Kenneth A. Grady

Adjunct Professor & Member, LegalRnD Faculty | Michigan State University

• Tell us a bit about yourself and how you came to be in (or a customer of) the legal business?

I came to the law literally by accident. I was in college and planned to go into an academic career in an area that today we call cognitive science. My senior year just before first semester finals, my mother was in an accident. She needed surgery and would be recuperating for a period of months. As the only child of divorced parents, I was going to be her caregiver. I took my finals, left college and went home to care for my mother and look for a job. I took a few courses at a local college to finish my degree and began to explore my options. As I looked more closely at an academic career, it became clear that the pipeline ahead of me was full. The chances of landing a college teaching position were low. After working in business for a year, I took a job as a paralegal in one of the largest U.S. law firms. I became familiar with the life of a big law firm lawyer and decided to go to law school. Because I lacked business knowledge, I did a joint degree program picking up my masters in management in addition to my law degree.

• What do you do for a living right now?

I work as an adjunct professor at Michigan State University’s College of Law. I also am the founder and principal author of the blog The Algorithmic Society (on Medium). It was named to the 2017 ABA Journal Web 100 as one of the top 50 law blogs. I write guest posts for many other blogs and articles for law journals and trade publications, I am working on two books and doing research in the area of machine learning and state and federal court appellate decisions with Dan Barnhizer, a professor at MSU. Finally, I give keynote presentations at private and public conferences around the world. So, while I “retired” in 2013, I’m as busy as I ever was.

• What has been your greatest triumph and your greatest success in the legal services field and what did you learn from each?

This has been the hardest question to answer (and the one I’m answering last). I’m going to give one answer: being a thought disruptor. Over almost 40 years in the industry and across the many roles I’ve played in it, I have watched the profession take a nosedive. I started in law just about the time it was changing from a profession into a powerful way for a few to make a lot of money. Of course, we did not know that at the time. What some saw was a shift that favored large, powerful legal organizations. The money went up: law school tuition, salaries, fees. I was a beneficiary, so I can’t claim I was on the side of access to justice from the start. But I was always uneasy in my corporate law role (law firm partner or in-house). I became more vocal for change over the years, leading to my triumph and success. I think I have raised awareness among lawyers of the perils of the path we have set for ourselves. We are in a self-destructive phase. I have educated some about what that means, and it means more than lawyers becoming an insignificant part of society. It means changing some of the fundamental notions of our society, the most obvious being the rule of law. So my triumph and success is through my writing-explaining complicated ideas in easy to understand ways and connecting the dots among many different trends in society and law.

• Do you think the legal industry is headed in the right direction, the wrong direction – or which direction?

I don’t think the legal industry has a direction. It is the soul wandering in a featureless desert. This is a bigger challenge than clients wanting value, efficiency, quality, or some other quality. It is a deeper question about what lawyers do and who creates the law under which our civilizations operate. The not-so-subtle shift has been away from government to corporations and away from lawyers to technologists. For most lawyers, the profession is a daily grind of making money. Some still love it. Many are confused  about where to go with their careers. In the meantime, adherence to the rule of law is declining and respect for legal institutions is near all-time lows. We definitely need to find our direction and re-define what we are and do.

• Who – or what – inspires you – and why?

Those individuals who dedicate themselves to being the best they can be at their craft. I use “craft” broadly, to include shoemakers, artisans, musicians, and anyone else involved in an area that respects personal commitment at doing what it takes to be the best they can be at what they do. I think this type of commitment has been on a rapid decline and getting by has become the mantra. In law, this getting by attitude seems to be the norm, with very few willing to devote themselves to excellence, stretching all the way from students through academics, partners, and others at the “top” of the profession.

• What advice would you give to the younger generation contemplating law as a career?

I would ask them to be honest with themselves about the reasons for considering law as a career. Many law students I see today are in law school as a default option. That has always been the joke – bright, liberal arts students had three choices: get an MBA, a JD, or a PhD. Those who didn’t like numbers had two choices (the MBA dropped out). Those who wanted to make money went the JD route. Law wasn’t a choice it was the default option. For the past 40 years, that made economic sense even if the career was not very satisfying. In the past 10 years, it hasn’t made economic sense.

Today, those interested in a legal career should be very realistic about what drives them and what a legal career offers. For those with a strong interest in helping others, who enjoy intellectual challenges, and who can avoid exiting law school with a crushing debt burden, it can be a satisfying career. But, if the goal is to make money, there are more lucrative career paths (and in many cases, much easier career paths). In other words, you should only go to law school if you have a personal commitment that drives you, a driving curiosity, a willingness to work hard at becoming the best you can be at your craft (writing!), and a willingness to keep reinventing yourself. Finally, consider what the profession will look like in 10 or even 20 years (extremely different from today) and ask if you are willing to go through constant re-invention to succeed.

• How ready for change do you think the legal industry is?

Not ready at all. Here, we need to distinguish between the traditional legal industry and recent entrants into the legal industry. The traditional players, all who have been around as organizations or individuals for more than 20 years, are not prepared for change. Their legal industry has been stable for over 150 years. They don’t know change and have neither the intellectual toolkit (education, experience, etc.) nor the emotional toolkit (change management skills, intense curiosity) for change. Those who have been at this for less than 20 years, have experienced some change. Most aren’t ready, but recognize that it is now part of life in law. We need to convert law schools to institutions that prepare students for constant change – something the law schools are (always exceptions) not prepared to do.

• Is more – or different – leadership required? In what ways?

In some ways, this asks whether we should heed Ben W. Heineman, Jr.’s call for a return to the lawyer-statesman, follow the current path of the lawyer-businessman, or find some new leadership model to pull us out of what many perceive as a downward spiral. The second question, of course, is even if we could settle on a model, is change feasible. This speaks to a bigger issue – the yearning for some role models. For almost 40 years, the list of the most prestigious professions has changed very little. If there is a common theme among them, it is that they tend to be service professions. In many cases, the jobs do not pay well and for several, the jobs bring great personal risk. Lawyers have not been on the list.

In law, it almost seems like we need two categories of lawyers. The first category, what might be called the lawyer of today, is focused on the business of legal services. The second category, Heineman’s lawyer-statesman, focuses on the “bigger” questions involving governance and society. They are the ones we look to for leadership. Perhaps they have a different level of education, additional training in fields pertinent to leadership, and are in roles that focus more on helping society than helping individual clients.

• How deep do you think will be the inroads of technology in the industry?

Technology will go as deep in the legal industry as it will go in any industry. Put another way, there are no natural barriers to technology use in the legal industry. The rate of diffusion, or substitution, of technology for manual labor will be slower than in some other industries. But, that is due to the challenges of developing technology to the point where it can replace humans on certain tasks.

• In ten years, do you see an industry much as it is – or do you see new players, new technology and an altered state?

The legal industry 10 years from now will not look completely unfamiliar to lawyers today. But, it will have moved substantially from what we see today. The choices clients will have for “legal work” will be more varied than today. We already see clients pursuing options to get the “legal work” done without lawyers. This trend will continue as long as lawyers refuse to adapt to the modern world. This goes back to the question, “what is a lawyer”? The longer we take to define ourselves and act on that definition, the more we will see others take over doing what was traditionally called legal work and the greater the altered state will be for the industry.

• Are consultants and lawyers looking increasingly similar? Should the distinction continue?

In a few ways yes, but in the important ways, no. Lawyers have boxed themselves into the role of technical masters and strategic novices. Consultants are problem solvers willing to pull from many disciplines to solve those problems. Lawyers still fight the multi-disciplinary approach. We need to learn that clients approach us with problems and law may or may not be part of the solution. At that point, we will become more like consultants, but with an edge because we possess the specialized legal knowledge.

• What are your thoughts on the increasing availability of data to guide client-side procurement of legal services

Data has become an important part of the legal industry, but mostly in the buy-sell equation. By that I mean, we have data on what services have cost (though with very poor definitions of the services) so that data will be used as a sword and a shield in negotiations. But, it is a distraction. It pulls the focus away from the real value content of what is being done or should be done. Rather than focusing on the work content, the data seduces the players to negotiate over the price of poorly done services. That isn’t of much value. I would rather see us gather meaningful data and use that to reform legal services, but that requires some work which, to date, neither side has been interested in doing.

• Lawyers have typically regulated to keep non-lawyer investors out but that’s a two-edged sword these days. What are your thoughts?

I liken this to two children fighting over who gets the last brownie, while the third child walks in, takes the brownie, and enjoys her treat. At the high-end (corporate) level, regulation is over. A state regulator will not bring a case charging Axiom Law with the unauthorized practice of law claiming it duped the general counsel of a Fortune 50 company. Those companies also can send their work around the world, and can structure all sorts of arrangements that satisfy their needs while stepping through (if they feel the need) the gaping loopholes in the regulatory structure.

One the low-end (individuals) the name of the game is to protect the monopoly, not the public. The regulators are losing the battle, but slowly. The real game is the end-around. Individuals, like other clients, are simply finding ways to do things without lawyers. They are the children who walk off with the brownie while others fight over a now-empty plate.

Eventually, we will go away from regulating status (who is or isn’t a lawyer) to regulating conduct. The only question in my mind is how much damage the pro-status regulation force will do to the profession before the change happens. Right now, that group is doing substantial damage while accomplishing very little in the way of protecting the monopoly.

• What’s the one most significant factor that will drive change in your view?

Lawyer apathy. It is hard to engage in a battle that will take a while to win (or lose). Most people choose note to engage (the same is true with people and voting). If not enough lawyers are willing to fight for the profession, then others will (and are) step in and take large chunks of the financial pie.

• Are we seeing the demise of the “profession” and the real emergence of the “business” of law?

We are seeing the demise of the profession, but the real emergence is of the rule of technology. Technologists are hard at work deciding what rules will govern society in the form of values built in to artificial intelligence. Those values (which will become de facto law) will replace laws written by lawyers. So, if you want to know who we are ceding our role to, check out the computer science majors.

• What do you consider is the greatest challenge facing the industry?

The large disconnect between cost and value. This starts in law school where the cost of law school is very out of alignment with the value received. It continues after law school with salaries and fees. Graduates need high salaries to pay back loans and lawyers charge high fees in part to provide high salaries. But, it is more complex than that simple story. The value that lawyers deliver today is based largely on time spent rather than substantive value delivered. The transition to aligning cost with value will be wrenching, and it is impeding progress on many fronts. It will probably take another 20 years to go through the change.

• What do you see as the greatest opportunity for the sector looking forward?

If lawyers can get past the cost/value misalignment, then the opportunity to do interesting, value-added work that helps society is enormous. The number and types of legal issues being raised as we go to a technology/data society are great and fascinating. The challenges of economic inequality, new governance models, defining the rights of individuals versus technology, are all driving questions that affect all aspects of our lives. Most of those questions are not being addressed by lawyers today. Yet, they are far more interesting than what most lawyers do. This is the sad part of the transition story. Lawyers are stuck doing boring, repetitive work that is well below their skill level, all to earn money. It has led to serious problems with substance abuse and mental illness in the profession. At the same time, there is a lot of interesting work to be done which lawyers are not doing because of an archaic value system.

• Do you think law can improve its track record on diversity and inclusion? How?

By becoming a desirable profession. People of all types will go into careers where they feel they have as much power as anyone else to make a difference and where there are opportunities to make a difference. Law does not offer those qualities right now. If law as a career offers attractive qualities, then we can improve our track record on diversity, because more diverse candidates will want to enter the profession.

• Will the current regulatory framework around law help or hinder it in the future?

It already is hindering it and it is harming clients. The only beneficiaries are those who enjoy the battle and lawyers who need the monopoly protection, because without their practices would die. We are doing little to regulate the conduct of lawyers, which is why we still have many problems (theft of client funds, etc.). The good news is that the regulatory framework is becoming irrelevant. Clients and technologists are finding ways to circumvent the vague regulations.

• Who do you think are the greatest influencers on the industry these days?

Technology disruptors. They are starting to show how easy it is to replace large chunks of what lawyers waste time on. As technology grows and our ability to do things with it expands, that trend will continue. It is one of the reasons lawyers are having trouble defining what it is they do that is unique. For most, their careers have been defined by doing a lot of tasks that now can be done better, faster, less expensively, by computers. There are lots of things computers can’t do, but lawyers have let their skills on those things lapse leaving lawyers in an uncomfortable position. We have generations of lawyers that need re-training, and new generations that need different training than law schools are providing. That leaves a big gap, and technologists are pushing through that gap disrupting the industry.

• If you had to do it all over again, would you? Or what would you do differently?

I don’t think hindsight exercises are very useful. We make the best choices we can given what we know at the time (at least I tried to do that).

• If a law firm was a startup pitching for investors, would you be an investor?

If a technology driven firm was pitching that it would provide legal services, I’d be very interested.

Wildcard questions:


• If you weren’t doing this, what would you be doing?

Writing or coding.

• What would you like to be known for?

Reawakening the notion that societies are built on people, not corporations or other institutions; that the rule of law is the defining force in a well-functioning society; and that creating a successful rule of law society requires more than building rules into programs, it requires people constantly inventing the value structures that fit the world they want not the world imposed on them.

• What would surprise everyone if they knew (they may now).

My original career path was to be a rock and roll/jazz drummer.

• What’s your favorite hobby or activity outside of law?

Vegetable gardening.

• What’s your favorite sports team?

Chicago Cubs.

• What’s your favorite city?


• What’s your favorite food?

Apple pie.

• What’s your nickname – and why?

Dreamsquasher. It is a horrible nickname, but one that captures something I learned early in my career. There was a time (hopefully one we have passed) when parents, teachers, and coaches handed out “participation” awards. Everyone on the team got an award for something. As the name implies, you got an award for just participating. As a result, we have a generation that wants rewards not for what they have done, but for simply being present. They avoid reality and only want to look on the bright side. That makes it hard to improve. If you don’t confront reality – the challenges you will face, the failures that happen, the things that did not go right – you will be stuck in the past. I was taught to acknowledge success, but focus on reality. So, when people present ideas I have a tendency to ask hard questions. I confront reality in the hope that we will find ways to overcome the challenges. To those not used to confronting reality, it seems like you are squashing their dreams. I prefer “realist” but “dreamsquasher” has been more fun for students and friends.