I recently met with a couple from Manhattan who had done everything “right.” They had a will, a power of attorney, and a healthcare proxy. The documents were drafted a few years ago by the same lawyer who handled their real estate closing. The problem? He was a real estate lawyer. Their documents were technically valid, but they did nothing to address the generational transfer of their primary asset—a multi-million dollar business. The plan was a box-checking exercise that completely missed the point. It treated their legacy as a transaction, not a transition.
This is a story I see play out far too often. Choosing an attorney to plan your estate is not like hiring someone to handle a traffic ticket or a property sale. You are not just buying a set of documents. You are selecting a counselor—someone who will guide your family through profound decisions and protect what you’ve spent a lifetime building. The selection process itself should be deliberate and intentional.
Beyond Drafting Documents: The Role of a Fiduciary
Many attorneys can draft a will. Far fewer are equipped to act as a true fiduciary and long-term advisor. The difference is critical. A document-drafter asks you what you want and writes it down. An estate planning counselor asks you questions you haven’t thought to ask yourself.
What happens if your chosen trustee predeceases you? What if one of your children develops a substance abuse problem or goes through a contentious divorce? How will you protect their inheritance from creditors or a future ex-spouse? What are the specific liquidity needs of your estate, and how will your executor meet them without a fire sale of your most important assets?
These are not comfortable questions, but they are essential. The work we do is about preparing for contingencies. It’s about building a framework that is resilient enough to withstand life’s unpredictable turns. This requires more than a passing familiarity with the law; it demands a practice dedicated to this specific discipline. The attorney you choose should be a steward, thinking generations ahead, not just about the signing ceremony.
At my firm, we view our role as custodians of a family’s intentions. The legal instruments—the trusts, the wills, the corporate structures—are simply the tools we use. The real work is in the thinking that precedes them. Stewardship.
Key Questions for Any Prospective Attorney
When you meet with a potential estate planning attorney, the conversation should be a two-way interview. You are evaluating them as much as they are evaluating your situation. I encourage clients to come prepared with specific, probing questions. Here are three I believe are non-negotiable.
1. What percentage of your practice is dedicated to trusts and estates?
This is the most direct way to gauge specialization. An attorney who spends 90% of their time on estate planning will have a depth of knowledge that a general practitioner simply cannot match. They will be current on recent changes to New York’s estate tax laws, familiar with the administrative quirks of the local Surrogate’s Court, and experienced in a wide range of family and financial situations. A generalist might know the basics, but they often miss the nuances that can make or break a plan.
2. How would a provision like EPTL § 5-1.1-A affect my plan?
This question tests two things: technical knowledge and the ability to communicate clearly. New York Estates, Powers and Trusts Law (EPTL) § 5-1.1-A gives a surviving spouse a “right of election.” This law prevents a person from completely disinheriting their spouse, granting the survivor a right to claim a significant portion of the estate—regardless of what the will says.
An experienced attorney should be able to explain this concept, its implications for your specific goals (especially in cases of second marriages or complex family structures), and how to plan for it. If they stumble over the explanation or dismiss its importance, it is a significant red flag. You need a guide who can make complex law understandable.
3. What is your process for funding a trust and keeping a plan current?
Creating a trust is only the first step. For a trust to be effective, it must be “funded”—meaning assets must be retitled into the name of the trust. I have seen countless families arrive in my office with beautifully drafted trusts that are completely empty, rendering them useless. This happens when an attorney drafts the document and sends the client on their way with a to-do list they do not understand.
A good firm has a formal process to guide clients through funding. They also have a system for periodic reviews. Laws change, families change, and finances change. A plan drafted in 2015 may be poorly suited for 2025. Your relationship with your attorney should be ongoing, not a single transaction that concludes when you sign the papers.
The Difference Between Price and True Cost
It can be tempting to choose an attorney based on the lowest fee or to use a cheap online form. But this is one area where “you get what you pay for” has profound consequences. An improperly drafted will or an unfunded trust does not reveal its flaws until you are no longer here to fix them. The “savings” of a few thousand dollars upfront can cost your children tens or even hundreds of thousands of dollars in litigation fees and unnecessary taxes down the road.
The cost of a poorly constructed plan is paid by the people you love most. It is paid in legal fees in Surrogate’s Court, in family relationships strained by ambiguity, and in assets lost to creditors or taxes that could have been legally and ethically avoided. A prudent plan is an investment in your family’s future harmony. The value is not in the documents themselves, but in the conflicts they prevent and the legacy they preserve.
Before you meet with any attorney, I suggest you perform a simple exercise. Sit down for fifteen minutes and write down the three most important things you want to accomplish for your family after you are gone. Is it providing for a child with special needs? Is it ensuring the family business continues? Is it funding your grandchildren’s education? Bring that list with you. It will be your clearest guide to finding the right counsel to help you achieve those goals.
