When Grief Meets Bureaucracy: Why Families Need Advocates During Estate Administration

Losing a loved one is difficult enough, but trying to navigate the complex maze of bureaucracy involved in managing and administering an estate, while deep in grief, can make things so much harder.

I am working with a client who was appointed as the personal representative of a Massachusetts estate in April. She needed just one document from Computershare (the 2024 Form 1099-DIV) to file the estate’s income tax return. What should have been a simple request quickly turned into an absurd bureaucratic obstacle course.

Here’s what we had already provided to Computershare:

  • Transfer Request with medallion guarantee

  • Estate mailing address

  • W-9 for the estate

  • Notarized Affidavit of Domicile

  • Letters of Authority

  • Death Certificate

And yet, we were told the form could only be mailed to the decedent’s old PO Box (a PO Box no one has access to.)

When I asked what else was required, the rep said: “a Letter of Instruction.”

I asked for their form — they don’t have one.
I asked what the letter must include — the rep listed information we had already provided, word for word, except for the phrase “please send the tax form.”

I asked if it needed to be notarized. She didn’t know.
Medallion guarantee? She didn’t know.
I asked her to find out.

So, I drafted the so-called “letter of instruction,” enclosed the Letter of Authority (again), and mailed it to my client for her signature.

This is the frustrating reality of estate administration: endless hoops, arbitrary rules, and confusing, time consuming paperwork at the worst possible time.

This experience highlights why many families hire advocates during the estate process. It’s not just about filling out forms; it’s about cutting through the red tape and ensuring the process moves forward smoothly. An advocate can help you navigate these complexities so you can focus on what matters: loving, honoring, grieving, and healing.

If you could use support navigating the estate administration process, click here to learn more about my services.

Reach out to me anytime: jill@deathreadiness.com

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From Problem-Aware to Solution-Aware: Why Families Get Stuck in Estate Planning

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