What Families Should Be Asking Their Estate Planners In 2026
A family is shown celebrating in a photo with Happy New Year 2026. Photo-Syda Productions
This month, I will be joining hundreds of estate planning professionals at the 2026 Heckerling Institute on Estate Planning in Orlando—one of the premier gatherings for advisors to wealthy families. I am going not just to listen but to ask the hard questions that my clients need answered, and that I suspect many other such families, and their advisors, should be asking themselves right now.
The estate planning landscape for families with $5 million, $50 million, or more, has never been more complex—or more consequential. Between shifting trust laws, new IRS scrutiny, evolving technology risks, and the looming 2026 estate tax cliff, the strategies that worked five years ago need serious stress-testing.
Here's what I'm focused on—and what you should be discussing with your own advisors.
Can Your Trust Structure Survive What's Coming?
For families, trust design is everything. The right trust in the right state can protect millions; the wrong structure can create tax disasters or leave assets vulnerable.
I'll be spending significant time in sessions on conflicts of trust laws and multi-jurisdictional structures, because I need answers to questions such as:
How aggressive can we be with trust situs selection before courts or regulators push back? "Situs shopping" for favorable tax and asset-protection rules has been common practice, but the legal landscape is shifting.
How do we draft dynasty trusts that stay flexible as fiduciary income tax rules and state laws evolve? Today's ironclad structure could become tomorrow's straitjacket.
What protections do dual SLATs and complex marital trusts need, if the marriage breaks down? With more couples using sophisticated spousal lifetime access trusts, we need clearer standards to protect both spouses—and their advisors.
Are Your Business Assets and Retirement Accounts Optimally Structured?
Many of my clients hold closely held businesses, qualified small business stock (QSBS), large insurance portfolios, and substantial retirement accounts. Each requires specialized planning, and the rules keep changing.
Key questions:
Which QSBS strategies will survive if Congress cracks down? The 100% gain exclusion on qualified small business stock is under constant scrutiny. We need to know which structures are reform-proof.
Do your legacy life insurance trusts reflect today's reality? Many families are funding trusts based on outdated illustrations and premium assumptions that no longer make sense.
What's the playbook for very large inherited IRAs? Post-SECURE Act, trustees managing eight- or nine-figure retirement accounts need sophisticated strategies around Roth conversions, separate accounts, and beneficiary communications.
How Do You Plan When Litigation Risk Is the New Normal?
I'm seeing more conflict, more scrutiny, and more vulnerable parties around large estates. When estate planning involves tens or hundreds of millions, every document may eventually be examined in litigation.
Critical issues:
How do you represent both spouses without creating future liability? Sophisticated joint planning requires bulletproof engagement letters and conflict waivers, drafted with an eye toward potential divorce proceedings.
How do you document capacity and intent? With undue-influence and elder-abuse allegations on the rise, best practices for documenting family dynamics and decision-making capacity are essential.
What's your protocol when you suspect financial exploitation? Advisors increasingly face situations where statutory guidance is unclear and families are resistant—yet the ethical and legal duties are real.
Can Your Charitable and Global Strategies Handle More Scrutiny?
Many clients I work with have either global assets, philanthropic goals, or both. Coordinating charitable remainder trusts (CRTs), foreign real estate, offshore accounts, and international business interests in an era of expanded reporting requirements requires careful choreography.
Questions on my list:
How flexible must CRTs be to stay viable as valuation rules and payout structures evolve?
What structures best balance confidentiality, control, and tax efficiency for cross-border families with operating businesses in multiple countries?
How should multi-national families integrate charitable entities across jurisdictions without triggering unintended tax consequences or regulatory red flags?
Is Your Firm Ready for the AI and Cybersecurity Standards of Care?
This may be the most overlooked area in planning. As both a trusts and estates attorney and a private fiduciary, I'm acutely aware that AI and cybersecurity aren't optional anymore—they're central to how sophisticated planning is delivered and how fiduciary duties are fulfilled.
What I need to understand:
How should firms vet and document AI use in drafting, analytics, and client communications? Technology can enhance our work, but only if used within clear fiduciary guardrails.
What cybersecurity protocols will courts expect from trustees holding sensitive financial, medical, and personal information?
How can multidisciplinary teams share information efficiently without crossing ethical or confidentiality boundaries? Modern planning requires coordination across legal, tax, investment, family office, and technology professionals.
The Bottom Line
The strategies that protect and preserve family wealth in 2026 and beyond must be more sophisticated, more adaptable, and more carefully documented than ever before. If you or your advisors aren't asking these questions, you may be building on assumptions that won't hold.
If you're a client, family office, or advisor with specific concerns you'd like me to explore at Heckerling—or you'd like to discuss how these themes apply to your situation—reach out at m.erskine@erskineco.com