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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: 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: 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: What to Do When You Are Feeling Overwhelmed at Work

I have been practicing law for a long time.  And even now, 30+ years into the game, there are still times when I find myself overwhelmed by everything on my plate.  And it’s just as shitty a feeling now as it was as a young associate at a big law firm or as general counsel dealing with – literally – bet-the-company litigation.  Fortunately, getting older comes with some advantages (besides the prospect of getting 50% off if I go to IHOP at 4:00 pm for dinner).  The biggest (non-IHOP) advantage being that I have developed a lot of different ways to cope with feeling this way.  And that’s good because one thing I hear a lot from the in-house lawyers I speak with is that they are having an increasingly hard time dealing with the incredible amount of work that keeps rolling down the hill – like a boulder crushing Wile E. Coyote when his ACME products backfire for the nine thousandth time.  Okay, that sounded better in my head, but I know you get the picture because you’ve all been there (and some of you may even be there as you are reading this).    

Given the increasing number of in-house lawyers edging ever closer to burnout, I thought I would spend some time talking through what you can do when feeling overwhelmed at the office.  I am going to focus on some practical, short-term solutions to help you get out of the muck and onto solid ground in the near term – as that is typically the most pressing need.[1]  What I am going to set out is all tested and true, and some combination of these ten things will very likely help you.[2]  How much they will help depends on how far you are willing to go to gain some control over the situation (and I know that is not always easy to do).  But hear me out and stick with me.  Today’s edition of “Ten Things” takes you through what you should do when you feel overwhelmed at the office:

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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: 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: Best Blogs (and Other Media) for In-House Lawyers (2024 Edition)

Hello everyone and season’s greetings from Dallas, Texas!  I would like to wish you all a terrific holiday season and all the best for 2025.  If you are looking for some fun in January (22-24), please join me and a host of others who will be presenting at Laura Frederick’s (of How to Contract fame) ContractsCon 2025!  I will be there discussing data privacy clauses, but the agenda is stuffed with lots of great speakers and topics. I hope to see you in person in Las Vegas in January (and please find me and say “hi”).

So, here we are in year 11 of the “Ten Things” blog.[1]  Like always, my last post of the year features all the other people you should be reading (or listening to) as part of your day-to-day in-house life. The hard part is choosing just ten to highlight for you.  And I have made it even harder on myself because, unlike past years, I have decided to weave in a few previous winners because they have consistently held up year after year and I want to make sure anyone reading this post is aware of them.  But, if you are interested in all of the past winners, you can start by reading last year’s edition of “Best Blogs (and Other Media) for In-House Lawyers.” I do, however, generally try to feature mostly new voices for you to check out and this year is no exception.  In case you were wondering, there is no particular order to my list (number ten is just as good as number one – I am just typing this up in whatever order I have jotted things down in my notebook or various scraps of paper lying around the “Ten Things” world headquarters).

I know you are excited to find out who made this year’s list so let’s get on with the 2024 edition of Best Blogs and Other Media for In-House Counsel!

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