In A Few Good Men, Jack Nicholson’s famous line, “You can’t handle the truth,” is not really about truth. It is about who must make hard decisions when the consequences are real and human, and about who must stand behind those decisions when things go wrong.
The distinction between providing information and exercising judgment is sharpening as artificial intelligence proliferates. This is particularly true in the uniquely human world of estates practice. Death, family dynamics, and emotionally charged decisions about inheritance mean that estate planning, estate administration, and estate litigation are rarely technical exercises. They are exercises in risk management, foresight, and human judgment.
This shift also underscores that the value of lawyers is in the exercise of judgment, refining opinions based on context, and taking responsibility for that advice. AI cannot do this.
The Strengths and Limits of AI
AI tools are extraordinarily good at summarizing, drafting and explaining black-letter law quickly and cheaply. Clients use these tools to obtain “second opinions,” to better understand our advice, and to ask more informed questions.
However, this pattern of use underscores the misconception that legal advice is primarily about arriving at the “correct” legal answer. In practice, most legal problems are resolved by balancing legal risk against cost, timing, reputation, relationships, and long-term consequences, by understanding and adapting to difficult personalities, and often by accepting that there may not be a “right” answer.
AI can identify options. It cannot meaningfully prioritize them in light of a client’s objectives, risk tolerance, and real-world constraints. It does not sit across the table from a client and absorb the nuance of what matters most to them. A good lawyer does.
Estate Administration: When Technical Answers Fall Short
A recent estate matter illustrates this point.
An estate trustee asked whether they should pay an invoice for services rendered to the deceased prior to the deceased’s passing. Because it had been more than two years since his death, the limitation period expired. An AI tool would have advised against payment on that basis.
Although that is the legally correct answer, in this context, it was the wrong advice. The amount owing was insignificant in the context of the overall estate. Defending the claim would likely have cost more in legal fees than simply paying the invoice, even if ultimately successful. More importantly, the claimant had other, ongoing business dealings with the estate that needed to be preserved. Refusing to pay a small invoice risked souring a relationship that mattered, causing unnecessary delay and cost on a more consequential issue.
Estate trustees are fiduciaries. They must balance competing beneficiary interests, preserve estate value, and administer the estate prudently and efficiently. They can be personally exposed to cost consequences if they act imprudently.
None of that changes the limitation period. It changes the advice though. Applying black-letter law in this situation would have been inconsistent with the trustee’s broader fiduciary obligations and practical risk exposure. While estate trustees are required to defend the estate’s interests, they are also required to allocate estate resources strategically.
There are also many circumstances where advancing a limitations period defence is the right course of action. This example simply illustrates that legal judgment is about applying the law in a manner that advances a client’s real-world objectives.
There’s the law, and then there’s reality.
Creativity in Settlement: Where Law Meets Human Reality
AI can estimate a reasonable settlement range based on precedent, damages, and probabilities of success. This method works if litigants are primarily motivated by money.
In estate litigation, however, litigants are more often motivated by sibling rivalries, perceived favouritism in a will, disputes about capacity or undue influence, long-standing grievances, family business succession tensions, and a host of emotional drivers that pre-date the estate itself. AI struggles to detect and account for these drivers.
Creative resolutions often reflect this reality. Settlements may involve charitable donations rather than direct payments, agreed-upon statements, governance changes, or future conduct undertakings. These solutions bridge gaps that numbers alone cannot.
These outcomes emerge through listening, reading the room, and understanding what motivates people. AI can calculate numbers. It cannot intuit dignity, closure, or reconciliation.
Estate Planning Isn’t Just About Templates
Estate Planning Lawyers also need not fear AI. AI tools can generate a will template in seconds. What they cannot do is assess family dynamics, anticipate how unequal distributions are likely to be received, evaluate litigation risk arising from blended families or prior promises, assess testamentary capacity concerns, or advise on how to structure a plan to minimize the risk of a future will challenge.
Accountability Still Matters
When a lawyer gives advice, that advice comes with accountability. Lawyers must balance zealous advocacy with duties to the court, confidentiality with disclosure obligations, and short-term advantage with long-term exposure. These are not matters of simple rule application. They require experience, judgment, and an appreciation of consequences.
Lawyers owe duties to their clients, are regulated by professional bodies, carry insurance, and can be called to account if their advice proves negligent or incomplete.
AI assumes no responsibility. For the moment, it is not a legal person and so it cannot be sued, disciplined, or required to stand behind its conclusions. It does not revisit its advice when facts change or follow through when a decision produces unintended consequences.
For clients, that distinction matters. Legal advice is not just about information; it is about having someone who is responsible for helping navigate uncertainty and who remains engaged as circumstances evolve.
Conclusion: The Lawyer’s Role Is Evolving Ever Upward
AI will change how legal services are delivered. It will reduce time spent on first drafts and routine research. It will compress timelines and challenge traditional billing models. But it will also allow lawyers more time to showcase the skills that set them apart from AI: good judgment, strategic and creative thinking, risk communication, and accountability.
Clients should feel free to use AI to better understand the advice they receive. Lawyers should welcome that engagement and rise to it. In the end, what clients need is not just someone who can handle the truth — it is someone who will stand behind it.