When someone dies, families expect to feel grief. What they rarely expect is the number of decisions, forms, accounts, and urgent conversations with banks and institutions that suddenly land in their laps. Even in the most organized families, the period after a death can feel like a maze. When the person who has passed left little or no guidance, that maze becomes even harder to navigate.
What an Executor or Administrator Actually Does
Executors and administrators are responsible for settling the financial affairs of the deceased. It can take months or even years and involves tasks like locating assets, gathering paperwork, filing tax returns, paying bills, and working with courts and financial institutions.
Most people never think about this role until they suddenly find themselves in it. An executor is named in a will to settle the estate. If there is no will, the court appoints an administrator to serve the same function. Because the job is often more involved than families expect, it can feel overwhelming at first. It includes locating accounts, gathering important documents, paying final bills, filing tax returns, canceling subscriptions, working with banks, and distributing property in accordance with the will or state law. It also includes sorting through personal items and digital records that may be scattered across a house, phone, or computer.
The emotional side can be just as challenging. People are grieving while also sorting through bank statements, investment accounts, closets, attics, and digital records. They may feel pressure to guess what their loved one would have wanted. In families where everyone gets along, this process is still draining. In families where there are disagreements, it can pull old conflicts to the surface. Preparation ahead of time does not eliminate grief, but it can greatly reduce confusion and conflict.
Why Probate Often Becomes the First Stop
Many estates end up in probate because few people create or update their legal planning documents. Probate is the legal process that validates a will and supervises the settlement of an estate. If there is no will, the probate court determines who inherits under state law.
The process works, but it is rarely smooth. It adds time, requires court filings, and often brings legal costs. Delays can occur if documents are missing or if no one knows where accounts are held. Families may even need a separate court order to open a safe deposit box containing the will. The public nature of the process also surprises many families who expected privacy. Because the executor cannot take action until the court authorizes it, even simple tasks can be delayed. Given the many downsides, it makes sense that people try to avoid probate whenever possible.
Probate only applies to assets that are considered “probate assets.” Many accounts and pieces of property can bypass the process entirely when ownership and instructions are properly established.
How Different Tools Shape What Happens
Estate planning is not one document. It is a set of tools that determines how assets move and who is in charge. The most common tools (summarized in the table below) serve different purposes and work together. Seeing them side by side can make the differences easier to understand.
Tool
What It Does
How it Transfers Assets
When it Takes Effect
Highlighted Benefits
Will
Lists who receives probate assets and names an executor
Through the probate court
After death
Clear instructions for the estate
Beneficiary Designation
Directs specific accounts to named individuals
Direct transfer by the financial institution
Immediately at death
Fast and avoids court involvement
Living Trust
Holds assets during life and distributes them under preset rules
Managed by the trustee according to instructions
During life and after death
Allows control and avoids probate if funded correctly
Testamentary Trust (Created by a Will)
Adds rules to gifts made through the will
Executor transfers assets into the trust after probate
After probate ends
Useful for conditions without a living trust
Each tool plays a role. Beneficiary designations are often the quickest way to transfer assets, but they must be updated regularly. Wills provide general instructions but rely on probate. Trusts allow more control and move assets more smoothly, but only if funded properly during life. A trust created through a will provides structure, but still passes through probate first.
The Practical Challenges Families Face
Even when someone’s wishes are straightforward, carrying them out can be complicated. Families often sort through decades of belongings without knowing what is valuable, sentimental, or simply clutter. They may struggle to agree on decisions or feel unsure about what their loved one truly intended. Digital records add another layer of difficulty. Phones, password managers, online accounts, and cloud storage now hold much of a person’s financial life, yet families often cannot access any of it without a digital legacy plan.
These challenges are common but preventable. Preparation ahead of time is not just a legal exercise. It is a practical safeguard and kindness to the people who will someday be responsible for handling your affairs. A little clarity now can prevent days or months of frustration later. It also gives your executor a realistic head start at a time when everything already feels heavy.
Putting Your Plan Into Action
Reducing future stress for your loved ones does not require mastering legal terminology. It simply requires understanding what you want and putting a few key pieces in place that reflect your current life situation.
Start by identifying your goals and sharing them with an estate planning professional. Create or update your will and ensure your executor can easily find the original. Review beneficiary designations regularly to ensure they reflect your current intentions. Think about whether a trust would help you avoid probate, manage distributions, or protect minors. Keep important documents accessible rather than locked away in places no one else can reach. Talk with your family so they understand your decisions. Revisit your plan every few years and any time you experience a major life change, such as a move, marriage, divorce, or the birth of a child. These steps reduce uncertainty, protect assets, and give your family a roadmap when they need it most.
Putting these steps into motion can feel daunting, but you do not have to navigate it alone. Our Legacy and Incapacity Planning workshop is designed to help you understand how the different parts of an estate plan work together. It shows you how to create a structure your family can rely on. The workshop builds on the same ideas explored here by emphasizing clarity, preparation, and care for the people who will one day carry out your wishes.
Planning ahead is not simply about distributing property. It is about removing avoidable obstacles during an already difficult time. When families have clear instructions and the right legal structure, the period after a loss becomes far more manageable. A thoughtful plan turns what could be a maze into a clear and navigable path.
Want to learn more? Listen to Ep. 206 of the Retire With Style Podcast.
