A client once told me he’d met with three other attorneys before choosing our firm. When I asked what made the difference, his answer was simple. “You were the first person who asked about my children’s personalities before you asked about my assets.”
That distinction is everything. You are selecting a custodian for your family’s future—a counselor who must understand the human dynamics at play just as well as the tax code. The initial consultation is your interview. The questions you ask will reveal whether you’re speaking with a document preparer or a true strategist.
Questions about fees and services are common. They are important, but they miss the point. The most revealing questions test an attorney’s philosophy and judgment.
Beyond Credentials: Gauging Real-World Judgment
Every licensed attorney has a law degree and has passed the bar exam. Those are the minimum qualifications—the price of entry. They tell you nothing about an attorney’s practical wisdom or their ability to guide a family through difficult decisions. To get a sense of their real experience, you have to dig deeper.
Instead of asking, “How many years have you been practicing?” consider asking, “Can you describe a complex family situation you’ve helped resolve?” or “What’s the most common mistake you see people make in their plans?” The answers will tell you more than a resume ever could. They reveal whether the attorney thinks in terms of legal mechanics or family outcomes. They show you if they have spent meaningful time in places like the Surrogate’s Court, observing what happens when plans fail.
An attorney who has only ever drafted simple wills may not have the foresight to anticipate the challenges a high-net-worth family in New York might face—from business succession to protecting assets for a child with special needs. You’re looking for someone whose experience matches the complexity of your own life.
The Strategic Conversation
A productive first meeting should feel less like a sales pitch and more like a strategic working session. The attorney’s job is to ask you thoughtful questions, but your questions should also guide the conversation toward what truly matters: the long-term stewardship of your legacy.
The conversation should quickly move beyond a simple checklist of documents—will, trust, power of attorney. These are merely the tools. The real work is in the design. I always look for a shift in the client’s thinking from “What do I need?” to “What do we want to accomplish?”
This is where we discuss the plan’s resilience. What happens if your circumstances change dramatically? A good plan is not a static document; it’s a framework built to adapt. For example, under New York’s Estates, Powers and Trusts Law § 5-1.4, a divorce automatically revokes any bequests to a former spouse in a will. That’s a clear statutory protection, but it doesn’t address the countless other contingencies—a falling out with a business partner, the birth of a grandchild, or a change in your financial situation. An attorney should be able to discuss how they help clients revisit and update their plans as life unfolds, so the documents continue to reflect their intentions.
The Nature of the Professional Relationship
Finally, you need to understand the nature of the working relationship you are about to enter. This includes fees, but the discussion should be much broader.
When you ask about fees, listen for the philosophy behind the answer. Does the attorney charge by the hour, or do they offer a flat fee for the planning process? I have always preferred flat fees for estate planning. It encourages open communication. Clients should never hesitate to call with a question for fear of being billed for a six-minute phone call. A flat-fee structure aligns our interests—our goal is to be thorough and create a prudent plan, not to rack up hours.
Ask how the firm communicates with clients and what the process looks like after you sign the engagement letter. Who will be your primary point of contact? How often should you review your plan? The answers define whether this is a transactional service or a long-term advisory relationship. Stewardship. That is the goal—a relationship that can last for a generation, providing guidance as your family grows and your legacy takes shape.
These questions are designed to move you past the surface and help you find a counselor you can trust with what matters most. The right attorney will welcome this level of inquiry.
If you are preparing for this conversation, I suggest you start by outlining your key family members and your primary goals for them. Bring that simple document to your first meeting. It will focus the discussion on your family’s future, which is where all good planning begins.
