Take This Stress Test: Top 10 Triggers for Ontario Estate Trustees Revealed

Were you named as Ontario estate trustee or estate executor? You may think this is an honour, as most people do. You may have been asked if you would handle an estate for a friend or relative. The job of being an estate trustee is often thankless and stressful. But, if you are also an estate beneficiary, it may be rewarding in many ways.

Here is a list of top 10 executor headaches that can make your job more stressful. You will require experienced legal advice to keep you out of trouble.

The estate is broke. Do the math and check if you have enough money to pay all the bills.
Real estate is always a headache. If you must sell real estate you have added responsibilities.
Investments and Commercial Real Estate. Does the estate include investments, including commercial real estate that requires attention?
Foreign Assets. Following the legal rules to probate an estate in another language and jurisdiction may be time consuming and complex.
Business Comes Before Pleasure. Is there an active business with partners or a corporation with shareholders in the estate?
Your Age Considerations. Does your age or health prevent you from starting and finishing your tasks over the next year or more?
Conflict or Conflict of Interests. Are there signs that the beneficiaries would disagree and give you headaches? Do you have a conflict of interest?
Contested Wills. Do you think that anyone will contest the will?
You Can’t Hire Help. Does the will prohibit you from hiring professionals to assist you with your duties?
Tedious Long-Term Trusts. Does the will require you to manage a Trust on a long-term basis, say over the next 5 to 10 years?

These and other executor headaches can make your job as estate trustee more stressful. Be forewarned. You will need experienced legal help to deal with these headaches.

How to Get Started

Need help during your journey as an Ontario estate trustee? Contact me for a meeting. I have helped estate trustees for decades by solving estate problems, going to court or through mediation.

I offer you a meeting to discuss your needs by Zoom or in-person in my Toronto west end office. Arrange your no-obligation meeting today.

I am a Certified Specialist in Estates and Trusts Law. I can give you expert tips to end your estate worries.

Posted In: Estates, Executors On: March 9th, 2026

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