Source:Danny Kahneman on Decision Hygiene,” Jury Analyst, July 22, 2021

Decision hygiene is to product and service selection as testing is to software development.  Skip them at your peril.


Decisions about technology can be noisy affairs.

(Please take a moment to relive one you were part of.)

As Daniel Kahneman, Olivier Sibony, and Cass Sunstein masterfully point out in Noise (2021), noise is different than bias. It’s an independent contributor to infelicitous results in professional (and other) judgments. Noise tends to be an invisible enemy. Bias, more obvious, moves decisions in particular directions; noise just adds errors through unwanted variability. Responsible decision-makers seek to minimize both.

The Noise authors provide vivid examples of judgments in which noise plays a role, including some in law, like judicial sentencing decisions, which have been shown to turn on such things as the outside temperature or whether the local city’s football team won its most recent game. Contexts like insurance underwriting can operate like lotteries. As the authors say, “wherever there is judgment, there is noise” (p 12).  We are all noisy.
Continue Reading Keeping the noise down in tech selection (325)


Unlike sharks, killer whales hunt collaboratively.  Is this the right approach to the legal tech vertical?


Why aren’t more law firms investing in startups and/or launching corporate venture arms? Is corporate venture capital (CVC) a good fit for the legal industry? If not, is there a better model? And then, finally, what does all of this have to do with killer whales?

In this essay, I’m going to attempt to answer each of these questions. I will start by giving a brief introduction to CVC and then I will outline the current models of law firm venture investments, highlighting both strengths and shortcomings. In the second half of this essay, I’ll suggest an alternative model, a collaborative industry-wide approach which I have dubbed “Investing like Killer Whales.” This is the strategy we used when we syndicated an investment in AI-based contract benchmarking startup TermScout.  See Abramowitz, “As Promised, Our Second #Legaltech Investment Announcement This Week,Zach of Legal Disruption, May 5, 2022 (describing collaborative syndicate approach and why worked well for TermScout).
Continue Reading Sharing my playbook for Legal Tech investment (324)


Four key elements: caps on total liability, exceptions to cap, limitations on type of damages, and exceptions to limits.


In recent posts, I have postulated that commercial contracting is on the following path of evolution:

  1. Reliable data as to what is market for key contracting terms will become readily available as utility models, powered by large data sets and AI, become prevalent. See Post 225 (“Can contract analysis operate like a utility?”).
  2. Companies will look to remove friction from their businesses by aligning their contract terms (and negotiating practices) with market, with some companies offering better-than-market terms in an effort to achieve competitive advantage. See Post 211 (“Competition based on better commercial contract terms”).
  3. Moving to market terms will lead to contract standardization, less contract complexity, and significant returns to the companies that adopt this approach, benefitting the economy as a whole.  See Post 228 (“The cost of contract complexity”); Post 236 (“Case study: impact of AI and Big Data on low-risk contract negotiations”); Post 292 (“The emergence of data-driven contracting: notes from the field”).

The critical foundation for this evolution is that all parties to a negotiation have reasonable access to information regarding what constitutes market.  (For a discussion of the problems associated with information asymmetry, see the works of Joseph Stiglitz.)
Continue Reading What is “market” for limitation of vendor liability? A look at the data (322)


Probably not, but we’ll see.  A surprising conversation with digital transformation expert Isabel Parker


It’s already been quite a year for law firm innovation.  Just last month, Norton Rose Fulbright launched LX Studio, a new “innovation-focused” subsidiary, and Wilson Sonsini unveiled Neuron, a proprietary SaaS platform for start-ups.  Exciting propositions, but the development that had the NewLaw cognoscenti scratching their heads was ‘white shoe’ firm Cleary Gottlieb launching of ClearyX, which the firm describes as a “platform for highly efficient, AI and data-driven legal services.”

What’s driving these unveilings? And, are these new platforms worthwhile?
Continue Reading Q: The first “White Shoe” law firm launched an innovation subsidiary. Does that matter? (315)

First-gen matrix for evaluating software options. Harvard Law School, circa 1985.

Oh, the Humanity!  We can choose to choose better.


My first serious experience choosing law-related technology was in early 1985. Personal computers had just been introduced in the Harvard Law School clinics (as part of Project Pericles) and we had to decide which software to use for word processing. (WordPerfect was around, but we somehow missed it.) So I typed up a chart on an electric typewriter and added lines by pencil. See above graphic.  We wanted to be sure our choice did things like automatically centering text.

Such charts are familiar to product choosers everywhere. Options on one axis; features or considerations on the other. Ideally incorporating some sense of the relative importance of the latter. (One defect of the above chart is that there’s a “How desirable?” column for each option. Perceived importance of factors may vary across decision-makers, but shouldn’t differ by option.)
Continue Reading The social life of legal tech choices (309)


Combing through the past to prepare lawyers for the future.


I’m offering a new course this fall at Suffolk University Law School in Boston called Shakespeare and Knowledge Technology.

Odd combination, right?  I know. But hopefully not as odd as you may think.

Especially in their final year of study, many law students are bored with academics and anxious to get out into paying practice. Courses that delve into seemingly unrelated subjects, like early modern literature, offer respite. Courses that provide hands-on exposure to cutting-edge legal technology kindle much positive energy. Why not both?!

Bear with me for a moment while I talk about Shakespeare. Then I will explain how he provides a great context for learning about knowledge tech.
Continue Reading Looking at legal knowledge technology through an unusual lens (301)


Maybe the ROI for legal tech comes from happier workers who stay.


Emily Chang: What do startups have to do in order to have a successful exit, whether it is an IPO or just building a great business?

Paul Graham: They have to make something that actually makes people’s lives better. It’s funny how straightforward it is.

Y Combinator’s Graham Says Startups Must Improve Lives,”  YouTube, June 17, 2011.

Here is my prediction: companies are about to spend more on legal technology, but not because they are trying to save money or be more efficient. Law firms and, to a lesser extent legal departments, are beginning to see investment in technology as a solution to unprecedented burnout and talent attrition. The further entrenchment of remote work will only amplify this trend. Smart marketers have figured out that this messaging is resonating. The deluge of messaging connecting tech and talent will shift how companies justify their return on investment. Technology does, in fact, have the potential to improve the day-to-day experience of the people on legal teams, but there is some important nuance. Let’s dive in.
Continue Reading People-driven tech: How new priorities and remote work are increasing #legaltech adoption (299)


This post is a digest of an important new article on the digital transformation of legal departments.


Me:  [Enthusiastically sharing new NewLaw literature with a friend.]

Friend:  “My first reaction is…that’s a lot of pages!”

It is a lot of pages. It is also critical reading, even for the newly acquainted. For those who want the bottom line without all of the pages, this digest is for you.
Continue Reading Q. What is digital transformation? A primer for legal professionals (289)


“Be engaged, interested in what others have to say. It’s more important to listen than to speak.”


I had the opportunity to discuss legal outsourcing with Colin Levy, who embodies the skills and mindset of the modern T-shaped legal professional.

Colin and I work on opposite ends of the spectrum: he’s an attorney who’s experienced first-hand how outsourcing to an ALSP can impact his career and place of employment. In contrast, I have expertise in helping law firms find and work with ALSPs. When law firms or legal departments choose to outsource to ALSPs, often, no jobs are lost. However, sometimes an ALSP can replace certain functions. I thought it would be interesting to hear one attorney’s perspective on whether ALSPs are a threat to attorney job security in the legal industry.

Below are notes from our discussion.
Continue Reading Legal careers in the age of outsourcing: A conversation with Colin Levy (288)


An emerging role in legal tech companies that ties together sales, marketing, and customer success.


At Legal Evolution, we often return to the above “five stages of evolution” graphic as a reminder that the legal industry has entered a period of profound tumult and uncertainty.

The tumult is driven by the cost, quality, and service delivery advantages of systematized & packaged legal solutions, which has set off a gold rush in legal tech. See Post 255 (Zach Abramowitz tracking legal tech investment).  The uncertainty is driven by the need for new business models combined with the lack of established, sales channels that enable end-users to buy with confidence.  Cf Post 279 (Jae Um observing that legal vertical is composed of multiple markets that are both fluid and segmented in nonobvious ways).

Well, what about solutions—is anything on the horizon?
Continue Reading How Chief Revenue Officers are making legal tech better (284)