Canadian Stewardship in Action

What does it really mean to be a “good steward” of wealth, and how do you actually do it across generations?

Stewarding Wealth Across Generations introduces the idea of stewardship as more than managing money; it’s about responsibility, awareness, and long-term thinking. It’s designed for anyone connected to family wealth, whether you’re just starting to engage or looking to participate more confidently. You’ll explore how wealth changes over time, what tends to erode or sustain it, and the role you can play in shaping better outcomes.

What You’ll Be Able to Do on the Other Side

• Understand what “stewardship” means in practice—not just preserving wealth, but managing it with intention
• See how wealth typically evolves (and sometimes fades) across generations, and where you fit into that story
• Recognize common pressures that quietly erode wealth, like spending, inflation, and growing family complexity
• Ask better questions about how wealth is being managed, even if you’re not the decision-maker
• Make more thoughtful tradeoffs between enjoying wealth today and protecting it for the future
• Move away from assuming wealth will “just be there,” and take a more active role in understanding how it’s managed and decisions are made
• Identify practical ways families sustain and grow wealth, including education, communication, and entrepreneurship
• Feel more confident participating in conversations with family, trustees, or advisors about long-term decisions

The Experience:
This course brings together a range of curated resources so you can learn from both experts and real family experiences. You’ll engage with selected chapters and writings from authors like Dennis Jaffe (Borrowed from Your Grandchildren), Barbara Blouin (The Legacy of Inherited Wealth), and Charlotte Beyer (Wealth Management Unwrapped), alongside podcasts exploring modern stewardship, family dynamics, and entrepreneurship.

This course is more than passive learning; you’ll also work through reflection prompts, interactive activities, and guided exercises that help you apply these ideas to your own situation. The experience is designed to build awareness, spark perspective, and give you a more grounded way to participate in conversations about wealth and responsibility.

Estimated Completion Time: 3 hours

What does it mean to be a beneficiary beyond just receiving assets?

Understanding the Beneficiary’s Role (formerly Beneficiary Fundamentals Module 1) helps you understand the “why” behind your role as a beneficiary. You’ll explore the meaning and values connected to wealth, how your motivations and influences shape your decisions, and how role models and mentors impact your development. It’s designed to help you move from uncertainty or assumption toward a clearer, more personal understanding of your role.

What You’ll Be Able to Do on the Other Side

• Understand the difference between "values and valuables" and why that matters
• Describe the purpose behind your trust in simple, personal terms
• Recognize the people and experiences shaping how you think about wealth
• Identify a mentor or role model worth learning from (and why)
• Ask more grounded questions about expectations and your role
• Start forming your own point of view on what being a beneficiary means

The Experience

This module brings together a curated set of resources so you can explore how meaning, values, and behavior connect in real life. You’ll engage with selected perspectives from voices like Dennis Jaffe (Borrowed from Your Grandchildren), alongside podcasts from experts such as Dr. Jim Grubman, Dr. Paul Edelman, and the Innerwill Leadership Institute.

Along the way, you will complete a values exercise and work through reflection prompts designed to help you connect these ideas to your own life. The experience is designed to build awareness, clarify what matters to you, and help you begin shaping your role with more intention.

Featured Resources:

• Podcast with Dr. Jim Grubman entitled, Meaning and Wealth and Its Connection to the Beneficiary
• Podcast with Dr. Paul Edelman entitled, Mentoring the Rising Gen
• Podcast with Betsey Fortlouis entitled, Exploring Value-Based Leadership
• Podcast with Chelsea Toler entitled, Collaboration, Communication, and Onramps for NxG Family Members
• Podcast with Patricia M. Angus entitled, The Beneficiary Primer
• "Discovering Your Core Values" by the Innerwill Institute
• Borrowed from Your Grandchildren by Dr. Dennis Jaffe
• "Ten Facts Every Trust Beneficiary Should Know" by Patricia M. Angus

What is your relationship with a trustee, and how might it change over time?

The Beneficiary-Trustee Relationship (formerly Beneficiary Fundamentals Module 2) focuses on how relationships between beneficiaries and trustees begin, develop, and sometimes become strained over time.

You’ll consider how the relationship is shaped by the beneficiary’s age and circumstances, the purpose of the trust, the type of trustee involved, and any relationship that existed before the trust became relevant. You’ll also examine why some trustee relationships are personal and developmental, while others remain primarily professional or administrative.

The module is designed to help you form realistic expectations, recognize sources of confusion or misalignment, and better understand how the relationship may evolve as circumstances change.

What You’ll Be Able to Do on the Other Side

• Explain how a beneficiary-trustee relationship may evolve across different life stages
• Recognize what may reasonably be expected from different types of trustees
• Distinguish among personal, professional, administrative, and developmental relationships
• Identify how the trust’s origin, purpose, participants, and existing dynamics shape the relationship
• Recognize how unspoken assumptions and communication patterns can create tension
• Analyze how earlier stages of a relationship may affect later decisions and interactions
• Ask clearer questions about the trustee’s role and how the relationship is intended to function

The Experience

This module combines practical frameworks, reflection, and a staged case study to show how beneficiary-trustee relationships take shape in real life. You’ll consider the relationship from childhood through adulthood, compare different trustee arrangements, and examine the factors that influence how personal, formal, collaborative, or administrative the relationship becomes.

You’ll also reflect on early experiences with money and responsibility through a guided activity and hear from Jeff Savlov on how childhood experiences can influence a beneficiary’s long-term relationship with wealth. An interactive crossword reinforces key terms, while the culminating case asks you to analyze how communication patterns and expectations formed over time contribute to a later point of tension.

Featured Resources: 

• Raising Financially Fit Kids by Joline Godfrey
• The Tamarind Learning Podcast, Raising Grounded Kids in a World of Wealth, Jeff Savlov

What does it look like to be a “good” beneficiary in practice?

Becoming an Engaged Beneficiary: Expectations, Responsibilities, and Trust Awareness (formerly Beneficiary Fundamentals Module 3) focuses on the personal side of being a beneficiary: how you show up, how you’re perceived, and how you make sense of expectations. You’ll explore the characteristics that support strong relationships, the pressures and assumptions that can get in the way, and how to align your behavior with both your values and your role.

What You’ll Be Able to Do on the Other Side

• Recognize the characteristics that support strong, trusted relationships with trustees
• Identify expectations placed on you—both explicit and unspoken
• Notice internal or external pressures that may affect how you show up
• Understand your role once you begin engaging with your trust, not just as a recipient, but as a participant
• See the importance of being informed about your trust, its purpose, and how it works
• Recognize the value of building financial fluency and understanding wealth management concepts
• Begin to see how you can participate in planning and conversations around your wealth more thoughtfully

The Experience

Becoming an Engaged Beneficiary brings together real-world perspectives and practical tools to help you understand how expectations, behavior, and self-perception shape your role as a beneficiary. You’ll engage with selected readings from The Myth of the Silver Spoon and The Beneficiary Primer, alongside expert perspectives from voices like Kristen Kefferrler, Dr. Jim Grubman, and Patricia Angus.

You’ll also work through reflection prompts and a guided worksheet to explore how a trust may impact your relationships, and where internal or external pressures may be influencing how you show up. The experience is designed to help you build awareness, navigate expectations more thoughtfully, and develop a more grounded approach to your role.

Featured Resources:

• The Beneficiary Primer: A Guide for Beneficiaries of Family Trusts Part 1 and 2 by Patricia M. Angus, Esq.
• "How Will a Trust Affect Your Relationships" by Dr. Kirby Rosplock
• Podcast with Jake Knight, The Gift of the Black Sheep: Belonging by Being Yourself 
• Podcast by Dr. Jim Grubman, Autonomy, Accountability, and Responsibilities Around a Trust
• Worksheet, How will a trust affect your relationships, Tamarind Learning

What does it actually look like to engage with your trust?

How do you move from understanding your role to participating in decisions, conversations, and planning?

Case Study: Beneficiaries and Sudden Wealth (formerly Beneficiary Fundamentals Module 4) focuses on the practical side of being a beneficiary. You’ll explore what it means to be informed, how to stay aware of your trust and its assets, and how to engage more actively with trustees and advisors. It’s designed to help you move from passive awareness to thoughtful participation.

What You’ll Be Able to Do on the Other Side

• See what it looks like for beneficiaries to engage with a trust in real life
• Understand what it means to become more informed about your trust over time
• Recognize how relationships with trustees and advisors evolve through engagement
• Feel more prepared to participate in conversations about your trust and your future

The Experience

This module is built around a detailed family case study, giving you a window into how beneficiary and trustee relationships play out in real life. You’ll follow the dynamics of a family navigating wealth, communication, decision-making, and evolving responsibilities over time.

Along the way, you’ll explore practical examples of how beneficiaries engage with their trusts—how they get informed, ask questions, build relationships with advisors, and participate in planning. The experience is designed to help you see what thoughtful engagement looks like in practice, not just in theory.

Who’s involved in a trust and what does each person actually do?

Introduction to Trusts (formerly Trustee Basics Module 1) introduces the main parties to the trust – the settlor, the beneficiary, and the trustee. Additional parties to the trust are introduced, such as advisors with specific oversight functions that may be required over several generations and common types of trustees and beneficiaries. The module concludes with applied learning, a helpful resource, and a concise summary of the trust concept, key terms, responsibilities, and duties of a trustee and beneficiary. This module is perfect for those with little or some basic understanding of the trustee role.

What You’ll Be Able to Do on the Other Side

• Identify the key parties in a trust and describe what each one is responsible for
• Recognize additional roles (like trust protectors and advisors) and how they show up in practice
• Map out the relationships between parties in a trust using a simple visual framework
• See how roles and relationships can shift over time as a trust evolves
• Reflect on how these relationships function—not just structurally, but in real life

The Experience

This module brings together foundational content and practical exercises so you can visualize how a trust works in real life. You’ll engage with selected readings from Family Trusts and The Trustee Primer, alongside expert perspectives from Patricia Angus.

You’ll also complete the Trustscape activity, mapping out the relationships between the different parties to a trust, and reflect on how those relationships show up in practice. The experience is designed to help you move from understanding roles on paper to seeing how they connect in a real-world context.

Estimated Completion Time: 2 hours

Featured Resources: 

• Podcast with Patricia M. Angus entitled, The Beneficiary Primer
•  Family Trusts: A Guide for Beneficiaries, Trustees, Trust Protectors, and Trust Creators by Hartley Goldstone, James E. Hughes Jr., and Keith Whitaker
• The Trustee Primer: A Guide for Personal Trustees by Patricia M. Angus

What makes someone effective in the trustee role, and what responsibilities come with it?

Trustee Responsibilities (formerly Trustee Basics Module 2) explores the qualities, duties, and challenges involved in serving as a trustee. It connects personal characteristics such as integrity, judgment, objectivity, communication, discretion, empathy, and accountability with the trustee’s core fiduciary responsibilities: administration, investment oversight, distributions, and beneficiary education. Learners examine both positive trustee behaviors and red flags, while considering how expectations, family dynamics, and legal duties shape the trustee-beneficiary relationship.

What You’ll Be Able to Do on the Other Side

• Evaluate trustee behaviors against key characteristics such as integrity, objectivity, communication, and accountability.
• Identify red flags that may indicate a trustee is not meeting fiduciary expectations.
• Understand the trustee’s four core duties: administration, investment, distribution, and education.
• Ask clearer questions about trust distributions, investment oversight, reporting, and communication.
• Prepare for trustee-beneficiary conversations with greater awareness of role expectations and boundaries.

The Experience

This module uses examples, matching exercises, reflection prompts, case studies, and practical worksheets to connect trustee traits with real-world conduct. Learners review scenarios involving communication, conflicts of interest, distribution decisions, documentation, and beneficiary engagement.

The experience asks both trustees and beneficiaries to reflect on their expectations, assumptions, and communication patterns. Through readings, prompts, and cautionary examples, learners build a more grounded understanding of what fiduciary responsibility entails and how trust can be strengthened or damaged by trustee behavior.

Featured Resources: 

•  Family Trusts: A Guide for Beneficiaries, Trustees, Trust Protectors, and Trust Creators by Hartley Goldstone, James E. Hughes Jr., and Keith Whitaker
• Trustee Candidate Checklist, Tamarind Learning
• Trustee Worksheet, Tamarind Learning

How do you decide what kind of trustee is right for a trust, and what role that trustee should play?

Trustee Types (formerly Truste Basics Module 3) helps learners look beyond trustee “types” and think more carefully about trustee fit. It explores how different trustee structures, including family member trustees, independent or professional trustees, corporate trustees, delegated and directed trusts, and private trust companies, may shape the beneficiary experience, family dynamics, decision-making, continuity, and long-term stewardship. The module invites learners to consider not only who can administer a trust, but what role the trustee is expected to play: technical fiduciary, neutral decision-maker, family steward, mentor, educator, or some combination of these.

What You’ll Be Able to Do on the Other Side

• Clarify what role a trustee is expected to play in a given trust, from administration and oversight to beneficiary support, education, and stewardship.
• Compare trustee models based on the needs of the trust, the family, and the beneficiary relationship, rather than relying on convenience or default assumptions.
• Assess whether a trustee’s strengths, limitations, independence, availability, and expertise match the role the family wants that trustee to play.
• Identify how different trustee structures may affect beneficiary engagement, communication, autonomy, and long-term preparedness.
• Prepare focused questions for advisors, trustees, or family decision-makers about trustee fit, authority, continuity, expectations, and potential conflicts.

The Experience

This module combines short explanatory readings, contributor perspectives, and practical reflection prompts to help learners examine trusteeship from both structural and relational perspectives. The experience includes key readings from James E. Hughes, Jr. and Patricia M. Angus on the role a trustee can play in supporting beneficiaries, along with a curated chapter from The Complete Family Office Handbook on developing the ideal trustee.

Learners compare family, independent, corporate, delegated, directed, and private trust company models while considering what each structure makes easier, what it may complicate, and how it may affect the trustee-beneficiary relationship. Reflection prompts and scenario-based questions invite learners to think through cost, control, expertise, family involvement, fiduciary responsibility, continuity, and conflict, so they can engage more constructively with trustees, advisors, and family decision-makers.

Featured Resources:

How do I prepare for a trustee to step into or transition out of the trustee role?

Sourcing a Trustee (formerly Trustee Basics Module 3) helps learners think through what it takes to set a trustee up for success at key transition points. It focuses on how to define the trustee role, evaluate fit, clarify expectations, and support a thoughtful handoff when a trustee is joining or leaving. Learners will consider the practical and relational elements of trustee transitions, including job descriptions, interview preparation, compensation expectations, onboarding practices, stakeholder communication, and continuity between outgoing and incoming trustees.

What You’ll Be Able to Do on the Other Side

• Draft a trustee job description that reflects the trust’s purpose, complexity, stakeholder needs, and desired trustee characteristics.
• Prepare interview questions that help evaluate whether a trustee candidate has the experience, judgment, temperament, and availability the role requires.
• Compare individual and corporate trustee candidates using consistent criteria tied to the needs of the trust and beneficiaries.
• Clarify trustee compensation expectations by identifying the responsibilities, complexity factors, and communication practices.
• Use onboarding and offboarding best practices to help a trustee enter or exit the role with clearer expectations, documentation, relationships, and continuity.

The Experience

In this module, participants work through the trustee transition process from defining the role and preparing for candidate conversations to supporting a trustee’s entry into or exit from the role. The experience uses practical examples, interview categories, compensation considerations, onboarding checklists, and transition prompts to help learners think through what should be clarified before, during, and after a trustee change.

Participants will be invited to consider trustee transitions from multiple perspectives, including the trust creator, beneficiary, incoming trustee, outgoing trustee, and advisor. Rather than treating onboarding and offboarding as administrative steps, the module emphasizes preparation, communication, role clarity, and continuity to ensure trustee transitions are handled with greater confidence and less ambiguity.

Featured Resources: 

• Sample job description template
• Sample interview template
• The case study Pitt v Holt
• Family Trusts: A Guide for Beneficiaries, Trustees, Trust Protectors, and Trust Creators by Hartley Goldstone, James E. Hughes Jr., and Keith Whitaker