Lawyers, including in-house lawyers, have a well-deserved reputation for over-complicating things. Don’t worry, this isn’t a sermon. I am standing in the dock next to you, guilty as hell! Still, I have spent time over the course of a long career in the law trying to figure out why this is. Why is it that lawyers make things so hard on themselves and their clients? I think it comes down to this: lawyers hate to be wrong. No, they fear being wrong, coupled with a belief that if you throw enough time, money, and words at a legal problem you can get to the answer or solve the problem. This explains why lawyers write in a way that no mere mortal understands. We have developed an uber-complex grammar structure that mystifies all but those foolhardy enough to plunge into the ocean of words, clauses, commas, “notwithstandings,” triple negatives, subparts, subparts to the subparts, and so on that make up modern-day contracts. Or why our litigation process (in the US) is now largely an exercise in trying to get documents from the other side and prevent the other side from getting your documents and working overtime to get the court to sanction the other side for not giving you documents or for trying to unfairly get your documents, or… well, you get the point.
If you spend any time thinking about it, you begin to see why business leaders appreciate practical lawyers – lawyers who can get things done quickly and who can communicate in ways the business can understand. The issue for in-house lawyers is that both demands tend to cut against all of our training and instincts, i.e., it’s hard! Building “Rube Goldberg” machines is in our DNA. Fortunately, it is possible to learn to be practical. And, while not a hard and fast rule, my experience is that in-house lawyers who are practical in their approach and advice tend to thrive at companies and become sought-after partners to the business. Those who are not, tend to be treated like lepers – feared and shunned. This edition of “Ten Things” brings the cure and discusses how to be a practical in-house lawyer:
1. What does “practical” mean? Your first lesson in practical-ness: start at the beginning. There, you are now an expert! Joking aside, in the context of being an in-house lawyer, “practical” is a way of thinking and approaching problems. It means actively seeking to avoid the overly complicated, inflexible, slow, or theoretical while striving to find answers that are timely, workable (under the circumstances), actionable, and that take into account the realities and goals of the business. In other words, legal advice in a vacuum from the top floor of the ivory tower is not going to cut it. Nor should it.
2. Decide you “want to.” Yeah, like most bad habits, you must make a conscious effort to break them. The same is true when breaking the habit of overcomplicating things. It’s actually easier to over-lawyer a problem than you may think. So, you begin with a commitment to start making things as simple as possible. Not everything can be made simple, but making a conscious effort to try is step one. As you get better at it, you’ll find that you have extra time to work on the more complicated issues and that you start to get more positive reactions and feedback from the business. They probably won’t say “Wow! This is way more practical than your usual crap, Sterling!” But, they will likely be pleased with what you provided, more apt to follow what you laid out, and encouraged to seek you out for help down the road. As an in-house lawyer, being in demand is a goal unto itself.
3. Agree on expectations with the business. Too often in my career I sat around and griped to myself (and select others) about the business and how unreasonable they were being or what critical priorities were being overrun by focusing on some low-value deal. Why didn’t they know? Why didn’t they realize? And one day a novel thought entered my T-Rex size brain – why didn’t I ask them? Yes, I was making things way more complicated than they needed to be. Instead of trying to figure it all out by myself, what if I reached out to the business leaders each week and asked them:
- What is the most important [project] for you this week?
- How should I prioritize the following [projects]?
- When do you really need this [project] done?
- What if we agree to the following deadlines and priorities?
The practical lawyer doesn’t make assumptions for the business, he or she simply asks them and makes everyone’s life much easier. For the most part (but not always) I have found business leaders to be pretty rational and fair. They understand the problem, once you tell it to them. They likely assume (there’s that word again) that if you are not saying anything you are fine with whatever deadlines and mixed up priorities they heave your way. So, speak up! Does it solve the never-ending parade of projects coming across your desk? Nah. Does it work every time? Nope. But it helps you get some peace of mind and, most importantly, aligns your work priorities with the expectations of the business.
4. Learn to prioritize. Speaking of priorities, you know you cannot do everything. No matter how smart, hard-working, and dedicated you may be, there are simply not enough hours in the day, days in the week, or months in the year to get to everything that comes into the legal department or your desk. Coming to terms with this basic fact of in-house life is a critical next step in honing your ability to be practical. Instead, and in conjunction with No. 3 above, you must learn to prioritize what’s on your plate every day. You can sit in the corner and try to figure it out yourself, or (hint) you can try this:
- Look at everything on your plate and
- Find out what on your plate is most important to the leaders of the business (e.g., head of sales, head of HR, or whomever). Their priorities should be your priorities (as they represent the priorities of the company);
- Find out what’s important to your boss (yes, your boss matters whether it is the CEO, the general counsel, the deputy general counsel, or whomever). Make sure they know what you are prioritizing and why (and that they agree); and
- Focus on the most important. Look at your prioritized list and pick the three most important things. Those three are now your focus for the day, i.e., a to-do list of three things.
This is the “Pareto Principle” in practice, i.e., 20% of your tasks should/will accomplish 80% of the value you generate. You can also plot projects in a 2×2 Eisenhower matrix where the upper right box is urgent + important. The projects that make this box are where you will get the most bang for your time. Will this make everyone happy? No. But, your efforts will be focused more on the most valuable vs. the less valuable and, over time, that will pay off. And, don’t always look for big wins. Usually, making small amounts of progress add up to big gains (see Ten Things: The Productive Power of Little Things). The practical in-house lawyer takes what they can get to keep things moving along.
5. Take a hard pass on perfect. Perfection is the mortal enemy of the practical. No one likes to be wrong, but in-house lawyers rarely have the time or budget to track down every possible thread that could get pulled to unravel their answer. Accept that “good enough” is usually good enough. If you can reuse material, don’t reinvent the wheel – use the wheels lying around the office. There will be times when you will need to spend more time on certain problems, but you can usually tell those apart from the run-of-the-mill problems that simply do not require maximum effort. If the board of directors is involved or it’s “bet the company” time, then by all means take the time you think you need to figure out the answer or solve the problem. But those instances are generally rare in my experience. Most of your day-to-day is about cranking out as much output as you can as fast as you can with an acceptable level of risk to the business (not to you). There might be an error in there somewhere (though a good checklist is a good way to avoid the most glaring errors). It happens. The sky will not fall. Get over it and move on to the next project.
6. Be judicious with “No.” No one likes Dr. No (especially James Bond). Practical in-house lawyers understand this and work hard at “no” being their answer of last resort. Yes, there are times when no is the answer, but rarely. For many lawyers, this means a big change in mindset. They are used to telling clients to do something and having the client do it, no questions asked. The practical lawyer welcomes questions about their advice because it may lead to a better answer or better result for the company. I realized early on that I just may not know everything about the business and someone pointing out issues with my analysis or recommendation is healthy, not an indictment. Also, come to grips with the fact that the legal department doesn’t run the business. We give advice, we give options, and we then do the best we can with whatever it is the business wants to do. This usually means you must get used to taking a lot more risk than you ever imagined you would. Trust me, it’s okay. The world is not going to end because you said, “I guess we’ll live without that cap on indemnity then…” In my view, things get overly complicated and bogged down because lawyers are afraid of being wrong and ungodly conservative about risk. I get it. No one likes to be wrong, but the only way to never be wrong is to never take any chances. A business that doesn’t take chances doesn’t get very far. This means its lawyers need to be comfortable taking chances as well. Risk must be thought out and the right people at the right level in the business need to make the calls around the bigger risks, but at the end of the day, you will get more done, and more done faster if you start thinking about things in terms of “yes, let’s do that” vs. “no frigging way we would ever do that!” Lock Dr. No up in a soundproof room and bring out Dr. Yes. Your life will be much easier.
7. Just roll with it. Do you know who lives a righteous life? Gumby. That guy is incredibly flexible and no matter what happens, no matter hard he gets smacked around (or thrown against the wall), he rolls with it and it turns out fine in the end. Be like Gumby. In other words, be flexible. Expect assumptions to change, expect the project to get more complex, expect the deadlines to move, and expect the other side in contract negotiation to be idiots. Just roll with it. Remember: WWGDD (What Would Gumby Do, Dammit?). Fighting against unexpected changes is like punching at an ocean wave. So, don’t waste your time or energy railing against the inevitable. As things change with your day or project or contract, breathe deep and take it in stride. Figure out how, if at all, you need to re-prioritize your day or your to-do list of three. If the change is big enough, get alignment from the business and your boss on what has to happen now that things have changed, and then just get on with it. You’ll be surprised at the amount of time, brainpower, and stress are expended fighting things you cannot control. I was a wave puncher early in my career, figuring I could – by sheer willpower – force everything back to the way I wanted it to be. Epic fail. WWGDD?
8. Live in the real world. Above, I talk about the importance of not giving legal advice in a vacuum from the top floor of an ivory tower. In other words, live in the real world when you are trying to solve the company’s problems. For any legal solution or advice you provide, work through the practical considerations of what you are suggesting. Doing so will help you tailor your work to what’s doable, i.e., cost, manpower, risk profile, and so on. Here is my list checklist to help come to a practical solution (note that not all the questions apply to every situation):
- What needs to be done? By when?
- What are the benefits/downsides?
- Can we afford it? What can we afford to do?
- Can we implement it? How long will it take us?
- What does perfect look like? What does good enough look like?
- What is actually required to get “this” done in the simplest, most cost-effective manner?
- How does this tie into the company’s goals and strategy?
- Whose input/buy-in do I need before coming up with an answer/solution?
- If we cannot get everything done now, what can we get done to demonstrate good faith and buy time?
- Do we buy it or build it? If we build it, what our all of our options?
- What problems do we face if we do not get it done? Can we live with this outcome?
- How have others dealt with this problem and can we do that?
It’s not a perfect list, but having some type of framework to analyze if what you are doing is practical or not is key to consistently delivering solutions that work for the business and aren’t ignored or get you laughed out of the room. Think about how you (and your team) can create your own checklist tailored to the needs of your company.
9. Listen for the other side of the story. When it comes to being practical always remember that there are two sides (at least) to every issue. If you work based on knowing just one side, you are missing opportunities to get things done better, faster, and cheaper. For example, it’s easy to fall into the trap of hearing how the other side breached the contract, screwed over the company, cost it millions of dollars in damages, and then rush to fire off a nasty demand letter or, worse, a lawsuit. Instead, actively seek out the other side of the story. Push back on the “facts” as they are being relayed to you, ask to see (and read) key documents – especially the contract and correspondence from the other side, talk to others in the company to see if you get the same story or if they tell a different tale. Then put yourself in the shoes of the other side and see how things look from that angle. You may find that your case kind of sucks and the company would be far better off trying to reach a quick deal vs. launching into an exchange of unpleasant letters or litigation. The same skills apply to negotiating contracts, investigating employment claims, etc. There is almost always another side and understanding that position will help you better craft practical responses and solutions.
10. Keep it simple. Our journey into Practical Land is almost over.  And I have saved the most important lesson for last. The easiest way to be practical is to keep things simple. Start off looking for the simplest path to get to the end result. Don’t climb a mountain when you can walk through the pass. As Leonardo De Vinci said, “Hey! You can’t park here, buddy!” He also said, “Simplicity is the ultimate sophistication.” Leading with simplicity brings clarity and focus, which in turn lead to higher levels of effectiveness. Additionally, I have written about writing skills for in-house lawyers and presenting legal issues to the business. Both deal with a fundamental paradox that when it comes to being a practical in-house lawyer you must stop acting like a lawyer! In other words, use your lawyer superpowers to think about and try to solve issues, but when relaying information or solutions to the business you must keep it simple, straightforward, and legal jargon-free. If your email to the sales team is 12-pages long, you need to stop and rethink it. If you are writing a lot of words but not giving the answer, you need to rethink it. If your sentences are like paragraphs, you need to rethink it. Learn to be short, punchy, and direct with your writing and presentations. Put the answer up front, layout options and risks, and make a recommendation based on what you know about the business generally, its financial situation, risk profile, and strategic goals. You do not need to cite sources or add footnotes or any of the legal drafting basics you learned in law school or at the firm. They simply don’t matter and are counter-productive for your audience, the business.
I hope the above is helpful, especially if you have been struggling with requests that you be “more practical” or if you have had a hard time coaching someone on your team to be more practical in their approach. You can even adopt a mission statement or department goal based on “Practical Legal and Business Solutions for the Company that Work in the Real World.” Remember: perceived value often comes down to marketing – always be marketing and telling the story you want to tell about the legal department. And one of the best things about adopting a maximum practicality mindset is that it almost always results in higher productivity, getting more done in the same amount of time. That’s a double dose of value for you and for the business!
April 27, 2022
My fifth book, Showing the Value of the Legal Department: More Than Just a Cost Center is available now, including as an eBook! As the ABA says, “Buy this book or the dog gets it!” The ABA is serious about this so just buy a copy of the damn book and help a dog out. You can buy it 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, ideas for a post, please contact me at email@example.com or, if you would like a CLE for your team on this or any topic in the blog, contact me at firstname.lastname@example.org
 Sorry, watched “Ben-Hur” recently and had the leper scenes on my mind. Yuck!
 Huddle meetings are a great way to do this en masse. See “Ten Things: Legal Departments and the Value of Huddle Meetings.”
 I dedicate a full section of my new book, “Showing the Value of the Legal Department: More than Just a Cost Center” to how to use matrices. Check it out!
 See, for example, this excellent article by Christine Uri in the Contract Nerds blog, “Perfect vs. Done: How Do You Know When a Contract is Ready?”
 One thing I asked of my teams when general counsel was to be the other side and come up with reasons why my theory, clauses, or whatever didn’t hold water or didn’t work. Basically, tear into my work product like you were the lawyer for the other side. We always came out with better work when we did this.
 I am creating my own game to compete with Candy Land so keep your greasy mitts off my new, cool name (trademark pending…).
 See “The Benefits of Simple Productivity” by Lou Macabasco.
I was looking for some good stuff on Legal topics and found your website while scrolling on Google.
I read your post and found it really interesting, especially I liked the way how you explained every point in detail.
The best part of your blog was the 8th point “Live in the real world” I strongly agree with this. It would be great if you publish more of such informative posts and give us a little more information on every aspect of law.
I appreciate the time and effort that you have put into creating this post that was helpful to me. Hope to read more good content from your blog.
Hi Sarah – thank you for reading the blog and taking the time to post a comment. There are about 150 posts on the blog and I have also written three books on legal issues (all tied to in-house lawyers but applicable to lawyers generally). Check those out. I’d like to go into greater detail but the theme of the blog is ten things and most posts come in around 3000-3500 words, which is a lot. But, hopefully the blog provides you with enough information to go deeper on any particular part. Regards – Sterling
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Thank you for sharing an amazing article.
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You are most welcome, Aaron!
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