Top Practices for Wealthy Families and Their Advisors

This volume turns thinking into practice. As in Wealth of Wisdom 1.0, we have gathered insights from leading practitioners from around the world from more than 60 of them to deliver a comprehensive collection of practical activities that advisors and members of wealthy families can undertake to ensure their continued success and development.
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Watch the video interview of co-editors Tom McCullough and Keith Whitaker




1. Four Profound Questions for Families
Ellen Miley Perry
2. Identifying Actionable Values for Family and Enterprise
Doug Baumoel and Blair Trippe
3. Values That Matter
Sharna Goldseker and Danielle Oristian York
4. A Framework for Family Wealth and Well-Being
Richard Franklin and Claudia Tordini
5. Understanding Identity and Social Power
Kofi Hope and Zahra Ebrahim
6. Tapping Character Strengths to Move Families Forward
Kristin Keffeler
7. Using the Ikigai Model to Foster a Legacy of Meaningful Engagement
Don Opatrny and Keith Michaelson
8. Stages of Wealth Integration
Courtney Pullen
9. Learning from Your Money History and Writing a New Story
Jill Shipley
10. Envisioning the Future
Jamie Traeger-Muney
11. Benchmarking Your Family Against Successful Global Families
Dennis Jaffe
12. Understanding the True Goals of Wealth Preparation
James Grubman
13. Advancing Flourishing: A 10x10 Learning Roadmap
Stacy Allred, Joan DiFuria, and Stephen Goldbart
14. Finding What’s Next for Your Family
Barton Parrott
15. Creating Impactful Learning Programs for Families
Greg Burrows and Ruth Steverlynck
16. Developing a Family Wealth Education Plan
Kirby Rosplock
17. Practical Tools for Building Healthy Families
Christian Stewart
18. Expressing Purpose in Your Trusts
John A. Warnick
19. Managing a Shared Family Property
Jamie Forbes
20. Creating a Family Bank
James E. Hughes, Jr.
21. Undertaking a Family Risk Assessment
Linda Bourn
22. Is Your Infrastructure Resilient?
Natasha Pearl
23. Creating a Family Owner’s Manual
Josh Kanter
24. Family Behavioral Health Wellness Assessment
Arden O’Connor
25. Building a Smart Aging Plan
Susan Hyatt
26. Managing the Risk of Diminished Capacity
Patricia Annino
27. Creating an Ethical Will
Scotty McLennan
28. Monitoring Financial Capital with the “Four Horsemen” Graph
Scott Peppet
29. Keeping Goals in the Spotlight with Capital Sufficiency Analysis
Joe Calabrese
30. Constructing an Investment Portfolio to Support Family Goals
Jean Brunel and Voyt Krzychylkiewicz
31. Investment Education for Family Members
Jim Garland
32. Assessing Your Family’s Financial and Family Management Needs
Scott Hayman and Tom McCullough
33. Finding an Advisor Who Will Help Your Family Thrive for Generations
Kathy Lintz and Ned Rollhaus
34. Choosing Trustees with Care and Wisdom
Kim Kamin
35. Assessing Your Readiness for a (Family Enterprise) Leadership Coach
Greg McCann
36. Understanding Advisors’ Fees
Mark Pletts
37. Balancing Entitlement and Responsibility in Children’s Birthdays
Joline Godfrey
38. A Ritual to Send Children off to College
Andrew Doust
39. Developmental Life Lessons for Grandchildren
William (Bo) and Suzanne Huhn
40. Deciding If You Should Join the Family Business
Josh Baron and Rob Lachenauer
41. How Can You Ensure the Success of Your Successors?
Dean Fowler
42. The Intergenerational Dialogue
Susan Massenzio
43. A Three-Step Process for Enhanced Communication
Keith Whitaker
44. Strengthening Your “Family Factor” to Deconstruct Conflict
Blair Trippe and Doug Baumoel
45. Using Genograms to Understand Family Patterns
Guillermo Salazar
46. Achieving New Insights and Possibilities through Generative Dialogue
Michelle Osry
47. How Powerful Are Your Questions?
Ian McDermott
48. Expectations versus Agreements
Mimi Ramsey and Stephanie Hardwick
49. Enhancing Sibling Relationships
Christian Stewart
50. Gamechanging
Matt Wesley
51. Hats Off to You!
Lee Hausner
52. How to Balance Family Stability with Resilience over Generations
James Grubman
53. Making Better Decisions by Telling Stories That Have “Already Happened”
Stacy Allred
54. Democratizing Family Decision-Making
Barbara Hauser
55. Using RACI to Determine Roles and Responsibilities in a Complex Multigenerational Family Enterprise
Kathryn McCarthy
56. Creating Internal Controls and Policy and Procedures for a Family Office
Eugene Lipitz
57. Leading Successful Family Meetings
Katherine Grady and Wendy Ulaszek
58. Establishing Ground Rules for Family Meetings
Keith Whitaker
59. Finding a Philanthropic Focus and Integrating the Rising Generation Perspective
Etienne Eichenberger, Małgorzata Smulowitz, and Peter Vogel
60. Facilitating Grandchild-Grandparent Philanthropy
James E. Hughes, Jr.
61. Helping Families Move Up the Philanthropic Curve
Leslie Pine
62. A Roadmap to Successful Philanthropy
Susan Winer


1. Thinking Through What Matters Most

We begin this book of tools and exercises at the beginning: with what truly matters to you. Of course, the aim of these chapters is not to tell you what matters or what should matter to you, but rather to help you and your family members discern and clarify what matters to yourselves.

The first Wealth of Wisdom volume (The Top 50 Questions Wealthy Families Ask) offered its readers questions to explore. This volume focuses on exercises or tools, but sometimes questions can be tools too. In the first chapter in this section, Ellen Perry offers four questions to discuss as a family:

1. What can I do more of that makes you feel close to me?
2. What can I do less of that makes you lean out emotionally?
3. What do you wish I understood more about who you are or what you value? 4. What are your favorite stories from childhood and why?

Sometimes the simplest questions are the hardest to answer and the most rewarding to discuss.

Many people express what matters most in the form of “values.” As a result, many families seek to clarify their shared values, as a guide to action. In the next chapter in this section, Doug Baumoel and Blair Trippe help readers discern their “actionable values,” that is, values that, in one’s experience, have led to specific outcomes or results. By focusing on actionable values rather than individuals’ beliefs (political, moral, or otherwise), families can mitigate conflict and identify powerful shared direction.

Sharna Goldseker and Danielle Oristian York also take up the subject of values, by offering readers a simple but powerful tool in the form of lists of values-words on cards that readers can sort for themselves and then use as a group to distinguish individual and shared values. This simple process can offer insights to families in fields such as philanthropy and enterprise governance and, most importantly, in simply understanding and appreciating each other.

In the next chapter, Richard Franklin and Claudia Tordini broaden the lens on what matters by taking up the subject of well-being. (The root of the word “wealth” itself points to “well-being.”) Franklin and Tordini offer readers ways to assess their own sense of well-being and to talk, as a family, about what well-being means to them, using different domains of physical, social, career, community, and financial well-being. Through these discussions, families can more clearly decide how to allocate their financial wealth to foster their true well-being.

Kofi Hope and Zahra Ebrahim focus readers on the topic of identity, which for many is an important element of their personal “wealth.” Using a wheel listing various forms of identity, and a process of first clarifying how you see yourself and then how the world sees you, they set up the basis for a family conversation about what identities members bring to shared work such as philanthropy or business.

Human beings have long recognized that character is absolutely essential to our happiness; as the distillation of our choices and habits, it becomes our destiny. Kristin Keffeler uses contemporary psychological tools to help readers identify their own signature character strengths, which then allows family members to see how their strengths may complement or conflict with one another, and to concentrate their efforts on developing desired strengths.

Another element of what matters most is a sense of purpose and meaning in life. In this chapter, Don Opatrny and Keith Michaelson share the Japanese concept of “Ikigai” (“a reason for being”) as a tool to allow readers to clarify the intersection of what they love, what the world needs, what they can be paid for, and what they are good at.

Financial wealth is no doubt something that matters—but, beyond paying for basic necessities, why does it matter? That’s a question that each of us would likely answer in different ways, and the answers matter to our sense of who we are and how we should use our wealth. To explore one’s relationship with money, Courtney Pullen offers a framework of stages in wealth integration. It is meant to be used by families in a half-day setting, in which family members can explore both the positive and negative aspects of their beliefs about financial wealth.

Another way to approach our relationship to money is through reflecting on the stories that we tell ourselves about it, stories that are often rooted in long-ago events or even in stories that we heard from our parents or grandparents. In the next chapter, Jill Shipley gives readers a process for identifying the beliefs they hold about money, locating the root of those beliefs in stories they tell themselves about financial wealth. She then shows how readers might reconsider their desired relationship to money and come up with new stories that foster that desired way of living.

In the last chapter of this section, Jamie Traeger-Muney brings together many of the threads of the other contributions into an exercise focused forward: the work of “Designing Your Future, Now.” This exercise is rooted in visualization, to move from past and present beliefs to imagining what you would like the future to look like, as it relates to your family, friends, work, leisure, contribution to the community, and other areas. This exercise allows “what matters most” not only to meet reality but to shape it.

2. Becoming a Learning Family

Many people think of learning as something that happens only in class (or, maybe, by Zoom) in the context of formal educational programs. One of the most important developments in the field of family wealth in the last decade is the realization that families who succeed over time do not limit their understanding of learning; instead, they make conscious choices to become learning organizations.

Dennis Jaffe starts off this section with a chapter devoted to helping you learn about yourselves as a family, through comparison with global families who have succeeded over time. Jaffe’s assessment—which focuses on three areas: Nurturing the Family, Stewarding the Family Enterprise, and Cultivating Human Capital for the Next Generation—reflects his extensive research into family enterprise success factors. It is a simple way to benchmark your family against these global success stories and identify areas where you want to grow and learn.

The next chapter, Jim Grubman’s contribution on “Understanding What Wealth Preparation Really Means,” moves us from the macro-level to very specific skills needed to manage financial wealth wisely in a family context. Grubman observes that family members often think they have the requisite skills, without knowing what they don’t know. His process connects the roles needed for wealth management with the skills needed to succeed in those roles; it validates the knowledge family members already have while pointing out areas for additional skill development.

Stacy Allred, Joan DiFuria, and Stephen Goldbart then position this work of learning across the developmental stages of an individual life. With their “10x10 Roadmap,” family members can pinpoint which of 10 competencies they want to work on, depending on where they are in a 10-part framework of life stages. This is a tool that provides individuals with direction while also allowing a family to map its members’ progress together.

Learning can be a path for connecting what is with what can be. That is the path Bart Parrott leads readers on in the next chapter, in which he lays out a simple but powerful set of questions for families to discuss when facing important choices: What’s true now? What’s possible? What’s our plan? This process of questioning and discovery can apply to choices all the way from the selection of an advisor to momentous decisions about selling a business.

The next two chapters bring the subject of learning back to a more familiar, curricular framework. First, Ruth Steverlynck and Greg Burrows give readers a structure through which to understand how your family could learn best, all the way from identifying the goal of the learning to determining what sorts of platforms or styles best suit family members’ learning needs. In the next chapter, Kirby Rosplock offers readers direction in creating their own wealth education plans, to help family members gain specific money skills.

Finally, in a chapter reprinted from the first Wealth of Wisdom volume, Christian Stewart gives readers a plethora of tools to help their families become learning organizations. These tools range from reflective exercises for each individual family member to exercises that allow the family as a whole to chart its future path and understand better the stories that have defined its journey thus far. Stewart also summarizes exercises families can use to promote a “thinking environment” and to manage difficult conversations.

3. Planning Thoughtfully

“Plans are nothing, but planning is everything,” holds a well-worn aphorism. It reflects the nature of reality: Things never turn out just as we expected. To quote a less-hopeful version, “Man plans, and God laughs.” Despite the divine laughter, going through the work of planning helps prepare the mind for whatever fortune throws its way.

Planning is an essential component of managing financial wealth. Typically, that planning takes place under the auspices of various experts: financial planners, estate planners, investment managers, business succession experts, and so on. As a result, many times families feel that their plans are something external to them- selves, not something they truly live. Sticking to a plan, or keeping it up to date, can be a real challenge.
The chapters in this section aim to address this challenge by providing exercises and tools in various aspects of planning that readers can easily apply, and reapply, to their own situations.

The section begins with John A. Warnick’s guidance on “Expressing Purpose in Your Trusts.” Families with significant wealth typically have a multitude of trust structures in which they hold their assets and transfer those assets to future generations. Far too rarely do they give any thought to the purpose of those structures, with often painful results for beneficiaries. Warnick’s exercise gives trust creators a clear path for discerning their purposes and then incorporating those purposes into their trusts or their instructions for future trustees.

In the next chapter (reprinted from the first Wealth of Wisdom volume), Jamie Forbes describes steps to take to maintain shared ownership of a family vacation home. This is a topic that many families struggle with, given the great emotional power that a beloved family gathering place can have. Forbes uses the experience of his family’s century-long stewardship of the island of Naushon, off Cape Cod, to offer practical guidance to any family seeking to preserve a home for generations.

Jay Hughes then turns our attention to the power of family financial assets to foster family members’ abilities (especially in communication and entrepreneurship), through the mechanism of the “Family Bank.” Though it doesn’t require a charter, a family bank works best when it combines attention to each family member’s needs and skills along with some formality of decision-making, whether that is in making loans or giving grants to family members for projects such as buying a house, starting a business, pursuing additional education, or the like.

Risk is a key element of planning, and yet it can often feel hard to evaluate. Linda Bourn offers readers a way to assess themselves regarding “What keeps you up at night?” in a variety of areas: cyber risk, natural disaster risk, private collectibles, personal security, and so on. Her assessment then points to specific actions to take, whether in the form of asset retitling or relocation, expert consultation, or insurance.

Every community requires infrastructure—families too. For a family with significant wealth, that infrastructure takes the forms of effective monitoring of assets, financial controls, expense and liquidity management, human resource management, and reputation management—to name only a few items. Natasha Pearl gives readers a mechanism to evaluate their “infrastructure” and its needs, to see where it is crumbling or nonexistent, and then to determine what steps are necessary to upgrade the system.

A common challenge for family members is to learn and keep track of all the operational details of managing significant family wealth. Due to specialization and confidentiality, many important documents and reports can easily become lost or siloed, making information very hard to deploy in an emergency. In the next chapter, based on his own family’s experience, Josh Kanter instructs readers how to create a “Family Owners’ Manual” that consolidates this crucial information in one place, with flexibility to add to or change the manual as time goes on.

Clearly, the most important assets in any family are the family members themselves, and the last four chapters in this section deal with planning as it regards their health, well-being, and values.

Arden O’Connor helps families take on the difficult task of assessing behavioral health challenges (e.g., around alcohol, drugs, or mental illness) as well as guidance of what to do in a behavioral health crisis.

Given that so many family members are living longer than past generations, Susan Hyatt then offers readers a “Smart Aging Audit.” Readers can think specifically about their medical information and needs, personal preferences and financial preparedness for the future, and end-of-life planning, by considering not only what they have in place now but “what if” different scenarios should come to pass.

Almost all families include members who suffer from diminished capacity as they age, a condition that can become even more challenging if the family member controls significant financial or business resources. Patricia Annino offers a list of steps to take before a family member’s capacity diminishes, as well as guidance for opening up the conversation of diminished capacity with key family leaders.

Finally, planning often involves one’s legacy—what one leaves behind. Most people consider their values to be a key part of their legacy, and yet they struggle with how to pass on those values. Scotty McLennan rounds out this section with a wonderful exercise—“Creating an Ethical Will”—that has stood the test of time and that gives parents or grandparents a way to express their most deeply held feelings and beliefs and to share those effectively with the people they love most.

4. Investing Wisely

Investing is a huge topic with a vast literature devoted to it. The goal of this volume is not to offer tools or exercises aimed at making money through investing. Instead, we approach investing here not from its quantitative perspective but from the qualitative one: What should family members be thinking and talking about to make sure that their investment process enhances their lives together as a family?

Perhaps the most fundamental skill with regard to financial wealth is to identify and track the factors with the largest impact. In the first chapter in this section, Scott Peppet shares a graph that families can use to provide themselves a “stewardship snapshot” of their portfolio, in the face of the “Four Horsemen” of fees, taxes, spending (including charitable giving), and inflation. This graph allows families to keep track of their financial wealth as well as to talk specifically about what is (and is not) in their control when it comes to stewarding that wealth well.

In the next chapter, Joe Calabrese moves us from tracking wealth to setting goals, by leading readers through the simple but powerful exercise of “Capital Sufficiency Analysis.” Since families have only four options with regard to financial wealth— create it, consume it, charitably give it away, or convey it to heirs—Calabrese’s exercise prompts members to think about which of those goals they want to pursue (and how to prioritize them), and then whether their current investment plan provides an expected balance of risk and return to achieve those goals (or whether they are likely to under- or overshoot them).

For families who want to pursue this line of thinking in even more detail, Jean Brunel and Voyt Krzychylkiewicz then expand on this framework with an exercise that allows readers to assign probabilities to the different types of goals they want to pursue (needs, wants, wishes, and dreams), as well as timelines for pursuing these goals. They then introduce the concept of dedicating sub-portfolios to these different classes of goals.

Many families seek to help their members become better stewards of their financial wealth through offering some sort of investment education. Our contributors share various tools and exercises related to family wealth education in the section entitled, “Becoming a Learning Family.” In this section, however, we have included a contribution by Jim Garland specific to family learning about investments. In it, Garland describes in detail the series of seminars that the Jeffrey family devised over several decades to educate family members about their financial assets, along with the methods of instruction and outcomes. This program provides an excellent blueprint for other families to consider and adapt to their specific needs and situation.

5. Seeking Sound Advice

Family wealth management is not a do-it-yourself activity, though many family members derive great satisfaction (and are quite skilled at) investing, managing companies, or having fun together. Nonetheless, the wide variety of expertise needed to manage all aspects of a family’s financial wealth outstrips even the most dedicated family members’ knowledge base. As a result, all families make use of advisors of some sort, which means that knowing how to select, manage, and evaluate advisors is a key qualitative skill for family members.

A fundamental question is, of course, what sorts of advisors a family needs. To help readers think through that question, Scott Hayman and Tom McCullough begin this section with a Family Self-Assessment Tool that allows families to rate their comfort with their organization and planning, their investment management, risk management, tax planning, estate planning, reporting/document management, philanthropy, family communication about various risks, and their advisors. The results from this assessment should give readers a clear sense of which areas a family should seek sound advice in and whether they need someone with a very specific skill set or an integrated holistic advisor.

Kathy Lintz and Ned Rollhaus then put the focus on selecting a comprehensive wealth manager. They offer a worksheet that families can use to think through that choice, involving evaluating prospective advisors in the areas of culture, people/ resources, alignment of interests, scope of services, fee structure, and typical client profile. They also offer recommendations on how to be a good client to the right advisor.

As time goes on and financial wealth transitions from one generation to the next, most families find that much of that wealth comes to be held in trusts. As a result, one of the most important choices family members must consider is that of trustee. Kim Kamin educates readers about the responsibilities of trustees and the different types of trustees—along with their respective pros and cons. She also offers extensive questions that readers can use when interviewing prospective trustees.

A key challenge for many enterprising families is leadership development. In the first Wealth of Wisdom volume, Susan Massenzio contributed a chapter to help readers think through what to look for in the choice of a coach or consultant to

6. Raising the Rising Generation

Most parents see their children as their greatest gift, and accordingly look at the task of raising happy, independent young adults as their most important work. At the same time, the special risks and concerns that raising children amid significant wealth brings cause many parents to doubt themselves, procrastinate taking action or communicating, and miss opportunities for passing on important life lessons.

The chapters in this section aim to resolve this dilemma, as much as possible. We begin with two chapters devoted to instituting new “rituals” in your life with your children.

In the first, Joline Godfrey describes steps that parents can take to introduce discussion of responsibilities and maturity into a “pre-birthday” ritual for each child. Starting even with young children, parents can connect the benefit of getting presents with the importance of taking on new responsibilities as a child ages. It is a ritual that can resonate powerfully when children are faced with receiving much larger gifts as part of parents’ estate planning.

Next, Andrew Doust outlines a college “sending” ritual that families can use to mark the special transition from life at home to life at college, which for many children marks the true beginning of adult life. This ritual involves inviting the young- adult child to reflect on what he or she wants to get out of the college experience and creating an agreement of expectations of what the college student will do and communicate with parents in exchange for the “scholarship” of family funds that are covering tuition. As with the pre-birthday ritual, this ceremony aims to connect the opportunity that wealth affords with responsibility, to militate against entitlement.

Much of the work of effective parenting takes place through offhand conversations that make the most of “teachable moments.” But as the two prior chapters show, intentional communication can be very powerful. This is the point of the next chapter as well, in which Bo and Suzanne Huhn relate the lessons they imparted to their grandchildren, using a thoughtful plan of written notes, humorous conversations, structured family dialogues, and video testimony. Over the course of years this intentional process of imparting “life lessons” deeply shaped their grandchildren’s character.

In many families, raising the rising generation also involves the practical consideration of whether members of the rising generation will join the family business. The next two chapters take up this dynamic, first from the standpoint of the rising generation member who is considering this choice and then from the standpoint of the senior family member who is trying to prepare his or her successors to succeed.

In the first, Josh Baron and Rob Lachenauer offer a checklist for the rising generation family member who is considering joining the family business. This list prompts reflections on everything from the young adult’s motivation, to past experience, to the nature of the ownership structure, to the alignment of the young adult’s goals with the current owners’ and managers’, and much more. The results of this self-assessment will help the prospective member of the family business decide whether, and at what speed, and with what support, to move ahead in this choice.

In the next chapter (reprinted from the first Wealth of Wisdom volume), Dean Fowler offers guidance to family business leaders on how to mentor their successors and prepare them to succeed. The checklist for these mentors includes ensuring that successors have developed their own sense of independence, that the family has enhanced its ability to talk about difficult topics, that there is a transition strategy in place that (among other things) addresses the liquidity needs of various family members, and that the successors have developed their own ability to assess, take, and manage financial risk.

If there is one ability that is central to long-term family success, it is the ability to communicate effectively among generations. The greatest obstacle to this communication very often is the belief that it has taken place. As a result, families commonly need to make time to foster intergenerational communication in an intentional manner. In the final chapter in this section, Susan Massenzio offers a simple but extremely powerful exercise for structuring an “intergenerational dialogue,” which family members can use to share their most important messages with each other, to learn from each other, and to practice communicating effectively within each generation as well.

7. Navigating Family Dynamics

Readers will no doubt notice that many chapters of this book would be at home in multiple sections. For example, the same exercise may touch upon What Matters Most, Planning Thoughtfully, and Making Shared Decisions.

This is especially the case with tools and practices devoted to enhancing a family’s dynamic, that is, its members’ ability to communicate, collaborate, and treat each other with respect, fairness, and trust. The chapters that we have collected in this section represent just a few of those that can help readers in this area.

To begin, Keith Whitaker offers a summary of a very powerful exercise first developed by Charles Collier, senior philanthropic advisor at Harvard University, and described by Charlie in the first Wealth of Wisdom volume. This “Three-Step Process” involves individual reflection, sharing those reflections with the other family members (and hearing their thoughts), and then identifying common ground for next steps. It can be used in its simplest form by couples, but it can also be applied to siblings, parents, and children, or even conversations among cousins or more distant relations.

Most families don’t recognize all the factors that keep them together; they observe these factors only in their absence, when conflict threatens to erupt. In the next chapter, Blair Trippe and Doug Baumoel give readers a construct by which to evaluate their “family factor”—the combination of shared history, shared vision, and trust—that allows a family to work together effectively. Based upon this evaluation, they also offer specific steps for building that family factor.

The family factor is one way to understand what ties families together. Another is through the genogram, a tool that Guillermo Salazar describes, which provides a graphical representation of family relationships, past and present. Family members can use this tool to better understand the source of certain beliefs or habits in their family history and, then, to identify ways to adapt current behaviors to enhance relationships and to redress old hurts.

Often these historical hurts or beliefs keep families from effectively discussing important choices, even in the midst of crisis. In the next chapter, Michelle Osry describes a process for communication—the Generative Dialogue Framework—that gives families structure for talking about emotionally difficult topics. This framework helps family members recognize when they are mired in “politeness” or stuck in “breakdown” and how to move the conversation to “inquiry” and ultimately “flow.”

The next chapter, by Ian McDermott, is not specific to family dynamics, but the practice it describes fits so well with the other tools and practices described here, that this section seemed its natural home. In it, McDermott describes the difference between two sorts of questions: “Problem-Frame” and “Outcome-Frame.” Neither is good or bad by itself, but McDermott shows how a problem-frame can often leave us feeling stuck, while switching to questions with an outcome-frame can make us and the people we’re talking with feel empowered.

One of the most common dynamics felt within families with significant wealth is the burden of poorly communicated expectations. Many family members feel (accurately) that benefits come with “strings attached,” which makes no one feel good. In the next chapter, Mimi Ramsey and Stephanie Hardwick offer readers a simple framework for evaluating how they are feeling in response to expectations, what unfulfilled expectations are causing these feelings, how they could request to clarify the expectations, and what agreements they could forge among family members to make all parties feel understood. This is a true journey from “problem” to “outcome.”

When it comes to family dynamics, parent-child relations probably receive the most attention, especially in the context of the transition of finances or power from one generation to the next. However, sibling relationships often generate the greatest heat, and in families where the founding generation has passed away, siblings are the ones who have to find ways to work together. That is why in this next chapter Christian Stewart gives readers a worksheet to evaluate their sibling relationships on measures related to shared values, trust, honesty, collaborative skills, and much more. The results of the worksheet provide direction for specific efforts to improve these crucial relationships.

Another way to describe family dynamics is the “game” that each family plays. Family games have very specific (though unwritten) rules, and participants know their parts. The family game can help the family through many tough spots, though inevitably there come times when the game no longer works so well. It’s at moments like this when Matt Wesley’s contribution on “Gamechanging” can prove most powerful. Gamechanging involves carefully observing the family game and then deciding what one change to the game could serve as a “pivot” to change the family’s behavior. It takes time and honest communication, but the model of gamechanging allows for fundamental reorientation rather than trying to change one practice or policy after another—only to see the “game” stymy these partial efforts.

8. Making Shared Decisions

One of the most challenging aspects of managing financial wealth together as a family is making shared decisions. All families make decisions. But the ways they make decisions are often left unspoken and unexamined. Perhaps there is one “true” decision-maker, the wealth creator or the eldest family member. Maybe whoever “pushes” the most drives the decision.

For families to succeed over time, they need to make, on balance, more good decisions than bad ones; they also need to decide how to decide—that is, in a clear and intentional way, think through how to make various decisions, decide what works best for them in which circumstances, and then communicate those decisions clearly. This work is sometimes called family “governance.”

The chapters in this section explore different aspects of governance. In the first chapter, Lee Hausner offers an exercise that helps families visualize their existing structure of decision-making. Through asking family members at a family gathering to don different hats based on their roles in the family—parent, child, trustee, beneficiary, business owner, manager, etc.—a family can quickly see where authority for different decisions resides. They can also begin to discuss what information and communication are needed to make effective decisions. To top it off, it’s a very fun exercise too.

Jim Grubman then offers a framework (first published in the first Wealth of Wisdom volume) for making wise decisions about different practices in the family. He asks readers to reflect on what family traditions, habits, practices, or ideas family members find helpful and want to preserve; which seem vestiges from the past and are no longer contributing to the family’s well-being; and what new practices or ideas the family could adopt that would help them adapt to the future. This backward-and-forward gaze honors the reality that every family is in the midst of a journey from the past into the future.

In the next chapter, Stacy Allred moves the focus from the big picture to more specific decisions, such as sharing information about wealth with an adult child or making a loan to a friend. She invites readers to analyze such decisions using, first, a “premortem”—in which one envisions all the things that could go wrong, and so identifies risks—and then, second, a “promortem”—in which one envisions what steps could be taken to ensure a successful outcome.

As mentioned, in many families, decisions are made by one or two family members, usually parents. This paternalistic approach can lead to problems as children mature and grow into adults themselves. In the next chapter, Barbara Hauser uses insights from the governance of nations to highlight three principles that are key also to family governance: transparency, accountability, and participation. If these three principles are honored in a family’s decision-making, the results are often more understood, more effective, and more long-lasting.

An extension of these principles comes in the next chapter, in which Kathryn McCarthy offers the “RACI” (pronounced RAY-SEE) framework to apply to decision-making in a complex family enterprise. This framework works best in a system where there are multiple boards or entities governing different parts of the family’s affairs (such as an operating company board, management, foundation board, trustees, etc.). RACI distinguishes among people who are Responsible, those who are Accountable, those who should be Consulted, and those who need to be Informed. McCarthy offers the example of a matrix in which a family enterprise can keep track of these different categories for different stakeholders. This is advanced decision-making, but for families with this level of complexity, it can be extremely useful.

One form of a family enterprise is a family office—whether a stand-alone “single family office” or a family office embedded within a family-owned operating company—which handles all the family’s financial affairs. In the next chapter, Eugene Lipitz takes up the important subject of developing internal controls and transparent workflows for the critical tasks of the family office. Development of such controls may sometimes feel too “formal” for an entity which is, after all, about the family—yet doing so can save a great deal of family confusion or conflict but also can guard against fraud or poorly informed decision-making.

One of the most valuable practices for families who are managing significant financial wealth or other assets together is to hold regular family meetings. These meetings can be for the purpose of educating family members about the finances, connecting with each other and having fun, or making shared decisions. Whatever the specific purposes, developing the habit of holding effective family meetings is a clear success factor for enterprising families.

That’s why we devote the last two chapters in this section to family meetings. In the first, Katherine Grady and Wendy Ulaszek lay out practical, step-by-step considerations for families who want to hold a productive family meeting. They move from the question of why meet, to who should be invited, to how to assemble the agenda in line with the meeting goals, to the crucial considerations of where to meet, for how long, with whose direction, etc. Even for families who have a tradition of meeting, this chapter will provide insights into enhancing meeting design and execution.

In the final chapter, Keith Whitaker focuses in on one aspect of family meeting management: the articulation of meeting ground rules. Ground rules may feel awkward for a family meeting: We’re family, after all! But experience shows that agreeing upon such rules at the beginning of a family meeting process can be invaluable for giving participants a sense that the meeting will be a safe place to discuss important topics, topics that sometimes come with strong emotional content. Sometimes in the heat of discussion, family members will break the rules, but then the group will be able to refer back to the rules and reaffirm the family’s norms. And over time the ground rules become just “the way we treat each other.” Deciding on meeting ground rules is one of the most important shared decisions a family can make.

9. Giving Together

One of the main findings in Wise Counsel Research’s “100-Year Family Study” (a study of over 100 families that had succeeded in transitioning a major family enterprise through at least three generations of leadership) is that “connection to communities beyond the family” is a key factor in each family’s success.

It is no surprise that many families intuitively turn to philanthropy as a way for individual members to make a positive difference in the world and for the family as a whole to feel connected through giving. As with any activity to do with families, self-understanding, communication, and empathy are crucial for this pursuit to go well.

In the first chapter of this section, Etienne Eichenberger, Małgorzata Smulowitz, and Peter Vogel offer a comprehensive approach for evaluating and enhancing giving together as a family. This process moves from understanding the family’s current focus and possible trade-offs it involves (e.g., between depth and breadth of impact), then to reformulating that focus based on input from family members. The authors also include a number of tips and insights for engaging rising generation family members in shaping the family’s philanthropic focus.

The rising generation is very much the focus for the second chapter, James “Jay” Hughes’ reflections on grandparent-grandchild philanthropy. Jay guides readers in a simple way to structure shared giving between these two generations (key step: parents stay out!). He also points out the numerous benefits beyond the charitable from grandparent-grandchild philanthropy, in the form of sharing stories, giving grandchildren a chance to explain their choices, and fostering true understanding across the generations. It is a fine gift for families to give to themselves.

As the example of grandchild-grandparent philanthropy suggests, giving as a family is never a static activity: it changes as the family members themselves grow and change. Families can also intentionally change their style of philanthropy. That is the insight offered by Leslie Pine in the third chapter in this section, in which she describes a “philanthropic curve”—from becoming a donor to becoming more strategic to, ultimately, achieving high impact. This curve is a useful tool for evaluating where a family is now in its giving, where it wants to be, and what steps are needed to get there.

If charity begins at home, then, by the same principle, one could say that giving starts with the giver. In the final chapter in this section, Susan Winer asks the individual philanthropist to step back and reflect on the reasons or motivations for his or her giving. This checklist of motivations then can flow into defining the scope of one’s giving and even a statement describing its principles. This process of individual reflection is fundamental to giving well.

Authors & Contributors

James E.
Hughes, Jr.
Oristian York
Ruth E.
John A.