inhouse

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: 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: 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: 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: 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.

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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: What to Do When You Don’t Know the Answer

Everyone likes to know the answer to questions that come their way at work, none more so than in-house lawyers.  Lawyers take special pride in being able to respond to practically any question, on any topic, at any time.  They can do this because they are, typically, very smart, well-read, and at ease with murky situations.  However, occasionally, and usually at the worst possible moment, someone in the business will ask an in-house lawyer a question and they will have no idea how to answer it.  This happened to me on more than one occasion and it was incredibly frustrating for me and whoever was asking the question – usually the CEO or a board member.  Why were they frustrated?  Well, because like most people on the business side they believe two things that make your job as in-house counsel even harder: 1) all lawyers know everything about all areas of the law regardless of their background or specialty, and 2) that there is a “Big Book of Law” we keep on a shelf that has all the answers to every legal question and all we lawyers have to do is take it down and find the right page.  Yeah, right…. So, what do you do when you get a question you don’t know the answer to (especially when they are looking right at you across the table)?  This edition of “Ten Things” set out some strategies to help you navigate this tricky situation:

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Ten Things: Creating a “Not-to-Do” List (Learning How to Say No)

Hello again everyone! I am very excited to report to you that my next book (number six) is in the hands of the publisher and should be out by this summer.[1]  The working title is The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done.  I think you are going to really enjoy reading this one, especially if you find yourself pressed for time to do all the things you need to do on your to-do list.  Which basically means anyone reading this.  The book is jammed to the rafters with different ways to squeeze more time out of your day with the goal of getting more done (and more important things done) in the time you have vs. working more.  While I am not going to go into too much more detail here (I do want you to actually buy it when it’s available), there is one section of the book I keep coming back to in my head.  What section is that you ask?  Well, thank you for asking!  It is the section on how to say “no.”  In particular, how to create a “Not-to-Do” list, i.e., a set of principles that guide how you will spend your time by setting out the things you will not spend time on (or spend significant time on).  I certainly cannot take any credit for the idea of a “Not-to-Do” list.  The concept has been around forever, and history is full of people wildly succeeding at not doing things, such as Emperor Nero standing by while Rome burned, my law school roommate, the Kardashian family, Congress… okay, enough of that.  But you get my point, and that is the blindingly obvious fact that one path to getting more done is to reduce the number of things you are doing (Hey, I never said this was rocket science).  One way to do that effectively as an in-house lawyer is to create a list of things you will not do – a “Not-to-Do” list.  Alas, yet another thing law school, law firm, etc. never teaches you how to do (though it is such a fantastic tool).  So, let’s fix that problem.  This edition of Ten Things walks you through how to create a Not-to-Do list (and how to use it):

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Ten Things: Asking For More Legal Department Resources (How and When to Go Big)

In my last book, Showing the Value of the Legal Department: More Than Just a Cost Center, I tackle one of the fundamental issues facing all in-house legal departments: it sucks to be a cost center.  You can check if you want, but I am pretty sure that’s what I said.[1]  Why does this matter? Because cost centers are places the business looks to cut when times get tough, or the numbers need “improving.”  And, historically, most legal departments have had a ”cut my budget” sign taped to their backs.  This is due partly to those evil bastards in finance, and in part because most in-house legal departments have not aggressively marketed themselves to the business.  It’s probably more the latter, but who’s keeping score?[2]  By aggressively market, I mean taking the steps necessary every day to show the value provided by the legal team, and, more importantly, showing how the department can create even more value if properly nurtured.  If you have been a long-time reader of the blog, you know that I have written about how to go about showing value and how to market the department.  Now I want to take on yet another task in-house lawyers often suck at (my early self included), i.e., how to ask for more resources (and not get laughed out of the room).[3]

I’ll lead off with it is not easy, but it can be done if you prepare the ground in advance of the ask.  And now that most in-house legal departments are heading into “budget season.” It’s the perfect time to rip the “cut my budget” sign off your back and replace it with a “we deserve more budget” sign – or button.  That’s right, this edition of “Ten Things” takes you through the process of how to ask for more resources and – on occasion – get them:

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