LegalTech – Lawyers’ need for perfection clashes with tech’s need for iteration

Sondra Rebenchuk reveals the hardest part of technology implementation

A title like “Legal Technology and Process Improvement” might bring to mind images of someone who has been coding and hacking since Grade 6. 

Luckily, the team at Blake, Cassels & Graydon LLP is not one for stereotypes. 

“I had really never before contemplated working in legal tech. I didn’t really understand what the industry was. I didn’t know any of the players. But [someone] asked me for help, and if I wanted to join her team and get involved,” says counsel Sondra Rebenchuk, who worked as an AI practice consultant before joining Blakes.

“I was just at a place in my life where I was saying yes to opportunities, so I said yes.” 

Rebenchuk came to Osgoode Hall Law School from the west coast, landing a role at Goodmans LLP. But while her start may have been traditional, she got creative from there, working at a communications firm that specialized in proxy battles and mergers, followed by a stint in South Africa with her husband’s family. From there she joined Kira Systems, a Toronto tech company which helps businesses parse unstructured contract data and perform due diligence. There, she worked on training artificial intelligence with legal data, eventually working with clients across North America before falling into her current role at Blakes.

“Working in this space meant that I was able to address a lot of the challenges that I personally faced when I practiced, and that was very rewarding to me,” she says. 

“And I think that there were a lot of moments in those years when I was practicing where I realized that there was really an opportunity to do things differently. But I didn’t know how. I hadn’t turned my mind to the fact that it could be technology.” 

Rebenchuk will be speaking at Canadian Lawyer’s LegalTech Summit on May 26 in Toronto, in a session focused on practical tips for choosing the right technology. The big challenges, she’s found, aren’t always around the obvious questions, like which tools to use to go paperless.

“Especially with something like going paperless, make sure that you have a really, really good internal communications plan at the very beginning: ensuring that you’re talking to everyone at the firm who could be impacted, collecting their feedback, understanding their needs,” she says. 

“When you’re out there, and you’re looking at different document management systems, making sure that you’re choosing a solution that isn’t just something that you’ve read about and think is interesting, but actually fits the firm.”  

Legal tech always seems to fall short of the fast and powerful consumer technology available today, she’s found. Lawyers can have an “all-or-nothing” tendency, she says: to prefer either nothing or a perfect, complete system, with no compromises.

“A lot of the new technology in the legal space is helping to address pain points in very specific tasks. So, whether it’s contract review, generating signature page packages, automating agreements that are drafted over and over and over again — these are all very tiny pieces of work,” she says. 

“So, start to get comfortable with the fact that the technology will not be perfect. It won’t be able to do exactly what you can do. Setting the right expectations will make people more successful.”

Luckily, says Rebenchuk, there are more resources than ever for lawyers to learn about technology, as more mainstream legal publications explore the issue, in addition to stalwart blogs such as Legal IT Insider and Artificial Lawyer. In-house counsel have an additional resource in outside counsel, she says, adding that her firm has offered legal technology information sessions for in-house teams. Soon, she hopes, law schools will be another hub keeping lawyers up to speed on technology.

“If you start to think about technology as something that you’re in control of, and is something that can actually help improve your practice — not just something that runs in the background, that sometimes crashes or is sometimes too slow — that can be really powerful,” she says.

Hear more from Sondra, who is a speaker at the upcoming Legal Tech Summit on May 26. Visit for more information.