Ten Things: ChatGPT and Generative AI (What In-House Counsel Need to Know)

Hello again everyone.  I suspect a number of you out there have been wondering when I was going to get around to today’s topic.  Hell, even I was wondering about it.  Back in January, I identified ChatGPT as one of my top ten things for in-house lawyers to pay attention to in 2023, but I must admit that I am shocked at how quickly it has overwhelmed the debate about legal tech.  To be honest, I was hoping for a moment when the pace of “new” ChatGPT information would slow down.  It hasn’t.  And likely won’t.  But I think it’s important enough of a topic to at least try to take a snapshot of where things stand today for in-house lawyers when it comes to ChatGPT (or more generically, generative AI).  Back when I was general counsel, I would have grabbed a few folks on my team and said, “Let’s jump into a conference room and whiteboard ten things we need to know about ChatGPT.”[1]  As I have been thinking about and using ChatGPT, I realize we may need two whiteboards – there is a lot to cover!  What I have done is read a lot about it and I have tried it out a number of times with many different asks.  All to put myself back in the chair of an in-house lawyer and cut through the clutter to make sense of just what this tool is and what can it do to help me and the legal department.  So, get your dry markers out, grab a big mug of coffee, and join me in the conference room as this edition of “Ten Things” tries to set out what in-house lawyers need to know about ChatGPT (and be sure to click through the links and check the footnotes for – a lot of – extra information):



Ten Things: How to Manage People… and Lawyers

There are several things that I rarely, if ever, expect to hear in-house lawyers utter.  These include, “Hey, I’m really excited about that new ‘Rocky’ movie!” and “Is $1,500 an hour enough for that Big Law third-year associate?” or, my favorite, “This suit from Sears fits perfectly!” Right up there on the Mount Rushmore of “No One Said Ever” is this, “I really love managing people – it’s the best part of my day!”  Okay,  that may be stretching things a bit, but, in all seriousness, managing people in an in-house legal department (like anywhere) can be a… umm, taxing job (yeah, that’s the right word, taxing).  For sure, there are days when managing people – even lawyers – can be very rewarding and enjoyable.  The challenging part is figuring out how to make days like that the majority versus the minority.  This is difficult because – like many things I discovered post-law school – no one teaches or prepares in-house lawyers for managing people. There seems to be an assumption that if you are a good lawyer, you are automatically a good manager.  As you probably know by experience, that is not true.  Many great lawyers suck at managing people.  It is just not the way their brains are wired.  And when you put bad people managers in charge of people, it can be a disaster.  I have had the benefit of having many terrific managers, both in-house and in private practice.  And I have had a few duds.  I learned important lessons from both types in terms of how to manage people, i.e., things to do and things not to do. Regardless, if you want to get ahead in the in-house world, especially if you aspire to sit in the general counsel chair, then it’s something you will need to learn to do and do well.  This edition of “Ten Things” shares my experience with what works best when it comes to managing people in an in-house legal department:


Ten Things: Alternative Fee Arrangements – What In-House Lawyers Need to Know

I had a different topic in mind for this post and then someone sent me a screenshot from a fee request filing on Pacer (the federal courts’ e-filing system).  Here’s just a snippet:


This is not a joke.  You are reading this correctly – $775.00 per hour for first-year litigation associate lawyers.  $1,205.00 per hour for a third-year!  In a world that often feels insane, we’ve reached a new level of rate insanity when it comes to legal fees, especially those demanded by the mega firms.  If you are like me, you looked at this chart and then fell out of your chair, unconscious and involuntarily flopping on the floor like a dying fish.  Or maybe that’s just me?  Unconscious or not, there is a lot wrong with these numbers, but I do not want to spend 3,000 words bashing the business model of the mega law firms.  I know you all get it.  Hell, even the folks at Big Law get it – they just can’t change the trajectory.  But, the bigger questions to me are: (1) is this rate insanity sustainable, and (2) what can in-house legal departments do about it?  Personally, I believe that the number of clients who can afford these rates (or have matters justifying these rates) is shrinking, like George Costanza at the beach house coming out of a cold swimming pool.[1]  In other words, is a reckoning coming?

I have no idea.  These rates may, in fact, be sustainable.  The legal services marketplace seems to be immune to pressures other businesses face.  So, let’s just set that question to the side.  Instead, today I want to talk about – once you stop flopping around and get back into your chair – what in-house legal teams can do in response to rates like this.  In particular, I want to discuss alternative fee arrangements as I have been asked about these numerous times over the past month or so and they are likely to be (if done correctly) one of the most promising ways legal departments can get some control over the cost of legal services, especially when economic times appear to be as uncertain as they do here in the first half of 2023.  This edition of “Ten Things” will tell you what in-house lawyers need to know about alternative fee arrangements:


Ten Things: How In-House Lawyers Can Survive and Thrive in Times of Uncertainty and Change

I do a lot of speaking with and presenting to in-house lawyers and legal departments.  It’s something I really enjoy doing because I get to share my “wisdom” with everyone (which is just a fancy word for “oldness”).  By this I mean I have been around a while and have spent most of my working years as an in-house lawyer.  And, like anyone who has completed the solar elliptical as many times as I have, I’ve dealt with a lot of different things as an in-house lawyer – some good, some bad, and some still defying categorization years later.  On the bad side of the continuum, I was there for the first internet tech bubble (and the second), along with the mortgage meltdown crisis.  I was in the travel business right after 9-11.  I have been through natural disasters, multiple layoffs, budget cuts, reorganizations, mergers, acquisitions, sales, going private, going public, and all the rest of it.  I oversaw bet the company litigation, where literally the livelihoods of 10,000+ employees depended on my team not losing a piece of litigation.  And most terrifying, I had a front-row seat for the incredibly shitty ending to Game of Thrones.  That is a season of television I can never get back.  Damn you, HBO.  Damn you to hell!  Sorry, I got off on a rant there.  Allow me to (cough) refocus.

So, here we are again.  Things feel shaky with the economy and there is a good bit of unease out there in the business world and, therefore, in the in-house legal departments that serve those businesses.  I wrote about some of it last month in my post on things to watch out for in 2023.  But even more so, over the past few months, I have been consistently asked to talk about/present on how in-house lawyers can succeed in an environment of change and uncertainty.  So much so that a couple of nights ago (as I was NOT watching HBO), I started putting some real thought into the question and realized that I have a lot to say about it (shock!).  So, this edition of “Ten Things” will discuss some of the things in-house lawyers (and legal departments) can do to survive and thrive in times of change and uncertainty:[1]


Ten Things: Essential Issues for In-House Counsel (2023 Edition)

Hello everyone and welcome to 2023!  Here we are well into year nine of the “Ten Things” blog.  I checked recently and see that there are over 12,000 followers of the blog.  Holy #$^%!  I never in my wildest dreams imagined that would happen.  So, thank you all for reading and sharing my posts.  I truly appreciate it.  And, as we start a new year, many of you know that my first post of the year is typically a list of issues I believe in-house lawyers should pay attention to over the coming 12 months.  This is something I started doing when I first became a general counsel way back when and something I kept doing over the course of my in-house career.  I still do it now as CEO of the Hilgers Graben law firm.  In short, I spend time thinking about developments, trends, issues that may have a material impact on the legal department/business over the course of the new year.  It starts with simply gathering information.  As general counsel, that meant speaking with in-house lawyers and outside counsel, reading newspapers, blogs, industry reports, attending conferences, sitting in on meetings within the business, asking business leaders at the company, asking my team what they were seeing, and just generally paying attention to what was going on around me (see Ten Things In-House Lawyers Should Read Every Day).  If you didn’t know already, information is gold to in-house lawyers, the currency of the realm.  Stock up when you can!  Once I spotted a potential issue, I looked at it from multiple angles and asked this question: How might this affect the company and the legal department?  Answering this question meant I had to understand the company’s goals and strategy so I could spot and manage risks (see Ten Things – Spotting, Managing, and Reporting Risk) and I had to be a strategic thinker, looking beyond just the legal issues that might be at stake (see Ten Things – The Strategic In-House Lawyer).  From there, I made a list of the most critical issues and worked them into the goals and activities of the legal department.

To assist me with this process, I created checklists to help quickly analyze the potential risk and strategic implications of the items on my list.  Here is a version of one checklist, and it’s a helpful filter when you look at things coming across your desk day in and day out:

  • Is this something that can create or destroy value?
  • How does this fit into my company’s strategic goals?
  • Could this be a game-changer and how so?
  • Is this something a regulator might care about/criminal?
  • Who is impacted by this: company, competitors, vendors, customers?
  • What happens if I apply game theory to this?
  • What is the regulatory regime around this?
  • How can we create a competitive advantage from this?
  • Have others had problems or success with this before/lessons already learned? 

How you answer these questions tells you a lot about the issue you are analyzing and whether it matters or not.  You do not need a checklist, but it’s a tool that can help you quickly sort through a lot of information quickly.  You could also use an Eisenhower Matrix (2×2) to plot issues, focusing on the ones in the upper right quadrant.  It’s really all about providing a consistent framework to consider whatever is in front of you.  All right, enough yapping and background.  Time to get on with another year of Ten Things You Need to Know as In-House Counsel. Here is my list of critical issues in-house lawyers should pay attention to and plan against for 2023:


Ten Things: Best Blogs (and Other Media) for In-House Lawyers (2022 Edition)

Hello everyone and greetings from Copenhagen!  Mrs. Ten Thing’s family is from Denmark, so we have been fortunate enough to spend these holidays in Switzerland and Denmark.  It’s been chocolate, beer, and a lot of eating!  And no matter where you may be, I wish you a fantastic holiday season and all the best for 2023.  Speaking of 2023, we are now into the ninth year of the “Ten Things” blog.  How did that happen?  (Hopefully, no one out there is screaming “unfortunate accident!”).  Seriously, thank you all for sticking around for the ride, for the suggestions for topics, and, most of all, for the encouragement to keep on writing!  I don’t think my shelf life has expired yet, so I plan to keep it going at least until the magic ten-year mark.  I am also starting to work on the “Ten Things” podcast.  But don’t get too excited just yet.  That is probably a project for later next year as first I have to bear down and get the next book – on productivity – into the hands of the ABA before they send around the goon squad to make sure I am feverishly writing away.  It is kind of a Charles Dickens vibe – if Charles Dickens was lashed to his desk with piano wire and reminded daily to get writing or else the dog, grandma, and Tiny Tim get it in the head.  But I did sign on the line so the ABA will get their &%$#@ first draft soon enough.

But I digress.  A lot.  As usual.  So, let’s right the ship and get back on course.  I am excited about the final “Ten Things” blog of 2022 because, like every year, I end it by writing about all the other people you should be reading (or listening to) as part of your day-to-day in-house life.  And, as always, there are a lot of great content generators out there fighting for your attention.  Like in past years I am going to highlight a few that I follow and enjoy.  But I cannot list everyone because I handicapped myself by calling my blog “Ten Things” and not “One Hundred Things” and I am nothing if not slavishly true to the numerical predicament of my own making.  Which is a very long-winded way of saying, I am going to just list ten.  And, like always, there is no particular order to my list and I will not list past “winners” – even if they are still some of my favorites (and they are, like Presnell on Privileges, Mel Scott’s Counsel podcast, and Contract Nerds).[1]  If you want to get more recommendations, check out past editions of my “Best Blogs (and Other Media) for In-House Lawyers,” starting with the 2021 edition.[2]  Okay, enough with the tangents and ABA bashing, let’s get on with the 2022 edition!


Ten Things: Becoming the Company Watchdog (Spotting and Dealing with Corporate Badness)

I assume most of you have been following the spectacular collapse of FTX, the cryptocurrency exchange that was once worth $34 billion and is now worth less than the coins in the cushions of your couch, with theft, fraud, and a host of other felonies thrown in for good measure.  If you’re like me, you probably had this reaction: “What the f**k happened here?!”  If you are a regulator or law enforcement, you might also be thinking (among many other things): “Where were the lawyers, and what did they do to stop this?”  Sadly, these are now common questions as expectations regarding the responsibilities of in-house counsel to spot and stop corporate malfeasance have changed dramatically over the past two decades.  These expectations (and new laws) are driving more in-house counsel to look for ways to beef up their role as the “watchdogs” of the company, on the prowl for trouble and wrongdoing – and one clear way to show the value of the legal function.  It’s not an easy task, however.  It’s can be fraught with risk and conflicting loyalties.  And it often seems like the in-house lawyers are bringing a water gun to a knife fight, i.e., they need more help.  Warren Zevon said it best way back in 1978:

“Send lawyers, guns, and money.  The shit has hit the fan!”

(Lawyers, Guns, and Money)

The problem for lawyers is that guns and money may not be enough (though they certainly help, especially the money bit).  They need a plan and a process for how best to identify problems and what to do if they uncover (or suspect they have uncovered) serious wrongdoing.  This edition of “Ten Things” walks you through a plan for doing just that:


Ten Things: Business Skills All In-House Lawyers Should Master

In my newest book, Showing the Value of the Legal Department, I include a section on the evolution of the role of in-house counsel.  I walk through the “dark ages” (lawyers in the basement alone and ignored) all the way to the current phase of “leaders/strategic thinkers” (using our lawyer superpowers to become valued partners to the business).   As I see it, the part of the role that has changed the most over the course of this evolution is the need for in-house lawyers to bring more to the table than just good legal skills.  Those are just your ticket to get into the circus.  To be successful, to be viewed as a partner to the business, and to get your seat at the big kids’ table with the filet mignon, you must also possess a set of key business skills.  How do I know this?  Well, I fumbled and bumbled my way through the process the hard way, i.e., I had to figure it out mostly on my own (but certainly – and thankfully – with the help of some key mentors along the way).  But I did figure it out and had a seat at the table as general counsel three times where I learned that the business had its own language (numbers) and way of doing things (business school) that were foreign to me given my legal background.  After thinking about it a bit, I realized that almost everyone at the table had a background in certain business skills that I did not possess.  Moreover, while everyone was more than happy to explain things if you asked; if you didn’t ask, they just assumed you were playing the same game they were playing, and it was on you to keep up with the class.  And, of course, like most lawyers, I was too proud to just up and announce that I had no clue about half the shit they were talking about.  Fortunately, I was smart enough to know I had to level up or I was soon destined for the little kids’ table and a nice Happy Meal of chicken nuggets.  So, level up I did.  And over the course of eight years of writing this blog, I have mentioned a wide assortment of business skills you need to succeed in the role.  But what I have not done is list all those skills in one post.  This edition of “Ten Things” corrects that oversight and sets out the ten essential business skills you must master to succeed as an in-house counsel.  And thanks to Marco Bijl, Head of Legal at Philips, for the idea:


Ten Things: The Art of Delivering Bad News

Most days being an in-house lawyer is a pretty good gig.  It has certainly gotten more demanding over the last ten years or so, but there have been corresponding gains in both compensation and prestige.  Those do not always offset the increase in expectations, but they are pretty nice!  When things are good and the relationship with the business is productive, your days are busy but manageable.  And when you get to deliver good news to the business, things can really take a positive turn.  Everyone likes to give and get good news.  Unfortunately, unless you work in a very magical, wonderful place, not all the news in-house counsel must deliver is good.  While hopefully infrequent, there comes a time when all in-house counsel must deliver bad news.  And, depending on the content and context, this can be both a painful and scary proposition.  Believe it or not, there is an art to delivering bad news.  For some, it’s instinctive.  For others (yours truly included) it must be learned.  This edition of “Ten Things” will walk you through the art of delivering bad news:


Ten Things: “Cool Tech” for In-House Counsel (2022 Edition)

Well, it’s August and that means lots of things.  If you live in Texas, it means you are seriously regretting your decision to move here because it is just stupid hot and humid.  Apparently, housing lots in Hell are sold out as Texans look to move someplace cooler.  August also means it is time for my annual “Cool Tech” blog – one of my favorites.  Somehow, this is the eighth year in a row where I will share technology and tech-related ideas that can make life easier (or a smidge better) for in-house counsel.  If you want to check out past editions of my “Cool Tech” blog, here you go:

There is a lot of great technology discussed in these past editions and they are worth reading to find a gem or two that works best for you.

You probably know that I am a bit of a technology geek.  Not that I have any special powers (I am as afraid of screwing something up as you are), but rather because I wholeheartedly believe that technology can make an in-house lawyer’s job easier, improve the capabilities of the legal department, and help show the value generated by the legal team.  In my “Cool Tech” posts, I generally try to discuss technology that is free (or very low cost) and adds immediate value.   While I think e-billing systems, matter management systems, document management systems, electronic signatures, and so forth, are table stakes for legal departments today, that is not my focus here.  If you do want to read about this type of big tech (and all in-house lawyers should), I suggest you check out this really cool fairly new site, LawNext.  LawNext is a comprehensive directory of legal technology products and buyer’s resources.[1]  I also recommend the CCBJ 2022 Directory of Leading Legal Technology and Project Management Solutions available here.  But, with one exception, we’ll stay small and focused, i.e., technology you can buy and start using today, much of which is free.  As always, I received nothing for recommending this technology to you.  I just think in-house lawyers will find the technology useful.  But, enough yapping, let’s get to the fun stuff.  Here is my Cool Tech for In-House Lawyers 2022 Edition: