Estates Made Simple

Welcome to the “Estates Made Simple” Podcast, hosted by Gordon VanderLeek, a licensed lawyer specializing in wills, estates and trusts, and Jenna Carvalho, an estate and trust consultant with over 10 years experience helping families secure their assets and plan for the future. We are a bi-weekly podcast that discusses the complicated and often confusing world of estate administration. Our goal is to provide you with the insight, knowledge and resources to help you navigate this complex process. Every episode we bring our unique perspective to provide listeners with unbiased information and practical tips to ensure success and mitigate risk. Even if you are not an executor, there will be topics of interest as you consider planning options for your own estate. Join us for helpful tips and important information on navigating estate administration so you can achieve peace of mind as an executor or administrator.

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Estates Made Simple

Estates Gone Badly (Part 2)

October 01, 2025 • Jenna Carvalho & Gordon VanderLeek • Season 1 • Episode 70

Episode Summary

In this episode, we’re joined again by Michaela Summers, associate lawyer at VanderLeek Law and head of the estate administration department.

This is part two of our “Estates Gone Badly” series. There were simply too many stories (and lessons) to fit into one episode, so in this episode we continue exploring real-life examples of estate administration gone sideways and what could have been done differently to avoid costly, stressful, or relationship-damaging outcomes.

Key Discussion Points

1. DIY and Hybrid Wills Gone Wrong

· The risks of mixing holograph (handwritten) and formal will requirements.

· Why having a beneficiary witness a will can void their gift.

· How courts may handle these cases and why family harmony often determines whether things turn out well.

2. Multiple Executors and Family Conflict

· When “treating everyone equally” creates more problems than solutions.

· Lessons on choosing executors based on skills, judgment, and ability to collaborate not just fairness.

3. The Power (and Absence) of Communication

· Why clear communication with family about your estate plan is one of the greatest gifts you can leave.

· The damage that secrecy and surprises in a will can cause, even when legally valid.

· Alternative ways to explain decisions - letters, videos, or conversations to help preserve family relationships.

Key Takeaways

· A small upfront investment in professional estate planning saves thousands in legal costs and heartache later.

· Don’t appoint multiple executors just to avoid “picking favourites.” Choose the right person for the job or consider a neutral third party.

· Communication with family members, whether through direct conversation or written explanations, reduces surprises, prevents conflict, and protects relationships. A strong executor is trustworthy, has time, and makes sound decisions.

Hosts:
Jenna Carvalho
The smartest way to choose an executor.
Guardian Estate Company
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Gordon VanderLeek
Give your family a legacy of protection - Wills, Estates and Trusts.
VanderLeek Law
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