Legal Technology

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: An Index to All the Posts (November 2014 – August 2025)

Hello again everyone.  I have been working on my annual “cool tech” post, but it’s not ready for prime time as I am still sifting through things.  The amount of tech out there (cool or otherwise) is amazing.  And since I want to give you my best recommendations, I am going to work on it for another week or so.  Instead (and because I am a big believer in keeping to a regular publishing schedule), I thought I would put out a current index to all of the “Ten Things” posts from post number one in November 2014 to last month’s post about things to think about before hitting send.  There are a lot of posts and this edition of Ten Things lists them all (which is kind of the point of an index but I digress):

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Ten Things: Travel Tips for the Busy In-House Lawyer

Hello everyone and greetings from 35,000 feet!  I am on the road again – my third trip in April.  I think I have spent more days sleeping in hotel rooms than I have at home this month.  I am not complaining at all, but I do spend a lot of time on the road.  And that got me thinking about all the things that have gone wrong over many years of hard travel.  It’s a lot.  But, like many of my blog topics, I screwed up and then learned the lesson.  The same is true with traveling.  I know not all in-house lawyers travel a lot, but they do travel.  And it is always better to be over-prepared than to get smacked upside the head by the cold, hard, fickle hand of Fate (she is indeed a tough mistress who enjoys smacking people upside the head).  I was going to write about mentoring programs, but (as I sit here on the plane) I decided this was a more interesting topic – at least to me.[1]  So, instead of mentoring tips, I am going to pass along some tips I learned (the hard way) over many years so you can travel better. I am writing this with the assumption you will carry on your luggage vs. checking a bag.  First tip: Never check a bag unless you have no choice.[2] See how easy that was?  But brace yourself, as there is more.  A lot more.  This edition of “Ten Things” sets out my top travel tips for the busy in-house lawyer:

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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: Essential Issues for In-House Counsel (2025 Edition)

Hello again everyone!  As I have done for the past several years, I want to share a list of issues I believe in-house lawyers should pay attention to over the coming 12 months.  I started doing this when I first became a general counsel way back when Julius Caesar took 23 stabs to the body (he should have read my blog about the Ides of March).  Even though I am no longer practicing in-house, the process of trying to spot key issues is something I do every year, including in my role as CEO here at Hilgers Graben.  Simply put, then as now, I like to spend time thinking about developments, trends, and issues that may have a material impact on legal departments/businesses over the course of the new year.  I realize this is not something they teach you in law school (or anywhere really), so I will start by setting out the steps I followed to create my list as general counsel (and you are welcome to laugh at it, use it “as is,” or modify it to suit your own purposes):

  • I started by just gathering information.  I would catch up with other in-house lawyers and outside counsel, read newspapers, blogs, industry reports, attend conferences, sit in on business meetings, ask business leaders at the company, ask my team what they were seeing, and just generally pay attention to what was going on around me.  Information is gold and, like Scrooge McDuck, I was (and am) pretty greedy about it.
  • Once I spotted an issue that intrigued me, I looked at it from multiple angles and asked this question: How might this affect the company and the legal department?  Answering this meant I had to understand the company’s goals and strategy so I could spot and manage risks and I had to think strategically (not just legally).
  • From there, I made a list of the most important issues I spotted and worked them into the goals and activities of the legal department for the upcoming year.  To assist me, I created multiple checklists to help quickly analyze the potential risks and strategic implications of the items on my list.  Here is a shortened version of one checklist.  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 for the company?
    • How does this fit into my company’s strategic goals?
    • What is the quantitative/qualitative impact of this?
    • Could this be a game-changer and how so?
    • Is this something a regulator might care about or lead to litigation?
    • Who is impacted by this – company, competitors, vendors, customers – and how so?
    • What happens if I apply game theory to this?
    • Who needs to know about this in the department/company?
    • How can we create a competitive advantage from this?
    • Have others had problems or success with this before and what are the lessons already learned?

The answers to these questions tell 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 useful tool that can help you quickly sort through a lot of information.  You can also use an Eisenhower Matrix (2×2) to plot issues.  Here is one option for such a matrix (though what you put on the X-axis and Y-axis is wide open): 

It’s a little clunky for sure, but it just depends on what you find most useful.  Regardless of what you use to help you think through the issues, it’s really all about finding a consistent framework and repeatable process.  Okay, enough of the background story – let’s get going!  This edition of “Ten Things” sets out my list of critical issues in-house lawyers should pay attention to and plan against for 2025:

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Ten Things: I Am On Two Podcasts This Month – How The Hell Did That Happen?!

It has been a fun month or so for me because I had the true pleasure of appearing on two of the best podcasts for in-house lawyers.  The first is “The Legal Department” hosted by Stacy Bratcher, CLO at Cottage Health.  The second is the “Legal Leaders” podcast hosted by David Lancelot, CLO at LawVu.  Stacy and I chatted in depth about productivity for in-house lawyers, including slaying the email monster and escaping meeting hell (as well as my go-to pump-me-up song).  David and I spoke about a variety of topics about practicing in-house, including technology and the keys to being an effective in-house lawyer (and if you listen closely you can hear my dog snoring blissfully in the background).  Both hosts asked outstanding questions and made it very easy for me to engage with them (and covering up my blathering).  So, grab some coffee and Oreos and give them a listen.  I think you will find a lot to like in both podcasts – mostly from the hosts.

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Ten Things: “Cool Tech” for In-House Counsel (2024 Edition)

Hello everyone and welcome to another edition of “Ten Things You Need to Know as In-House Counsel!”  This is one of my favorite posts of the year because every summer for the past nine years or so, I have written about “cool tech” for in-house lawyers – and this year is no exception.  If you would like to see past editions of the “cool tech” edition, check out footnote 1 below.[1]  As always, I have been scanning the technology horizon like Captain Ahab, searching for the most elusive prize of all – useful technology that will make in-house lawyers more productive (in addition to making work easier and – hopefully – more fun and interesting).  In my new book on productivity for in-house lawyers, I have chapters on technology generally and ChatGPT specifically.  And if you have been reading my other books, this blog, or my LinkedIn posts over the years, you know that I am a big fan of technology, especially technology that enhances the productivity of the legal department and its value to the business.

As always, I like to find and highlight technology that is easy to use and low cost – delivering big value with little effort or expense (though occasionally – like today – I will highlight something that is a bigger lift cost-wise but likely to pay big dividends).  As usual, I make no promises or warranties of any kind, implied or express (got to cover my ass when I can) and 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 time checking them out.  Ready to get into it?  Great, here we go with my “Ten Things” cool tech 2024 edition:

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Ten Things: Cool Tech for In-House Counsel (2023 Edition)

Hello again everyone and welcome to another edition of “Ten Things You Need to Know as In-House Counsel.”  This is one of my favorite posts of the year because every August for the past eight years (really?) I have written about “cool tech” for in-house lawyers – and this year is no exception![1]  Once again, I have been scanning the (virtual) horizon for the most useful technology that will – hopefully – make you more productive, make your life easier, or may just be fun and interesting.  If you have been reading my books, this blog, or my LinkedIn posts over the years, you know that I am a big fan of technology as a way to increase productivity and enhance the value of the legal department.  The good news is that the technology needed to make this happen does not have to be overly complicated or expensive.  In fact, I deliberately try to find low-cost – or free – solutions that are easy to adopt and use.  As usual, I make no promises or warranties of any kind, implied or express (sorry, just covering my bases here – you can’t be too careful, especially with the ABA breathing down my neck about some book I’m “supposed” to be sending their way soon).  I can assure you, however, that I get nothing for recommending the technology below.  I just think these are all useful tools and worth checking out.  So, with no further ado, this edition of “Ten Things” sets out my cool tech for in-house lawyers in 2023:

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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):

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