A family from Brooklyn sat in my office last week. They had a folder of financial statements, a list of assets, and a question I hear often: “What kind of trust do we need?” It’s a logical question, but it’s not the right place to start. I told them what I tell every family I meet. Before we talk about legal structures, we need to talk about your life, your values, and what you want for the people you love. The documents are the end result—not the beginning.
Choosing counsel to oversee your family’s legacy is one of the most significant decisions you will make. This relationship can span decades and generations. You are not hiring a document preparer; you are selecting a counselor who will be there when your family needs guidance most. The quality of that relationship depends on asking the right questions from the very first meeting.
Beyond Experience: What is Your Philosophy?
Nearly any attorney can list their credentials or years in practice. That information is a baseline, not a differentiator. The more telling questions probe their philosophy. You are looking for a steward, not just a technician. The conversation should feel less like an intake form and more like the beginning of a long-term advisory relationship.
I suggest starting with a simple, open-ended question: “How do you view your role in this process?”
Listen carefully to the answer. Do they immediately talk about wills, trusts, and tax codes? Or do they talk about families, communication, and protecting your legacy? At my firm, we see ourselves as counselors first. Our work is to translate a family’s intentions into a clear, legally sound plan that functions in the real world—especially during times of stress and grief. The legal instruments we draft are simply the tools to achieve that outcome.
Another crucial question is about the team. Ask, “Who besides you will I be working with, and who will be there for my family in 10 or 20 years?” A solo practitioner might offer personal attention, but what is their succession plan? A larger firm might have more resources, but will your family be passed from one junior associate to another? You need to understand the firm’s structure and its plan for continuity. Stewardship is generational.
From Documents to Strategy: How Do You Plan for Contingency?
A basic estate plan can handle a straightforward inheritance. But life is rarely straightforward. An effective plan anticipates and addresses life’s contingencies—divorce, disability, creditor issues, or a beneficiary who isn’t ready for a large inheritance. This is where an attorney’s strategic thinking matters.
Your questions should test for this foresight. Instead of asking “What documents do I need?” ask, “What are the most common points of failure you’ve seen in estate plans, and how do you plan against them?”
An experienced attorney will have stories—not of their successes, but of plans they’ve had to untangle for other families. They might discuss the importance of trustee selection, the use of spendthrift provisions, or the critical need to fund a trust properly. They should be able to explain how they protect inheritances from a beneficiary’s potential divorce or creditors.
This is also where we can discuss specific points of law. For example, under New York’s Estates, Powers and Trusts Law (EPTL) § 5-1.4, a divorce automatically nullifies any bequests to a former spouse in your will. That’s a good statutory backstop, but it isn’t enough. A prudent plan goes further. What about asset designations on a 401(k) or a life insurance policy? What about the ex-spouse named as a trustee? A thorough plan addresses every component, ensuring no loose ends are left for a Surrogate’s Court judge to sort out.
The Working Relationship: How Do We Communicate?
Finally, you need to understand the practical nature of the relationship. This includes fees, but it’s about more than the final number. It’s about value and communication.
Ask, “What is your fee structure, and what does it include?” Many firms, including ours, work on a flat-fee basis for foundational estate planning. I find this encourages open communication. Clients can call with questions without worrying that they are “on the clock.” An hourly billing arrangement can sometimes create a barrier, discouraging the very conversations that lead to a better plan. You should be clear on what the fee covers—the initial design, the drafting, the signing ceremony, and the critical process of funding your trusts.
The other side of this coin is ongoing maintenance. Ask, “How and when do we review my plan?” Laws change. The federal estate tax exemption fluctuates. Your family will grow and change. Your assets will evolve. An estate plan is not a “set it and forget it” document. We have a formal review program to check in with our clients, but we also encourage them to call us after any major life event—a birth, a death, a marriage, a significant change in assets. Your counsel should have a clear process for keeping your plan current.
Finding the right fit is an intentional process. The goal is to find a professional you trust not only with your assets, but with the well-being of your family. The right questions will lead you to the right counsel.
The first step is often the most difficult—organizing your thoughts around your assets, your people, and your ultimate goals. To aid in this, we provide our prospective clients with a confidential family legacy guide. It is designed to help you frame these initial thoughts before any legal documents are ever considered. You can call our office to request a copy and begin the process of deliberate planning.
