artificial intelligence

Ten Things: “Cool Tech” for In-House Counsel (2025 Edition)

Hello my friends and welcome to another edition of “Ten Things You Need to Know as In-House Counsel!”  Every summer for the past ten years, I have written about “cool tech” for in-house lawyers.  It is one of my favorite posts and over that time I have stumbled upon a number of great bits of technology that in-house lawyers should check out.[1]  Over the course of the past 12 months, I have been keeping my eyes open for useful technology that will make you more productive (in addition to making work easier and – hopefully – more fun and interesting).  In my latest book, productivity for in-house lawyers, I devote a lot of space to how technology can increase productivity, reduce costs, and make your life as an in-house lawyer better. Simply put, I am a big fan of technology.  I say that with full disclosure that I am not particularly skillful with it.  I just like to bang away and see what works and what doesn’t, keeping the good and moving on from the bad.  Pretty much just “Joe Average” when it comes to understanding how it works – but good at finding ways to capitalize on the stuff that does work.

I know most legal departments operate on a tight budget, so when I am putting this post together I like to find and highlight technology that is easy to use and low cost – delivering big value with little effort or expense (though I also highlight at least one bit of technology that is a bigger lift cost-wise but likely to pay big dividends – and I do that again this year).  No shock, but a lot of the technology I highlight here in 2025 has some basis in AI and I think that will pretty much be the course for next several years if not more.  As usual, I make no promises or warranties of any kind, implied or express and you assume all risks associated with reading further (and I have an army of savage litigators at my disposal should something go off the rails – so keep those lawsuits to yourself…). I can also assure you that I get nothing for recommending the technology below.  I just think these are all useful tools and worth your checking them out.  Ready to get started?  Great, here we go with my “Ten Things” cool tech 2025 edition:

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Ten Things: Ten Questions To Ask Yourself Before Hitting Send (Lessons From the Trenches)

I was cleaning out some old files in a filing cabinet (yes, that’s still a thing) and I came across some plastic cards we had made up when I was head of litigation at a large technology company many moons ago.  My team and I created the cards to help the business focus on key compliance issues, i.e., providing them cards with lists of easy-to-remember rules that could help keep them – and the company – out of trouble.  They were about the size of a business card (that may not be a thing anymore…)[1] and were laminated so they would last forever.[2]  And here in front of me were several different cards we had prepared close to twenty years ago.  They included tips on competition law compliance, how to report a violation of the company handbook, and (my personal favorite) how to write smart emails that won’t end up as Exhibit A at trial.  I remembered why we created these in the first place, especially the email card:  If you have ever lived through big litigation (or any litigation for that matter), you understand just how deadly a poorly drafted email can be.

And deadly is right.  I lived through several painful and protracted litigated disputes, and I can attest that emails (ours and theirs) were front and center, blowing up in faces like Wile E. Coyote-endorsed ACME product.  The only thing missing was a sign for free birdseed. There were lots of lessons learned by unfortunate executives (and yours truly).  Back then, I decided to take those lessons and create something useful to showcase basic rules to help the business – and the lawyers – write smarter emails (and other documents).  As I read through the card, I realized that I had forgotten some of the lessons.  And, yes, that failure has bitten me in the ass more than a few times.  So, I decided it would be a good idea to write them out here for you – and for me.  This edition of “Ten Things” sets out questions you should ask yourself about the email before you hit send:

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Ten Things: 100 Practical Generative AI Prompts for In-House Lawyers

Over the course of 2024 and the first part of 2025, the questions I get most frequently from in-house lawyers are about Generative AI and how legal departments can use it to improve productivity.  There is a lot of pressure from the C-Suite on legal departments to adopt AI and show meaningful productivity gains.  While this is a noble goal, there are a number of issues with Generative AI that – rightfully – are causing legal department leaders to want to “go slow.”  Chief among them are concerns about 1) confidentiality, 2) attorney-client privilege, 3) trustworthiness, i.e., trusting the results, and 4) how do I draft “prompts” that get me useful results.  All valid issues that should not be taken lightly or dismissed out of hand.  Second, there is an almost overwhelming amount of information out there about Generative AI, making it hard (exhausting?) to stay on top of the latest developments in the field – so why not wait until things settle down before adopting?  Lastly, the technology is changing quickly, too quickly for most legal departments to understand the changes (and the implications) without a dedicated AI team – something beyond the reach (and budgets) of most in-house legal teams.  In other words, it’s really f$#@ing hard to figure out how to use Generative AI effectively!

So, how do we solve this problem?  In my experience, there are many simple and practical things you can do with Generative AI right now that can drive real productivity gains for in-house lawyers.  And while there may be an ever-growing list of more sophisticated and complicated uses for it, most legal departments are just looking to crawl and not sprint.  For most, crawling is perfectly fine and will get you a lot of useful results from Generative AI.  All of this is a big wind-up for me telling you I think I can help get you started crawling (in the “good” sense)[1] and that’s what I intend to do.  While thinking about this post, I realized it needs to flow differently than a typical “Ten Things” blog.  I’ll still give you ten things to focus on (in this case practical “prompts”), but it will take me a bit to build up to that part because there is some background we need to dwell on first.  Bear with me – I promise we’ll get to the good stuff!  For now, just sit back, grab some coffee and a Cinnabon roll, and set your brain to “learn.”  This edition of “Ten Things” will walk you through practical prompts for in-house lawyers:

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Ten Things: Artificial Intelligence – What Every Legal Department Really Needs to Know

[Note: this is a summary version of a four-part series I wrote for Thomson Reuters earlier this year with some key updates and new sections.  You can find the full series by clicking here]

Some of the best scenes in the television show Star Trek (the original version) involve the crew members asking the computer a question and the computer spitting out the answer in the form of a conversation.  I was utterly amazed by this and, of course, wanted my own computer that would “answer” my questions.  Alas, I was ahead of my time.  But, I was recently reading an article comparing the Google Home with the Amazon Echo, two devices that allow you to ask questions and get an answer.  From a computer.  Just like Star Trek!  This brought back two important memories from the TV show: 1) intelligent computers that can talk and answer questions; and 2) never be the crewman in the red shirt.  I always lived by the latter and now, it dawned on me, I could start to live by the former too.

Artificial Intelligence (“AI”) is just beginning to come into its own in terms of uses by lawyers.  We are on the cusp of a revolution in the practice of law led by the adoption of AI computers – in particular by in-house lawyers.  Much like email changed the way we do business every day, AI will become ubiquitous – an indispensable assistant to practically every lawyer.  This edition of “Ten Things” discusses what you really need to know right now about artificial intelligence:

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Ten Things: 10 Essential Legal Department Issues for 2017

There are an amazing number of issues, trends, and headaches to keep track of as in-house counsel.  So much, that it can be difficult to know what to focus on.  When I was General Counsel I made time each year to step back and try to take a look at the big picture, i.e., given everything going on in the world, what should I and my department be spending time on right now?  Certainly, I wanted to make sure things that were important to the goals of business where high on our list.  But I also wanted to “benchmark” my team and make sure we were aware of what other legal departments were doing.  I would gather information from many different sources and then come up with my own list of current essential “issues/best practices” that I thought we needed to focus on.  Generally, my list contained items dealing with risk reduction, technology needs, management practices, key analytics, and ways to enhance the value of the department to the business.

Though I have not been GC for a little while, I keep my eyes and ears open to what’s going on in the world and how might it affect in-house lawyers.  I thought I would highlight some of the important things I see out there right now — things that should be on every in-house lawyer’s “watch list.”  This edition of “Ten Things” discusses the essential items I would be focused on right now if I were running a legal department in 2017:

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