business

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: 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: 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: Solving Problems (It’s Different In-House)

One of the reasons I wanted to become a lawyer was to solve problems.  The added bonus was the expectation that someone would pay me (a lot) to read and write stuff to help solve those problems.  How cool is that?[1]  Law school and then working at a law firm for a number of years post-graduation were both fantastic training for how to solve problems.  Well, how to solve legal problems.  When I finally got my chance to go in-house, I learned pretty quickly that all my “legal-problem-solving-skills” were useful but many of the problems I was called upon to help with involved only a small amount of legal-ness and a lot of “other stuff” – I’ll just call that other stuff “business issues” to save time (but if you work in-house, you know exactly what I am talking about).  Unfortunately, this meant that a lot of what I thought I brought to the table was useful only part of the time, i.e., solving problems as an in-house lawyer is very different from solving them as an outside lawyer.  Skip forward a few centuries, and I can proudly say that I have been a lawyer for a long time with most of that time spent in-house – I survived the crucible of fire and walked away with my sanity (and all of my toes).  Some don’t.[2]  Why?  Because, even now, one thing I consistently see from many in-house lawyers is an inability to grasp the very real difference between what the company needs from them when it comes to solving problems vs. what it needs from outside lawyers.  Many lawyers (in-house or law firm) tend to fall back on the mind-numbingly rigid dogma[3] of treating every problem like a law school exam.  More troubling, even when they know it’s not a legal problem they are trying to solve, they simply don’t know the way forward and fall back into the same pit of despair and anguish.  Fortunately, I screwed this up enough times over the decades (and am still coated heavily in despair and anguish) that I can share a little knowledge with you here today.  That’s right.  This edition of “Ten Things” discusses something I bet no one has raised with you before — how to solve problems as an in-house lawyer:

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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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