Discussing Death with Family, Business Estate Assets and How to Argue Less and Talk More


Your Estate Matters Newsletter

Your Estate Matters Podcast

Episode 23: How Discussing Death Can Enrich Family Relationships

In this week's episode, we engage in a compelling discussion with Alyson Jones, a renowned therapist, educator, and bestselling author. Alyson shares her extensive experience as a therapist, focusing on family dynamics, separation, divorce, grief, and legacy planning. The conversation highlights the importance of building resilient families, navigating grief, and fostering open discussions about death and financial matters. Alyson emphasizes transparency in estate planning to mitigate family conflicts and underscores the value of therapy in managing life's significant transitions.


Your Estate Tip

Navigating Business Ownership as an Estate Executor: a Concise Primer

When someone appoints you as their estate executor, they're placing immense trust in your judgment and capabilities. But what happens when the deceased was a business owner? Suddenly, you may find yourself temporarily at the helm of an enterprise - a responsibility few executors anticipate.

Serving as executor for an estate containing a business requires careful navigation of legal, financial, and operational challenges. By understanding your authority, making timely decisions about business continuity, managing risks effectively, and leveraging professional expertise, you can fulfill your fiduciary duty while preserving the business's value.

Whether the ultimate outcome is continued operation, sale, or orderly dissolution, your diligent management during this transition period is crucial to protecting the interests of all beneficiaries.


Your Estate Read

Clear Communication and Estate Planning: Insights from Jefferson Fisher’s New Book

Navigating conversations about estate planning is often one of the most delicate aspects of preparing for the future. These discussions can be emotionally charged, touching on deeply personal subjects such as finances, family expectations, and end-of-life wishes. In his book which came out this week, The Next Conversation: Argue Less, Talk More, Jefferson Fisher offers a framework for addressing high-stakes conversations - making it especially relevant for those engaged in estate matters.

Jefferson Fisher is not a traditional communication expert. A practicing trial attorney based in Texas, Fisher initially gained widespread attention by recording short, insightful videos—often filmed from the front seat of his truck—where he shared simple, practical advice on how to manage everyday conflicts. His straightforward delivery, grounded in empathy and clarity, resonated deeply. As his social media presence grew into the millions, so too did the impact of his message: we can all learn to communicate better, even in the most challenging moments.

While wills, trusts, and incapacity documents provide the structural framework for an estate plan, communication is what gives these plans strength and meaning. Even the most carefully constructed estate documents can become a source of confusion - or even conflict - if they are not accompanied by clear, open dialogue with loved ones.

Fisher’s approach offers practical strategies that can help make those conversations smoother and more effective. Key principles from The Next Conversation that are particularly relevant to estate planning include:

  • Remain in control of your tone – Calmness fosters cooperation. When emotions escalate, clarity often disappears.
  • Use language that connects, not divides – Thoughtful phrasing can help loved ones better understand your intentions.
  • Acknowledge concerns without surrendering your decisions – Validating others’ emotions creates space for respectful discussion.
  • Prepare before speaking – Clarity and confidence are often the result of forethought and intentionality.

These tools are not about avoiding difficult conversations—they’re about approaching them with greater emotional intelligence and respect.

A well-executed estate plan does more than distribute assets: it protects the relationships that matter most. For many individuals, the real challenge is not in drafting documents, but in discussing their wishes with children, spouses, or beneficiaries. There may be disagreements, surprises, or emotional responses. Jefferson Fisher’s communication philosophy offers a roadmap for navigating those moments with grace.

By initiating open, calm, and compassionate conversations now, you reduce the likelihood of misunderstandings and family disputes later. In this way, effective communication becomes a vital part of your legacy.


Here are some ways you can work with us:

  1. Book a free consultation with Heritage Trust.
  2. Download our free checklist “Essential Steps for Estate Planning.”
  3. Purchase our course "The Estate Organizer for Canadians."

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