Finding the Time; The British Barrister/Solicitor Divide; Apparently Nothing Is Tougher than a Diamond

The main reason I’m coming around to the idea of seed funding

There are a lot of benefits to solo bootstrapping. You don’t have investors or co-founders or employees breathing down your neck.

No timelines. No deadlines. Low stakes.

A lot of that, though, is as counterproductive as it is cushy. The lack of stress and accountability means there’s no urgency. This is part of the 90 day exercise I’m in the middle of - trying to manufacture some artificial urgency (although, when it’s your wife who’s given you the deadline, it may not be so artificial…).

I’m much less of a baby in this space than I was two years ago, and my views on a lot of things have changed. I’d like to work with others (not so easy to find), and I’d like to take it all a little more seriously.

But the major thing I’d love is the freedom to work on it all full time.

That’s not what part-time bootstrapping is about. I have a variety of income sources I cobble together to pay the bills, from part-time duty counsel work to an increasing load of contact legal research/drafting I’ve been taking on for colleagues. I don’t mind it - it keeps my head in the law game, and let’s me innovate and test out some of the legal tech I’m building, as well as affords me access to early users.

But my god does it take up a lot of time.

I would be shipping and iterating on the things I’m building 1000% faster if I could work on it full-time. I used to think about raising funding only as a means of hiring, scaling, and/or paying gigantic upfront costs. What never really hit me until recently was that it could pay for my full-time attention. That would be pretty cool.

It’s Really Two Jobs

In North America, a litigator preps the file, does the research, brings in and manages the clients, drafts materials, interviews witnesses, goes to court, etc., etc., etc. That’s what I did when I was in private practice, and I was pretty darn good at it.

On the other hand…

There’s something to be said for the specialization of the classic british barrister/solicitor divide. As I understand it, over there the jobs of managing and preparing the file, and then actually doing the negotiating/litigating in court, are distinct sub-specializations within the legal profession. This makes a lot of sense for a bunch of reasons.

Reason the first

It’s really two jobs. Wading into the nitty gritty of a mountain of disclosure/productions, cross-referencing details, and then swan-diving into the sea of case law and secondary source material out there (if done at a very high level) is a full-time gig. Or could be, particularly with a respectable case load.

Similarly, perfecting the double-art of advocating outside, and then inside, a courtroom is itself a full-time gig. Negotiating, mediating, and settling cases is an enormously useful skill akin to great poker playing, and takes years to learn to do well. Advocating inside the courtroom is, in many ways, a very different kettle of fish, and also takes a lot of reps to master (and, unfortunately, it is increasingly rare to find litigators who have really gotten the level of on-your-feet experience to get quite good).

Now obviously there are plenty of great lawyers in North America who are able to do both at a high level. But there are way, way more who really only excel at one side of that coin (and an unfortunate amount who excel at neither).

And splitting up the work would ultimately be a good thing, because…

Reason the second

Specialization breeds quality. We live in a world of increasing specialization, and specialization of task is an important version of that.

Take my area of criminal defence. Getting down to the business of reading a disclosure package and issue-spotting all of the potential missing disclosure, evidentiary issues, and Charter applications is itself a highly complex exercise that one could get very, very good at if they spent all of their time doing it.

Similarly, knowing your local Crowns, judges, court staff and procedures can often make the difference for the quality of result your client gets on a resolution or at a trial. And that’s to say nothing of the skill of actually writing and delivering great examinations/submissions, or perfecting the art of informal folksy advocacy inside judges’ chambers.

Getting good at one or the other of those specialized skillsets is tough. Getting good at both, simultaneously? Tall order for many counsel. And it’s the clients that suffer. If you had a nice team of lawyers tackling each in tandem though, you’d greatly improve the overall quality of work on files not only because of the specialization aspect, but because…

Reason the third

Litigation is a team-sport frequently played solo. Lawyers, and particularly litigators, tend to be individiualistic, A-type professionals who prefer to work alone and be accountable to as few people as possible. The problem with that is that law is hard, different lawyers have different strengths and experiences, and sticking two (or more) heads on a legal problem almost always yields superior results. One of you will catch something the other missed. Or think about it a different way. Sometimes, it’s just great to have a sounding board and hear your ideas and strategies out loud.

This is why it’s such a shame that the lawyers lounge has turned out to be one of the primary victims of Covid and the pandemic. Even isolationist litigators would tend to converse with their colleagues whilst sitting on the well-worn couches of a good counsel lounge, and their clients results would tend to be all the better for it. But you won’t find those crotchety barristers making the effort to seek out their colleagues advice nearly as often, if at all, in the new world of virtual courts.

The solicitor side is ripe for technological innovation

One of my side gigs involves getting hired by more and more of my colleagues to do classical british solicitor-type work on their files. Now I was pretty darn good on my feet in the courtroom, and even better in the judges’ chambers. But I wouldn’t say I was passionate about advocacy.

The solicitor side, on the other hand, is both fascinating and really fertile ground for some good new tech. So much of reviewing files and doing legal research can be automated in ways that would necessarily increase the quality of legal work that I can’t believe more hasn’t been done in this area.

By the end of my time in private practice I became convinced that 95% of that side of the job could be automated and standardized according to set of well thought out checklists and flowcharts put together by someone with experience in the area. Why that hasn’t been done, and stuck in a simple web app, is beyond me.¹

All of that is to say, I’m enjoying this little solicitor-side practice I’m building. And the lawyers I work with? They love it even more. They tend to be the type to really enjoy excelling at the barrister-side of the job - negotiating, examining, shooting the shit with the judiciary, and all of that jazz. What they hate is pouring over hundreds of pages of handwritten notes, and then cross-referencing them to page 345 of tab 34 of bla, bla bla bla… Particularly because I find there tends to be quite an overlap between ‘poker-playing, gun-slinging trial lawyers’, and the ‘almost completely technolocially inept’. It takes me 5 minutes to prep or research something it might them take all day to do. No wonder the team model works so well.

I think the tech is coming that will make this type of arrangement more and more of a reality. Maybe not always an actual person like me doing the solicitor-side, but at least a kind of techno-solicitor AI specialized to assist barristers in their particular area of law. Hell, I’m building a bunch of it myself. Tools to generate appropriate boolean queries, semantically search through results to find relevant passages and compile the best results in a mini-memo. Tools to recursively examine a disclosure package or transcript with natural language queries and compile relevant results to be cross-referenced against each other. Hell, even tools to one-click-create your application records, book of authorities, whatever. The stuff’s not rocket science.

The real winner is the client

I know that I’m cynical. But the truth is, the quality of legal work being done out there, writ large, is not as high as it should be. And for once, that’s not meant to be a knock against my colleagues. It’s been technologically possible to build tools that would systematically raise the level of legal services delivered to the public for a long time - it just hasn’t been done.

It should very much be the case that anyone taking on an impaired driving case, for example, has an affordable tool available to them that in 5 clicks or less:

• tells what disclosure they should have/request for this type of case

• sets out a checklist of all of the common issues they should be on the lookout for, and how to find them

• gives them current, high level law on each issue, and

• affords them an easy way to save the results and refer to them later

If that existed, you’d have to work pretty hard not to do at least an adequate job representing your client, and getting respectable results.

Maybe then, people might have a little more respect for lawyers writ large. Then again…

I guess there really is nothing tougher than a diamond

For anyone keeping score, the seeming end to the long-running Diamond and Diamond regulatory action is a $100,000 fine and 3 months off from the practice of law for head honcho Jeremy Diamond. For many both inside and outside of the profession, that’s pretty disappointing. For a guy with the means and prospects of Jeremy Diamond, it’s pretty hard to call that anything more than a slap on the wrist.

I won’t get into the issues here - the Toronto Star has been reporting on all of the controversies around the firm for years, and I’m sure does a better job than I could.

What I will say is that the message sent out by that result for most will be that the law society lacks teeth as a regulator. The self-regulating status of the law society is a hot topic out there, particularly in the upcoming Ontario bencher election. It’s actually a hot topic across the world of licensed professionals, with many in the public wondering why people who practice in areas as impactful as law and medicine should get to set and enforce their own rules, as opposed to being subject to some form of external regulation more directly accountable to the public they serve.

That’s a complicated topic I won’t get into just yet. But definitely food for thought.

Notes