A new client once sat across the desk from me in my Manhattan office, pushing a thick binder forward. It was filled with documents from a previous law firm—a will, various trusts, powers of attorney, a healthcare proxy. He looked exhausted. “I paid a lot for this,” he said, “but I have no idea what any of it actually does for my family.”
I see this scenario more often than I’d like. It is the product of legal service focused on documents rather than outcomes. The papers are technically correct and the signatures are in the right places, but the human element is missing. The work answers, “What can we draft?” but not the more important question: “How will this protect the people you love?”
Finding the right counsel to manage your family’s future is one of the most significant decisions you will make. You are not searching for a technician; you are searching for a steward. In my practice, I have found the most effective attorneys share core qualities that have nothing to do with their law school rank and everything to do with their character.
Beyond Technical Proficiency
A deep understanding of New York’s Estates, Powers and Trusts Law (EPTL) is the absolute minimum. It’s the price of entry. But the law is just a toolkit. A master craftsman knows not only what each tool does but also when—and why—to use it. The best estate planning attorneys possess a practical wisdom that cannot be learned from a textbook.
They exercise foresight. They anticipate not just tax implications, but family dynamics. They ask the difficult “what if” questions. What if your chosen trustee passes away unexpectedly? What if one of your children has a difficult divorce? What if a beneficiary develops a substance abuse problem? A stack of documents cannot account for life’s unpredictability, but a prudent plan builds in the flexibility and protections to handle it.
This is the difference between a drafter and a counselor. A drafter sells you a will. A counselor helps you create a plan that can withstand pressure—one resilient enough to serve your family a generation from now.
The Standard of a Fiduciary
In law, a “fiduciary” is a person who acts on behalf of another, putting their client’s interests ahead of their own. Your trustee is a fiduciary. Your executor is a fiduciary. At my firm, we believe your attorney must embody that principle in every action. A fiduciary mindset is not optional.
This is not just a matter of professional ethics; it is woven into our state’s laws. For example, New York EPTL § 11-1.7 expressly forbids any clause in a will that would exonerate an executor from liability for failing to exercise “reasonable care, diligence and prudence.” The law itself demands a high standard of care from those entrusted with an estate. Your attorney should hold themselves to that same unwavering standard.
When you speak with an attorney, listen for this. Do they talk more about their services or your family? Do they explain what a trust is, or do they explain what a trust can do for your children? The focus of the conversation reveals whether their priority is the transaction or your long-term well-being.
A Counselor for the Long Term
Creating an estate plan is not a one-time event. It is the beginning of a relationship. Your life will change—you’ll have more children, your assets will grow, you might sell a business. Your plan must be a living thing, capable of adapting.
This is why the relationship with your attorney is critical. A good attorney does not just create a plan and send you on your way. They stay with you. We regularly review plans with our clients, especially after a major life event, to ensure the structure still serves its original purpose. We become a resource for the family, someone they can call years later for guidance.
This is the work of stewardship. It is the recognition that our role is to serve as a custodian for a family’s legacy, ensuring that what they have built is passed on intentionally and prudently. It is a profound responsibility—one we take personally.
When interviewing a potential attorney, ask yourself if this is someone you can imagine your spouse or children calling for advice in 20 years. Are they building a relationship or just completing a sale? The answer is critical.
Before you engage any attorney to plan your family’s future, I suggest you ask them one simple question: “How will this plan evolve as my family’s life changes over the next two decades?” Their answer will tell you whether you’ve found a document drafter or a genuine counselor for your legacy.
