Pretty much everything was a counterintuitive curveball.


In April of 2006, more than 15 years ago, I wrote a memo to file that would go on to exert a disproportionately large impact on my thinking and career, albeit many of the lessons took years to come into focus and were far from what I expected.

The topic was Moneyball as applied to law firm associates—in essence, sketching out the data and methodology necessary to identify under and overvalued attributes of law firm associates, akin to the selection methods used by Oakland Athletics in the famous book by Michael Lewis.
Continue Reading Moneyball for law firm associates: a 15-year retrospective (257)

Source:  Gravity Stack [Click on to enlarge]

Sophisticated investors are betting on contract tech. It’s about business, not the intricacies or importance of law.


Today’s post (256) and last week’s (255) are a two-part series on the burgeoning legal tech sector.

Whereas Post 255 focused on the explosion in the legal technology market over the past year—five new #Legaltech Unicorns, three companies go public—this post looks contract tech, which is arguably legal tech’s hottest subsector.
Continue Reading Because Everyone Else Cares: Why legal should be paying attention to contracts (256)

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Five New #Legaltech Unicorns.  One Unicorn Nearly Doubles in Value.  Three Companies Go Public. 


It might be unfair to say that legal technology arrived in 2021. After all, law firms and law departments, the primary target buyers of legal tech, have been preparing for the impact of AI and automation.

In 2018, Amlaw 100 firms like Reed Smith and later Wilson Sonsini began creating dedicated tech-focused subsidiaries. See Post 213 (Zach Abramowitz’s overview of law firm-led legal tech.  In late 2019, the chairman of an AmLaw 50 firm told us, “We know there is new stuff, we know that our clients know about the new stuff. The question is how we become proactive so that our clients don’t bypass us on the way to the new stuff.”
Continue Reading How the first half of 2021 signals the maturity of an ecosystem (255)


Making lemonade out of lemons.


It’s sometimes hard for those of us working in professional services or the legal profession to fully and completely walk in the shoes of our clients.   Sometimes it takes a bit of real-world experience to get us there. 

My spouse, Mila Jones (we call her Miles), was recently involved in a controversy that had the potential to result in class-action litigation involving several sophisticated parties.  As a loving and supportive spouse whose household was personally affected by the alleged wrong—and someone who earns his living in the litigation business—I had the experience of walking in the shoes of a prospective client.  And no surprise, it was eye-opening.
Continue Reading My walk in the shoes of a prospective client (254)


A. NewLaw is a mindset.


NewLaw is a mindset. It is a movement. NewLaw’s enemy is the adage: “because that’s the way we’ve always done it.”

Whether coined by Eric Chin, see Post 242, or Jordan Furlong, see Furlong, “An Incomplete Inventory of New Law,” Law21, May 13, 2014, the original definition circa 2013 was: “any model, process, or tool that represents a significantly different approach to the creation or provision of legal services than what the legal profession traditionally has employed.”
Continue Reading Q. What is NewLaw? (253)


Len Fromm’s lawyer shares what he’s learned.


Positively Conflicted is the right book for any lawyer seeking a rich and fulfilling life, which is a larger category than one’s career.

According to the author, lawyer-meditator Sam Ardery, we get to this highly desirable endpoint by getting good at conflict. On one level, this makes sense, as we’re all in the conflict business. But Ardery’s definition of conflict is remarkably broad and includes the tensions and traumas of our personal, professional, and familial relations as well internal conflicts, where we stew over our inadequate supply of power, security, esteem, and comfort.
Continue Reading Positively Conflicted (book review) (252)


“One of the biggest myths in legal education is that there is more than enough well-paying work for anyone who has a law license.”


About ten years ago, through a connection made by Bill Henderson, I was invited to a gathering of law-school professors in Northern California.  I was still a manager of a global law firm at the time, and Bill thought that it would be useful to add a practitioner to the group, which otherwise comprised solely academics from around the US.  I remembered this conference recently as I read about the focused efforts of the Debevoise & Plimpton law firm starting in 2012 to bolster demand for its services after years of no growth or decline. See Dylan Jackson, “Debevoise Faced a Demand Crisis. Its Solution Required Change From the Ground Up,” Law.com, July 1, 2021.

The reason for the flashback was my laughed-at suggestion that law schools should add a course in sales and marketing to their curricula. 
Continue Reading Would sales & marketing in law school cross a red line? (251)


Will expert systems disrupt the legal value chain?


In the first installment of this book review series on AI (Post 232), I argued that AI will not reduce employment in the legal sector, and in fact, the extensive deployment of AI tools might well increase total legal employment significantly. In the second installment (Post 237), I reviewed a children’s board book, considered weaponized ostriches, and concluded that AI tools are powerful complements to human lawyers but will not soon replace many – or perhaps any – of them.

In both pieces, the point is that AI – while very cool and very powerful – is also just a labor-saving device like anything else.  AI should extend the reach of legal services to a broader audience, and there is little to suggest that AI will reduce employment in the legal sector overall.

This is not to say that AI will leave the legal market’s very settled pecking orders undisturbed.  AI turns a service into a product, and that can have powerfully disruptive effects in an industry.
Continue Reading “My new Volvo is a Mazda”: Part III of book review series on AI in law (250)


Yvonne Nath shares what she’s learned (so far!).


Any good strategic planning process takes into consideration how to optimize the existing resources you have and what you will decline to pursue. You must be able to make important decisions without having all the information (i.e., you’ll need to take some risks).

The pandemic gave me some time to rethink and revise the strategic plan I have for my life. Not my entire life, of course, but I did map out how I want to live the next 1-2 years of it. You see, strategic plans need to be flexible because the future is not linear. One can plan and prepare for the future yet still be surprised and unprepared by contingencies in life. Ten years ago, I would have never dreamed I would be where I am today. Likewise, my life looks pretty different today than it looked just one year ago. Could you say the same?
Continue Reading 16 lessons learned from a digital nomad (249)

Source: Rob Saccone, Nexlaw Partners

We’re on the ground floor of digital services.


I didn’t like Alexa at first. If she were my assistant, she would have likely ended up on a performance improvement plan had our working relationship not improved.

Over time we grew to better understand each other, and we now converse multiple times a day about news, weather, sports, music, and impulse purchases. My wife and kids have also become everyday users, and in a twist of fate, I occasionally find myself scolding my teens for yelling at Alexa as if she were a family friend instead of a glowing tube of snark and overnight deliveries.
Continue Reading Platform (r)evolution: how the convergence of talent and technology will reshape service organizations (248)