By Brittany Kalsky, CFP®, CRPC®
Most families have a will. Some have a trust in place. A few have gone through the full estate planning process with an attorney and feel reasonably confident the legal documents are in order.
What far fewer families have done is had the family meeting and open dialogue with their loved ones.
Not the meeting with the attorney. Not the signing of the documents. The actual conversation, the one where you sit down with the people who matter most to you and talk honestly about what you have, what you want, and what you hope for them.
Do my children know what I actually own and where it is held?
Have I told them what I intend and why?
If something happened to me tomorrow, would they know what to do?
These are the questions that tend to stay unasked. Not because families do not care, but because the topic feels uncomfortable, premature, or simply like something that can wait.
At Brandywine Oak Private Wealth, we have seen what happens when it waits too long. And we have seen what happens when families get it right. The difference is almost never about the legal documents. It is almost always about the conversation that did or did not happen before they were needed.
Why the Documents Are Only Half the Plan
Estate planning attorneys do important work. Wills, trusts, powers of attorney, and healthcare directives are the legal instruments that carry out your wishes. They are necessary. But they are not sufficient on their own.
A trust that your heirs do not know exists cannot be acted upon quickly in a crisis. A will that reflects intentions from fifteen years ago may no longer reflect who you are or what your family looks like today. A power of attorney that names someone who does not understand your financial picture creates confusion at exactly the moment clarity is most needed.
The legal documents give your plan structure. The conversation gives it meaning. And without both, even the most carefully drafted estate plan can create more friction than it resolves.
What Tends to Go Unsaid
In our experience working with affluent families across multiple generations, there are a few areas where the silence tends to be loudest.
What you own and where it lives. Many spouses, let alone adult children, do not have a clear picture of the full financial landscape. Which accounts exist, where they are held, who the beneficiaries are, what the login credentials are, whether there is life insurance and with which company. This information does not need to be shared broadly, but at least one trusted person needs to know where to find it.
The values behind your legacy planning. If you want your beneficiaries to understand the reasoning behind your decisions, or the values you hope to pass on to the next generation, it’s best to have those conversations now. Whether one child is receiving more, a family business is being handled differently, or a charitable organization plays an important role, providing context today can help avoid confusion or unintended feelings later.
Your wishes for care, not just for assets. Healthcare directives and powers of attorney address what should happen if you cannot make decisions for yourself. But the documents alone cannot replace a real conversation about what you value, what quality of life means to you, and what you would and would not want in difficult medical circumstances. The people who may be called upon to make those decisions on your behalf need more than a legal form. They need to understand you.
What you hope the wealth will do. Beyond the mechanics of who receives what, there is a deeper question that most estate plans never address directly: what do you hope this money accomplishes for the people you love? That answer shapes everything from how trusts are structured to how conversations with heirs unfold over time.
The Timing Question
One of the most common things we hear when this topic comes up is some version of “we will do that eventually.” And we understand the instinct. These conversations feel heavy. They require vulnerability. They surface questions that do not have easy answers.
But the families who wait until a health event forces the conversation are almost always the ones who wish they had started sooner. At that point, the emotional weight is heavier, the cognitive bandwidth is lower, and the time to course correct is gone.
The right time to have the estate planning conversation is not when something is wrong. It is when everything is fine, when there is space to think clearly, speak honestly, and revisit the conversation over time as circumstances change.
For many of our clients, we suggest starting with one focused conversation rather than trying to cover everything at once. Begin with the basics: where the key documents are, who the key contacts are, and what the immediate steps would be if something happened tomorrow. That single conversation removes an enormous amount of uncertainty and creates a foundation for the deeper discussions that can follow.
How to Begin
The hardest part of this conversation for most families is simply starting it. A few approaches that tend to work well:
Frame it as a gift, not a transaction. The goal of the conversation is not to distribute wealth. It is to give the people you love the information and clarity they would need to handle things without you. That framing tends to make the conversation feel less like a legal exercise and more like an act of care.
Use a specific trigger to open the door. A news story about a family dispute, a friend’s experience navigating a parent’s estate, a milestone birthday, or even this article can serve as a natural entry point. You do not have to announce that you are having “the estate planning conversation.” You can simply start talking.
Involve a neutral third party. For families where dynamics are complex or where certain topics feel especially charged, having a trusted advisor present can help keep the conversation focused and productive. At Brandywine Oak, we often serve in that role. Not as a legal authority, but as a steady presence who can help facilitate the conversation and answer financial questions as they arise.
Keeping the Plan Current
Estate planning is not a one-time event. Life changes through marriages, divorces, births, deaths, business transitions, shifts in tax law, and shifts in family relationships, and the plan needs to keep pace with all of it.
A review of your estate documents every two to three years, or after any significant life event, is a reasonable minimum. Beneficiary designations on retirement accounts and life insurance policies should be reviewed on the same schedule, as they pass outside of the will entirely and are easy to overlook.
The conversation with your family should evolve on a similar timeline. What was true five years ago may not be true today, and keeping the people closest to you informed of meaningful changes is part of what makes the plan work in practice, not just on paper.
The Role Your Advisor Plays
One of the most valuable things a wealth advisor can do in the context of estate planning is serve as the connective tissue between the different professionals involved. The attorney drafts the documents. The CPA handles the tax implications. The financial advisor holds the picture of the full financial landscape and can make sure all of the pieces are aligned.
At Brandywine Oak Private Wealth, we work closely with your estate planning attorney, or with the estate planning counsel we have on retainer, to make sure your documents reflect your current wishes and your current financial picture. We also help families think through the conversation itself: who should be in the room, what should be covered, and how to handle the questions that tend to come up.
If your estate plan has not been reviewed recently, or if the conversation with your family has not happened yet, we would welcome the opportunity to help you think through both. Call (484) 785-0050, email contact@BrandywineOak.com, or schedule a meeting online. You can also visit our client testimonials page to hear how we have helped other families navigate these conversations with clarity and care.
Frequently Asked Questions About Estate Planning Conversations
What should be covered in a family estate planning conversation?
At a minimum, the people closest to you should know where your key documents are stored, who the primary contacts are (your attorney, financial advisor, and accountant), which accounts and assets exist and where they are held, and what the immediate steps would be if something happened to you. Beyond the logistics, it is also valuable to share the reasoning behind significant decisions in your estate plan, particularly any that might be surprising or feel unequal, so that your intentions are understood before they need to be acted upon. At Brandywine Oak Private Wealth in Kennett Square, PA, we often help clients think through both what to cover and how to frame it.
How often should I update my estate plan?
A review every three to five years is a reasonable baseline, but certain life events should trigger an immediate review: marriage or divorce, the birth or adoption of a child or grandchild, the death of a beneficiary or named executor, a significant change in assets, or a major shift in tax law. Beneficiary designations on retirement accounts and life insurance policies deserve particular attention, as they are often updated less frequently than the will itself but carry significant weight in determining where assets go.
Do I need to share the details of my estate plan with my children?
You are not obligated to share specific dollar amounts or every detail of your plan. But there is real value in making sure the people who may be called upon to act on your behalf, whether as executor, healthcare proxy, or power of attorney, understand enough to fulfill that role effectively. Surprises in estate documents, particularly unexpected distributions or omissions, can create conflict that outlasts the estate process itself. A candid conversation while you are here to provide context is almost always preferable to leaving interpretation to others.
What happens if I die without a current estate plan in place?
Without a valid will, your assets are distributed according to your state’s intestacy laws, which may not reflect your wishes. In Pennsylvania, this means assets pass to a surviving spouse and children in proportions set by statute, without regard for your specific intentions or family circumstances. Without a healthcare directive or power of attorney, decisions about your care and finances may fall to a court-appointed guardian rather than someone you would have chosen. The absence of a plan does not mean nothing happens. It means the state’s default plan applies instead of yours.
What is the difference between a will and a trust, and do I need both?
A will directs how your assets are distributed after your death and goes through a legal process called probate before it takes effect. A trust can hold assets during your lifetime and transfer them to beneficiaries outside of probate, often with more specificity and privacy. Many families benefit from having both: a trust to handle the primary transfer of assets and a will to address anything not covered by the trust. The right structure depends on the size and complexity of your estate, your privacy preferences, your family dynamics, and your goals for how wealth is transferred across generations. This is an area where the guidance of both an estate planning attorney and a financial advisor working together tends to produce the most thoughtful outcome.
About Brittany Kalsky
As a Private Wealth Advisor with Brandywine Oak Private Wealth, Brittany brings a decade of experience guiding wealthy individuals and families toward their financial goals using a tailored, strategic approach. Brittany specializes in creating comprehensive financial plans that address a wide range of needs, including tax planning, retirement cash flow management, charitable giving, and estate planning. Her expertise helps clients navigate the complexities of their financial lives while working toward their objectives with greater confidence and clarity. Brittany holds the CERTIFIED FINANCIAL PLANNER™ certification awarded by the CFP Board of Standards and the Chartered Retirement Planning Counselor℠ (CRPC®) designation.
Brittany enjoys cooking, gardening, and spending time down the shore. She lives in Audubon, NJ with her fiancé Dan and golden retriever Osborne.
Brandywine Oak Private Wealth is a registered investment adviser. Registration does not imply a certain level of skill or training. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and, unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial adviser and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance.
