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Trustees today are expected to navigate far more than compliance and administration. They must adapt across borders, manage digital risks, and balance the intentions of settlors with the realities of beneficiaries. Just as important, they also need the ability to listen well, adjust in the moment, and build trust through authentic connection.
This month’s feature highlights an unexpected perspective: how principles from improv can strengthen family conversations and trustee decision-making. Alongside this, we’re sharing resources on cross-border complexities, cybersecurity, AI in fiduciary practice, and the evolving role of letters of wishes. And don’t miss Tamarind Learning’s new Trustee Preparedness Survey. It’s a chance to benchmark current practices and identify opportunities to strengthen stewardship across generations.
Finally, don't miss an opportunity to join us at the upcoming Mastering Multigenerational Wealth Conference. More information and a special discount code are available below. | | | |
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Whose Trust Is It Anyway? The Intersection of Family Wealth, Estate Planning and Improv with Mark Shiller | |
This episode of the Tamarind Learning Podcast features estate planning attorney and author Mark Shiller, who brings unexpected lessons from improv into the world of trusts and family wealth. He shares how listening, adapting in real time, and building together can improve family meetings, estate planning, and intergenerational trust. Thoughtful, engaging, and filled with practical insights. | | | |
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Artificial intelligence & Trusts and Trustees: a new dawn of investment opportunities and risks? |
This article from Trusts & Trustees examines how generative AI is entering investment management and the duty-of-care questions it creates for trustees. It highlights both opportunities and risks, urging fiduciaries to set clear governance standards for AI use.
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Cybersecurity for Trustees: How to Reduce Risk and Respond to an Incident |
This piece from Woodruff Sawyer outlines practical steps trustees can take to protect against cyber threats, from secure communications to incident response planning. It offers timely guidance for trustees facing increasing digital risks to family wealth.
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Trusts and Dynastic Planning: Letters of Wishes and the Limits of Trust Flexibility |
This piece from Charles Russell Speechlys explains how settlors’ letters of wishes influence trustee decisions and where their legal limits lie. It underscores the importance of careful drafting and regular updates in long-term dynastic planning.
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Navigating U.S.-Canada Cross-Border Trust Regulations | Serving our cross-border audience, this article from Cardinal Point Wealth Management explores the tax and reporting differences between U.S. and Canadian trust regimes. It provides trustees with a roadmap for managing cross-border complexities when families and assets span both countries.
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Upcoming Event: Mastering Multigenerational Wealth Conference | |
Join Kirby Rosplock at the Mastering Multigenerational Wealth Conference for a one-of-a-kind gathering for successful multigenerational families and the professionals who serve them. This unique conference offers a rare opportunity for both groups to learn with and from each other—sharing best practices, lived experience, and forward-thinking strategies for preserving family unity, | | | |
purpose, and wealth across generations. Whether you're part of a thriving multigenerational family or a family seeking to build the culture and structures necessary for long-term success, this event is designed for you.
If you're a professional, advisor, attorney, trustee, therapist, consultant, or coach serving legacy-minded families or looking to enter this field, you'll gain invaluable insights from both client families and the cross-disciplinary experts who support them. Get 30% Off with the Code TL15 | |
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Brought to you by Tamarind Learning
Editorial Mission: To provide monthly news, education, and professional guidance that help families, advisors, and trustees become extraordinary stewards of wealth. | |
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