Second opinion

I’ve been thinking about my expertise lately, and the information I’m best equipped to share with you here. I read fewer decisions than I used to, but I talk to far more lawyers about the realities of running a practice.

So, this newsletter is now a source for all the hard-won lessons I’ve learned from Inn Laws — our community of entrepreneurial lawyers. I’m surrounded by people who run their practices like a business, share openly with peers, and are quickly finding themselves in the top 1% of AI adoption (safely and sanction-free). You deserve a window into everything we’re learning together.

Don’t worry, I’ll still be rounding up all the stuff readers loved about Hearsay from days of old, including the latest Canadian legal cases, news stories, and cautionary discipline tales.

But you’ll also get a slice of the tactical work we do each week inside our community.

Thanks for allowing me this reintroduction. Let me know what you think about the new Hearsay.

— Dylan Gibbs

• Questionable courthouse convos

• Swearing about the King (still)

• AI-powered second opinions

• Foreign buyers

• Copy-pasting

MAKING HEADLINES 

👑 The SCC will decide whether the Law Society of Alberta can require new lawyers to swear allegiance to the King. The Alberta Court of Appeal held that the oath infringes religious freedom, and the province is appealing. There’s somewhat similar litigation brewing in Quebec, over the oath for provincial legislators. Quebec made the oath optional in 2022, which the Public Interest Litigation Institute says effectively amended the Constitution.

💰 The Federal Court will need to figure out whether parliamentarians can refuse a pay raise. Conservative MP Mike Dawson doesn’t want the extra $8,800 granted to federal legislators earlier this year. The House of Commons says he doesn’t have a choice, but Dawson wants the Court to take a closer look.

🥤 Quebec’s new energy drink law tripped up McDonald’s this week. The fast food chain started selling Red Bull everywhere else in Canada, but they’re delaying the Quebec launch until they can figure out how to navigate the law that bans energy drink sales to consumers under 16 years of age.

🏛️ Congratulations to Chief Justice Geneviève Cotnam, who’s now spearheading the Quebec Court of Appeal. Outgoing Chief Justice Manon Savard went supernumerary earlier this week.

IN FOCUS

Did I say ChatGPT could read my advice?

A lawyer recently told me about a clicking noise that kept interrupting her client meeting. Every time she spoke, the client paused before answering.

Click. Click. Click.

Before long, she realized the client was feeding every word she said into his AI tool of choice. He challenged her advice, extending the meeting beyond reason and testing the lawyer’s patience.

I hear some version of this story almost every week now. Claude and ChatGPT held out as experts. Clients clogging their lawyer’s inbox with AI-generated slop. Lawyers left sorting out the mess.

So what, if anything, should we do about this?

After a year spent running a community of entrepreneurial lawyers, I’ve seen several different approaches. Some lawyers prohibit client AI use in their retainer agreements. Some charge extra to review AI-generated material.

I think we can do better. But it starts with trying to understand the gap these clients are trying to fill.

Most people with a legal problem are facing what might be the most difficult problem of their lives. They’re overwhelmed, and discomforted by how little they know about the legal system. They’ve also watched AI conquer nearly everything else they’ve thrown at it.

From the client’s perspective, avoiding a tool that feels like magic would be absurd. Telling clients to do so is quickly becoming a position so extreme that it almost certainly won’t be respected. And a disrespected boundary is worse than no boundary at all.

Instead, I propose that you accept the fact that clients will use AI to help with their legal problems. Instead of trying to eliminate AI from the conversation, aim to make its involvement as non-adversarial as possible. Instead of banning your clients from using these tools, advise them of the risks.

Learn enough about AI that you can tell clients where it shines — and where it comes up short. Know enough that you can be their trusted expert in this domain too. I suspect it will serve you better than arguing with them.

If you want a starting point, I put together a letter I’d send to clients if I were practicing. Feel free to steal it, tweak it, or use it as a source of inspiration.

And if you need help on the AI expertise front: reply and let me know. Inn Laws has that covered.

FROM THE COURTS

1. There’s such a thing as too much copy & paste
   Lounge Medical v. DermaSpark, 2026 FCA 135

It’s one thing for a judge to endorse a proposed order. It’s another thing to mirror the order so closely that the judge’s final order ends up including the same errors as the draft. The latter led the Federal Court of Appeal to overturn a Federal Court decision that awarded $50,000 in “nominal damages” (later corrected to “punitive and exemplary damages” ).

2. New life for termination clauses
   Baker v. Van Dolder’s Home Team, 2026 ONCA 568

The Ontario Court of Appeal finally ruled on whether using the phrase “at any time” in a termination provision violates the Employment Standards Act. To the chagrin of the plaintiff-side bar: it doesn’t. Some lower courts held that this sort of provision is offside, because employment standards legislation spells out certain “times” when you definitely can’t fire an employee. The Court of Appeal’s approach had a bit less “well, technically” in it:

3. End of life for privative clauses 
   Democracy Watch v. Canada, 2026 SCC 28

Lawmakers can no longer prevent courts from reviewing administrative decisions. Many statutes include a privative clause, saying that courts can’t get involved through judicial review. For example, the federal Conflict of Interest Act says courts can’t review decisions made by the Ethics Commissioner. According to a recent SCC decision, that’s no longer allowed. And that means there’ll be a bit more scrutiny on Justin Trudeau’s ties to WE Charity.

BY THE NUMBERS

15%: Ontario’s foreign buyer tax back in 2022, which stung the former head coach of the Toronto Raptors to the tune of $697,500. Nick Nurse is now challenging that bill in Ontario’s Superior Court of Justice, arguing that he lived and worked in Ontario (and won us a freakin’ championship for Pete’s sake).

$1M: the maximum administrative penalty for those who fail to register under Canada’s new foreign influence registry, launched this month. Lawyers get a carveout: privileged advice to foreigners doesn’t require registration.

257: the number of professionals the Law Commission of Ontario surveyed before concluding that protection orders in the province are routinely breached and rarely enforced.

FROM OUR COMMUNITY

I ran a bunch of live workshops this spring, teaching lawyers how to supercharge their use of AI tools like Claude. One attendee said I should be selling it to law firms as a several-thousand-dollar session.

Instead, I decided to record the whole thing as a self-paced course and put it inside Inn Laws — free for members. Our AI Bootcamp has 16 lessons so far, with about three hours of content, and more coming each week.

Many lawyers are still stuck on whether you can put client information into an AI tool at all, so that’s where we start. By the end, members will have everything they need to run their own AI executive assistant.

I tell the people who take my training that they’ll enter the top 1% of legal AI users. But you don’t need to take it from me. Thirty-nine lawyers filled out the feedback form after our live workshops. Twenty gave it a ten out of ten. Here’s one of the comments I appreciated most:

THINGS NOT TO DO 😤

Don’t chit-chat with the junior lawyer applying for your recusal.

A newly-minted lawyer went to court to collect an audio recording of a past hearing involving New Brunswick Justice Frederick Ferguson. His firm planned to use it as evidence in a pending recusal motion.

Justice Ferguson learned the lawyer was in the courthouse and struck up a conversation, attempting to contextualize what the lawyer would soon hear on the audio recording. He also mentioned that there might not be time to get the recording in as evidence. Even though Justice Ferguson said he wasn’t trying to gain favour, it made the young lawyer nervous.

The CJC ordered a written apology.