For many families, the estate planning process might look something like this: Your wills get signed. Your trust is funded. The attorney drafted everything you asked for, and you left the meeting with the sense that something important had been handled. But your partner wasn’t really active in the conversations. And the estate plan reflects it. 

Later, someone notices that the beneficiary designations on your retirement accounts don’t match your trust. The CPA, reviewing year-end statements, flags a tax problem that the trust structure didn’t anticipate. Your partner who wasn’t at the attorney meeting still doesn’t fully understand what was decided. 

Your documents may be correct, but the financial picture they reflect may be incomplete.  
An estate attorney’s job is to draft documents that hold up legally. That requires knowing what the client wants. It doesn’t require knowing the client’s complete financial picture, because that information isn’t typically in the room. A financial advisor who works alongside your estate attorney can bring the pieces together: the accounts, the tax exposure, the liquidity needs, and the family dynamics that determine whether the legal structure actually fits the family. When both your estate attorney and financial advisor are present and coordinated, the estate plan is more likely to hold up in practice, not just on paper. 

The Estate Plan Is One Piece of the Picture 

Estate attorneys are trained to draft legal documents that ensure assets are protected and distributed according to the client’s wishes. What they draft is based on what the client tells them. The problem is that many clients can only tell them part of the story, because there wasn’t coordination with the financial advisor, and/or the CPA wasn’t consulted before a legal structure was chosen. 

The result is an estate plan that’s legally sound but financially incomplete. 

Three gaps appear in too many estate plans which are drafted without a financial advisor to guide them: 

1. Beneficiary designations that contradict the will. Retirement accounts and life insurance policies pass directly to whoever is named on the account. That designation overrides the will entirely. Many families haven’t reviewed those forms since the accounts were opened, and they are stale. 

2. A trust structure with unintended tax consequences. The type of trust, which assets fund it, and when distributions occur all carry tax implications. Without the full financial picture, the attorney is effectively blind while making structural decisions. 

3. A power of attorney with no roadmap. The document names someone to act on your behalf but tells them nothing about the accounts, the advisors, the passwords, the goals, or what decisions are likely to come up. 

For couples, estate planning adds another layer of complexity. Two people often bring different levels of financial involvement, different relationships with the beneficiaries named in the will and trust documents, and different ideas about what goals the plan is supposed to meet. One may be thinking about tax efficiency, the other about making sure the children are treated equally, and neither may have said that out loud during the planning process. When one partner handles the process and everything gets built around their understanding, those differences don’t come up during the planning. They surface when the plan is activated: at death, incapacity, or major family transition. 

What Multigenerational Wealth Planning Actually Requires 

Many families approach estate planning as a distribution question: who gets what, how do we make sure it transfers efficiently, and are the people we love protected? Focusing on distribution may be the right framework for an estate attorney, but incomplete for a multigenerational family since multigenerational wealth transfers not just assets but context. The families who do it well give their heirs both. 

What The Portfolio Strategy Group has observed over 35 years is: the families who navigate wealth transitions well didn’t start the conversation at the attorneys’ office. They started it earlier, and vetted it with their advisors. They addressed what the money meant, what legacy they hoped their heirs would build with it, and what assumptions had never been named out loud. By the time the legal documents were signed, the family already understood the intention behind them. 

Multigenerational wealth management starts in the conversations that happen with everyone still present, well before the inheritance happens. 

A Word on Families with Young Children 

For families with minor children, estate planning carries a layer that, in our opinion, rarely gets the attention it deserves. 

Guardianship provisions tell the court who raises the children. That’s essential. But those provisions say nothing about what that guardian should know about the money: how to manage it, what values should guide decisions about the children’s upbringing, or what they should receive as adults. 

These aren’t legal questions. They’re human ones that an estate plan can’t answer on its own. That conversation has to happen well before the estate documents are written, so there is no ambiguity about protecting the people you love. 

Legacy Planning Is Built on Financial Decisions, Not Just Values 

Financial legacy planning asks a different set of questions than estate planning. Not just who receives what, but what they receive it for. What your family hopes the money makes possible. What you want the next generation to understand about how it was built. 

Estate and legacy planning are not the same thing. Many families treat them as one. 

Estate Planning	Legacy Planning
Addresses the legal transfer of assets	Addresses the meaning behind the transfer
Done by an estate attorney	Requires the whole financial and relational picture
Often left alone once documents are signed	An ongoing conversation that begins before the estate documents are drafted and continues long after

Legacy financial planning is the work that lives between the attorneys’ office and the first family conversation about what this money is actually supposed to mean. Many families have done the first. Not all have started the second. 

The Retirement Window 

For families approaching retirement, estate planning carries a specific urgency. 

The decisions made in the five years before and after retirement have the potential to reshape the financial and tax picture for the next generation: how accounts are structured, when distributions begin, which assets get passed and which get spent. Estate planning for high-earning families nearing retirement, such as many living in Westchester, NY, is one of the areas we address directly with clients, before those decisions get made by default. 

What a Financial Advisor Actually Does to Guide Your Estate Plan  

A financial advisor who helps with estate planning isn’t meant to replace the attorney. It’s to make sure the attorney has the full financial picture and identify gaps between the estate structure and what the family’s finances actually require. It’s meant to make sure nothing slips through the cracks, and that the drafted documents reflect the family’s unique goals and intentions. 

In practice, that means different things depending on where the family is in the process. If you haven’t started: we offer to come to the first–and every–attorney meeting prepared, with a full account inventory (once provided), a review of existing beneficiary designations, and specific questions for the attorney to answer for the structure to work. 

If you already have a plan: we will review what was drafted against what actually exists, identify any gaps, and work with your attorney and CPA to close them so you have a plan that reflects what you want. 

What That Coordination Looks Like in Practice: 

• Preparing the agenda and supporting documents for estate attorney meetings 

• Reviewing beneficiary designations on every account against the will and trust 

• Coordinating with the CPA on trust structure, asset placement, and distribution timing before documents are finalized 

• Walking both spouses through the plan so each has the context to make decisions and knows who to call with questions 

For the family, the outcome is simpler to describe: fewer surprises, fewer conversations that start with “I didn’t know that,” fewer moments where the legal structure and the financial reality don’t match. 

The Portfolio Strategy Group doesn’t only work with families in Westchester or near White Plains–we work with families across the country with exactly this kind of coordination. Fee-only, which means we don’t earn money from products, referrals, or recommendations. The family’s situation is the only thing that drives advice. 

If you have an estate plan and aren’t sure whether your financial picture is reflected in it, that’s a conversation worth having. 

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