because of a sense of duty to do so, because it was a message I received constantly while growing up.

I was lucky that I did feel like I belonged, in both the family and the business.

Once we sold the operations, though, I worked mostly alone for a couple of decades, which did not suit me, but I didn’t know how to get myself out.

Now that I’m working with other families and with great colleagues, I’ve found the place where I belong once again.

Comparing and Contrasting these Roles

As I write these words I’m on flight PD 386 back to Montreal from Calgary.

I just completed a busy couple of days at the Family Enterprise Canada 2024 Symposium, where I reprised my role as co-Emcee for the third year running.

So I decided it’d be fun to compare the role of Master of Ceremonies to that of Meeting Facilitator, which is more along the lines of my usual work.

I managed to jot down nine similarities on the back of my boarding pass, which I’ll share.


Managing Flow and Timing

A big part of the role of the Emcee at a conference is making sure everybody’s where they’re supposed to be, when you want them to be there.

There’s a flow designed into the schedule, and good Emcees recognize the importance of keeping things on schedule, with an orderly flow of all proceedings.

When facilitating a meeting, it’s a bit different, because the flow and schedule fluctuate more widely, and you have more flexibility in leading the discourse.

But flow and timing are part of your purview in both cases.


My Process, NOT My Content

At the Symposium I just worked, I had zero input on the content, which is nice, because I then don’t feel any responsibility for the outcome, aside from all of the transitions.

If you had input into the content, you’re in a possible conflict, where you might favour some parts of the day and give unfair sway to some presenters over others.

When running a meeting as a neutral outsider, it’s all about process, and you can do a better job if you let the participants supply all (or at least most) of the content.


More About Who I Am than What I Do

I refer to the Being Vs Doing dichotomy from time to time, and it certainly fits here.

I believe that my success as both an Emcee and as a meeting facilitator is more about who I am (or more specifically, who I’ve become) than about any specific thing that I do or say.

Knowing and accepting my role comes first.


Maximizing the Experience for All Participants

That last point creates a nice segue into this one. A major goal of mine in either scenario is to maximize the experience for all participants.

Whether I’m up on the stage or at the head of the table, I adopt a service mentality, whereby the others in the room are the focus.

I know I’ve done well when everyone got the most out of our time together, even those who may have been sceptical going in.


Thinking Fast on Your Feet

The ability to think on one’s feet is a key success factor in both roles. Admittedly, when leading a meeting, especially with an enterprising family, this can be even more of a differentiating factor, because one never knows what might arise, and as a facilitator, it is our job to get things back on the rails.

But even in an Emcee role, there are always hiccups, changes in plans, new info to share, and unexpected delays that you have to be prepared for.


Passing On Key Messages

The need to pass on key messages also occurs in both roles, but is quite different.

From the stage, the messages come from the event organizers, and are to be relayed to the people in the audience, and everyone gets that.

In many family meetings, a prepared moderator will know about some subjects that need to be raised, and can help them come out onto the table, but the way that’s done needs to be much subtler.


Works Better as a Pair

Working as a pair on a stage has many benefits, assuming you and your partner understand your roles and get along well.

In a meeting scenario, having a second pair of eyes and ears is always useful, and 1 + 1 = 5 in terms of the results.


It’s Harder than It Looks

Doing a good job in front of a crowd is not as easy as it looks, and making it look effortless is part of the challenge.

Leading a family meeting is also not easy, and when it is done well, it should look easy, even if it is anything but.


It’s Not About Me

Many of the eight points above boil down to the fact that both these roles are examples of servant leadership, and if you think it’s about you, you’re doing it wrong.

Family Governance Is a Contact Sport

Transitioning a family’s wealth from one generation to another is my beat, and every week I take a stab at adding some useful perspectives to this work.

Doing this work is rarely easy, and I like to think that all of those who work this space like I do, in support of families trying to succeed, can and must learn from one another.

Recently in Building Processing Time into your Process, I noted how one peer group I’m part of likens family work with skiing only the double black diamond runs.

In my weekly posts I often share things I learn in peer groups, but I just realized that one of my regular conferences offers something I don’t get anywhere else.


A Conference Like No Other

I just returned from the annual conference of the Institute for Family Governance in NYC and once again, it did not disappoint.

But I’m only now coming to grips with what makes it so different from the other annual family enterprise events on my calendar.

I get a lot out of Family Enterprise Canada’s Symposium, the RendezVous of the Purposeful Planning Institute and the Family Firm Institute’s annual conference.

But IFG is different and it’s because it’s just so damn real.

The organizers manage to bring together real people from real multi-generational family businesses, who share real stories.

Because family governance is very much a contact sport, some of these stories are not necessarily all butterflies and roses, as you might guess.

But somehow at IFG, they tell the real stories and really share, warts and all.


Strictly Obeying the Chatham House Rules

The IFG Conference runs on the basis of Chatham House Rules, which means that I’m allowed to share much of what I heard there, so long as I don’t share who said what.

I can easily share some snippets of words shared during talk at my table between presentations, though.

A man beside me noted that he did not recall hearing the word “A-hole” so many times in one day at a conference before, and I had to agree.

I shared a comment with a young woman on the other side of me at the end of the day, where I told her not to expect to hear the sharing of such frank stories at other conferences.


A Spirit and Culture of Blunt Sharing

The stories we heard typically involve families whose wealth has already successfully transitioned a few times from one generation to the next, and yet still there are some elements involving conflicts that got resolved, seemingly against long odds.

We can learn from the successes of other families, but we may even be able to learn more from their failures.

The stories shared involve a lot of successes that were required to build the wealth of the families, and then the hiccups along the way as that wealth was being shared by the family.

The blunt sharing of the less beautiful aspects of those transitions is what makes the IFG conference special, as the culture has been created where that’s a safe space for family members to share.


Families and Their Wealth Grow at Different Rates

One of the issues that can arise is that the wealth can continue to grow at some reasonable rate, but when you go down a couple of generations, the growth in the number of family members can expand exponentially.

As a generous amount of wealth is expected to be available to more and more people, that can become problematic.

Who gets to decide how the wealth is managed and shared?  See Who Gets to Decide Who Gets to Decide from 2017.


Pruning the Family Tree

Building wealth is difficult enough, but learning how to keep it and share it as a family is probably even harder.

It shouldn’t be surprising to learn that many of the stories we heard about from families where the wealth was first created over a century ago, were able to transition it a few times by limiting the number of family members who shared in it.

This sort of “pruning” of the family wealth tree is simple to explain, but not necessarily easy to implement, assuming that you value harmonious family relationships.

The IFG conference did a nice job of normalizing the fact that families can face a bumpy road on this journey, but when we learn to share the good, bad and ugly, we can help others to be forewarned.

A Relation Beyond the Rhyme

Many of my weekly missives begin with the inspiration behind them, and that makes this one a bit tough for me.

There’s often some kind of story behind how an idea came to me and why I then choose to write about it here, in the context of how if relates to my work advising families around their wealth or business transition challenges.

Regular readers know I use a simple Gmail folder to store ideas that come to me at any given time, and for this one I even needed to look at the date of the email to recall when the idea struck me.

That’ll help a bit, perhaps, but what I do recall is that I awoke early one morning with the idea of “curious, not furious”, but without any clue as to from whence it came.


Inspired by My Colleagues?

The date on which I emailed myself the idea was the Saturday of a weekend-long peer meeting I’ve written about here at times, where colleagues gather to share how we do our work with families, in order that we may all improve.

We began on Friday afternoon, and for some reason when I awoke on Saturday morning, I had “curious” and “furious” on the brain.

I don’t recall any particular discussion from the previous day that might have caused this, but alas, here we are.

I have to believe that just being with these colleagues was somehow responsible for this.

Now my challenge is to turn this into something useful, while being entertaining at the same time. Here goes.


Curiosity as an Antidote

A couple of years back in Curiosity as the Antidote to Assumptions in Families, we looked at how getting curious and asking questions can be a great way to get out of the rut of sticking with our assumptions, which are so often wrong or simply just outdated.

But it now strikes me that when I’m angry, which is not as bad as furious, I can usually walk myself back from the ledge by thinking about why someone might do what they did which has now angered me.

I touched on some of this last year in Stop Assuming the Worst – Using the MGI Method. There, we looked at how forcing oneself to think of the “most generous interpretation” (i.e. MGI) can be useful in lowering our own anxiety.

Trying to come up with such an interpretation cannot be done without getting curious.


Important Family Discussions Can Create Tension

A huge part of my work involves helping families have important conversations they need to have.

They know deep down that they need to have such discussions, yet despite this, they almost always have difficulty starting them and then having them go well, when left to themselves.

Having a neutral third party in the room can do wonders, and so I am often the person who brings my curiosity out first, and then encourage others to follow suit.

In a similar way, I often flex my calm, in the hopes that it too will become contagious. See Calm Is Contagious from 2018.

Discussions about how things will need to evolve and change going forward are fraught with emotions, and it’s not unusual for things to get charged, and inevitably someone may become angry, if not furious.

Those who experience these strong emotions typically don’t even know exactly why they’ve been riled up, because the thinking part of our brains is not where the emotions are regulated.


Curiosity to the Rescue

As the unrelated party in the room, it’s much easier for me to inquire as to the source of the emotions.

I can and do ask questions about what’s at the root of the outrage, because I’m genuinely interested in learning the answer.

The person in question can often be perplexed by my intervention and desire to know, but the mere fact that I’ve asked can be enough to interrupt the tension long enough to provoke some necessary reflection on their part.

On some occasions the self-reflection can be outright surprising to everyone, and if the space feels safe enough, others in the room may offer their own answers too.

Much of the success of such interventions comes down to a positive attitude that an experienced facilitator brings, so as to properly hold the space for productive dialogue.

And genuine curiosity is always a huge component of success.

Things Always Take Longer – And That’s Okay

It’s now been a bit over a decade since I discovered and entered the family enterprise transition world as an advisor to families.

Having come from my own family’s journey and closely followed that of my wife’s family, I came at this with lots of lived experience but not much else. (Okay, plenty of passion and curiosity too.)

Diving deeply into training in coaching, facilitation, conflict resolution and family systems, I was looking for any and every way to learn to do this work well.

Having decided to specialize in the family circle (as opposed to the business or the ownership areas) I had some catching up to do.

Regular readers will also know that I have latched onto every possible peer organisation as well, as my interactions with those have inspired many of my weekly missives here.


Hanging Out with a Bunch of Psychologists

One such peer group was founded thirty years ago by several psychologists who were hoping to create a place where those with that training, who’ve also developed a practice serving enterprising families, could come together and form a learning community.

A few years ago, a couple of its members approached me, suggesting I could make an interesting addition to their group.

At first I declined, stating that I was not a psychologist, so I was likely not “qualified” to be a member.

A couple of reassurances, arm twists, and Groucho Marx quotes about “being a member of a club that would have me as a member” later, and I was in.

I just returned from my third annual in-person weekend meeting with them (after 2 years of virtual encounters thanks to you-know-what) and want to share some of my thoughts.


Appreciating the Process

It’s amazing to me that a decade into this work, I still have plenty of A-Ha moments.

Spending quality time over a weekend with like-minded professionals who are all trying to learn to do this work better was chock full of them once again.

Working with families as they prepare to transition their wealth to the following generation is all about process, as opposed to content.

The “deliverable” is thus quite hard to define.

Psychologists, in their individual practices, typically see clients one-on-one, or sometimes as a couple.

The deliverable for their clients is also difficult to define, but those clients (patients?) are typically able to discern whether or not continuing to see their mental health professional is worth the time, effort and expense.

They spend time sharing thoughts with their doctor and work through how they are doing and what changes they can and should think about making in how they live their lives.

Making time to regularly visit someone like this is all about process.


Respecting Everyone’s Processing Time

Similarly, in my coaching work with clients, I help them think through what’s going on in their lives, give them a fresh perspective, and encourage them to make positive changes in their day-to-day actions.

While their time with me might last an hour, the weeks between sessions are where most of the processing takes place.

And different people process things at different speeds.

Much of the complexity that arises when working with a whole family comes from the fact that the members rarely process the required changes they need to make at the same speed.

During that recent weekend with peers, one of them noted that working with a whole family is like heading to the ski hill and seeking out only the double black diamond ski runs.

If you can survive those, everything else is a walk in the park.

Not only are we dealing with the family emotions, we layer in a family enterprise, and there’s a lot at stake in every meeting.

The rising generation family members in their thirties and forties have much different desires and priorities than their parents who are in their sixties and seventies.


Guiding the Process for the Family

Working with a family on their transition is a lot like being a tour guide. See Choosing your FamBiz Tour Guide

A good guide adjusts their speed to allow each person to process the journey and keeps everyone together.

The most difficult part can sometimes be slowing down those who want to move quickly.

Making sure that everybody has had enough time to process changes will always help.

Owning a Family Enterprise Has Many Facets

This week we’re going to look at a topic that affects every family business, even if it doesn’t get discussed very often.

I write a lot about the overlap of the family and the business circles, but less often about who owns the company.

See Ownership: The Forgotten Circle in Family Business

That’s partly because the people who work in and own most family enterprises don’t talk about this subject very often either.

Of course that doesn’t mean that they shouldn’t, or that these conversations aren’t important, far from it.

It can get pretty complex at times, but I want to just bisect it into its two most essential elements: value and control.


Beyond Tradition, Pride, and Duty

When people involved in a family owned enterprise do actually talk about what ownership means to them, they often talk about intangibles like tradition and pride.

That makes plenty of sense, of course, but it often just puts off the discussions about what really is at stake, i.e. who can derive the value from the business (financially) and who gets to call the shots.

Many people who are part owners of a family enterprise feel like it’s part of their duty to keep the business in the family, and they adopt a stewardship mindset, which is often also rightly praised.

But while the family and business circles move quickly, changes in the ownership circle often drag.

See Varying Time Factors in Each of the Three Circles


Who Can Profit, Who Gets to Decide

Where families sometimes get stuck in discussing what the best ownership structure should look like, they sometimes fail to make the distinction between the two main elements I’m highlighting.

I’ve lost count of how many parents I’ve heard saying that they want to treat all of their offspring equally, even as they recognize that they are certainly not equal in many important respects.

I’ve yet to meet a family with even just two next gens who are equal in ability, work ethic, motivation, education, availability, contribution…. 

You get the idea.

Where they often run into problems is when they get stuck in the belief that allowing all of their children to benefit from the family’s ownership of the business also means that every one of them needs to end up with an equal say in how it will be run.


Learning to Share All Over Again

Growing up together as siblings, the parents surely spent some time teaching them to share, whether it was about food on the dinner table, clothing, sports equipment or even just the TV remote.

See Who Gets to Decide Who Gets to Decide

Figuring out how the family should best share both the benefits of owning the business and control over business decisions is yet another tricky subject that needs to be worked out.

But it all begins with getting unstuck from the idea that the default of “everyone needs to be equal” can often lead to disastrous consequences.

When a particular ownership structure has been in place for a while, a certain amount of homeostasis sets in, meaning it’s difficult to introduce change without meeting resistance.


Leadership for Important Discussions

Undertaking such discussions requires courage and leadership.

It can be difficult for families to do this by themselves, so outside assistance, facilitation, and guidance can certainly help.

Preparation for this is key, which requires plenty of time, intention, and effort.

 

This is not a subject you want to just throw on the table and see what happens.

Those who currently own the shares need to put a lot of thoughtful consideration into how they see the future and establish their perspective first.


Not a Fait Accompli!

At this point, a fulsome discussion with the next generation can begin, presenting what the current owners have in mind, and why they think their ideas make sense.

You don’t want to present this as already done, or a fait accompli.

The final version needs to be co-created by the family, so that everyone is heard and feels like they were part of the decisions.

You cannot realistically expect this discussion to be done quickly, rather a series of meetings is quite likely going to be required.

It’s more important to end up with a result that everyone has bought into than to get this over with so you can cross it off your to do list.

Everyone needs to get something, but nobody should expect to get everything.

You are looking for consensus here, not unanimity.

Two Key Elements Working Together

As someone who shares my thoughts weekly on a variety of subjects relating to intergenerational wealth transitions, I need to have an eclectic array of inspirations.

Since the Covid pandemic has largely receded into the rear view mirror, I’ve noticed how in person meetings can develop into deeper discussions that more easily trigger ideas for these posts.

Such was the case when I recently had breakfast with a colleague who happened to be in town on other business.

This man has experience as a lawyer and a family office executive, and he is enamored with the idea of a “family bank” as a strong foundation for successful family governance.


What’s Right for THIS Family?

As we discussed his thinking and how a family bank can be exactly the right structure around which some families can and should build their legacy, the conversation took some interesting turns.

At one point he was in the middle of a sentence about what a family bank can bring and in my mind I jumped ahead and filled in my own word, assuming he would say the one I was thinking.

As you might guess from the title of this piece, we had different words.

I assumed he would say “structure”, but instead he said “discipline”.

Hmmm, I thought…. And this is exactly how many of my blogs are born.


What Angle Am I Taking?

Let’s take a minute to consider the angle one would be coming from to choose between those words.

I was coming from a big picture view of creating some structure around how a family might consider setting things up, in order to bring some necessary formality to the decisions they will want to make regarding the funding of various ideas that are expected to come from certain family members.

My friend was instead focussing on the discipline that having such a structure naturally imposes on those who wish to partake in a request for funding their idea.

Neither is necessarily better than the other, and in fact, they are complementary, hence my decision to highlight these synergies in the title I chose for this post.


Somewhat Like Engagement and Alignment?

The contrasting of structure and discipline reminded me of another pair of words that I like to look at together, engagement and alignment.

See Family Engagement and Family Alignment – Chicken and Egg

Regular readers know that I like to pay close attention to the words I use, and I also appreciate conversing with people who also choose their specific vocabulary with care.

In a similar way that alignment and engagement can be seen as two sides of the same coin, I think that structure and discipline also work well together.

When my friend said “discipline” while I was expecting “structure”, it probably mostly had to do with the fact that I feel like imposing discipline on people seems more judgemental that I think is necessary, whereas structure feels more neutral.


Back to the Synergies

Stepping away from how “judgy” these words are, let’s get back to how they work well together.

Structure is about the way you put something together, and some formality is inherent in the process, because we’re not talking about a physical structure, but a theoretical one.

The discipline is more about what that structure naturally imposes on those who want to interact with the structure, which includes some elements of formality, preparation, and diligence.

I’m flashing back to something I learned a decade ago in my Family Enterprise Advisor training, “Formality is your friend”.


Perfect for Certain Kinds of Families

A family bank can provide both structure and discipline, and for some families, it’s a great foundation for the family’s governance needs.

Other families will be better served with a different foundation, depending on where they are in their evolution and what their major activities and priorities are.

Some families anchor their governance to a philanthropic mission, others will base theirs around an operating business, while others will use a family office as their base.

What they all have in common, hopefully, is some basic structure, which then imposes some discipline for the family to organize around.

It’s important to find the right balance that can serve the needs of the largest group of family members who need to come together to make decisions together in the interest of the entire family.

Some structure and discipline are always required.

Sometimes Less Really Is More

This week we’re looking at a topic that’s actually pretty common with family enterprises, but that most people don’t like to discuss.

We’ll get into some tricky areas where family members all work together, and even though that can be great when it works well, when it causes problems, those problems get bigger in a hurry.

The expression “addition by subtraction” is pretty self-explanatory, but just in case it has eluded you, I’m talking about making an improvement in something (the business) by actually removing something (or someone).

In that specific context, I think you can all imagine why this can get tricky, especially when the person you need to subtract is a member of the family.


No Simple or Magic Solutions

Now lest you think that you will read this post and walk away with the silver bullet to make this easy to do, let me disabuse you of that notion.

Situations like this are never simple to deal with and there’s no magic answer here.

What I do want to share is that situations like this should not be ignored because they cause follow-on problems throughout the company.

When an underperforming employee is tolerated and held to different standards just because they have a certain last name, the work culture takes a hit.

The longer that persists, the worse the culture gets.

You may pretend that others don’t notice and are unaffected, but you are almost certainly wrong.


The Family Enterprise Model

Regular readers may recall that I’ve been redoing all of the courses of the Family Enterprise Advisor program (FEA), as part my new role as a project team advisor.

This has re-introduced me to a visual called the “Family Enterprise Model”, which I want to share here, as it can be part of the answer when faced with this kind of challenge.

This model is actually so simple that my friend Mr. Google came up empty when searching for a shareable version here.

It basically just shows that while a family may own a business, they also typically own all sorts of other assets as part of their enterprise, such as real estate, liquid investments, a foundation, vacation properties, heirlooms, a family office, etc.

In such cases, there may be other areas where the employee you need to subtract from an operating business may be more suitable for employment.


Ownership Versus Employment Compensation

Another consideration that families need to keep top of mind, especially when employment in the business is not a good fit, is to really think about how family members can gain from being part of a family that owns a business.

Employees get paid to do work, whether they are family members or not.

Owners of a business can also collect dividends, presumably when the business has made a profit. Such owners may also be employees, or they may simply be owners who do not work for the company.

When family members are owners who also work in the business, this distinction of whether they are being paid to work or are receiving compensation as an owner needs to be clear.

Confounding these two ways to benefit can cause problems.

The negative culture effects of a poor employee may make it so that paying someone to not come to work and having them simply collect a dividend may make more sense economically.


Sooner Is Better Than Later

When an underperforming family member is tolerated and not held to the same standards as others, it can become contagious.

The sooner you decide to deal with this the better, because it won’t fix itself on its own and it will probably get worse with time as others eventually become infected.

Honest feedback isn’t easy to deliver, but is necessary. 

In the end, the goal is for the family member to come to their own conclusion that continued employment is not working out and that a change of scenery will be better for everyone.


The Best Thing That Could’ve Happened 

You often hear stories about people whose careers took an unexpected turn, where the person is shocked to have been fired but then later looks back and admits that it was the best thing that could’ve happened to them.

That’s what I hope you’ll be able to achieve by confronting such a situation.

It’s not easy, but it is necessary.

There Are Lots of Ways to Get Started

Over the years since I had my calling to do this work with families, I’ve sought out and even created peer groups where colleagues come together to discuss particular cases they’re involved with professionally.

The way that one family handles the work of transitioning their business or wealth to the next generation will differ markedly from the way another handles the process, for lots of good reasons.

As someone who advises families and helps guide the process, I can tell you that this is not something you can learn from a book.

When there’s a good deal of complexity involved with the family system and in the assets they want to transition, there are always a number of places you can begin, and figuring out where to start involves plenty of discernment.


Recognizing That It Will Evolve

One aspect of this work that can go unrecognized is that it can be very difficult to predict how things will actually unfold.

The technical part of wealth transitions, like the legal, financial, estate and tax planning and execution that more people are familiar with, can be comparatively straightforward, compared to the family and relationships part where I specialize.

Quite often much of the technical work will have been done before the family recognizes their need for some support in learning how to govern themselves together going forward.

It’s so important to get families started on discussions about this early on, while recognizing that a timeline and exact steps will be almost impossible to predict in advance.

See, for example, The Evolution of Family Governance.


Looking for Some Small Wins Early On

Back to the various peer groups in which friends and colleagues from various fields discuss real cases we’re dealing with, it’s always interesting to hear the variety of viewpoints, ideas, and tactics we suggest to each other.

One of the angles I typically come from is emphasizing the importance of moving slowly, so as not to “scare” the family too much, while also trying to make sure that we make some quick progress and get some small wins relatively early on.

This field continues to mature and many tools are available for us to put into our toolboxes, and being flexible is an important element when doing this work.

The discernment required to read the situation and figure out what should be done next is always part of wonderful discussions with colleagues.

See On Discernment and Resourcefulness for Family Clients


On Setting Expectations and Timeframes 

Another aspect of family governance work that’s often underappreciated is how difficult it is to set a realistic timeline for the work.

This can become frustrating for practitioners early on as it’s always nice to promise the client family that the process won’t take too long.

I try to be extra careful in setting proper expectations whenever I begin working with a new family.

It is a process, and it will take time. And, trying to do it quickly can be a huge mistake.

The family needs to learn a lot and needs to become engaged in the process, and each family member has their own pace and ability for both of those.


My Favourite Arthur Ashe Quote

A couple of years ago in Starting a Family Council – Some Assembly Required, I shared some great yet simple wisdom that I like to remind myself, my clients, and my colleagues of, a quote attributed to Arthur Ashe:

                                                  “Start where you are.

                                                    Use what you have.

                                                    Do what you can.”

I’ve loved it since the first time I heard it, and it’s a great reminder when working with families.

In most cases the mere fact that you’re getting a family started is more important than exactly where you begin.

And of course at every juncture there needs to be a lot of thought and discussion around what comes next.

You can’t expect straight line progress either, as there are always some unexpected roadblocks and missteps along the way, which is par for the course.


More Art Than Science

Peer groups that include professionals who practice mostly in the structural content space are always interesting, because they often suggest great ideas, but may not appreciate the difficulty in executing them with a family.

This work is much more art than science.

I think of myself as a guide, helping the family make progress together, but where the pace of the work depends so much more on the family members than it does on me.