soft skills

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:      

(more…)

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):

(more…)

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:

(more…)

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:

(more…)

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:

(more…)

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.

(more…)

Ten Things: I Am On Two Podcasts This Month – How The Hell Did That Happen?!

It has been a fun month or so for me because I had the true pleasure of appearing on two of the best podcasts for in-house lawyers.  The first is “The Legal Department” hosted by Stacy Bratcher, CLO at Cottage Health.  The second is the “Legal Leaders” podcast hosted by David Lancelot, CLO at LawVu.  Stacy and I chatted in depth about productivity for in-house lawyers, including slaying the email monster and escaping meeting hell (as well as my go-to pump-me-up song).  David and I spoke about a variety of topics about practicing in-house, including technology and the keys to being an effective in-house lawyer (and if you listen closely you can hear my dog snoring blissfully in the background).  Both hosts asked outstanding questions and made it very easy for me to engage with them (and covering up my blathering).  So, grab some coffee and Oreos and give them a listen.  I think you will find a lot to like in both podcasts – mostly from the hosts.

(more…)

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:

(more…)

Ten Things: How to Develop “Good Judgment” – What In-House Lawyers Need to Know (and Do)

Hello again my friends.  Now that the new book on productivity is finally available to buy, I have had a bit more time to go back through the “Ten Things” mailbag.  I get lots of emails from all over the world asking me questions or suggesting topics.  And I love it (so please keep doing that)!  One email stood out.  Someone reported that they recently had a mid-year review and one area of improvement for them is to develop “better judgment.”  They asked me for some tips on how to go about doing this.  Fortunately, I have a few tips to scatter about here today.  As usual, most of these were learned the hard way, i.e., by screwing up and stumbling along over the course of many years as an in-house lawyer.  My judgment certainly needed improvement early in my career (and to some extent even today, e.g., why did I think eating half a bag of Oreos last week was a good idea?  It wasn’t…[1]).  While I screwed up a lot, I did (and do) have a knack for learning the lesson the first time.  So, over time, I started to figure out what I needed to do to hone my judgment.  Want to get wiser than King Solomon?  Want to put those smug bastards Plato and Aristotle in their place?  Then keep reading as this edition of “Ten Things” walks you through what in-house lawyers need to know about developing good judgment:

(more…)