writing

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: All the Podcasts!

Hi everyone!  Well, I’ve been working on a new “Ten Things” blog about what to do when you feel overwhelmed at work.  It’s almost finished, but I got a bit sidetracked when I took a short break (something I write about in that particular blog) and listened to an old podcast where Mel Storey interviewed me from Australia.  It was a lot of fun, and she did an amazing job.  But it got me thinking about some of the other times I have been invited to speak on a podcast.  It was more than I remembered.

So, I went down the rabbit hole, and guess what? No new “Ten Things” blog on how to overcome feeling overwhelmed.  I was, however, able to locate all of the podcasts, and for this semi-new edition of “Ten Things,” I thought I would list them out for you in a post.  Not so much for hearing me babble on about stuff (though that may be interesting), but so you can discover all of these great podcasts and podcasters for yourself.  Hopefully, you’ll subscribe to one or two and gain a lot from all of their terrific guests (present company excluded).  Anyway, I suspect you will find a few nuggets in all of these if you give them a listen, and if not, I will happily refund your money:

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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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