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Leaning into Family Leadership, Together

Thoughts on Who Leans In and Who Leans Out

Most of the posts I write here weekly are based on ideas that have been simmering in my head for a few weeks or even months before I write about them for public consumption.

Every once in a while, like this week, they stem from an urge to quickly try to process a confluence of many recent ideas, before the potential magic they may contain begins to dissipate.

Leadership of families is often top of mind, but this week some conversations that included the ideas of “leaning in” and “leaning out” added to the mix, and so here we are.

Let’s see how I can tie something coherent together that is both useful and entertaining.

The First Family Meeting Is the Hardest

I should first set some important context though, because I recently had the privilege of working with a family for a number of months in preparation for their first in-person family forum.

When these go well, as this one did, there’s a magic that happens in the room, as the family comes together to discuss important topics as a group for the first time, and they typically begin to discover what’s possible for them going forward.

Too many families know that they should be discussing these things, but because they’re not sure how to start, or they fear that they’ll accidentally kick a hornet’s nest, they put these discussions off for “yet another year”.

So I was coming off a high, where I’d been with some people who had a new sense of possibilities for their future.

Yet Another PPI Call Inspires Me

As has occurred many times over the years, attending the weekly PPI Tuesday call was an additional source of inspiration.

The subject that week was women and philanthropy, and the guest mentioned that women need to learn to “lean in” to get more involved.

My friend Amanda, who was hosting the call and knew that I was in attendance asked if I had any comments, and of course I did (!)

They opened my line and I highlighted the concept of leaning in, and the fact that sometimes others, who have been leaning in, need to start to learn to “lean out”, so that others can play a more prominent role.

This applies to both women and men in philanthropy discussions, as well as to the Rising Generation and the Incumbents in families who are hoping to transition from one generation of leadership to the next.

How About the Outside Professional Advisors?

Part of the magic in a family forum comes from the fact that participants begin to realize that sharing of leadership is both welcome and required over the long term.

But the idea of leaning in and out is not just limited to the family members. 

As the outside facilitator of the meeting (and the only non-family person in the room), I also need to be aware of my own presence in the room, and to try to make sure I allow the family system to manage itself.

I may begin each part of the meeting by taking some leadership in teeing up a discussion or activity, but then I absolutely must lean back and let things happen organically, and only step back in as necessary.

If I try too hard to make everything work in a way that seems perfect, because I’m worried about looking good, I’m no longer properly serving the family.

My goal is to get the family members to lean in and put in the work required to build the connection and understanding with each other.

Sharing Leadership as a Family

The goal for many families is for their wealth to transition successfully from one generation to the next, and because that typically involves more people in subsequent generations, it’s important for everyone to learn to make decisions together in as democratic a way as possible.

Having all of the leadership and decisions concentrated in the hands of one person or a very small group can be a recipe for trouble.

There are usually more aspects of the family that require some leadership than they realize, and because everyone has different strengths, it makes sense to share roles among as large a group as possible.

And the parents first need to learn to lean back, and then the offspring need to lean in.

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The Importance of Enrollment for Family Success

Family Governance Is the Ultimate Team Sport

Shortly after writing My “Role / Goal / Control” Life Hack last year, I came up with another rhyming word that I could have added to those three, and I made note of it so that I could someday write this week’s post about it.

Looking at the title I chose for this week’s blog, you may have already guessed that that word is “enroll”.

I’ll quickly recap the initial post, which highlighted a three step way of looking at a challenge one faces.

I suggested taking a moment to first consider the role one was playing in the particular situation, then to think about the goal they’re trying to achieve, and then finally being realistic in understanding that there are only so many elements that one can actually control in any set of circumstances.

Moving Away from the “What” Questions

You may have noticed that all three of those questions normally begin with the word “what”. What is my role; What is my goal; What can I control.

Today, I want to add a different question, and this one starts with Who.

As in “Who can I enroll in this project?”

Some tasks are best handled by a single person, but many others have a higher likelihood of success when a leader is able to enroll the support and participation of others.

I write about challenges that families face as they prepare to transition their wealth from one generation to the next, and so it shouldn’t come as much of a surprise that I think that overcoming family challenges is particularly well suited to such group involvement.

Going Far, Going Together

A family “project”, as I call it with some of the families I’m privileged to work with, is by definition something that works best when several people are involved in it.

I can’t believe it was over 6 years ago that I wrote Going Far? Go Together.

That remains one of my favourite blogs, and is based on the African proverb:

                            If you want to go fast, go alone. 

                           If you want to go far, go together.

Needless to say, if you want to have people join you on your quest, it helps if you’re able to enroll them in it.

Some Definitions Are Useful

As often occurs when I write these missives, I end up Googling important words along the way, to make sure I’m as precise as possible getting my points across.

With “enroll”, I came up with some interesting angles:

  • “officially register as a member of an institution or a student on a course”

That one wasn’t exactly what I was going for, but just below that I hit pay dirt:

  • recruit (someone) to perform a service.

I like the part about recruiting, because it highlights the fact that there is often some outreach required from the leader in order to attract other parties to the task.

In Service of the Family

The “service” is also part of it, although perhaps less noticeably.

The person who is attempting to enroll others needs to convince the others that the “service”, or what’s to be gained, is for the benefit of the others, and ideally the whole family.

When one member of a family begins to take this task seriously it typically feels a bit lonely and even overwhelming in some respects.

Once they’re able to enroll one accomplice, it gets easier, as I discuss in The Exponential Magic of Family Collaboration.

The secret to doing this is to not have high expectations that it will be quick or easy to get others on board.

It really is a marathon and not a sprint, and various family members will each take their own time to understand what’s involved and why their enrollment is important to the success that the family is hoping for.

This Is NOT for All Families

For many families, all of this work is simply a bridge too far, and for most families it’s more work than they’re prepared to do.

But, for some families, it is exactly what they need to be doing, in order for the wealth they have accumulated to be successfully transitioned from one generation of their family to the next.

It truly is for exceptional families, in the true sense of the word, i.e. they are the exception.

I write a lot about family engagement and family alignment, and a big part of both of those is family enrollment.

It takes a lot work and patience to get everyone on board.

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Direction Comes Before Destination for Families

Admittedly a Little Bit Counter-Intuitive

In last week’s blog I talked about the latest super-spreader event that I attended in 2022, and enough time has passed that I can safely confirm that I emerged unscathed once again.

I did leave the latest RendezVous of the Purposeful Planning Institute with lots of good stuff, of course, as has been the case each time I’ve attended since 2014.

There was a small nugget in the opening keynote presentation that made me jot down one single word, and I’ve been reflecting on its importance ever since.

That word was “direction”, and even though I can’t recall the exact context in which it was shared, it resonated with me, and so now I need to share some of my thoughts about that.

 

Fundamental Human Connection

The theme for this year’s conference was “The Fundamentals of Human Connection”, and our opening keynote was wonderfully delivered by Akasha Saunders, from Cultivating Leadership.

When he noted the importance of direction it hit me like a lightning bolt, as if it were the missing link to a number of disparate ideas in my head.

I write about families who face the challenges of transitioning their wealth or their business from one generation to the next, which is never simple or easy work.

When I’m engaged by a family as a resource to them to guide them on that journey, they often ask me lots of questions about the destination we are trying to get to.

I don’t like to get into “destination” type talk, preferring to focus on the “journey” instead.

The idea of focusing on “direction” appeals to me, probably because it’s even simpler than the journey, and is in fact a small subset of it.

 

But Doesn’t the Destination Give You the Direction?

I wrote about this 4 years ago in There IS No Destination which was inspired by a great quote I’d read: 

                                          There Is No Destination.

                                                It’s ALL Journey.

                                                    All. Of. It. 

That remains one of my favourite posts, and now I’m please to be able to revisit it and add the importance of direction.

Just because it’s a journey, that doesn’t mean it needs to be random.

You have a general idea of where you want to go, and that helps you and your family to point yourself in the right direction.

 

In a Hurry to Get to the End

I recently ran a first in-person family meeting with a family I’ve been working with remotely in 1-on-1 calls over the past 6 months, and as we wound up our successful time together, we ended with a look ahead at what could be the next logical step on our journey together.

Some of the family members seemed in more of a hurry than others, as the idea of tackling formal governance appealed to them.

I discouraged them from trying to “jump ahead” too quickly, and we decided together that working on defining the family’s shared values made more sense.

I explained my penchant for attaching the adjective “evolving” to the term “governance”, and they agreed that this sounded prudent.

See The Evolution of Family Governance, among other posts.

 

Shared Values Help Provide Direction

Uncovering a family’s shared values provides a great foundation, and that helps inform the logical direction that the family members need to take.

Getting everyone pointed in the same direction, and then starting to slowly move the proverbial train down the track is how I like to explain it.

Are you heading west, or south? 

You don’t have to know exactly where you are trying to go to begin to overcome the inertia that keeps too many families stuck in neutral.

Sticking with the train metaphor, there are lots of places where a train can deviate from straight ahead and take on a new direction.

The flexibility component of not simply looking rigidly ahead to a specific destination should not be understated.

 

Engagement and Alignment – Redux

In Family Engagement and Family Alignment – Chicken and Egg we looked at these two key elements and how interdependent they are.

We can now add direction, and perhaps even momentum, as key areas for families to focus upon, as they work to overcome the many challenges involved in successful intergenerational wealth transitions.

Most families have a good general idea of what it could/should look like, but that doesn’t mean that the exact destination is known or even achievable.

Simply making sure you have the direction right is something worth thinking about from time to time

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Starting Fast and Moving Slow, Overcoming Resistance in Family Systems Conversations

Read more
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Fantastic Parts, an Even Greater Whole Community

Coming Down from a Rocky Mountain High

Over the years since I’ve been sharing my thoughts in this space on a weekly basis, there is one particular source of inspiration upon which I have drawn far more ideas than any other.

Regular readers can likely guess that I’m referring to the Purposeful Planning Institute, whose members long ago became my “tribe”.

I first attended PPI’s annual RendezVous in Denver in 2014, where it became evident for me that this community was unlike any other group of professionals I’d ever encountered. (I’ve yet to come across anything else even close to it since either.)

Having just completed our first in-person RendezVous since 2019, I’m coming down from my Rocky Mountain high and will share my experience.

Highest Membership Numbers Yet

I should explain my role with this group a bit further before I expound upon the “humble brag” that I’ve already set up here.

I’ve been serving on the Wisdom Expedition for RendezVous for 5 years now, including the past two years as its leader. 

Wisdom, along with its sister expedition, Experience, both sit below the Vision Expedition, which is responsible for each annual RendezVous gathering. 

The result is that the organisation benefits from a leadership group numbering a couple dozen committed believers, and that breadth has always been a hallmark of PPI’s success.

So when John A. Warnick, PPI’s founder and our fearless leader, shared that PPI’s membership is now over 450 people, there were many people in the room who beamed with pride, as this is the highest number since PPI’s initial RendezVous in 2011.

Pent Up Demand for Connection

Reconvening with one’s tribe is always great because although we’ve remained connected virtually in the interim, this is a group of “huggers” and many were long overdue.

And, at the same time, there were so many new faces this year too, and that bodes well for the future.

Our theme was well selected, “The Fundamentals of Human Connection” and I’m quite sure we won’t stray too far from that in the future either, as it is what sets the PPI community apart.

What we all have in common is a desire to better serve the families we work for, and doing so requires that we go deeper, and connect not just with our heads but also with our hearts and souls.

A Community and Its Members

Between sessions over the three days, there are lots of long breaks built in, during which relationships can be built and or rekindled.

By the final day, I kept returning to the same comments in my discussions: 

The whole of our community is greater than the sum of its parts, for sure, AND, so many of those parts are really fantastic to begin with.

As I often remark, the way we think about our professional community also happens to have many parallels to the work we all do with families.

Not all families realize how important it is for them to work on developing all of the human capital they have at their disposal in their family.

As we have the privilege to work with such families, part of what we often need to do is to nudge them in this direction, and encourage them to consider every family member and their individual development, and not simply be satisfied that the family remains wealthy or that their business continues to succeed.

A Few Highlights for Good Measure

Following RendezVous each year I typically blog about some of the highlights, but I didn’t leave myself much room this time.

From our opening keynote from Akasha to the closing salvo from David York, there were many other great moments in between.

The Dream Building session featuring Amanda, Cathy and Marlis was off the charts, the FRED Talks that I was honoured to introduce were all home runs, and the two Purposeful Connections speeches were wonderfully touching.

I was looking forward to finally meeting my friend Cindy Radu in person, but thanks to a late Covid diagnosis, she was forced to submit hers on video, and she blew everyone away nonetheless.

I always go to RendezVous to refill my proverbial “pitcher”, from which I pour for the other 51 weeks of the year.

As usual, the many firehoses that were present made it overflow and I left all wet, and very fulfilled.

See you again next year.

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Starting a Family Council: Some Assembly Required

Figuring Out Who Belongs Where

Working with families who are in the early stages of trying to establish some governance, there are always many areas of uncertainty involved, and some doubts about just how to proceed.

Often families expect that the steps and answers will be simple and easy to follow, but that’s rarely the case in my experience.

And that’s actually a good thing, because every family is different, and you can’t just look at a similar family who are a decade ahead of you and assume you can copy them and save ten years of work.

Of course there are likely plenty of experts who will try to tell you that it’s doable and charge you a hefty price for the shortcut, and some of you will buy into the mirage, unfortunately.

Regular Family Meetings Come in Many Forms

One good place for me to begin sharing my views on this subject is to look at a couple of the most basic kinds of meetings and structures that many families use to form key parts of their family governance: the family assembly, and the family council.

Regular readers will recognize my penchant for wordplay, and the title of this post definitely went there, as I found a way to (cleverly?) combine both of those into my headline, and ended up with more than I bargained for.

While a “family assembly” is a popular term for what many families create, the “some assembly required” does double duty in underscoring how much work is typically required when a family goes down the road to creating their governance structures and procedures, which must evolve slowly over time to actually have a high probability of success over the long haul.

From a Large Group to a Small One?

But not every family evolves in the same direction, as I will now discuss.

Sometimes a family will begin by having a large gathering, where everyone who’s related is invited to spend some time together, often like a reunion, and where the festivities might last longer than one day.

If those are the characteristics, then I would put that under the heading of a family assembly.

This is usually the largest and most inclusive group of people invited to get together, and includes many possible stakeholders, including in-laws, and many who will never work in or own any part of the family enterprise.

At some point down the road, such a family may decide to convene an smaller, more select group of family members who can then make some decisions for the family.

From a Small Group to a Large One?

Other times a small group is the starting point, where a select few, carefully chosen family members come together and begin to make some important decisions that affect the family and how its members interact with the family’s enterprise(s).

They may begin to make some major strategic decisions that start to form the building blocks of the family’s governance.

This approach is one I would label a family council.

At some point, this group might decide that a much larger meeting would be useful to share information and educate a larger group of family stakeholders, and they might decide to hold such a gathering, which may then become something that also reoccurs on a regular basis.

Neither Is Necessarily Better or Worse 

Last week in Looking Forward Together as an Enterprising Family, I ended by noting that the most important idea is to get into the habit of having regularly scheduled family meetings.

I did not get into whether those meetings might be an annual family assembly or a quarterly family council meeting, because either one might make the most sense for any particular family at any point in time.

All of this, no matter which direction it goes, requires some leadership and intentionality.

Writing about this has just sparked my memory of a favourite quote of mine, which I have yet to share in a blog post, so here goes.

From Arthur Ashe

Arthur Ashe was an American tennis player who faced plenty of adversity. Here are his wise words:

                        “Start where you are. 

                         Use what you have. 

                         Do what you can.”

I love the simplicity of those words, and they apply quite nicely to any family beginning their family governance journey.

They can also come in handy in a variety of other life situations, so make sure they’re never far away whenever you need them!

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Looking Forward Together as an Enterprising Family

Are We All Looking Forward to the Same Thing?

Recently while dealing with a family where some of the members kept wanting to rehash events from the past, it became nearly impossible for me to get them to concentrate on leaving old squabbles behind and instead try to focus on looking forward instead.

That got me thinking about how simple this can sound, yet still be hard to get people to buy into.

There are of course many reasons to look backwards on occasion, but if you drive your car while staring at the rear view mirror, you will run into trouble (or something else) relatively quickly.

So this week, I want to share some of my thoughts about the whole idea of looking forward as a family.

 

Setting the Past Aside – At Least for Now

I’m not suggesting that families never think about or talk about the past.

There are plenty of times and occasions and reasons to do that, but if you spend too much time there, when you really should instead be trying to work productively towards some common desired future, those looks backward too often end up usurping all of the positive energy you’ll need to make progress.

There are times when you need to agree to set the past aside, at least for now.

I wrote about this many years ago in There is No “Rewind” Button.

 

“As a Family” Changes Over Time

As we turn our focus to looking forward “as a family” I guess the first musing I have is that the idea of looking forward as a group of people can get a bit tricky, because each member of the group has their own pair of eyes with which they do their own looking.

So the group, the family in this case, needs to do some work to try to establish a common future towards which they are all looking.

This is important work that I think many families should undertake because the results will usually be useful in making sure that everyone understands where they are trying to go together, so all of their efforts can be aimed in the same direction.

Okay, so let’s say the family does that today and they all agree, are they then set for life? I assume you recognize a rhetorical question when I ask it.

Of course that common vision of where the family is looking to go needs to be revisited often, as each person’s view will also differ a bit over time as the family advances.

 

By Generation, By Individual

One way to try to tease out the variety of viewpoints is to look separately at members of the same generation, who at least are progressing through their life stages on a similar timeframe.

When the rising generation in a family enterprise is in their 30’s and 40’s, most of them will have at least some common views that will differ from their parents’, who are likely in their 50’s and 60’s.

However, fast forward a couple of decades, and those rising gen members will now likely view certain things in a way similar to how their parents saw things not that long ago.

And of course, each of the individuals in each generation will have their own unique things that they are looking forward to as well.

 

Re-Calibrating the Vision – It’s a Process

As any family sets out towards a future together, the simple passage of time, along with daily, weekly, and monthly events and happenings all combine to change where they are now.

Hopefully they will be closer to where they were planning to go, but things don’t always move forward as planned, nor do they always move in a straight line.

Figuring out if you are all still looking forward to the same thing requires frequent re-calibrating of that vision.

 

Looking Forward Together Regularly – Family Forums

Some regular readers may already see where I’m headed, and that’s to make sure that you don’t just have occasional, ad-hoc meetings as a family.

You need to develop a habit of having regularly scheduled meetings as a family, as noted in Live from the Forum – Successful Transitions.

Families who get together regularly (often quarterly or annually) can easily take stock of where they are, how they got there, and where they’re trying to go next.

Refocusing together also re-energizes everyone.

There’s always something to look forward to, and figuring it out together, over and over again, will help you all get there.

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