January was a busy month on my LinkedIn. Birthday and a work anniversary. The automatic notifications prompted some splendid exchanges with old friends. And I received a few questions worth answering more publicly.

Where you been?

Working. Took the new job at the beginning of 2019. It was exciting at the time. Even more exciting now. But I wanted to do something before I said something. When you spill ink decrying the lack of substance underpinning many discussions of innovation in legal service delivery, you set yourself up to be indicted on charges of hypocrisy (a misdemeanor). I’ve mostly kept my head down and gone about the business of demonstrable progress (to be continued).

When will you write/speak again?


What about?

So much to say. But I’ll start with a shibboleth that continues to burrow deeper into my brain despite the fact I’ve been repeating it for years.

Obvious ≠ Simple ≠ Easy

Everything is obvious—once you know the answer (great book, btw). But what is obvious is not always simple. And what is simple is not necessarily easy. Since it’s resolution season, I’ll use the ubiquitous ‘diet and exercise’ as my real-world example with guest appearances by old acquaintances like innovation, AFAs, and artificial intelligence to bring it home to our space.

It’s obvious but not that obvious. While a huge swath of the population acknowledges they should eat healthier and exercise more regularly, most of the thinking beyond that gets hazy despite no shortage of generally recognized motivations. Look better. Feel better. Live longer. These are admirable but amorphous goals that remain mostly aspirational save some short, intermittent efforts to ‘do something’. Relative to the popularity of the topics, the actual incidence of sustained, effective commitment to improved diet and exercise are vanishingly small (far different from nonexistent—in raw numbers, there are many success stories). People have other present, pressing priorities.

Innovation in legal services is similarly admirable and amorphous. It is an aspirational abstraction to which few raise objection. We witness innumerable, repeat vows to innovate (and countless examples of real innovation). But relative to the supposed attention to innovation, the felt impact consistently disappoints. Legal professionals have other present, pressing priorities.

Other present, pressing priorities should not be dismissed. Family, emotional health, work, etc. are legitimate consumers of personal energy and attention. Actually delivering legal services to the people and businesses who need them today rightfully has pride of place among legal professionals. The fundamental attribution error and blame-based narratives are unhelpful in telling the story of clinging to current behavioral patterns.

But it’s not merely being busy. It is also the fact that when you decide to pursue change, the question of how to change gets complicated, in short order.

It’s not so simple. At a high level, ‘eat healthy’ is quite simple—and beyond vague. Imagine tackling the question for the first time and finding, as has been observed by others, that for every diet there is an equal and opposite diet.

Exercise selection is equally taxing (running, lifting, yoga, etc.). Consider the variations (sprinting, 5Ks, marathons; cross fit, powerlifting, Olympic lifting; Ashtanga, Anusara, Bikram) and infinite, often conflicting, advice on training protocols from people locked in internecine squabbles incomprehensible to outsiders. So many people purport to have the answer. Yet the number of answers to sift through is practically infinite.

Then there is the inconvenient facts that weight loss is not the same as fat loss and being lean is not the same as being healthy. People not surviving marathons. The extreme misery of fitness competitors. Yogis hurting themselves. If you are the type of person who wants to do things well, let alone perfectly, you will quickly suffer from information overload. A swift return to the couch is not without its appeal.

Again, plenty of people have successfully improved, and are improving, various aspects of their lives through better diet and exercise habits with a focus on progress rather perfection. The point here is that when the simple notion that ‘something’ should be done gives way to actually deciding what that something is, complexity often intrudes. Complexity can be discouraging for the well-intentioned novice with other pressing, present priorities.

Worse, the conflation of obvious and simple, tends to drive people towards magic bullet (or magic pill) thinking.

Alternative fee arrangements (AFAs) are an example of a pricing innovation from our space. It is obvious enough to lament the drawbacks of the billable hour—or even declare it dead. But when accurate analysis of the shortcomings of hourly billing gives way to devising a suitable alternative, complexity rears its heads.

There are many different fee arrangements, each with their own mix of tradeoffs. The competing options lend themselves not only to different types of matters but to different preference profiles. The lawyer who wanted a simple alternative to the billable hour instead discovers a decided lack of simplicity. Nor is the associated effort without downside risk—poorly calibrated fee arrangements can go very wrong. It is no wonder that so many revert to the default. Hourly billing is immediately familiar and accessible to anyone under pressure to get moving on the matter itself.

Selecting the right AFA entails hard thinking, hard choices, and, often, hard conversations. Not impossible. These occur every day. Successful AFAs are common enough. But there are comprehensible reasons their penetration comes nowhere close to the revolution that has been consistently predicted for the last four decades.

Moreover, even the successful implementation of AFAs is not a panacea so often imagined. Change the incentives, change the world. The interplay of incentives governing legal service delivery is far more intricate than simply switching fee structures. Many complementary conversations and attendant behavioral changes remain necessary. There are no magic bullets.

It’s not that easy. Determining an optimal diet and exercise plan may not be simple, but there are still many small, simple choices that have a positive impact on health outcomes. For example, in almost every instance: don’t eat the donut.

If you are trying to eat healthier, it is obvious you shouldn’t eat the donut. It is also quite simple. Just don’t eat the donut. But it isn’t easy. Donuts are delicious.

It isn’t easy Monday morning when the donut is fresh. It’s even less so Monday afternoon when a crazy day and a lunch salad have left you peckish. It isn’t easy on Tuesday when, instead of the donut, cookies presents themselves. Or Wednesday introduces a co-worker’s birthday cake. Or Thursday brings your colleagues’ invitation to happy hour. Or Friday screams out for comfort food after a long week. Or Saturday…

Adherence is often a far greater obstacle than diet selection. Our environment of caloric abundance conspires against our best intentions. Through millennia of scarcity, we evolved to eat what is in front of us. Now, delicious, calorie-dense food is constantly in front of us—most of it expertly engineered to light up our dopamine receptors like a Vegas slot machine.

Our work environment is similarly calibrated. We are trained to do the work in front of us. And there is always work in front of us.

Take the perspective of a busy legal professional and start to stack all the seemingly simple tasks we pile on top of one another. Capture your time. Upload documents to X repository using Y naming convention. File your matter-specific emails here. Contribute to this KM initiative. Attend, and pay rapt attention in, these trainings. Read and process these organizational updates. Keep up with trends in your practice area(s). Serve on this committee….oh, and, constantly innovate while simultaneously adopting and adapting to the innovations introduced by others!

In isolation, all simple and doable. In aggregate, overwhelming while also being subordinate to the work itself.

Which is not to say we can never expect people to modify their behavior or build new habits. Rather it is to observe that sustainable change is far less straightforward than merely recognizing benefits will follow therefrom. Sustainable change at the organizational level is an order of magnitude more challenging. Sustainable behavioral change often requires a new mindset grounded in a shift in identity. It requires new skillsets in navigating complex environments and coping with constant change. It requires new systems that eliminate waste masquerading as necessity. It requires tradeoffs, prioritization, and discipline. It is feasible. It is achievable. But not obvious. Not simple. Not easy. There are no magic bullets.

An exercise in empathy. Would-be change agents can quickly become frustrated and fall back into self-righteousness. There is a natural tendency to focus on how right we are—and, correspondingly, how wrong everyone else is for not listening to us. But anyone familiar with my writing knows I am keen to reflect on how wrong I’ve been. In particular, I try to interrogate the gaps in my mental models that lead to inaccurate predictions about the pace, scale, scope, and shape of change in the legal market.

Self-reflection engendered my affinity for Obvious ≠ Simple ≠ Easy. My  operating assumption is that anything obvious, simple, and easy is already in effect. Thus, if I look at a particular problem and think to myself the solution is all of those (happens frequently on a gut level), I am the one in error (so critical to not believe everything you think). I then use the lens of O≠S≠E to work through the problem and identify the errors in my thinking—not to dismiss my initial thought, but to refine it in order to make it workable.

A supposed antidote to natural stupidity. I’ll conclude with artificial intelligence as a final example.

At a certain level of abstraction, the proposition that AI should be applied to the delivery of legal services is obvious enough. AI automates knowledge work. Law is knowledge work. Therefore AI should have an impact on law.

Fair enough. But also fairly facile. To identify actual actionable overlaps, you need to know a decent amount about both law and AI. Most people focused on the day-to-day delivery of legal services do not possess such knowledge—nor should we expect them to. Thus, anyone who has observed (as I surely did once or twice in my wayward youth) that the application of AI to legal work is obvious is making a uselessly broad statement, has no idea what they are talking about, or is omitting a key qualifier: “obvious to people like me.”

Moreover, the constant refrain that the introduction of AI to legal service delivery is obvious has the effect of making it seem simple to the uninitiated. You just buy some AI, turn it on, and reap the rewards of the resulting magic. But anyone who has actually been involved procuring an AI solution can attest to the rigor required to identify a tool fit to purpose given the diversity and variety of options (see here). Simple it is not.

But even if you identify the right tool, it won’t be easy. You need clean data. You need to test and train. You need workflows and quality controls. You need to design, build, and iterate a well-structured process that maximizes the upside and minimizes the risks of the particular tool selected and ensure it is calibrated to context of the specific job to be done. Ultimately, you want to make this feel effortless and intuitive to various stakeholders. But the effort required to make work seem effortless can be extraordinary. It is not easy.

It’s been done. It’s been done well. Repeatedly. We have decades of successes. We have many more successes in front of us. But those successes have been, and will be, hard earned. What can be said of AI, can also be said of AFAs, knowledge management, workflow automation, contract lifecycle management, and all the other ‘basics’ of modern law practice. Even project management—which I may need to address soonish given how much territory in my brain that topic now occupies.

The hard thing about hard things. We do hard things well all the time. We, however, have a natural inclination to then present them as more accessible than they are. Wanting innovation to spread is an act of generosity. Indeed, many innovations exist because some well-meaning soul was initially convinced it was obvious, simple, and easy, then learned it was none of those but persisted anyway.

My aim is not to discourage all happy talk. I do, however, think we need to become better storytellers. We are drawn to tell innovation stories along the lines of this is great, quick, and easy as a way to make the journey attractive to potential fellow travelers. The countervailing impulse to share our struggles, however, tends too far towards this is inhumanely difficult (and therefore praiseworthy) to a degree that runs counter to our collective interest in promoting better behaviors. The sweet spot of this is hard but doable and worthwhile does not always land but is effective when it does.

We (well, me) need to get better at constructive realism not only in the stories we tell but in how we react to the stories others tell themselves. I have been guilty of offering unqualified encouragement to someone who wrongly thought the path before them was obvious, simple, easy. I liked their destination and did not want to be a buzzkill. I have likewise been guilty of accurately pointing out the flaws in lovely plans for the same reason—I wanted to help them avoid pitfalls. But I’ve introduced real talk in a way that dampened the innovation impulse rather than redirected it.

Not all failures are failures of imagination. Not all failures are failures of willpower. We fail for many reasons. Fit. Timing. Design. Planning. Execution. Change management….We succeed for the same reasons. That’s the hard thing about hard things. There are few easy answers. Nor many obvious or simple ones. But there are answers. Obvious Simple Easy. Yet:

Complicated Hard Impossible


Photo of Casey Flaherty 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…

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.