Last month I attended the annual New York Advisen Cyber Security Conference. The event which this year had over 900 attendees is frequented by insurance representatives, brokers, risk managers and, yes, a handful of lawyers, all of whom work in the cyber and cyber insurance space. Its probably the premier conference of its kind.

It’s funny. I’ve been attending this conference for about 5 years. When I first started coming, the conferance was all about sales, marketing and underwriting. I remember sitting at a table my first year having lunch with a handful of 20 something underwriters who were gushing over their new insurance product called cyber insurance. They trumpeted the freedoms the lack of forms provided and how they could even make up policy language as they went along. When I spoke up and said what about future claims, it was as if I was speaking in a foreign language: they were completely baffled.

Fast forward 5 years.  The theme of this year’s Conference was “Solving The Cyber Risk Equation”. The Conference was devoted primarily if not exclusively to what to do about claims and the enormous and uncertain risk cyber poses under the policies. Things have a way of evolving along a natural course.

The good news is that the attendees and speakers have become much more sophisticated about exactly what carriers are getting into when they write cyber policies and what kinds of risk they are biting off. They are also beginning to look long and hard at the future and the problems and issues that the proliferation of data through the internet of things and data analytics may pose for all insurance- not just cyber.

The Conference kicked off with a Keynote address by Adm. Michael Rogers, Director of the National Security Agency. Director Rogers talked about his view of the cyber landscape and the threats. He made the point that cyber carriers and, for that matter, society as a whole are dealing with a highly fluid and ever changing cyber threat where past data does not correlate well with future outcomes. In short, a potential insuring nightmare. But Director Roger’s other conclusion: cyber insurance is in a unique position to strengthen cyber security practices of insureds by incentivizing sound cyber practices.

This all sounded well and good. But as the day went on, what this may actually mean practically has a potential dark side that may or may not be acceptable to society.

For example, Nicole Eagen of Darktrace, a cyber security analytics firm, noted in her panel presentation that many cyber attacks occur due to human missteps and errors. According to Eagen, we now have the ability, though, through artificial intelligence and data analytics to take a virtual look at a company’s employees, and determine from that look what is normal behavior for each of them. Analytics can then figure out when those employees aren’t acting consistent with their norm. This then could signal actions that decrease cyber risk and steps to stop improper behavior before it causes harm. That in and of itself is kind of spooky. How much do we really want our employers monitoring our every step and labeling what we do normal or abnormal?

But what happens when insurance becomes involved. Should insurance carriers who insure against cyber risk have access to this data? Should they insist on having it?  That would certainly enable a carrier to put into place protections to reduce the risk of data breach.  And what if a carrier offered a premium discount to a business that allowed this kind of access

? Most businesses would jump I think at the chance to in essence sell their employees’ information in exchange for reduced premiums and better protection.

Mark Jenkins of PaloAlto Networks, a cybersecurity protection and detection firm, kicked off the next panel and raised the possibility that a carrier could use data collected from IoT devices to make real time algorithmic decisions about coverages and premiums. Jenkins laid out a hypothetical where data collected by your auto and communicated to your carrier would signal if you were driving too fast too long. Or the auto data could show you frequented areas of town where the risks of accidents or theft were high. Your carrier could then use this data to make real time adjustments to your premium based on your behavior. Mark thinks this not that far off.

These ideas did not go without push back however. In the same panel, Adam Cottini of Arthur Gallagher, an insurance brokerage firm, pushed back and asked is this something we really want? Do we as a society and as insuring consumers really want to give up our privacy and allow our carrier to know where we go and how fast for this kind of monitoring and decision making? He thought many would not. And later in the day, Shiraz Saeed of Starr Insurance raised the same issue: “you have to have some level of anonymity in this country. Our Constitution guarantees it. We have all made mistakes in life we would just as soon not everyone know about.”


“You have to have some level of anonymity in this country. Our Constitution guarantees it. We have all made mistakes in life we would just as soon not everyone know about.”


So the day quickly morphed from a cyber insurance conference to, in part, a philosophical debate about whether insurance companies should have and use analytical tools to reduce risk and premium or whether that so far invades basic human privacy to be unacceptable. And it raises related questions of who owns data, what is it value and who controls it. I recently interviewed Kathleen Dooley, GC of, a company whose mission is to use the block chain to enable consumers to make decisions about their health data such as who can access it and to even sell it if the so desire. Dooley made the point that personal health data is property and we have certain inherent rights with respect to it.

I actually predicted many of these very issues in a post from 2016. In particular, I was interested in how business and insurance carriers could use data to reduce costs to all. I focused, for example, on a new electric toothbrush that would communicate to your dentist how often you brushed your teeth. I postulated that this same information could be communicated to your health care provider who could in real time change your premium. Would that change behavior? It would mine. Do I really want Delta Dental to know this? Depends I suppose on what its worth-how much would I save? Implicit in my analysis is that my tooth brushing data does have value-I can trade it for reduced premium.


My guess is that people and businesses will elect to buy cheaper insurance if all it means is giving up some level of privacy. Indeed, we make this election every day


My guess is that people and businesses will elect to buy cheaper insurance if all it means is giving up some level of privacy. Indeed, we make this election every day. (How many of us trade privacy for the communication abilities offered by Facebook in order to get that free service?). Meaning that we will make choices based on the implicit monetary value of our data. Looking at how we have willingly, consistently and even happily given up privacy rights for convenience and cost, its inevitable this is where we are headed.

But this isn’t all bad. If my insurance company monitoring my teeth brushing habits means I will brush my teeth more, have less cavities and be more healthy in the end so much the better. The fact that insurance pays for filling my cavities doesn’t make going through the process any less an ordeal.



The Best Lawyer You Can Be. A Guide to Physical, Mental, Emotional and Spiritual Wellness By Stewart Levine


Stewart Levine’s new book reminds of the Whole Earth Catalogue written a number of years ago by another Stewart-Stewart Brand. For those too young to remember, the Whole Earth Catalogue  was magazine and product catalog published several times a year between 1968 and 1972, and occasionally thereafter, until 1998. While it was directed mainly to a non mainstream, sort of countercultural audience, it did contain all sorts of product information, how to instructions and  other valuable information. The goal of the Catalogue was to introduce those who were interested to some unique tools and information on topics not well addressed other places. Its theme was “access to tools” and that’s by and large what it delivered.


Stewart Levine’s new book. The Best Lawyer You Can Be similarly is a collection of various essays and short pieces from others, access to tools if you would, that will help us be better lawyers. Better not  in the substantive senses-this is not a book about legal topics— like the rule against perpetuities, God forbid—but how we can be better from a physical, spiritual and emotional sense. Like the Whole Earth Catalogue, it is counter cultural in a sense, at least from a mainstream lawyers’ standpoint and attempts to introduce us to tools we can use but may not know about it.


So, for example, there are sections on mindful lawyering, collaboration, emotional intelligence, well being, finance, managing stress, even physical activity and nutrition, among others. There are number of essays in each section that are designed to introduce the reader to topics and whet their appetite for more.  Many of the authors are well known in the field and each could probably write a book on their topic


The book doesn’t pretend to provide an in-depth, comprehensive of each component but is instead designed to introduce the various topics to us for further reflection and study. It’s an excellent starting place.


Lawyer wellness has been a topic that has received increasing attention of late particularly in light of the high levels of substance abuse, depression and even suicide among lawyers. It’s a topic that is a bit antithetical to the image of the hard charging, take no prisoners, Rambo lawyer that was popularized in the late 80s and continues to bedevil us even today. Stewart has taken the concept of wellness for lawyers and tried pretty successively  to give us a nice sampling of all the various component of lawyer wellness in one place. The book doesn’t pretend to provide an in-depth, comprehensive analysis or discussion of each component but is instead designed to introduce the various topics to us for further reflection and study. It’s an excellent starting place.


Much of the information here I had read about before and I know many of the writers, including Stewart. So for me, there was not a lot new. But if you haven’t kept up to date with lawyer wellness or are just curious about what that means and includes, this book is a good introduction of many of the topics. And it can point you in the right direction if you want to know more.


While Stewart has done a good job grouping the topics, because this is a collection of article written by some 29 authors (if you count Stewart), it can be a little disjointed. Many of the articles are relatively short and of course the writing styles of the various authors differ which perhaps leads to a bit of disjointed nature. But given what Stewart was trying to do, it’s to be expected and is not horribly distracting.


One criticism. You have to know Stewart: he is a likable, humble, self-effacing guy with perpetual good natured twinkle in his eye.  The kind of guy who would give you the shirt his back if you asked for it. (More about Stewart is found below). He is not prone to seek the spotlight and prefers to help others more than himself. He has been in the lawyer wellness space a number of years and probably knows as much about it as anyone. Yet his writing in the book is pretty much limited to introducing the various topics and authors. Knowing Stewart, I know he has a lot to say and wish he had said more of it here. Perhaps he will give us that next time.



Like the Whole Earth Catalogue, this is a book you will probably refer back to and to some extent use a reference tool for yourself and others.


The book can be purchased from the American Bar Association at a cost of $39.95 for non-ABA and Law Practice Division members and $29.95 for Division members. Sadly, it is not available electronically. While a little pricy, like the Whole Earth Catalogue, this is a book you will probably refer back to and to some extent use a reference tool for yourself and others. So, in that regard, it’s not that expensive. And where else could you get the advice of 29 writers all in one place?


The last edition of the Whole Earth Catalogue ended with a picture of a country road and the phrase “Stay hungry. Stay foolish”. My guess is that Stewart Brand and Stewart Levine are kindred spirits: Staying young and foolish in spirit might just be a good first step to lawyer wellness.


About Stewart Levine

Stewart Levine is the founder of ResolutionWorks, a consulting and training organization dedicated to providing skills and ways of thinking needed to build strong organizational cultures. He spent ten years practicing law before becoming an award-winning marketing executive serving the legal profession at AT&T where he was recognized as a pioneer “intrapreneur.”  He uses his approach to form teams and joint ventures in a variety of situations.  Stewart has worked with large and small law firms, legal departments and government agencies across the country.

Stewart served on the Council of the American Bar Association Law Practice Management Section where he was Chair of the Education Board 2000-2003. He was a founding editorial member of the ABA Law Practice Management Ezine where he wrote a monthly column, “Management By Agreement” from 2003-2008. He was featured in an article about “Trend Setters” in the Legal Profession in Law Practice Magazine.

His book “Getting to Resolution: Turning Conflict into Collaboration” (Berrett-Koehler 1998) was called “a must read” by Law Practice Management Magazine. It was an Executive Book Club Selection; Featured by Executive Book Summaries; named one of the 30 Best Business Books of1998; endorsed by Dr. Stephen Covey, author of “Seven Habits of Highly Effective People” and featured in “The Futurist” magazine. It was a finalist for the 2009 Center for Public Resources book of the year. “The Book of Agreement” (Berrett-Koehler 2003) has been called more practical than the classic “Getting to Yes, ” and named among the best books of 2003 by CEO Refresher.  He co-authored “Collaboration 2.0” (HappyAbout 2008.) He is a frequent contributor to Legal Publications.

Stewart is an Honors graduate of Rutgers Law School where he was the Student Writing Editor of the Law Review. He served as a Deputy Attorney General for the State of New Jersey and was a Law and Humanities Fellow at Temple Law School where he was a law teacher.


In October 2010 Stewart was inducted into the College of Law Practice Management. He served as an adjunct member of the faculty at the University of California Berkeley Law School.



Photo Attribution

Rosa Menkman via Flickr


Today was yet another big Apple Event to announce new products. This one was held interesting enough in Brooklyn at the Brooklyn Academy of Music instead of in California which is where Apple typically holds it announcements. The show opened with a short video ironically extolling New York (“ I happen to like New York”) instead of Brooklyn; I assume Apple does know the difference. In any event, the video was pretty well made and definitely one of the cooler things Apple has done recently.

Continue Reading Today’s Apple New Product Announcements: What’s In It For Us Lawyers?

I read with interest Bob Ambrogi’s recent post  on the lack of change in the legal industry. Bob’s view is that while many of us talk and talk about the great changes in store for the legal profession that will move us forward, nothing seems to happen. It’s as if we are housed in a giant echo chamber.

My own view is that until the clients demand change, us outside lawyers ain’t gonna.

Continue Reading If I Were King: Five Things I Would Demand of My Lawyers

Today, Google held its #madebygoogle event in New York City and announced 3 new products. While none of these were particularly surprising since they had all been rumored for some time (some tech writers had already been sent some products to review), the announcement was still interesting. And while all three of the new products are primarily designed for home and general customer use, I can see some useful applications for us lawyers.

Continue Reading Made By Google: What’s In It For Lawyers

Sometime ago, I read an article about a former biglaw litigator, Kathleen Dooley, who left biglaw to go in-house for is dedicated to enabling individuals to claim legal ownership of their inherent human data as property (i.e., doing good for the world).

Since I, too, was a former biglaw litigator who recently left for something else, I reached out to her to see what prompted her to make the change and how she went about it. I found her to be a fascinating person who gave her change process a lot of thought. Here is my interview of her in which she candidly talks about her change, what she’s doing now and the state of women in law. I hope you enjoy it as much as I did doing it.

Continue Reading Kathleen Dooley: Her Journey From BigLaw to Doing Good and More

I listen to a lot of podcasts when, as in the past, I was driving to and from my law office: now, since my office is just a couple of steps down the hall from the kitchen and I have no commute, I listen while I am exercising. Some of my usual podcasts are good and some average but every now and then, I get one that really makes me see things in a new light and inspires me to do something. Such was the case with the most recent podcast of Dennis Kennedy and Tom Miguel on the Law Technology Today blog entitled Disruptive Innovation in a Law Practice.

Continue Reading Forget Disrupting Law. Disrupt Yourself

Why do some law firms give away content while others wallow in silos?

For most of this week I have been attending the annual trade show of the International Legal Technology Association or ILTA for short. Like most trade shows, ILTA offers a very large and interesting exhibit hall with hundreds of vendors displaying their wares. Continue Reading Sorry Sir: You Have to Buy Something to Get The Socks

Today’s morning keynote at ILTA was a topic near and dear to the heart of most legal industry observers and pundits: the so called Dramatic Shifts in Legal Services. A panel of esteemed luminaries including John Elbasan of Wilkie Farr, Zabrina Jenkins, Starbucks in house counsel, Dan Linna of Northwestern University, Jeffery Schwartz of Hinshaw and last but certainly not least for reasons that will become apparent below, John Fernandez of Dentons. Unrepresented on the panel, ironically, was anyone actively practicing with a law firm which, in and of itself, is emblematic of the continuing gap between those of us who believe there is a better way to provide legal services and those who provide them. Continue Reading Lawyers and Innovation: Let’s Talk About the Elephant In the Room