I once met with the children of a successful Brooklyn business owner a few months after he passed away. They brought in their father’s will, drafted a decade earlier by the same lawyer who handled his commercial real estate closings. On paper, everything looked correct. The document was properly signed and witnessed. But as we read it, a disaster unfolded in slow motion. The will created a trust for his grandchildren, but it was structured in a way that completely overlooked the generation-skipping transfer tax. It was a multi-million-dollar mistake—one that a dedicated estate planning attorney would have seen from a mile away.
This family’s story gets to the heart of what I believe is the single most important decision in estate planning. It’s not choosing between a will and a trust. It’s not deciding how to divide your assets. The most critical decision is choosing the counsel who will guide you through all the others.
Beyond Documents to Judgment
Anyone with a law license can download a template and draft a will. The mechanics are simple. But estate planning is not about filling in blanks. It is about foresight, judgment, and anticipating the pressures a family will face during a time of grief. It is about understanding the personalities, the relationships, and the potential for conflict. This is the work of a counselor, not just a document preparer.
The real value is in the questions we ask before a single word is written. What happens if your chosen executor is also grieving and unable to act? What if one of your children has a special needs child? How do we protect a beneficiary from a future divorce or creditors? How do we structure the transfer of a family business without igniting a war between the siblings who work there and those who don’t?
Answering these questions requires a deep and narrow focus. The law of estates and trusts in New York is a world of its own, governed by the Estates, Powers and Trusts Law (EPTL) and the Surrogate’s Court Procedure Act (SCPA). A general practitioner who spends their morning in traffic court and their afternoon on a contract dispute cannot maintain the specific knowledge required to give prudent advice on generational wealth transfer. The plan they create may be technically legal, but it will likely be fragile.
The Standard of Stewardship
When you create an estate plan, you are appointing fiduciaries—executors, trustees, guardians. These individuals or institutions will have a legal and ethical duty to manage your legacy with prudence and loyalty. Your choice of attorney directly impacts how well those fiduciaries can perform their duties and how well your plan protects them and your beneficiaries.
A thoughtfully constructed plan provides clear instructions, anticipates conflicts, and gives a trustee the flexibility to adapt to changing circumstances. A poorly constructed one can place an honest fiduciary in an impossible position, exposing them to liability and forcing the estate into litigation. The law is clear on this. For instance, New York’s EPTL § 11-1.7 expressly forbids any provision in a will that grants an executor or testamentary trustee immunity from liability for failing to exercise reasonable care, diligence, and prudence.
The law demands a standard of care. Your estate plan—and the attorney who drafts it—must honor that. An attorney’s job is to build a structure that upholds this fiduciary duty, not one that ignores it. This is the essence of stewardship. We are not just distributing property; we are ensuring its careful management for the next generation.
What to Look For and What to Ignore
When evaluating an attorney, I suggest you ignore the grand claims and focus on the substance of their practice and their approach.
First, ask what percentage of their work is dedicated to estate and trust matters. If the answer isn’t “all of it” or close to it, that is a significant warning sign. The world of estate planning is too deep for a part-time focus. We see the consequences of this every day in Surrogate’s Court.
Second, pay attention to the first conversation. Does it start with a checklist of your assets, or does it start with a conversation about your family, your values, and your concerns for the future? A plan built on a simple inventory of assets is just a list. A plan built on an understanding of your life’s work and your family’s dynamics becomes a true legacy.
Finally, a plan must be built for contingencies. A plan that seems perfect today may be unworkable in ten years as laws, markets, and families change. The right counsel builds a structure that can endure, giving trustees the flexibility to respond to new laws, changing market conditions, and evolving family needs.
The documents are just the final output of a much deeper process of intentional planning. The quality of that process, and the foresight it contains, comes directly from the experience and dedication of the professional guiding you. Choosing that guide is the first, and most important, step in securing your legacy.
If you have an existing will or trust, I encourage you to read it again. Then, schedule a meeting with the attorney who drafted it—or a new one—and ask them one question: “Can you walk me through the three likeliest points of failure for this plan and explain how the document protects my family from them?” Their answer will tell you everything you need to know.
