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Estate planning is rarely straightforward, but it can become even more complicated when parents find themselves dealing with a grown child whose behaviour or circumstances pose a risk to the family's wealth.

Maybe an adult son or daughter has a history of refusing help for self-destructive behaviour, or perhaps the relationship is strained or has grown toxic beyond repair.

Ads for banks and financial-planning firms often show images of multiple generations coming together to talk about what happens to a family's assets once Mom and Dad have passed on. But reality is often messier than that. Sometimes parents must contemplate cutting that difficult adult child out of their wills.

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Vancouver lawyer Julia Barsel, who specializes in wills and estates, has seen it all: broken relationships, severed ties, unforgivable actions. Children with constant money troubles are bailed out time and again by the folks.

Those in control of family fortunes have many options, but cutting someone out of an inheritance is usually a last resort.

"It all depends on to what extent the black sheep is black," Ms. Barsel says. "You have to think it through. Sometimes it's really, really difficult. And it's always emotional."

When estate planner Lisa Handfield, of MacMillan Estate Planning Corp. in Calgary, meets clients who say they want to cut a child out of their will, she first begins to tamp down emotions.

She begins by asking why they have come to that decision. They discuss the circumstances as openly as possible; context is crucial for estate planners should a will ever be challenged in the future. Then she sets up another meeting a few weeks later, to give clients the chance to mull things over.

If, after that, they are still determined to go ahead, Ms. Handfield then arranges a subsequent appointment to sign the documents.

"The most important thing to remember – and what we always advise clients – is that this shouldn't be taken lightly," she says. "This is a big decision. Sometimes people want to do things a little bit hastily. We want to make sure they have time to reflect on it.

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"We also like to do a tummy test," Ms. Handfield says. "If they can't sleep at night, we say, 'Maybe you should wait before you cut them out.'"

People making out wills should remember that they are public documents that can go through probate proceedings, Ms. Barsel says. So those who have opted to deny an adult child an inheritance should consider a separate memorandum. Such a document can explain the reasoning behind the decision in a discreet manner, as it's not a public document like the will but rather can be seen only by interested parties. Ms. Barsel recommends that people go into extensive detail and provide documentation to protect themselves and their estate.

"If a child has been cut out from the will for no good reason, the court would do anything to fix the situation and give them something," she explains. "The court would usually urge the parties to come to some sort of agreement. But if the parent is adamant about not leaving anything to that child, they need to be prepared for litigation. Chances are the child will dispute the will."

Parents should be prepared for that, Ms. Barsel notes. "In the memorandum, they should explain things like, 'We gave John this amount of money 10 years ago, this amount of money seven years ago, this amount of money five years ago. This is the part of my estate they would have received, but they have already drawn it, and I want to be fair toward my other children and keep it equal.'"

If parents have evidence of disbursing funds in the past, such as copies of money transfers, cheques or paid debts, Ms. Barsel says they should be included in the memorandum in case a lawsuit arises.

Estate planning can be even more complicated and heart-wrenching when drug or alcohol abuse is involved. Parents might worry that handing over a large sum of money could exacerbate the issue.

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One way to cope with that is a testamentary trust, which provides explicit instructions for how the money is disbursed. It might require that money be spent specifically on accommodation, transportation, medical costs or rehabilitation, Ms. Handfield notes. For instance, if that person required a car, trustees could arrange to pay a dealership directly.

People also need to be aware of varying laws among the provinces and other jurisdictions, says Norman Ewing, a colleague of Ms. Handfield's at MacMillan Estate Planning. For instance, owners of investment or recreational property in another part of Canada or south of the border could be subject to other probate and inheritance rules.

Ensuring that an estate is legally sound is just one part of a planner's role, Mr. Ewing notes. The other is the human element.

"Sometimes people are pretty passionate about something and may want to be a bit vindictive," he says, "and that's just asking for further complications or challenges. We want people to understand their options.

"We take on kind of a counselling role at times to make sure we get the best results."

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