Ten Things: Ten Questions the Legal Department Should Ask the Business Right Now (2026 Edition)

Hello everyone and hello 2026!  It’s time to kick off another year of “Ten Things You Need to Know as In-House Counsel.”  For a number of years, I started January with my “essential issues” for in-house lawyers post, i.e., things I thought were important for in-house lawyers to watch out for over the upcoming year.  It was something I did as general counsel; a good exercise to go through to help put the legal department at the front of the pack when it came to spotting risk and opportunity for the company. Last year, I changed things up and did my first “New Year’s resolutions” for in-house lawyers where I set out a number of things in-house lawyers could do over the course of the year to make themselves better lawyers and more valuable to the department (and the company).[1]  I enjoyed that one, but since I like to mix things up, I am going to try out something different again this year.

I want to go back to the basics of being an in-house lawyer.  For me, that means being attuned to what is going on at the company and asking lots of questions.  Questions are often the most important tool in your in-house survival kit.  The right questions at the right time can reveal problems that can get solved before they become big problems. Nipping things in the bud is an undervalued skill most in-house lawyers bring to the table.  I think it’s undervalued because many legal departments don’t know how to market why their early intervention is so valuable to the business.  You can find out more about how to solve that problem by reading my post on how to market the legal department.[2]  Besides marketing skills, in-house lawyers need to spend time thinking about what types of problems may be lurking out there that can cost a lot of blood and treasure to fix.  In other words, what questions should I be asking the business here in January 2026?  This is the difference between legal being the brake pedal (reactive) vs. the gas pedal (proactive).  You want to be the latter!  I have been thinking about this over the past several weeks and have come up with a list of questions that I think all in-house lawyers should be asking the business right now.  This edition of “Ten Things” sets those questions out for you, along with why they matter (to legal and to the business) and, more importantly, potential next steps:

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Ten Things: The Best Blogs, Podcasts, and Other Media for In-House Lawyers (2025 Edition)

Hello everyone and welcome to the end of 2025.  It’s been a jammed packed year for me and the blog.  As usual, I like to end the year with my list of the best blogs, podcasts, and “other media” for in-house lawyers.  And, no surprise, there is a lot of great content – and a lot of great content generators – out there that deserve your attention.  This is a far cry from what was available when I started the “Ten Things” blog back in 2014.  It was pretty bleak to be honest.  There were few, if any, specific resources for in-house lawyers then.  Generally, there were law firm client alerts (meh…) and the Association of Corporate Counsel (not bad, but you have to pay for it…).  This in-house counsel “wasteland” was a driving factor in my creating the blog.  And, looking back, I have been able to stay pretty true to my goals at the time: free, practical content covering issues that matter to in-house counsel written from the perspective of someone who has sat in the chair.  I continue to be source agnostic, i.e., if someone has something good out there, I will share it with you.  I am happy to promote anyone’s content that helps get my points across to you or otherwise deserves your attention.

But what was a wasteland in 2014 is now a rain forest! And seeing how in-house lawyer-focused content has exploded is pretty incredible.  I hope to occupy my small sliver of this space for a while longer but, as I have said before, my shelf life will expire at some point and I will simply hang up my cleats and enjoy all of the new voices coming online every week.  That time is not now and I know I have at least one more year of “Ten Things” in me, so stick around for a bit longer!  But enough about that, let’s get onto today’s topic.  I am going to structure this post a little differently than my typical list of ten because (as I look over my notes) it just makes more sense to do that – and if there is one thing I firmly believe it is not staying wedded to a particular way of doing things if something else might work better.  Similarly, in the past I tried to avoid picking my “best of” from blogs and writers whom I selected in the past.  But, I realize that each year is different and someone who is an excellent writer should be recognized in 2025 just as much as in 2023 or 2024.

Lastly, before we start, keep in mind that there is nothing stopping you from making your voice heard.  Starting a blog or a LinkedIn newsletter has never been easier.  Write about what you know and what you love, do it consistently and, over time,  your audience will find you.  In other words, if you have something to say, say it (just be respectful and courteous because we need way more of that in the world today).  Okay, time to get off the soapbox before it caves in and I get carted off to the hospital.  Without further ado, here is my list of the best blogs, pods, and other media for in-house lawyers for 2025:

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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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