legal department

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: 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: New Year’s Resolutions for In-House Lawyers (2025 Edition)

I know that I usually start the year with my list of things that in-house lawyers should be watching out for over the course of the coming year.  I will still post that blog in the next week or two.  To be honest, it’s been kind of crazy watching national and global events unfold over the past couple of weeks, so I am still refining my list (and waiting to see what else pops up in the next few days).  I also wanted to mix things up a bit to keep the blog fresh and not feel I have to do everything exactly the same as I have done things in the past.  This first post of 2025 started with a conversation with an in-house lawyer about things they could do to be more effective this coming year.  Which, as always, got me thinking about what I would do if I were in their shoes. Like most of my ideas (good, bad, or wildly shitty[1]), it just popped into my head that, in addition to the typical goals everyone creates for the year, every in-house lawyer should consider starting the year with some “New Year’s resolutions” designed to help them enhance their effectiveness, well-being, and contributions to the legal department (and the company). Unlike most New Year’s resolutions, I wanted these to be practical, manageable, and realistic. So, I put pen to paper and started to sketch out a few resolutions.  After about 15 minutes, I had way too many, which is a recipe for getting nothing done.  So, I just stopped writing and started culling.  These are the ten that made the list for 2025.  If I do this again, 2026 will likely be very different but you’ll have to stick around for 12 months to find out (how’s that for quality foreshadowing?).  But, enough of this blather.[2]  Let’s get going!  This edition of “Ten Things” sets out ten New Year’s resolutions all in-house lawyers should consider adopting:

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Ten Things: Things You Can (and Should) Delegate

I have written a lot about delegation, both in the blog and in my last two books, Showing the Value of the Legal Department and The Productive In-House Lawyer.   Specifically, I write a lot about why delegation is important and how to do it.  This past week or so it has dawned on me that I have not really spent any time talking about what to delegate other than a few asides thrown in here and there.  That is an oversight I would like to correct.  Like many of my blog posts, one of the first things I do is search to see if anyone else has already written on the topic.  I really couldn’t find anything written on what in-house lawyers should delegate.  This generally means I have a pretty wide-open field to play in, which I plan to take full advantage of![1]  I decided to do what I almost always do and that is reach back to my past and think about the things that were delegated to me as a young in-house lawyer (some), things that I asked to have delegated to me (a lot), and things that I delegated to my team once I was in a position to do so (plenty but should have been more).  All of what you read below is pretty specific to my in-house experience – though I suspect they are universal to any in-house lawyer in any legal department anywhere in the world.  So, fill up the coffee mug and get ready to go deep into the world of delegation as this edition of “Ten Things” takes on the task of setting out things in-house lawyers can (and should) delegate.

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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: What to Do When You Don’t Know the Answer

Everyone likes to know the answer to questions that come their way at work, none more so than in-house lawyers.  Lawyers take special pride in being able to respond to practically any question, on any topic, at any time.  They can do this because they are, typically, very smart, well-read, and at ease with murky situations.  However, occasionally, and usually at the worst possible moment, someone in the business will ask an in-house lawyer a question and they will have no idea how to answer it.  This happened to me on more than one occasion and it was incredibly frustrating for me and whoever was asking the question – usually the CEO or a board member.  Why were they frustrated?  Well, because like most people on the business side they believe two things that make your job as in-house counsel even harder: 1) all lawyers know everything about all areas of the law regardless of their background or specialty, and 2) that there is a “Big Book of Law” we keep on a shelf that has all the answers to every legal question and all we lawyers have to do is take it down and find the right page.  Yeah, right…. So, what do you do when you get a question you don’t know the answer to (especially when they are looking right at you across the table)?  This edition of “Ten Things” set out some strategies to help you navigate this tricky situation:

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Ten Things: Creating a “Not-to-Do” List (Learning How to Say No)

Hello again everyone! I am very excited to report to you that my next book (number six) is in the hands of the publisher and should be out by this summer.[1]  The working title is The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done.  I think you are going to really enjoy reading this one, especially if you find yourself pressed for time to do all the things you need to do on your to-do list.  Which basically means anyone reading this.  The book is jammed to the rafters with different ways to squeeze more time out of your day with the goal of getting more done (and more important things done) in the time you have vs. working more.  While I am not going to go into too much more detail here (I do want you to actually buy it when it’s available), there is one section of the book I keep coming back to in my head.  What section is that you ask?  Well, thank you for asking!  It is the section on how to say “no.”  In particular, how to create a “Not-to-Do” list, i.e., a set of principles that guide how you will spend your time by setting out the things you will not spend time on (or spend significant time on).  I certainly cannot take any credit for the idea of a “Not-to-Do” list.  The concept has been around forever, and history is full of people wildly succeeding at not doing things, such as Emperor Nero standing by while Rome burned, my law school roommate, the Kardashian family, Congress… okay, enough of that.  But you get my point, and that is the blindingly obvious fact that one path to getting more done is to reduce the number of things you are doing (Hey, I never said this was rocket science).  One way to do that effectively as an in-house lawyer is to create a list of things you will not do – a “Not-to-Do” list.  Alas, yet another thing law school, law firm, etc. never teaches you how to do (though it is such a fantastic tool).  So, let’s fix that problem.  This edition of Ten Things walks you through how to create a Not-to-Do list (and how to use it):

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Ten Things: Best Blogs (and Other Media) for In-House Lawyers (2023 Edition)

Hello everyone and season’s greetings from the penthouse of the “Ten Things” world headquarters in Dallas, Texas![1]  I will start this post by wishing everyone a fantastic holiday season and all the best for 2024.  As most of you know, 2024 is year 10 of the “Ten Things” blog and it is also the year the long-awaited(?) productivity book comes out.  I am in the final stages of submitting everything to the ABA.  More news on that as things progress. And if you are looking for some fun in January, please join me and a host of others who will be presenting at Laura Frederick’s (of How to Contract fame) ContractsCon 2024!  I will be there discussing indemnity clauses but the agenda is jam-packed with far worthier speakers and topics. So, I hope to see you in person in Las Vegas in January!

But, on with the business at hand.  Like every year, I end 2023 with a blog featuring all the other people you should be reading (or listening to) as part of your day-to-day in-house life.  For me, the hard part is choosing just a few to highlight.  There are so many great content generators out there fighting for your (and my) attention.  Unfortunately, I cannot list everyone (and I rarely repeat listing anyone I have listed in the past, i.e., I just assume you know they are still worth your time – they are!). [2]  And, if you are interested in past winners, you can start by reading last year’s edition of “Best Blogs (and Other Media) for In-House Lawyers.” Instead, I try to list some new voices for you to check out.  And, same as always, there is no particular order to my list (literally I am just typing as I find things in my Post-it notes, faulty memory, and Google Keep folders).  Okay, where was I…? Right, enough yakking, let’s get on with the 2023 edition of Best Blogs and Other Media for In-House Counsel!

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Ten Things: Creating Standard Operating Procedures for the Legal Department (Just a Fancy Way of Saying “Checklists”)

If you have been a long-time reader of the blog or my books, you know that I am a huge fan of checklists.  There is perhaps no tool as humble and simple as a good old-fashioned checklist.  There is also nothing more powerful than a checklist, especially when it comes to productivity for in-house lawyers.  Early in my in-house career, I had a friend and mentor who told me we needed to create some new standard operating procedures for the legal department.  I got very excited as this sounded like a cool, exotic assignment.  And it was about time my talents were utilized for just such a task.  Then he pulled out a one-page document with a list of tasks and tick-boxes next to each one.  I was kind of puzzled and said, “This is just a f*&%$# checklist.”  He paused for a moment and then smacked me upside the head, “Say that with respect newbie.  A good checklist can save your ass someday!”  Okay, that’s not all 100% accurate.  He did not call me “newbie” – it was something much, much worse.  But, seeking to avoid further disorienting blows to the cranium, I became a fast convert to the power and beauty of a good checklist … ummm, standard operating procedures.  Over the years, I created hundreds of checklists for myself, for my team, and for others.  I still use them literally every day.[1]  Like many things with the practice of law in-house, no one teaches you why a checklist matters or, more importantly, how to create one.  You’re just expected to know how.  I realized that while I write about them a lot, I have been remiss in not explaining the “why” and the “how” of checklist magic.  This edition of “Ten Things” corrects this state of affairs and we will get elbow-deep into the slimy, bloody guts of creating a good one:

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