Things Lawyers Know

This is my first post in a new “category” of posts that I plan to offer from time to time. I’ll generally post these to instead of posting them directly to my social media accounts. You can thank me later. (They might be long, like this one.)  Here’s the concept:  Lawyers see a lot of interesting things in the course of representing a variety of clients.  That experience shapes us and makes us (or helps us to) look a the world through a lens that is, well, “lawyerly.”  For moral people who are thinking about public issues, that lens might be helpful sometimes.  Let’s find out.

We sometimes joke that doctors have a hard time at cocktail parties because everyone wants to ask some questions, get a little free advice. “I’ve had a cough lately. What do you think it is?” “What do you think about that new medication I’ve seen advertised?” “Don’t you think this mole looks like George Washington?”

Lawyers get the cocktail party questions, too: “Can I set up my will to accomplish this or that?” “My car lease says X. What does that mean?” “I was thinking about doing this or that with my business. How would I go about getting started?” Despite the general public’s ordinary aversion to talking with lawyers, friends still come to us with their law-related questions all the time. Especially if you’re the approachable, chubby, bearded (yes, I’m led to believe the beard makes us more approachable, and anyway it half-hides my second chin), non-fire-breathing kind of lawyer. I don’t often breathe fire. And friends do bring me their general legal questions. I’m glad they do. I’m happy to be helpful. (Side note: Here comes some “legalese.” I can’t/don’t give actual legal advice unless I’m formally engaged as someone’s lawyer. Otherwise it might violate our professional rules. I only represent companies and other kinds of entities, anyway. Neither this post nor others in this series is “legal advice.” Ok?)

There’s a reason folks ask questions to their lawyer friends: Lawyers know stuff. But if there’s one response I give more than any other, it’s this: “I’m not that kind of lawyer.” You see, good lawyers know that they don’t know everything. The law is a vast and complicated thing. We take bar exams to ensure that licensed attorneys know a little bit about a lot of legal topics, but, candidly, the law is so complicated that any reasonable attorney has to choose a field of focus. You can’t be good at very many things, and you can be great at only a few things. When friends ask me about real estate investments, I refer them to colleagues. When friends ask about their wills, I claim ignorance. Yes, I passed the bar exam (in New York and Virginia), which means I learned “enough” (by someone’s definition) about those topics, but good lawyers know that “enough” isn’t greatness or expertise. So, when offering legal advice, I stay within the fields I know very well. In my case, I focus on transactions related to creation, commercialization, and regulation of information technologies and large aggregations of data. Yawn, right?

But you’d be surprised what that entails. The things I’ve had to learn in order to be good at my job are, at least to most folks, unexpected. In particular, I’ve had to learn a lot about ethics. That’s good, because I became a lawyer in the first place in part because of my interest in ethical questions, because of my sense of “calling” to be a positive force for good in my community. When we say that “lawyers know stuff,” it might surprise you that most of us lawyers have to think about ethical questions pretty commonly. I know, I know – there are some awful human beings out there who practice law, and they give the profession a bad name sometimes. Those few bad apples might not be beacons of ethics. But most lawyers become lawyers because they actually care about justice, the public good, and ethics.

For this first post in the “things lawyers know” category, I want to talk about the difference between legality and ethics. While not all of these posts will have political relevance, let me warn you that this one certainly does. However, I hope you’ll also see that this isn’t a partisan essay. On the contrary, one of the “things I know” as a lawyer leads me to be a little more circumspect about political arguments and, sometimes, a little more forgiving of politicians. Here we go:

You might paraphrase one of the most common questions my clients ask as “Is this legal?” Despite pervasive public cynicism about big businesses, I find that most of my clients will go to great lengths to comply with the law. So when there is a legal issue confronting their business, they naturally want to know what they can and can’t do. They come to me. For example, most of you know that online businesses capture a lot of data about the consumers who visit their websites. Over time those databases are huge! All around the world, governments regulate what businesses can do with that data, because, for example, we want to protect consumers’ financial information and other privacy interests. Businesses are eager to know what they can lawfully do with these data assets. They want to obtain the maximum benefit that’s legally possible. (Can they, e.g., send marketing emails to those website visitors?) But they definitely don’t want to cross the line into illegality. So they come to me with such questions.

In our personal lives, most of us follow this same approach to the law. For example, we want to claim the maximum number of deductions on our taxes, because we don’t want to pay more taxes than the law actually requires. What can we lawfully do to reduce our tax payments? We want to go “as far as we can,” but we definitely don’t want to break the law. There’s generally nothing wrong with that approach — we’re sincerely and responsibly trying to comply with the law, but we don’t have any interest in voluntarily paying more taxes than necessary.

That seems like a simple, obvious observation, I’m sure.   “How far can we go?” is an ordinary and responsible question. There’s a line that separates legality and illegality. We sometimes want to walk right up to that line, but we don’t want to cross it.

Often times, because the law is complicated (and constantly evolving), it’s difficult to say with certainty where the “line of legality” actually sits. Will the regulators agree that this or that marketing communication complies with the new regulatory requirements? Is it ok to take that tax deduction? Due to such difficulties, sometimes clients cross the line. Unintentionally. For example, the Federal Trade Commission might conclude that Company X’s privacy policy doesn’t adequately disclose the Company’s practices, so a fine is levied. Or perhaps the IRS determines that a particular deduction on a Company’s tax return is not allowed, so the IRS requires payment plus a penalty. I think non-lawyers often assume that it’s not this way, that figuring out the legality of some activity is more-or-less a matter of looking up the answer in a book. If things worked that way, we wouldn’t need lawyers. But life is too complicated, and the law is too non-specific, so we still need attorneys to give their best advice.

What I’m trying to say is this: The first thing lawyers know is that regular people (often via the companies they own/manage) sometimes cross the line, even unintentionally and despite their reasonable efforts to comply. Sometimes, when matters are especially complicated, the line gets crossed even despite very careful, more-than-reasonable efforts to comply. In those instances, good companies make corrections, resolve not to make the same mistake again, and move forward.

The second thing lawyers know, as a result of that first thing, is that sometimes people who have crossed the line are not unethical or dishonest people. Quite the contrary. Sometimes they are the finest people we know, doing their best to follow the law. They make mistakes, nothing more.   They are not morally defective simply because, despite their good faith efforts, they tripped.

This perspective has implications for how I view the political sphere. And the implication is bipartisan:

For example, I look back at the Whitewater saga and imagine the Clintons consulting their attorney or broker about a potential investment: “How far can we go with this?” Maybe they crossed a line, maybe they didn’t. We can say, however, that despite several tens of millions of dollars of independent investigation, the prosecutor concluded that they didn’t break the law with respect to that investment. (Of course, the prosecutor and Congress did allege that the President broke the law when he lied under oath about his affair with an intern. That’s a different matter, and I’m not minimizing it, but it’s unrelated to the Whitewater investment itself.) Through the years I’ve seen numerous investment transactions in which honest folks, attempting to comply with the law, have navigated lots of regulatory complication and made mistakes. It happens. So I don’t need to reach a conclusion as to whether the Clintons’ Whitewater investment crossed a line. The prosecutors took care of that investigation, and I’m working on the basis of my own experience, which teaches me that honest people can sometimes venture past the line, even when they aren’t trying.

So, too, I can entirely understand when a complex business enterprise, like the Trump organization, makes reasonable efforts to comply with tax law and nevertheless unintentionally crosses the line. During the 2016 campaign, it was reported that Mr. Trump was found to have broken the law by failing to pay required taxes, and his organization was fined. I didn’t view his tax problems as automatically equating to unethical behavior. He made a mistake. That’s as much as I could say based on the available information. It happens. I could cite a thousand examples of this principle. I’ll bet you could, too.

Legal mistakes are not automatically unethical or dishonest behavior, especially when the subject matter is legally complicated.

But this is where the issue stops being simple. As I’ve noted, non-compliance with the law doesn’t always equate to unethical behavior. The reverse is also true, and maybe more important: Compliance with the law is not always enough to be ethical.

When my clients come to me and ask whether some proposed course of action would be lawful, I try to answer their question, but I also often lead them to a bigger question: Is it ethical? The law often fails to outlaw things that are unethical – I’m sure we’ll all agree. Once upon a time it was lawful in the United States to discriminate against persons based on the color of their skin, but it was never ethical to do so.

You might be surprised to learn how many of my clients are very sensitive to ethical concerns. They ALL are.  They are good people who want to manage their businesses profitably, but only if they can do so ethically.

Especially in industries where the law is always several steps behind the latest business developments – like the tech economy in which I work – it is always possible for businesses to “get away” with things that the legislators haven’t yet addressed (and often haven’t yet noticed). Innovative profit-seeking businesses will always find ways to conduct business when the transactions are so complicated that the regulators haven’t caught up. (Ethical companies will nevertheless always act ethically, no matter what might be possible to “get away with.”)

For example, I assure you that state and federal regulators in the United States care about consumer privacy. They are competent, smart people who do their homework and make every effort to be very well informed about current business practices. They craft regulations designed with the interests of individual consumers, the business community, and the general public in mind. And despite all that, they can’t possibly keep up with the latest developments in technology. As a result, when a business comes to me and asks whether some activity, newly possible due to some technological innovation, is legally prohibited, I sometimes answer “The law doesn’t prohibit it, but do you really want to do it?” That kind of conversation usually arises when a company has discovered or created some way to stay within the “letter of the law,” while ignoring the “spirit of the law.”

Sometimes we don’t really want to walk right up to the line between legality and illegality. Sometimes, to be ethical, it’s better when we keep a little distance from that line.

Like regulators struggling to keep up with the creativity of ambitious business folks, the general public also has a hard time assessing both the legality and the ethical implications of complex business practices. People can’t be faulted for not knowing what they don’t know, but they can be criticized for rushing to judgment when they ought to realize that they don’t fully grasp the complicated issues. As an example, I recently got into an argument with a friend, also a lawyer, when we were discussing a particular tech company. He concluded that the company was doing something unethical, but when he tried to explain his justification for that conclusion, all he did was prove to me that he didn’t understand the technology that was the subject of the debate. Had he understood the technology, there was no way, in my opinion, that he could have reached his conclusion. Because I did understand the technology (it’s my field of work), I reached the opposite conclusion. How often does this kind of thing happen when the general public looks at public issues (like elections) where ethical issues are involved?

For purposes of my observations here today, I’m thinking about the way the public assessed the behavior of candidates in the 2016 Presidential election. There were so many accusations of illegal and/or unethical behavior, from each party, directed at both candidates, and my humble opinion is that the general public 1) was ill-equipped to assess some of the very complicated questions, 2) public figures with adequate understanding either failed to help or weren’t heard when they tried, and 3) as a result, large segments of American society – good, well-intentioned people – reached inaccurate conclusions about some very important issues.

This is where “things lawyers know” come into play. As a lawyer, I viewed some of the public debate through lawyer’s eyes, through the lens of experience with business operations like both Clinton’s and Trump’s. In the posts that follow in this series, I want to explain how I see some of those issues, and my hope is that you’ll want to discuss (respectfully, of course) the conclusions we might reach about the ethical worldview of the candidates, their parties, their platforms, and their voters. To be clear, I have no interest in re-hashing the election. We’re all tired of that. However, we all have an interest in being better next time. Let’s learn to talk about these things now.

For the past 7-8 months, I’ve been posting periodically in efforts to encourage healthy conversation about important topics that matter to all of us. Based on the responses I’ve received so far, my observations are these: Many of you think it’s a bad idea to talk politics. Many of you have that point of view because of your religious convictions. Many of you do, in fact, hold your political views because you claim to hold core values consistent with mine (or even religious convictions like mine), but somehow you have reached very, very different conclusions about your/our role in shaping our communities, via politics and otherwise. Because I respect you – strike that, because I love you as my brothers and sisters – I’m willing to put my thoughts out there, on the record, willing to invite your thoughtful, charitable responses (even criticisms, if they’re thoughtful), but I confess I’ve been disappointed so far. There are a lot of folks who share my place on the political left-right spectrum, and I get plenty of “attaboys” from them, but from others I’ve received either unfruitful emotional reactions or silence. It’s precisely those of you who disagree, who care enough to want to get this citizenship thing right, whom I want to hear. To play ball, all you have to share is your reasoning, and I’m inviting you to do so.

So, with that introduction to the “things lawyers know” series, here’s what’s upcoming:

  1. When the public learned that Mr. Trump had lost roughly $1B in one year, and that those losses could be used to offset taxes that his other businesses might owe, I think most folks zoned out. Speaking as a lawyer, I’m going to try and explain how that stuff works. As you saw above, I have already confessed that I fully expect honest business people to optimize their taxes, and I don’t think doing so is automatically unethical. I will try to do the explanation in a cold, analytical way – that is, I’ll do my best to curb my biases while giving the explanation. And then I’ll ask some hard questions about the ethics of his business model. I don’t think that is partisan – you’ll be the judge, and I hope you’ll participate in that conversation.  Watch for the post, coming soon.
  2. I represent some companies who possess enormous pools of consumer data, and I assure you that they strive to use that data only in careful, ethical ways to help their customers do marketing campaigns. So I’m involved in a lot of issues related to “big data” and online advertising. Based on that experience, I will outline how online “influencer campaigns” work, generally. Done responsibly, such marketing programs are both legal and ethical, and they are highly effective. Statistics don’t lie. If, say, somebody (like Russia) were to deploy the same tactics in an effort to affect U.S. elections, it is entirely predictable that those tactics would have an impact. I have the sense that most Americans hear vague reports that Russia attempted to interfere in the 2016 election, and, other than the heavily reported theft of data from the Democratic National Committee, most folks have absolutely no idea what the interference was.  Again, I will try to present this online “influencer business model” in an editorial-free manner, and then we can explore out loud the public discourse that has surrounded allegations of Russian interference with the 2016 election. After you understand the business model, I think you will stop denying that such a thing happened (if you’re one of those folks who denies it), but – spoiler alert – although reasonable folks will no longer be able to say that no votes were swayed, sadly we will all still be left asking “how many,” having to make our best guesses about the extent of impact on votes.  Watch for that post, too.
  3. The practice of law has changed a lot in the past 30 years. When I began practicing with a New York firm, many of the country’s prominent firms still practiced in an old model. Today EVERY successful firm has changed how it organizes itself, following a lesson that the Apostle Paul tried to teach us two thousand years ago: Each of us has a specific role to play, and not one of us is good at everything.  Many parts, one body, Paul would say. In big law firms, we’ve learned that, because the law is very complicated, and because our clients need us to get a lot of complicated things right, we have to utilize the expertise of lots of “specialists,” professionals who focus on particular fields, and then we have to work together in effective teams. Reflecting on that business model in law firms, I’ll talk about the public’s obsession with electing “outsiders” who have no experience with government or governing. I’ll also ask about the ethical implications of constructing an administration comprised of non-experts, political allies, and mostly white men.  Coming to a blog post soon.

Remember, these are more than mere political discussions. I’m approaching all these topics as a Christian man who has a particular point of view. I don’t have any illusions that I can’t be wrong – I welcome your insights that will help me improve my own thinking! But I am clear on one thing: I approach YOU, my discussion partner, from a starting point of respect and charity. That’s yours to build on, or yours to squander, but I invite you to participate in this dialog. You don’t have to share my perspective, but I’m confident that our communities and nation will be served well by healthy conversations that build relationships and that advance efforts to craft real solutions to issues.

As a reminder (as if the length of this post weren’t enough), I work as a part-time law professor, too (I’m on the adjunct faculty at Georgetown), and I sometimes get a bit academic without realizing it. I don’t want this to be an academic discussion. Let’s work on changing minds or growing them. Let’s model the kind of discussion that we want the broader community to embrace.

Post your comments and tell me you’re in!  I’ll look forward to the conversation.







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