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:

1.  Be curious.  To start, to solve problems you must be curious about the problem and the solution.  Without curiosity, you are just going through the motions.  With it, you are more inclined to ask the right questions and take the right steps to get to the root of the problem.  Curiosity unleashes creativity, the most important skill in problem-solving. It does so because curiosity encourages you to seek out information from varied sources (e.g., new ideas) and drives experimentation, i.e., you are not using the same old tools in the same old way to solve every problem.  This keeps things fresh and makes your job more interesting and appealing.  Curiosity also means being proactive.  If you come across a problem, get busy solving it or finding the right person to solve it.  Don’t ignore it.  Don’t sit on your ass and hope it goes away or wait for someone else to step up.  For me, the harder the problem, the better.  If it was easy, then anyone could do it and what’s the fun in that?

2.  Understand the problem.  And I mean really understand the problem, not just a cursory quick pass.  Carve out an appropriate amount of time to just think about the problem.  Turn it over in your head.  Whiteboard it. Look at it from multiple angles – and more (see below).  Why is this so important?  Here are five reasons:

  • When you truly understand the problem, you avoid taking actions that address the wrong issues. This ensures that time, resources, and energy are directed toward solving the real problem rather than symptoms or unrelated issues.  As my granddad used to say, “Measure twice.  Cut once.”  And he passed on with all his fingers so pretty damn good advice.
  • Understanding the problem’s “root cause” helps inform the choices around a solution. It allows you to come up with targeted and tailored strategies that are more likely to solve it, as opposed to more generic approaches that may miss the mark.  When you know the root cause rather than just the symptoms, you can help prevent the problem from arising again.
  • It facilitates communication with the business (always a good thing). Most importantly, if you understand the problem, you can explain it to others. This allows you to pull in additional brain power and ideas.[4]
  • Knowing the problem reduces ambiguity, allowing for a more structured approach to problem-solving. It also helps identify potential risks and challenges early on, making it easier to plan for and mitigate them.
  • You make better decisions because you can better understand the pros and cons of potential solutions when you understand the issues.

3.  Leverage others.   At some point in my in-house legal career, I realized that the smartest person in the room was probably not me.  I may have been the smartest lawyer in the room (if I was the only lawyer) but when it came to solving business problems, let’s just say there were others out there on the corporate org chart more qualified than me to do that.  But I had a superpower that many others lacked: I was smart enough to recognize my limitations and smart enough to know I had to go out and find the smartest people in the company and drag them into the room (conscious or not) to help me solve problems.  In high school, I called this “running to get help” which was my highest and best use if some type of gang fight broke out.[5]  In other words, be humble enough to recognize the value of others and bring them to the table, and leverage them to help solve the problem.

4.  Ask smart questions.  For me, to solve any problem (legal or business) you need to know what questions to ask.  For starters, realize that when you ask someone on the business side to describe the problem or goal, what they tell you may not really be the issue or the problem they are trying to solve.  They just think it is.  Your job, as in-house counsel, is to not accept anything at face value and dig in.  This means asking smart questions.  My favorite questions start with “Why…”  When I was four or five, I drove my parents crazy because no matter what they told me, I would always ask “why” that was the case.[6]  As an in-house lawyer, you need to unleash your inner five-year-old and annoy the shit out of the business by asking “why.”  A lot.  “Why” is your scalpel and your wrecking ball.  It is your extra course grit sandpaper to help you get down to the nub.  No other word will get you to the root cause of the problem like the word “why.”  So, keep it handy and use it as needed to cut through the bullshit.  What are these “smart” questions you ask?  That is a smart question!  Here is the checklist I used to get started digging in on pretty much any type of problem I faced as an in-house lawyer:

  • What is the core (real) problem?
  • What are the root causes?
  • Why do we want to do this/stop this?
  • Who needs to be here to help figure this out?
  • Who needs to be part of the team to solve this?
  • Who cares about this problem?
  • What are the business implications if the problem is not addressed?
  • What are the people implications if the problem is not addressed?
  • What are the legal implications if the problem is not addressed?
  • What is fact and what is opinion?
  • What constraints or limitations must be considered?
  • What does a successful outcome look like?
  • Who wins and who loses?
  • Who is the decision maker here?
  • What has been tried before and did it work or not?
  • Why did it work or fail?

There were, of course, many other questions I could ask depending on the circumstances, e.g., “When’s lunch?” But this group of questions was always part of my problem-solving process.

5.  Think like a business person (not like a lawyer).  One of the core lessons you learn quickly as an in-house lawyer is that business people look at problems differently than lawyers do.  Don’t get me wrong, lawyers add a lot to the problem-solving game.  We are methodical, cool with ambiguity, take great notes, and don’t panic easily.  The downside?  Lawyers frequently look at problems only from the legal angle and when that analysis is done, they tap out, i.e., “Here is the legal analysis.  You decide what to do.”  Nothing to be ashamed of, it’s how we are all trained.  Here is a very high-level way to look at the differences between how business people solve problems and how lawyers solve problems.  Successful in-house lawyers adopt a lot (not all) of the business view on problem-solving:

Of course, these are generalizations, and it is not always this simple or black and white, but hopefully, you can see the need to start shifting your mindset to the column on the right to be an effective in-house problem solver.[7]

6.  Bring everything in the toolbox to the table.  For me, the best part about trying to solve tough, complex problems in-house was not limiting myself as to what “tools” I could use to figure out the answer.  I could talk to anyone I wanted to.  I could get information from any source.  I could attack the problem from any angle I wanted.   I loved a good old-fashioned brainstorming session more than just about anything else I got to do.  My overriding principle? “No idea is too wild.”[8]  I put a question mark after everything (i.e., always asking “why”).  Here is why brainstorming and bringing everything to the table is so helpful.  To start, gathering and encouraging different perspectives brings unique insights and well-rounded solutions.  Second, you get a broad range of ideas to work with as everyone feels empowered to pose solutions, even unconventional (“weird”) ones. Third, there is a better balance of “risk/reward” for the company, i.e., you move beyond just legal risks and consider the business gain (or loss) potential of every idea.  And fourth, you ultimately surface the most feasible solutions as all ideas have gone through a gauntlet of different perspectives and priorities and what’s left is the best of the lot from both a business and legal perspective.  An additional benefit of this approach is that everyone who participated now “owns” the solution, i.e., it’s not just the legal department’s idea it is the group’s idea.

7.  Engage in critical thinking.  As you may be able to tell, the preceding paragraphs build up to something really important, i.e., the need to engage in critical thinking when trying to solve problems.  I have also referred to this as “strategic thinking” in past blogs and in my books but the concepts are the same when it comes to how in-house lawyers need to reorient their mindset. Critical thinking is a way to look at problems from multiple viewpoints and to question assumptions (asking “why”).  For me, it has always started with this: Am I thinking strategically about the company and its business goals and objectives while I work? Am I advancing those goals and that strategy?  If not, I am missing a big part of my job.  To do this properly, in-house lawyers need three things: (i) a deep understanding of the business and its goals/strategy, (ii) comfort with basic corporate finance, and (iii) a willingness to build real relationships with the business (and not just rely on sending out emails from deep in your cave).  There are other things you can do but mastering these three will position you nicely to bring that big brain of yours to the table in a way that solves business problems and not just for spotting the legal issues lurking in the shadows.  As many of you long-time readers know, I created a checklist to help me think strategically about the problems coming across my desk.  Here is a slightly updated version in case you have not seen it before:

 

You can print this out, adapt it to your own needs, throw darts at it, or line the bird cage.  All I can tell you is that a list like this works and will dramatically boost your ability to solve problems and not just spot legal issues.

8.  Give options and your recommendation.  When it comes to problem-solving, in-house lawyers need to remember two things: give options and give your recommendation as to what the business should do.  Pointing out problems is not solving problems.  If there is one thing in-house lawyers do that frustrates the business to no end it is telling them there is a problem without proposing any type of solution.  A close second is bringing only one solution to the table even if there are other paths to choose from, i.e., the lawyers self-select the path they think is best (usually the least risky) and present it as the only option.  The better path is to bring as many viable options as possible to the discussion and discuss the pros and cons of each.  You can (and should) recommend the option you think is best (and set out why) but don’t be shocked if the business picks another option.  It doesn’t mean they think you are stupid or have failed,[9] it’s just exercising their prerogative of how much risk and which direction they want the business to go.  And as long as the right people are making the decision and it’s not criminal, etc., then your task as in-house counsel is to fall in line and do everything you can to help implement the plan while doing your best to minimize potential problems.  I know you have read it here many times but the thing to keep top of mind is this: legal doesn’t run the business.

9.  Set out the plan.  After you have gone through all of the above and you and/or the business have decided on the right course of action to solve the problem, don’t just wing it from there or start jabbering on about the plan.  If there is any complexity at all to the solution, create a written plan setting out key steps, key deadlines, who is responsible for what, etc.  I know this sounds really basic but that is why it works.[10]  A written plan with key components broken down into manageable steps and with a timeline containing built-in “check-in” points keeps things moving, keeps everyone aligned, and gives you an early warning if something is going off the rails.  A written plan also gives stakeholders confidence that the team is solving the problem (showing me the plan is better than you telling me there is one).  Lastly, a written plan gives you a road map (or template) to reuse to solve similar problems in the future. If you have trouble getting started with this one, try Magic To-Do from Goblin Tools which provides a free tool to break down tasks (among a lot of other neat offerings).[11]

10.  Did it work?  No matter how good or bad you are at solving problems, there is no guarantee that your solution will work.  Or, perhaps, it solved the problem, but created others?  Or maybe it was a slam dunk winner.  This is why you must take time to evaluate how things worked out.  This is sometimes called a “post-mortem,” a gruesome term but befitting.  This evaluation can be short and simple, or it can be more elaborate, it really depends on the complexity of the problem and the solution you came up with.  Post-mortems are important because they:

  • Help determine what aspects of the solution were effective and what fell short. This helps you recognize and replicate what worked while learning from (and avoiding) what did not.
  • Permit continuous improvement, i.e., helping you refine processes and approaches based on actual outcomes (and not what you or others “think” might happen).
  • Provide an opportunity for deeper exploration of the root cause(s) of the problem and the solution’s effectiveness. This ensures that underlying issues are addressed rather than just treating symptoms. This, in turn, can help to mitigate risks down the road and provide insights into potential pitfalls (and how the business can avoid them).
  • The findings from a post-mortem can be documented and used as a reference for similar situations in the future, e.g., a checklist or early warning system for the business and the legal team.  Institutional knowledge, especially when reduced to writing, benefits the company over time and is a real value added by the legal department

*****

As you can see, solving problems as an in-house lawyer is very different than solving them as an outside lawyer.  The latter are generally focused on legal issues and giving clients the lowdown on legal risks, often stopping right there.  While that is helpful, it is only part of the equation.  Where you can excel as an in-house lawyer is by filling in the rest of the equation and not limiting yourself to pondering just legal issues but seeing the whole forest and adopting a “business person” mindset – including proposing solutions.  As you start to plan for 2025, consider making time for a team exercise to work through how the legal department can more systematically help the business solve problems.  If everyone in the legal department is thinking the same way and taking a similar approach to problem-solving, your ability to make a real impact goes up (as does the business’ satisfaction with the work of the legal team).

Sterling Miller

October 29, 2024

My new book (number six), The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done, is now available for sale!  The New York Times calls it, “Eeh, pretty good.  Cool cover.”  With an endorsement like that, how can you go wrong?   You can buy your copy (and a copy for all your friends, siblings, and random strangers) here: Buy The Book!

My fifth book, Showing the Value of the Legal Department: More Than Just a Cost Center is available now, including as an eBook!  You can buy a copy HERE.

Two of my books, Ten Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies and Ten (More) Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies Volume 2, are on sale now at the ABA website (including as e-books).

I have published two other books: The Evolution of Professional Football, and The Slow-Cooker Savant.  I am also available for speaking engagements, webinars/CLEs, coaching, training, and consulting.

Connect with me on Twitter @10ThingsLegal and on LinkedIn where I post articles and stories of interest to in-house counsel frequently.  

“Ten Things” is not legal advice nor legal opinion and represents my views only.  It is intended to provide practical tips and references to the busy in-house practitioner and other readers.  If you have questions or comments, or ideas for a post, please contact me at sterling.miller@sbcglobal.net, or if you would like a CLE for your in-house legal team on this or any topic in the blog, contact me at smiller@hilgersgraben.com.

[1] Americans kind of hate lawyers, but they pay them well.  Gotta love the USA!

[2] Sanity? Toes?  Pants? You pick.

[3] Another bucket list word used in print.  Score!

[4] Kind of like Tom Sawyer getting his friends to paint the fence.  Interestingly, they edited out the part where his friends later realize they have been duped and come back that night and beat the living shit out of him with 2x4s.  Even Becky and Huck get a few punches in during all the chaos.  Yeah, Random House always leaves out the good parts.

[5] Don’t laugh.  York, Nebraska can be a real hell hole.  I once saw a guy get killed with a trident. Or did I see that in a movie…?  Let’s call it inconclusive for now.

[6] The big five are who, what, where, when, and why  – with “why” being the most important for in-house lawyers trying to get to the core of a problem.

[7] Just to be clear, I am not saying you need to abandon the legal analysis or raising legal issues that have an impact on the answer.  I am saying that this cannot be the only thing you bring to the table.  Business decisions that involve a lot of risk require the lawyers to ensure the right people within the company are making the final decision and if the path is illegal, fraudulent, can cause serious injuries to people, or causes you to violate an ethical cannon you have a responsibility to push back hard.

[8] There is a wing at the Smithsonian for my shitty ideas (closed on Mondays).

[9] Though with me, it was always touch and go on this point.

[10] See, e.g., my “Ten Things” post on legal project management at https://tenthings.blog/2017/07/31/ten-things-legal-project-management-for-beginners/

[11] For example, you can use Goblin Tools to formalize text, create a to-list from a “brain dump,” or estimate how long something will take to accomplish.  Love this tool!