Technology

Ten Things: Dealing with Business Executives (Where the Wild Things Are)

If it seems like it has been a while since I wrote a “Ten Things” post,[1] that’s because it has been!  I have been out on the road for most of October and November speaking at conferences, off-sites, street corners, church pulpits, casinos, bus stations, or wherever they will have me.  One thing I enjoy about doing this (other than the glamor of flying)[2] is getting to meet so many in-house lawyers and talking about what is on their minds. And that is where the inspiration for today’s post comes from. While on the road, I heard from many people that one of the hardest parts of their job is “dealing” with business executives, from front-line managers all the way up to the C-Suite.  In particular, people asked me why it is such a chore to get executives to focus on legal issues or take legal issues as important problems to solve vs. something that the lawyers are “dealing with” down in the basement but somehow requires them to spend part of their limited time helping with: “Why can’t you just make it go away and stop bothering me?”  I get it.  I had similar problems when I was starting out as an in-house lawyer and when I was general counsel, i.e., it never changed. I just got better at dealing with it.  How?  Because I spent a lot of time thinking about the best way to make an impact with my business colleagues.  And, over time, I figured out a number of things I could do to solve what is, apparently, still a very common problem even here in 2025. 

It will come as no surprise that it starts with understanding that working with business executives as an in-house lawyer is different than working with them as outside counsel. And, for those who arrive at the in-house world from a law firm, understanding that you are not the center of the universe.  If you are lucky, you may be the demi-planet Pluto or a large asteroid.  For many, this is a shock to the system, and some never recover or adapt.  We call those people former in-house lawyers (or really bad ones).  Second, and even more importantly, being successful at it requires a change in tactics and expectations.  I have compared the process to visiting the island of the “Wild Things.”[3]  And like Max, you must prepare yourself for a wild rumpus!  So brace yourself as this edition of “Ten Things” discusses how to best deal with the Wild Things… uh, I mean business executives:      

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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: 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: The Newest and Bestest Book on Productivity For In-House Lawyers is Out!

The wait is over!  Well, maybe just for me.  It took a while, but my sixth book, “Productivity for In-House Lawyers: Tips, Hacks, and the Art of Getting Things Done” is now available for purchase.  If you are struggling to manage everything on your plate or just want to be more efficient day-to-day, I have collected all of my best tips and hacks for increasing productivity in the unique world of practicing as an in-house lawyer (though anyone can probably benefit from the book).  You can buy it here:  Productivity Book.

Productivity Book Cover

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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:

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Ten Things: Cool Tech for In-House Counsel (2019 Edition)

Well, it’s that time of year again.  Every August for the last several years I have devoted a “Ten Things” blog post to talking about super useful technology for in-house lawyers.  Fortunately, there is always more cool tech to talk about and this year is no different.  That said, if you want to go back and revisit some of the past cool tech blogs click here (2016, 2017, 2018).  The ground rules are the same as always: (1) I receive no compensation for these recommendations, they’re just things I think in-house lawyers (any lawyers really) will find useful and helpful; (2) I try to focus mostly on free or low-cost technology – no breaking the bank for the most part; and (3) generally, everything I discuss should work for in-house lawyers anywhere in the world, not just the USA (if there is an exception, I’ll note it).[1]

With that in mind, this edition of “Ten Things” discusses some of the coolest technology out there for in-house lawyers, things that will make your life a little easier and, hopefully, more productive:

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Ten Things: “Cool Tech” for In-House Lawyers (2017)

I was a panelist at the 16th Annual Advanced In-House Counsel Course in San Antonio, Texas on August 18, 2017.  I was joined once again by Jason Smith of Apttus and Jane McBride of Optimus Legal to discuss ways lawyers can work smarter and not harder – a worthy goal if ever there was one!  Of course, one of the main ways to accomplish this is through the use of technology which we all touched on at some point during the discussion.  If you follow this blog regularly, you know that I have recently written on the impact of artificial intelligence on in-house legal departments as well as ways to slay the “Email Jabberwocky.”  Both highlight ways technology (and common sense) can help you do more in the same or less time.  You also know that I enjoy writing about the use of technology generally by in-house lawyers.  And now that I have gotten back in the General Counsel game after two years of private practice, I am focusing even more intently on ways technology can make my and my team’s lives easier.  What all of this means is that it is time for my annual “Cool Tech” blog post.  You can read my past posts for Cool Tech 2015 and Cool Tech 2016 (and I still recommend all of the technology mentioned there), but this edition of “Ten Things” will discuss an all-new list of cool tech for in-house lawyers.  As always, I do not receive any compensation or anything to endorse these products, it’s just my opinion about technology I think in-house lawyers might find useful:

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Ten Things: Increasing Efficiency in the Legal Department Through Technology

One goal set out in my sample legal department goals for 2015 was to increase efficiency (and reduce costs) in the legal department.  One of the easiest ways to do this is through the use of technology.  This can mean anything from apps for your smartphone to sophisticated software programs running on servers at your company.  For some, using technology can be daunting and frustrating.  For others, it is as easy as falling off of a log.  But, to be a successful in-house lawyer or general counsel you need to embrace technology and make sure your team does as well.  So, if you are afraid of technology, you need to get past that.

One issue with using technology is that the choices are almost endless and it can be difficult to distill things down into a useful list.  This edition of “Ten Things” takes on the task of listing some key technology that can help you increase your own efficiency as well as the efficiency of your team or the department overall.  I am going to assume you know how to use Microsoft Office products (free and pay) and Google products (free), so those tools — certainly very useful — are not included.  That said, if someone asked me to list my ten key technology tools for an in-house lawyer, here they are:

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