Navigating Complexity in Modern Estate Planning
Estate planning continues to grow more complex as tax rules evolve, client situations become more nuanced, and technology reshapes how advisors work. In this wide-ranging webinar, Martin Shenkman and Alan Gassman explore a series of practical topics that estate planning professionals should be paying closer attention to, regardless of discipline.
Rather than focusing on a single technique, the discussion highlights real-world issues that affect day-to-day practice, from asset protection and trust administration to client vetting, defensive planning, and the expanding role of artificial intelligence.
Asset Protection and Lessons from Recent Cases
The webinar begins with a discussion of recent developments involving Delaware domestic asset protection trusts. While a Delaware court upheld a DAPT in the CES 2007 Trust case, subsequent litigation underscores that even valid trusts can be vulnerable when transactions are handled improperly. The speakers emphasize that poor administration, fraudulent conveyances, and disregard for court orders can undermine otherwise sound planning.
A key takeaway is the importance of ongoing review and coordination among a client’s advisory team. Asset protection planning is not a one-time exercise, and clients who treat it as such may expose themselves and their advisors to unnecessary risk.
Using AI for Client Due Diligence and Risk Management
One of the most practical segments of the webinar focuses on how artificial intelligence can be used to improve client intake and risk assessment. The speakers demonstrate how AI tools can efficiently gather background information on prospective or returning clients, helping advisors identify potential red flags before a professional relationship begins.
Uniform application of due diligence is emphasized as a best practice, both to improve decision-making and to reduce exposure to ethical or professional liability concerns. When used thoughtfully, AI can provide deeper insights in minutes, supporting better-informed conversations and safer practice management.
Reviewing and Improving Existing Estate Plans
The discussion also explores how AI can assist in reviewing existing trust documents. By generating summaries and highlighting key provisions such as powers of appointment, administrative flexibility, and potential tax issues, technology can help advisors gain context quickly before conducting a deeper legal review.
Importantly, the speakers caution that AI is a starting point, not a substitute for professional judgment. Human review remains essential, particularly when evaluating fiduciary duties, beneficiary interests, and long-term planning implications.
Planning Numbers, Illustrations, and Defensive Practice
The webinar concludes with a detailed look at planning illustrations and modeling. By running multiple scenarios and adjusting assumptions, advisors can help clients better understand the long-term impact of different strategies, from gifting and installment sales to GRATs and charitable planning.
Beyond client education, this approach also supports defensive practice. Presenting multiple options, documenting assumptions, and clearly explaining trade-offs can help reduce the risk of hindsight-driven claims and strengthen professional documentation.
Key Takeaways
Throughout the discussion, a consistent theme emerges: better planning today requires flexibility, collaboration, and a willingness to adopt new tools thoughtfully. By combining technical expertise with careful administration, clear communication, and responsible use of technology, advisors can deliver stronger outcomes for clients while protecting their own practices.
Watch the full webinar above to explore these topics in depth and gain practical insights you can apply immediately in your planning work.