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:
1. Get old. I am sorry to tell you this, but I am suffering from something called “oldness” (or in Latin, senectus maximus). It gets a bit worse every day, it is terminal, and there is no cure. And it’s highly contagious, so you are probably experiencing some of the symptoms right now as you read this. The good news is that it sounds worse than it is. I have enjoyed getting older. One reason – this cool greyish tinge to my hair. Another plus? I have judgment oozing out of every pore. Yes, simply having been around for a while is the single best way to develop good judgment. The more you see, the more you know, and the more you do, the better your judgment becomes. Experience matters when it comes to judgment. It just works that way and it’s pretty great. It’s a bit like the day you realize your mom and dad were not total morons and actually knew what the hell they were talking about. Better yet, you don’t really have to do anything other than survive. Which, here in Texas, is definitely a lot harder than I thought it might be ten years ago.[2] So, while you cannot necessarily hurry it along, bide your time, pay attention, and good judgment will very likely come your way.[3]
2. Make (lots of) mistakes. I do realize that this is not the greatest start to a blog, i.e., talking about getting old and now about making a shit ton[4] of mistakes. But I put them as numbers one and two on my list because these are, swear to God, the most important ways to develop good judgment. If you make a mistake and figure out/understand what you did wrong, you instantly take a giant gulp from the good judgment mug. Sure, it’s bitter and tastes like warm goat piss,[5] but learning the hard lessons that come from making mistakes hones good judgment into a Ginsu steak knife of goodness. So, drink up. The more mistakes, the better! Of course, there is a caveat here. Most of the mistakes in-house lawyers make are relatively minor in the grand scheme and provide you with most of the fodder needed to help develop your judgment. Super, colossal, disaster screw-ups, however, can be very bad for holding on to your job. But it does happen. If it does, you will have to take the consequences, but you will probably have the greatest single judgment-honing moment of your career right there. So, that’s a plus. If it happens again, you may be in the wrong job. Two more things about making mistakes:
- If you are the boss, encourage your team to trust themselves and their judgment to make the right call. Be there to help them when they ask for help (but don’t do their thinking for them) and be understanding when mistakes arise. It’s the only way to learn. A team that never makes mistakes is way, way too conservative and unimaginative to be successful as a value-adding in-house legal department. And bosses who don’t tolerate any mistakes are not very good bosses. Don’t be that person.
- If you make a mistake, own it. Don’t blame others. Don’t make excuses. Don’t deny it. Just acknowledge that something went wrong, and you will go figure out why and learn from it to be a better in-house lawyer. You really can’t do any better than that. Most people in the business and the legal department will understand, as it has happened to everyone. In fact, many businesses tout a culture of encouraging mistakes because of the lessons they teach. But if you are part of a legal department or business that cannot accept any mistakes (or just talks the talk but doesn’t walk the walk) you are in the wrong place and you will be better served working somewhere else. Otherwise, you walk on eggshells and give the most risk-averse advice humanly possible. There is literally no fun or glory in that type of in-house existence
3. Understand the business. Okay, enough of the “depressing as hell” topics. Let’s move on to some more interesting and effective ways to start to build out good judgment. One pillar is understanding how the business functions. In particular, developing a deep understanding of a) the company’s business model (including how it makes money), b) the industry it operates in, c) its business goals, and d) its strategic goals.[6] No surprise but it is difficult to give good advice (legal or strategic), let alone exercise good judgment, if you don’t really understand all these facets. Giving legal advice in a vacuum is clunky and ill-fitting, like a suit from Sears. The business will instantly recognize (and appreciate) advice from (and judgment of) a lawyer who understands the realities of how the business functions, the competitive landscape, the financial realities, and the risk profile of the company. The more you learn about the business the better your judgment and ability to solve challenging problems or give useful advice. This all requires that you are curious by nature and specifically about the company you work for. Lastly, as I often say, the language of the business is numbers and in-house lawyers need to speak it to be effective. You do not need an MBA, but you need to be able to understand the basics, i.e., how to read a balance sheet, an income statement (P&L), and a cash flow statement. In the in-house world, good judgment and “business math” are intertwined.
4. Be well read. If you are an in-house lawyer and do not like to read, you must live in a world of deep hurt. Good judgment rests on so many things but few are more important than being a well-read person. Not just about the law (that’s expected – and key) but about the industry the company operates in, the world in general, current events, politics, literature, history, and so much more. Understanding and appreciating (but not necessarily agreeing with) different viewpoints is a big part of developing good judgment. The wider and broader your viewpoint the better – have a go-to list of things to read every day. Likewise, the ability to engage in a discussion with someone you disagree with but not turn it into a cable-news-talking-head-food-fight will serve you well. You will constantly draw from the knowledge you developed from reading many different things to help you think through the issue in front of you in creative ways.[7] This means you must be open-minded about what sources you get your information from and what you read. If you only read or listen to things you agree with or support your viewpoint, you are missing out on an easy way to develop and enhance your judgment. You don’t have to agree with everything you read or hear but understanding the basis for different positions, and the “why” people say or write what they do will help you analyze the problems and issues you face more completely and deeply.
5. Be an active listener. While we generally express our good judgment orally or in writing, it all starts with being a good listener or what is more commonly called being an “active listener.” Active listening is a communication technique involving:
- Giving the speaker your undivided attention. This involves maintaining eye contact, nodding, and using body language that shows you are engaged.
- Understanding and comprehending the message being communicated. You do this by asking clarifying questions or paraphrasing what the speaker has said to ensure you have understood correctly.
- Giving useful feedback to the speaker. This can include verbal affirmations like “I see,” “I understand,” or “That’s interesting,” as well as asking follow-up questions that show you are interested and engaged.
- Retaining the information shared by the speaker for future reference. Being able to recall the information when later engaging with the speaker shows respect and attentiveness.
- Demonstrating empathy by acknowledging the speaker’s feelings and perspectives. This involves showing that you understand and appreciate their emotions and viewpoints – even if you don’t agree.
- Understanding your own biases and how they may impact your decision process, i.e., be self-aware of how your unconscious preferences and motivations influence your actions and advice.
All of the above means giving your full, undivided attention to the meeting, the call, or the discussion and not letting your mind wander (or play with your phone, check emails, or otherwise try to multitask when engaged in a conversation with someone).[8] In-house lawyers who have mastered the skill of listening more and talking less are well on the way to developing their judgment.
6. Hone your analytical skills. Now it starts to get a bit harder. Honing your analytical skills is the next step after gaining experience and taking in information in the various ways discussed above in numbers 1-5. In a nutshell, honing your analytical skills means enhancing your ability to analyze complex legal and business issues. You do this by looking at a problem or issue from many different angles, not just the legal angle. Specifically, it requires some combination of the following:
- Evaluating information and arguments logically to identify strengths, weaknesses, and the range of potential outcomes.
- Identifying the key issue, determining its cause, and developing solutions that work in the real world.
- Gathering, reviewing, and interpreting data (quantitative and qualitative) to draw conclusions.
- Investigating questions or problems thoroughly to gather necessary information and insights, i.e., stress testing what people are saying or what you are reading.
- Noticing small but important details to better ensure accuracy and completeness in your analysis.
- Using game theory to break down problems into manageable parts and considering the potential impacts of different courses of action, including both best-case and worst-case scenarios and the implications of each – and strategies to deal with each.
7. Assess risk properly. While related to honing your analytical skills, I am giving “risk assessment” its own spot. Understanding, evaluating, and discussing “risk” is core to developing and enhancing your judgment. For in-house lawyers, this means the ability to weigh the legal and business risks against business needs and objectives in a fair and pragmatic manner. When doing so, there are several things to keep in mind. First, not all risk is “bad.” Companies take risks all the time as a path to maximizing profits and shareholder value. If you only think of risk as something to avoid, then you are missing half the equation. Second, must understand the risk profile of the business and not substitute your risk tolerance for that of the business. Lawyers tend to be very risk-averse, but the company may have a much bigger appetite for risk. Your job, in part, is to understand this, lean into the risk tolerance of the company, and work from there. Third, when analyzing the risk of a strategy, idea, position, action, or whatever, consider both short-term and long-term consequences of the same and look to balance legal considerations with business goals – looking to find practical solutions that support the company’s success. Fourth, be pragmatic and flexible, understanding that “perfect” legal compliance is not attainable, especially when balanced with business realities.[9] Fifth, focus on solutions over yammering on about the “list of horribles.” That’s great for a law school exam, but, in the real world, things rarely end up with the best case or the worst case. Don’t spend an inordinate amount of time discussing (or opining on) the highly unlikely. Focus your energy on the “most likely” scenarios This ability to focus on the most likely is foundational to good judgment. It doesn’t mean you ignore the super bad or super good, you just acknowledge that those are less likely to occur, and more effort should be spent on the path the company is most likely to take.
8. Learn to communicate effectively. Since, for the most part, your good judgment will be expressed through written or oral communication, learning how to be effective at both is important. A few things to consider:
- Stop writing and talking like a lawyer and start writing and talking like a business person. When you work in-house, that’s what you are, i.e., a business person whose skillset is primarily (but not only) legal analysis. Forget pretty much everything you learned about writing in law school or at the law firm because that is all pretty irrelevant now.
- Keep things simple and straightforward. Your goal is clarity and reducing complexity. If your advice is cloaked in legalese or muddled by too many caveats or by the love most lawyers have for spotting and discussing every possible permutation you’ve lost your audience (and your opportunity to show good judgment).
- Don’t be defensive if someone challenges your thinking. Welcome the questions and the pushback, it can only make your advice better. Likewise, speak up when you have a point to make and think is worth the business considering. But be calm and persuasive, not rattled and abrasive. How you present information and your thoughts is equally important to what you are saying when it comes to convincing the business you are bringing good judgment to the table.
- Learn to communicate with data. Numbers matter to the business so they must matter to you. Making a point buttressed by math is going to have much more impact than just spit balling or appearing to make it up on the fly. While it’s not always possible to have the math handy, don’t ignore it. A decision tree is your best friend!
- Observe and learn from the decision-making processes of other senior executives and experienced colleagues. Molding your style to fit with the style of the executive team is a terrific way to get heard. Being the bull in the China shop or the wallflower in the back of the room is simply not an effective way to communicate your ideas or your presence.
9. Be a team player (not the Lone Ranger). Sure, the Lone Ranger is a pretty cool dude. He wears a mask, uses silver to make his bullets (which is also key in warding off werewolves), and has a buddy named Tonto who will gladly take a severe ass-beating in town if it helps Kemo Sabe save the day. Not bad. But, if you want other leaders and departments to respect you (and the legal team) as purveyors of good judgment, ditch the Lone Ranger act and join the team! Work closely with others in the business to solve problems together. Collaboration is key here. Talk to the business every day and stay engaged with them as a colleague. Another way to go is to look for opportunities to participate in cross-functional projects to develop business skills, gain experience with the business, hear diverse perspectives, and make friends outside of the legal department. Understanding the different viewpoints, needs, concerns, biases, likes, and dislikes of different parts of the business helps you gather information and build out your emotional intelligence; allowing you to add your experience into the mix to help develop answers and solutions that make sense, work in the real world, and – most importantly – help create value or minimize value destruction for the business. Sadly, many in-house lawyers (and legal departments for that matter) tend to be standoffish and prefer to be “away” from the business – working on legal issues and too busy (or important) to work on anything else. That attitude will not get you far these days and will likely backfire spectacularly when the business (rightfully) sees you as an outsider vs. one of the gang. People are naturally suspicious of – and discount – the advice of outsiders. The viewpoints of teammates are usually welcomed and sought out. That’s the goal.
10. Hold the line. Lastly, when it comes to developing good judgment, build out your ethical core. Even if you are “one of the gang” that doesn’t mean it’s a free-for-all and anything goes. Understand that as a lawyer you have an obligation to the company to protect its interests at all times, even at the expense of personal relationships. You need bedrock core principles that you will not give up to get others to like you or think highly of you. They will think more highly of you if they know that you will be the conscience of the organization – the watchdog – if need be. That doesn’t mean you need to be the unbending nit-picking prig, but you must be prepared to challenge groupthink and decisions of actions that can lead to bad results, including damage to the company’s reputation, shareholder value, employee morale, and worst of all litigation or regulatory enforcement (including prison time for executives – and in-house lawyers – caught on the wrong side of the fence). I have thought about this a lot as general counsel, and I had a list of questions I developed and kept handy for when it felt to me like the business might be playing too fast and loose with their plans. Here is that list of questions. I didn’t ask all of them at one sitting but, generally, a few would pop out as the right questions to pose to help pull folks back from the brink of the abyss. And remember, tone is as important as the questions here. Don’t be holier-than-thou, be a partner trying to solve tricky issues and protect the interests of the company:
- “Even if we can do this, should we?”
- “I like the idea but let’s take a moment to think through and discuss the possible reactions to our taking this action?”
- “How might this decision impact our reputation with customers, employees, and other stakeholders?”
- “The short-term benefits seem good, but what are the possible long-term consequences of this decision? How does this decision align with our long-term strategic goals?”
- “How would we respond if this decision became public knowledge? Are we concerned”
- “Could this action set a precedent that might be difficult for us to manage in the future?”
- “We seem really focused on one course of action. What alternatives have we considered or ignored, and why are they being dismissed?”
- “Is this decision aligned with our company’s core values and ethical standards? Could this action be perceived as unethical or unfair by outsiders?”
- “Let’s consider what happens if this goes badly. Could this action expose us to lawsuits or other legal actions? What are the potential financial implications, including fines or litigation costs?”
- “How will this decision affect our culture?”
- “We focused on the best case. Let’s flip it and consider what is the worst-case scenario if we proceed with this decision?”
- “What measures can we put in place to mitigate potential downside risks?”
- “How might this impact our relationships with regulators and authorities?”
Asking the hard questions (but doing so in a way that doesn’t make you come across as Barry Butthead)[10] is an excellent way to help make sure all of the right factors are considered before an important decision is taken. If you take nothing else from today’s post, this is the essence of good judgment.
*****
Well, that’s all I have for today. Lots of good stuff in the hyperlinks so check those out. That said, I noticed that there are lots of articles talking about the need for good judgment, but not very many that tell you how to do that. Hopefully, today’s post helps fill that void for in-house lawyers. The bottom line is that developing good judgment involves a wide combination of experience, strategic thinking, relationship building, and knowing when to pose the hard questions – in the right way. There is no “one way” to go about it. Judgment depends a lot on the circumstances and personalities at play. Ultimately, if you are looking to develop and/or hone this incredibly valuable soft skill, your goal is to gain experience with a myriad of issues, e.g. legal, business, or a combination of both. In the end, what the business wants (and your goal) is to be another educated, thoughtful, and strong voice at the table, in particular, a teammate who is looking for solutions and not just pointing out problems or hyperventilating about risk.
Sterling Miller
July 10, 2024
My sixth book, The Productive In-House Lawyer: Tips, Hacks, and the Art of Getting Things Done, is now available for sale! In-House Lawyer Monthly Puzzle Book calls it “… the greatest book on productivity for in-house lawyers ever published anywhere in the universe.” You can buy your copy (and a copy for all your friends) 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.
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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] As the old knight guarding the Holy Grail in Indiana Jones and the Last Crusade said, “He chose… poorly.”
[2] I think Texas may be the largest free-range insane asylum in the world. And I’ve been to Canada!
[3] If not, you can do what everyone with sketchy judgment does – run for Congress.
[4] This measurement is actually part of the metric system. Seriously. Go check it out. It’s in one of the last chapters way in the back.
[5] Please, no questions about how on earth I possibly know this. Damn fraternity…
[6] In case you were wondering, business goals are specific, short-to-medium-term targets that an organization aims to achieve. They are typically concrete and quantifiable. Strategic goals are broad, long-term objectives that align with the company’s vision and mission statement. They generally provide a roadmap for achieving the company’s overarching aspirations.
[7] I know a lot of folks bash the value of a liberal arts education but I think it is critical for thinking, writing, analyzing, and communicating in today’s world. So, play with your computers and test tubes all you want, but someone has to translate all of that science into concepts the business (and customers) can understand. One big hug for the liberal arts!
[8] For horrors of multitasking see my new book or this article Why Multitasking Sucks… And Wastes Time.
[9] To be clear, I am not talking about criminal activity or when lives are at stake. Then 100% compliance is essential.
[10] I was going to say “Alvin Asshole” but I’m trying to cut back on the profanity.