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Archive for the ‘Legal Technology’ Columns

Is LinkedIn All It Was Cracked Up to Be?

Our friend and colleague Bob Ambrogi thinks LinkedIn is losing its luster – and we agree. He wrote a blog post recently on this subject. So we tip our hat to Bob before we begin.

Author Simek isn’t active on any social media other than LinkedIn, largely because he is a professional testifying expert on IT and digital forensics topics – and he didn’t want to risk being hung by his own petard because of something he had posted on other kinds of social media. But LinkedIn, in its original incarnation in 2002, was pretty much a resume site and . . . [more]

Posted in: Legal Technology

Please Don’t Try to Disrupt Anything, Just Build Useful Stuff That Helps People Work Better

Once in one of my law and technology LL.M. classes at UdeM, we had a dare: how many times can one possibly include the word “mayonnaise” in a class presentation. I feel that there is something similar going on with the word “disruption” in law-related talks.

The following are random thoughts about building and positioning products for the legal market which are drawn mostly from lessons learned (read: things that didn’t work out), but also from some stuff that turned out not so badly.

In order to not sound skeptical, I will deliberately not go into my memories of how . . . [more]

Posted in: Legal Technology

Elementary My Dear Lawyer

When “dear” is an opinion on pricing held by the 80% of society who do not use a lawyer to solve a legal problem, then we have a challenge and an opportunity. Both are big, as is the gap between what clients think they can afford to pay, and what lawyers think they need to charge to be profitable.

Around 25 years ago, Apple was advised that Librarians, Journalists and Lawyers would be the biggest users of IT. Because their raw materials were digitised, and their output could be delivered in electronic form, it was thought that Librarians, Journalists and . . . [more]

Posted in: Legal Technology

The Internet of Whose Things?

Much talk is heard, many tweets are generated, about the Internet of Things. Interconnected devices are everywhere, from your car to your home to your clothes to your body. This interconnection, it is alleged, will lead to great benefits, though sometimes it is hard to tell how, except for the people who build them.

We have looked at the questions of security they raise and their impact on privacy, as the Net connection pumps out data about your stuff, and by not-very-distant implication about you, to … just whom? With what restrictions?

The privacy authorities in Canada and . . . [more]

Posted in: Legal Technology

Encrypt or Lose

We all want to be the reasonable person. It’s a figment of the legal imagination but it’s a nice middle ground. Lawyers can protect their client confidential and private information using encryption and securing it with a strong password. At what point is a lawyer not longer acting reasonably when they don’t?

How Do I Get Encrypted?

Since the early 2000s, we have had free full disk encryption software (TrueCrypt) and password managers (KeePass). Cost has not been an obstacle, although you might have needed some technical chops to use them. Then Apple and Microsoft put full disk encryption in . . . [more]

Posted in: Legal Technology

Vivaldi, the Web and the Return of Browser Wars

Eons ago, I wrote one measly post on Slaw (for a 2008 legal tech article, it aged surprisingly well!) and since then have not posted here for seven years, while remaining a regular (but silent) reader.

As the new CanLII CEO, I was offered the chance to end this long hiatus and contribute again to Slaw. I was happy to oblige.


Let’s jump back in time:

At the time of my last contribution to Slaw, I was a very opinionated web user and thought that Internet Explorer 6 was the most evil thing that ever happened… to computers at . . . [more]

Posted in: Legal Technology

Style Makes the … Contract?

Why do lawyers write so badly? Save and except, without limiting the generality of the foregoing, writers and their heirs, successors, and assigns whose right, title, and interest in and to the aforesaid subject matter is or may be, with the giving of notice or the lapse of time, … Sorry, that sentence got away from me!

The push towards plain language drafting is, of course, nothing new. Joseph Kimble, Emeritus professor at WMU–Cooley Law School, has been writing on the topic for more than 30 years. He has written two books, including Lifting the Fog of Legalese and . . . [more]

Posted in: Legal Technology

Ashley Madison and the Deep (And Sometimes Dark) Web

There are lawyers – mostly family and criminal defense lawyers – who know at least a little about the Deep Web and the Dark Web. But the average lawyer? Not so much. In fact, after the Ashley Madison breach, a lot of family law colleagues began asking us questions about the Deep Web and the Dark Web – where the full steamy contents of the Ashley Madison breach were published in many places. Most had no clue that there was any distinction between the Deep Web and the Dark Web.

So what is the Deep Web? Think of the Web . . . [more]

Posted in: Legal Technology

Evidence vs Privacy?

Can efforts to avoid charges of spoliation of evidence involve violation of privacy norms?


Data storage has become very inexpensive. Finding information among masses of data is steadily becoming more manageable – one can turn loose the power of Google or other search engines on one’s own business data. One can use various forms of predictive coding to sort files for particular topics or for degrees of sensitivity: what’s relevant, what’s privileged, and so on.

On the other hand, it can be dangerous not to keep data. The rules of evidence have always included sanctions against spoliation. In days . . . [more]

Posted in: Legal Technology

Lawyers + Software: The New Partnership Model

On 26 August 1996, Business Week asked: “What’s Wrong With The Internet”? One criticism was that “Good Stuff Is Hard To Find”. Their suggested solution was: “Artificial intelligence will make search engines more discerning.”

One year later along came Google. It found the stuff you were looking for, without scaring you off with talk of artificial intelligence. Google helped more of us join the information revolution.

Meanwhile, today we should be on the road to driving nirvana via real automobiles. A problem for too many is that the “driverless car” is as scary as the “horseless carriage” would have been . . . [more]

Posted in: Legal Technology

Wade Into Windows 10

The latest Windows operating system has started rolling out. Unsurprisingly, reactions to its new update method and privacy functions are mixed. If you were on Windows 7 like most lawyers, it will be an easy upgrade and – despite the negative early chatter – worth taking advantage of the free upgrade.

The Upgrade and Updates

If you have any version of Windows other than Enterprise or Windows RT, you can get the new operating system free. You may have been invited to register for a copy, in which case you’ll get a notification e-mail. You can also just grab . . . [more]

Posted in: Legal Technology

Twelve Tips for Effective Tech Presentations

Let’s face it – whether you are talking about securing your data or describing the functions of legal IT products, the average lawyer audience may regard your presentation as useful, but hardly as “sexy.” Since we have been successfully lecturing on multiple topics for 18 years now, we have amassed a number of tips for making our presentations entertaining as well as educational. A friend suggested we share what we have learned. Here our twelve of our best tips:

  1. Be a storyteller. Cold hard facts have very little allure. But everyone likes a good story. When we lecture on cybersecurity,
. . . [more]
Posted in: Legal Technology