Photo of Casey Flaherty

I am the co-founder and chief strategy officer at LexFusion, the go-to-market collective of legal innovation companies (tech and services). I am also the co-founder of Procertas (competency-based tech training). I was a BigLaw litigator and then in-house counsel who went into legal operations consulting before one of my BigLaw consulting clients hired me full-time to help them build the biggest and best legal project management team in world. A Lean Six Sigma black belt, I tend to think in terms of scalable systems that properly leverage people through process and technology. I am deeply experienced in legal operations, legal tech, strategic sourcing, process improvement, systems re-engineering, and value storytelling, in addition to spending over a decade in the legal trenches as a practitioner. I've long served  as a mesh point between law departments and law firms to promote structured dialogue that fosters deep supplier relationships (read about that here). I am a regular writer and speaker on practical legal innovation.

I had the good fortune to attend the first in-person CLOC Global Institute in three years. It was an extremely positive experience. Unfortunately, I came home to find I was different kind of positive (new reality; unsurprising after three weeks of travel). I was therefore not able to timely complete my final CGI Dispatch for Artificial Lawyer. Blogs, however, have no deadlines.

To recap:

Dispatch #1 discussed the rise of legal ops in the context of ever-increasing scale, organizational complicatedness, and legal complexity.

Dispatch #2 covered the stellar pre-conference Legal Ops 101 session, highlighting the importance of education when most legal ops roles are net new and, therefore, being filled by individuals with no prior experience.

Dispatch #3 reported on the first day of CGI, which was bookended by sessions on storytelling (one of my favorite topics).

Dispatch #4 was to be a reflection piece. While I could have done without the multiple days of fatigue and brain fog, I am glad I had the opportunity to truly reflect.

Let me set the scene.


The presenters are lined up on stage at the end of a three-hour session built around the CLOC Core 12. The Q&A session is commencing. I am part of a sold-out audience of 170+.

Question: At a company where legal ops is new, which of the Core 12 would you start with?

Presenter1: Well, I began by getting the DMS under control.

Me (mouthing silently): What? No?

Presenter2: Typically, ebilling and outside counsel rates get attacked first.

Me (shaking head and whispering): But…but…

Presenter3: Knowledge management.

Me (clutching table and muttering compulsively): No! No! You start with the business! The business!

Presenter4: Department budgeting.

Me (spontaneously combusts)


The above is not a literal transcript. But it is a fair recounting of the conclusion of the excellent Legal Ops 101. What was unfair was my reaction.

While I have been wrong many times before (here, here), I stand by my substantive point in this instance. I am a broken record (most recently, here) about the importance, and unfortunate absence, of centering business needs in law department planning.

But being right is different than being fair.
Continue Reading CLOC Global Institute – Reflection (Delayed)

Tropes around tech utopianism are attractive fictions that promise quick wins and deliver long-term pain, ultimately undermining our efforts at effective value storytelling (series recap, plus prior screeds against tech-fixated magical thinking here, here, and here)

A new bombshell lawsuit against a contract lifecycle management provider offers a stark reminder of the promise and peril of CLM—and therefore an unfortunate but instructive example of how tech-first solutioning can go terribly wrong.

Bad contracting processes have consequences. At the center of the complaint is a ~$5m contract for CLM services and tech. The plaintiff claim they terminated the contract early for alleged uncured breaches thereof and then mistakenly continued to make ~$1.7m in payments to defendant.

Isn’t it ironic (in the Alanis Morrissette sense of the word) that in a lawsuit centered around a disastrous effort to improve contract management a substantial percentage of the alleged damages are due to alleged failures in contract management.

The business value of better contracting is not in question. As discussed previously, a 20% improvement in contracting efficacy has, on average, 32x the business impact of cutting outside counsel spend by 20%. Tech has an important role to play. But tech should not be the star of the show, especially in the beginning.

When tech is not the primary problem (or the primary solution). The complaint begins its retelling in October 2019 when the defendant gave an in-person platform demonstration. In June 2020—seven months later “following a rigorous selection process”—the parties entered into the $5m contract only to terminate it in April 2021, ten months post execution. Suit was filed in November—more than two years after the demo (which is unlikely to have even been the beginning of this ill-fated journey).

Important for our purposes, the plaintiff specifically alleges only one tech-related misrepresentation giving rise to their claims (the ability to “apply a single contract amendment to multiple agreements simultaneously”). Beyond that, every issue raised in the complaint relates to the enormous amount of work required to properly implement CLM.

Characterized as inadequate in the complaint:

  • Staffing
  • Availability of key resources
  • Status tracking
  • Training
  • Documentation
  • Discovery
  • Design
  • Feedback
  • Data mapping
  • Data conversion
  • Data migration
  • Data validation
  • Template harmonization
  • Contract sorting
  • Clause matching
  • Implementation
  • Integration

The tech is not the central grievance. The gravamen of the complaint is the absence of expertise:
Continue Reading Tech-First Failures – Value Storytelling (#6)

Start with Why. Value storytelling is essential (series summarized here). But, as storytellers, we’re not experimenting with the form. We should tell simple, compelling stories with no mystery as to the What, How, and Why.

What is outputs. How is inputs/process. Why is purpose, outcomes, and value.

What, How, and Why all matter. But, for our business audience, legal’s What and How are inherently uninteresting. Always start with their Why.

Why is the subject of the previous post. Business value is the one true Why. The call to action. The hook. The propulsive force. But the framing of Why is context dependent. The way we talk about business value will often need to be calibrated to our subject matter and our target audience—identifying our target audience and understanding what messaging resonates with them is quintessential to mastering our own context.

The stories we tell must cohere with the stories our audience tells themselves about their own starring role in the business’s journey. We must present ourselves as allies in the same cause. Which we are. This sense of shared purpose is most crucial when we are engaged in productive disagreement and accountable for persuading our allies of unpalatable truths—whether seeking to rejigger their perspective on value preservation (e.g., refining their legal-risk/business-reward calculus) or recommending that finite resources be allocated to the legal function despite the very real opportunity costs.
Continue Reading Start with Why – Value Storytelling (#4)

I interrupt our regularly scheduled programming—the continuing series on value storytelling—with a rant inspired by my pending Continuing Legal Education deadline.

Despite the temptation to satisfy everyone’s daily outrage quota by taking on a soft target, I consider our collective (and my personal) annoyance with CLE a minor symptom of a major problem. Our culture of learning is broken. This has all manner of downside implications, including for innovation.

But, first, a little rantastic fun. Can you spot what’s missing from this ad I received in the mail?

I am getting CLE right now. While typing these words, a CLE audio file is playing in the background on mute. I felt compelled to acquire hard evidence before launching into a tirade.

What’s missing from the advertisement is any suggestion I might learn. No mention of quality or relevance. Rather, the repeated, bolded promise of “no final exam” struck me as an assurance there would be no requirement I pay attention—i.e., I could avoid learning anything at all. A promise made; a promise kept.
Continue Reading CLE is Broken (as is our approach to learning/innovation)

Business value is business-centric. Law departments frequently ask me about metrics. My response is not nearly as definitive as they desire. I recommend they start with the customer—incorporating the metrics the business is already using and then proceeding accordingly to develop the complementary, internal (to the law department) metrics necessary to manage the department in supporting business objectives.

Talk to most (not all) law departments, you find the inverse. Most law department metrics are law-department centric, full stop. Most track their spend, consistent with a savings-centric narrative, the pitfalls of which I discussed last post. Spend with law firms. Spend v. budget. Internal v. external spend. Necessary. Fine. Limited.

You can also find excellent content online on how a more sophisticated law department can, and should, measure itself. Matter volume. Matter velocity. Cycle times. Better. Rare. Still law-department-centric.

To ground the conversation, we require some metrics on metrics. The most common law department metric is Total Spend By Law Firm, in use at 90% of law departments. No other metric cracks 60%. Cycle Time, by contrast, is near the bottom, tracked by only 16% of law departments. Legal Spend To Revenue is in the middle of the distribution at 29% penetration.

Critically, excepting diversity, these metrics are essentially meaningless from a business perspective. The CEO cares as little about how many matters the law department handles as they do about how many tickets the IT help desk closes, despite the fact both are essential to running the business. These are useful measures for managing workload within a specific function but irrelevant for managing the business—unless and until they are translated into actual business impact (i.e., value storytelling).
Continue Reading Defining Business Value – Value Storytelling (#3)

Me: Which “genius” decided savings should be a prime objective and metric of success for law departments?

Jae: [purses lips & tilts head]

Me: But…

Jae: [rolls eyes]

Me: No…like…well, actually…but see…what had happened was…

Jae: [sighs]

Me: Fine. I’ll recant and

I posit that the most valuable skill that every corporate law department needs in 2021 and beyond is the executive art of the business case….The reasons for this are many, but I’ll give just one: This is a task that cannot be outsourced.  Without the ability to secure the budget and investment required by the demands on the function, corporate clients will remain forever trapped in a never-ending cost-cutting exercise, to the detriment of everyone involved.  Worse yet, sustained strain on the corporate legal function and its outside supply chain introduces net-new risk — legal, financial and compliance risks — not only for the enterprise but for the social system to which we all belong.

Jae Um

I concluded my last post, on ever-increasing demand and our resulting productivity imperative, with the observation, “Some law departments simply need more money. Not all of them will get it.” In what may be a mini-series of follow-up posts, I try expand some on the value of value storytelling with a bias towards the uncomfortable and controversial. As I have been recently helping some GCs with annual budgeting, my primary orientation here is in-house but many lessons are more generally applicable.

It depends (on context). As Jae says, the business case cannot be outsourced. While good questions tend to be universal, good answers are almost always context dependent. We are responsible for achieving mastery of our own context. Mastery entails being able to navigate our context successfully, a higher bar than issue spotting for outsiders as to why “that won’t work here.” Having an information advantage over outsiders is meaningless. Your audience, and your competition, are inside your organization.

This is supposed to be hard. The Australian women smashed the world record in the 4x200m freestyle relay during the 2021 Summer Olympics—and still only won bronze. Falling short is common when competing against the best in the world. In seeking to secure finite resources within a world-class organization, we likely face world-class competition.

Maybe, just maybe, don’t be MacGyver. When we are under-resourced, the temptation is to fill in the gaps through extraordinary effort augmented by ingenuity. Yet any system predicated on extraordinary effort is unsustainable.

In one sense, it is laudable to meet several unfunded mandates with a paperclip, chewed bubble gum, and some duct tape, while working nights/weekends. Then again, if our organization is accreting operational risk by underfunding mission-critical work, it is our responsibility, as a conscientious steward of said organization, to make this manifest and pursue adequate resourcing. Superhuman gap filling can be counterproductive. We undermine our own case. Extraordinary yet unsustainable performance masks deficiencies and gives outsiders the illusion we have all we need—almost no one cares how busy we are perpetuating the illusion.

I recognize not doing things that, ideally, should get done demands uncomfortable choices and uncomfortable conversations. That’s the job. Sometimes, it is incumbent upon us to be correct, consistent, and persistent (Andy Dufrensene) rather than heroic (MacGyver).

Be prepared to say “No” and “I told you so” often (and ever so politely). Not being MacGyver requires saying No more often, and more clearly. I am deeply familiar with the angst this triggers. Many legal professionals have rightly cultivated a service mentality and are committed to doing everything in their power to meet the multifaceted (and multiplying) needs of their organization. Saying No reeks of disappointment, if not outright dereliction of duty.
Continue Reading Maybe, Don’t Be MacGyver – Value Storytelling (#1)

My partners and I made a thing. We hope you enjoy it.

We poke light fun at lawyers (which all three of us are) for remaining too analogue in an increasingly digital world. Our central premise is that digital transformation is inevitable (and already happening and good and hard and we at LexFusion can help). Underpinning the premise are some hypotheses about the shape, pace, and drivers of change in legal service delivery. We might be wrong. But our bets match our predictions. We all left excellent jobs to push our chips in on an accelerating growth curve in legal innovation. In short form:

  • The absolute demand for legal expertise is increasing; this will continue
  • The relative cost of legal services is also increasing; this will continue until we dramatically improve productivity
  • The uptick in demand powered the rise of BigLaw for decades; this peaked in 2007
  • Next came in-sourcing to meet demand, somewhat keeping costs in check, largely through labor arbitrage; this has likely peaked, or will soon
  • Now, to satisfy growing demand while truly bending the cost curve, we must also materially improve productivity—i.e., innovate through process and tech (the trend LexFusion is betting on)
  • Innovation is necessary but hard; we need to upskill in many respects, including value storytelling

As is appropriate here, I nerd out slightly on our hypotheses below (for an even deeper treatment, let me commend to you the inimitable Jae Um, one of our advisors, from whose magnificent five-part series I borrow liberally–or check out Jae’s recent Tweet storm).

Cost 🡹 The clip hits on the general dissatisfaction with how lawyers operate in the modern age, seemingly not taking full advantage of tools that have transformed much of our world.

The world has changed; lawyers, not so much.

For $600, Amazon will next-day deliver a pocket computer (phone, camera, browser, word processor, gaming device, rolodex, clock, calendar, calculator ….) that remains constantly connected to a searchable repository of nearly all human knowledge (real and fabricated). This technology barely existed in recognizable form twenty years ago. My favorite piece of context: less than a decade after their introduction, iPhones were 120,000,000x faster than the $23,000,000 computer that weighed 600 lbs. and guided Apollo 11 to the moon. (“The iPhone is nothing more than a luxury bauble that will appeal to a few gadget freaks” – Bloomberg, 2007 😂)

Alternatively, also for $600, a junior BigLaw associate will allocate one heavily discounted hour to a client matter. Despite the apparent opportunity to be tech enabled, this associate hour is hard to distinguish from the same associate hour that cost $200 two decades ago. And because legal complexity has outpaced productivity, the number of hours required has also gone up.

Clients “feel” they get less for their legal spend dollars because they do—relative to the trajectory in electronics, logistics, consumer goods, transportation, clothing, food,  etc.

Law suffers from a cost disease, previously covered here:

This is Baumol’s cost disease, an economic phenomenon that undercuts the classical theory that wages rise with productivity. The classical theory: the more productive you are, the more you are paid. The reality is that (across industries, as opposed to within them) the less productive you are, the more we need to pay you (unless there is a glut of qualified workers competing for your job). Unsurprisingly, the eponymous Baumol identified “legal services” as subject to the cost disease. And recent scholarship has concluded, “Legal services are decidedly in the stagnant sector.”

Continue Reading Explaining the joke: lawyers lagging behind