Chapter 16: Lessons from Two Decades of Practice

This chapter is different from the rest of the book. It's not about patent policies or governance structures or voting mechanics. It's about the soft side of the practice of law — and it may be the most important chapter in the book.

The technical frameworks matter. The legal analysis matters. But the principles that determine whether you're effective — whether your advice gets followed, whether your clients trust you, whether you build the relationships that make everything else possible — are the ones in this chapter.

Some of these emerged from standards work. Most apply to legal practice and leadership generally. They're offered as one practitioner's perspective, not as universal truths. Take what's useful. Leave what isn't.

People and Relationships

Law is easy, people are hard. The legal analysis is rarely the difficult part of any engagement. The statutes, the case law, the contract provisions — these are learnable, analyzable, and usually within a range of well-understood outcomes. What's hard is the people. Understanding their motivations. Managing their expectations. Navigating their internal politics. Earning their trust. Getting them to act on your advice. If you can do the people part, the law part follows. If you can only do the law part, you'll produce technically correct advice that nobody acts on.

Empathy is a tool, not a weakness. Understanding what everyone at the table needs — their business constraints, their internal politics, their competitive position, their personal incentives — is strategic intelligence. The more you understand about others' interests, the better you can identify trades, build alliances, and anticipate objections. This applies whether you're negotiating a deal, structuring a partnership, or managing a team. Empathy isn't about being nice. It's about being informed.

Don't go for the jugular — these are repeat players. In any professional community — legal, technical, industry — you encounter the same people again and again. The relationship you build — or destroy — in one engagement carries into the next. A reputation for fairness, competence, and good faith is the most valuable asset in any long-term career. Once lost, it doesn't come back.

Don't push people back on their heels. This is the in-the-moment cousin of the jugular point, and it's worth its own line because it gets violated constantly by smart lawyers who think they're being effective. Remember that this isn't litigation. There's no judge to rule in your favor. You need to convince the other side to come to your position willingly, and people who feel attacked dig in. They stop evaluating your argument and start defending their own. There is a real difference between marking up someone's document and explaining all the reasons they're wrong — which almost never works, and works even worse when their client is in the room — and asking a question. "That's interesting that you said that, because I was thinking it would work like this — can you help me understand?" That single move turns a confrontation into a conversation. It gives the other side room to reconsider without losing face. It's also genuinely curious, which means you sometimes find out you were the one missing something. Either way, you end up closer to a position you can both live with than you would have by being right out loud.

You need friends before you need friends. Build relationships, goodwill, and trust before you have a specific need. Support others when it costs you nothing. Show up consistently. Be helpful without being asked. When the time comes that you need support, it will be there — because people remember who helped them and who didn't.

It's all about the chits. Early in my career, I wanted something from another team and I wasn't getting anywhere with them. My manager — the son of a southern tobacco farmer and the only person who wore a three-piece suit in a company where flannel was considered formalwear — took me aside and said, "Son, it's all about the chits." Holding out both hands, he said, "If you want something in this hand, you need to cash in the chits you've earned in the other hand. And you don't have any chits." Once I got past the condescending tone, I realized it was some of the best advice I've ever received. The only way to get chits is to earn them — by showing up, by helping others, by being fair, and by doing it before you need something in return.

When you're in someone's backyard, let them know you're there and give them the opportunity to scream. If you're working across organizational boundaries — different teams, different departments, different companies — you're going to be playing on someone else's turf. Let them know you're there, what you're doing, and why. Give them every opportunity to raise concerns. Most people will welcome you and help you navigate their particular terrain. Don't ever surprise anyone, especially in front of their stakeholders.

There's plenty of credit to go around. The instinct to claim credit is natural but counterproductive. Share it generously. Help others look good in front of their management and their clients. The more credit you give away, the more people want to work with you. As Truman is often quoted: "It is amazing what you can accomplish if you do not care who gets the credit." Do the work. Help others succeed. Your reputation will compound over time, even if — especially if — you're not the one claiming it.

Negotiation and Strategy

It's Model UN, not litigation. Any time you're working in a multi-party setting — whether it's a standards body, a joint venture, an industry consortium, or a regulatory negotiation — the dynamics are diplomatic, not adversarial. You're building coalitions, managing relationships, and trading concessions across multiple dimensions simultaneously. The skills that make someone effective in a courtroom — aggressive advocacy, clever argument — actively hurt in collaborative settings. There's no judge. You can't compel a result. And the person you went after today will be across the table from you tomorrow.

Play 3D chess — lay the groundwork and let others carry your position. The most effective work in any collaborative setting happens before the meeting. Informal conversations. Alignment sessions. Understanding where the support is and where it isn't. If you've done the groundwork, others will advocate your position for you — and it carries more weight coming from them than from you. If you haven't done the groundwork, you're improvising in real time, which is a much harder game.

The most powerful word is "no" — not "no, because." In any negotiation, once you explain your reasons for saying no, the other side will solve your stated problem and come back with a revised proposal that you may find harder to reject. Sometimes the strongest position is the unexplained one. "No" is a complete sentence. Use it sparingly, but when you do, don't dilute it with rationale that invites workarounds.

This extends to how you manage your time. Just because someone raises an issue doesn't mean you need to address it. I've seen too many hours wasted on non-issues because lawyers wouldn't say no — to a client who wanted to relitigate a settled point, to a counterpart who raised a theoretical concern with no practical consequence, to an internal stakeholder who wanted a memo on a question that didn't matter. Protecting your time — and your team's time — requires the discipline to evaluate whether an issue is worth engaging on before you engage on it.

Create the rules — once they're playing on your gameboard, you've already won. Spend time shaping the environment before you need it. Whether it's a governance framework, a contract template, a process workflow, or an organizational structure — if you're the one who designed it, you understand it better than anyone, and the dynamics favor your position. The people and companies that are most effective in any collaborative context are the ones that shaped the playing field before the game started.

Focus on what truly matters — let other things slide. You can't fight every battle. You can't perfect every clause. You can't win every point. Identify the two or three issues that genuinely matter and focus your energy there. Concede gracefully on the rest. Losing on something you don't care about preserves your credibility and your relationships for the fights that count.

Drafting and Legal Craft

The range of reasonable. In any negotiation — standards, M&A, licensing, partnerships — most terms fall within a range of reasonable. The range is wide, and there are real differences within it, but the truly unreasonable provisions are rarer than you'd expect. Your job isn't to find the perfect deal. It's to identify when something falls outside the range and flag it. Whether you love what's inside the range is a different question. But distinguishing "I don't prefer this" from "this is outside the range" is a core skill for any transactional attorney.

Oxygen expands to the size of the room. Give any project, team, or initiative an open-ended scope, and the work will grow beyond what anyone anticipated. This isn't malice — it's the natural dynamic of ambitious people without external constraints. The antidote is clear scoping at the outset and the discipline to re-scope when the work drifts rather than letting it expand silently.

Terms travel, context doesn't. Language from one agreement migrates to the next — copied, adapted, carried forward. But the context that created that language — the specific negotiation, the specific problem it was solving — doesn't travel with it. Future readers see the clause and have no idea why it exists. If you're drafting, document the rationale. If you're reviewing, don't assume a clause is meaningless just because no one can explain it — but also don't be bound by it just because it's there. If a provision doesn't make sense for the current situation, fix it or remove it. Inherited language that nobody understands is a liability, not a tradition worth preserving.

Be an expert in your space — but don't be bound by precedent. Understand the common practices, the standard terms, the typical governance structures. Know why they exist and what problems they were designed to solve. Assume they were put in place by smart people with good reasons. But don't treat them as sacred. Every procedure, every term, every mechanism was designed for a specific context — and that context may not be yours. The fact that every agreement you've seen has a particular provision doesn't mean your agreement needs it. Question what you see. Understand the purpose behind the precedent, then decide whether that purpose applies to what you're doing now. The practitioners who add the most value are the ones who know the conventions well enough to know when to break them.

It's OK to be paranoid sometimes. When you're drafting any agreement, consider the worst case. What happens if a party acts in bad faith? What happens if the relationship breaks down? What happens if someone uses the process as a weapon? You don't design for bad faith as the default — that would make every agreement unusable. But you build in safety valves that address bad faith when it occurs. The agreements that survive crises are the ones that anticipated them.

The corollary is equally important: draft for collaboration as much as for protection. Law school teaches you to anticipate disputes. Real practice teaches you that disputes are rarer than you'd expect. Most parties engage in good faith most of the time. If you draft every agreement as if litigation is inevitable, you create friction that makes collaboration harder — and the collaboration is usually the whole point. Draft provisions that make good-faith participation easy and rewarding. Draft governance that facilitates consensus rather than just resolving conflict. Build structures that assume the best while preparing for the worst. The balance between paranoia and optimism is what makes an agreement actually work in practice.

Contracts are the starting point for negotiations when things go wrong. A mentor taught me this early in my career, and it's shaped how I approach every agreement since. Nobody reads the contract when things are going well. The contract matters when the relationship breaks down — and at that point, it's the starting point for the conversation about what happens next, not the final answer.

This means the agreement doesn't need to be perfect. Litigation around contracts is rare. The relationships aren't. Most disputes get resolved through conversation, not courtrooms — and that conversation starts with what the contract says, even if it doesn't end there. So draft with care, but don't let the pursuit of perfection delay the work or damage the relationship. An imperfect agreement that everyone signs and moves forward with is worth more than a perfect agreement that takes six months to negotiate. That said, don't be cavalier either. The provisions that matter most are the ones that govern failure: withdrawal, dispute resolution, IP survival, and termination. Get those right. Let the rest be good enough.

A lot of what we do is theater. This applies far beyond standards. In any client-facing practice, perception matters as much as substance. How you present advice, how you frame a risk, how you position a deal — these are acts of communication that shape whether your advice gets followed. Sometimes the legally optimal approach isn't the best approach. Sometimes a simpler framework that people trust matters more than a complex one that's technically superior. Understanding the theater doesn't make you cynical. It makes you effective.

Make your legal advice human-readable. Most clients don't want a five-page memo outlining legal risks. They want to know what to do. We transformed our open source license guidance from lawyerly analysis that left engineers wondering what to do into short checklists that made calls. The volume of requests we could handle went from hundreds per month to hundreds of thousands — not because the law changed, but because we made the advice actionable. If your advice requires a law degree to understand, it's not advice. It's a research paper.

Send a demand scroll, not a nasty-gram. Lawyers default to the demand letter — "We represent Client X, here's the detailed legal analysis of everything you've done wrong, you must stop immediately, and we're prepared to sue." It's the reflex. It's also rarely the best tool. Bud Light set a better standard. When a small brewery started using the "Dilly Dilly" trademark, Bud Light didn't send a nasty-gram. They sent a costumed town crier to deliver a "demand scroll" on parchment, politely asking the company to stop — and invited them to the Super Bowl. Bud Light preserved its rights, got the infringement to stop, generated terrific PR, and made a friend instead of an enemy. Before you fire off the default cease-and-desist, ask whether there's a Dilly Dilly version of the same communication. You can almost always preserve the legal position while choosing a tone that leaves the relationship — and your client's reputation — better off.

I don't want your five-page memo — I want your judgment. This is what I tell outside counsel. I don't need a comprehensive survey of the legal landscape. I need your judgment call. What would you do? What's the risk? Is it worth taking? The ability to synthesize complexity into a clear recommendation — rather than presenting options and leaving the decision to the client — is what distinguishes a trusted advisor from a research service.

Leadership and Career

All ideas are bad — but you need 100 bad ones to get to one good one. This is about leadership and creating an environment where people contribute. If the bar for sharing an idea is high — if every proposal has to be polished and defensible — people hold back. They self-censor. They wait for someone else to go first. But if the starting assumption is that all ideas are bad, the bar drops to zero. Everyone contributes, because there's no risk in sharing a bad idea when that's the expectation. And if someone critiques your idea, it's fine — it was a bad idea anyway. No harm done. The magic is that with enough bad ideas on the table, patterns emerge. Fragments from one bad idea combine with fragments from another. Someone builds on something that was thrown out casually. And eventually, a good idea surfaces — one that nobody would have reached if the first person in the room hadn't been willing to say something imperfect. Good ideas are hard to come by. The way to find them is to make it safe to generate a lot of bad ones first.

You have apparent authority — don't be afraid to use it. As a subject matter expert, you often have more influence than your title suggests. People seek you out because you add unique value. They defer to your judgment because you've been right before. That apparent authority is real, even if it isn't on an org chart. Use it. Make decisions when decisions need to be made. If you wait for someone with formal authority to act, you'll wait too long.

Strive to be best in class. Not just good enough. Not just competent. Best in class. In any specialized legal field, being the person that others turn to — inside and outside your organization — is the most durable form of professional security. It takes years to build. It's maintained through continuous learning, generous engagement, and consistent delivery. There's no shortcut.

Give generously of your time and expertise. When someone asks for help — even if there's no direct benefit to you at the time — help them. Share what you know. Make the introduction. Review the document. Take the call. Not because you're keeping score, but because generosity builds the reputation and relationships that sustain a career. The people you help today become the people who think of you when an opportunity comes up, who vouch for you when your name is mentioned, who return the favor when you need it. What goes around comes around — not transactionally, but over the arc of a career.

Develop expertise — build a practice, don't wait for a mandate. Don't limit yourself to what's in your job description. If you see an emerging area that nobody is covering — and that needs covering — cover it. One of the most impressive things I've seen is a colleague who became interested in open data. It wasn't formally part of her job. She learned about the emerging topic, engaged across the company, and quickly became the legal open data expert at one of the largest companies in the world — because she decided to.

If you manage ambitious people, give them room to run. If you're a manager and someone on your team is building something new — exploring an area nobody asked them to explore, developing expertise that doesn't fit neatly into their job description — give them the space and protection to do it. Take away half their formal job and let them create the job they want. Maybe they'll fail, and that's OK. One home run can change everything for the better — for them, for the team, for the organization. I always told my team they should spend 20% of their time on experiments, new ideas, and stretch goals. Most didn't. So when you find someone who does, embrace them. Protect them. Clear the path. These are the people who will do great things if you let them — and who will leave if you don't.

Don't be confined to your wheelhouse — make your clients smarter. Lawyers often think they need to confine themselves to "legal" issues. The hard truth is that most of your clients don't care about indemnification and warranty clauses. That's a lawyer problem they expect the lawyer to handle. Your job is to make your clients smarter — whether they're lawyers, engineers, or business people. Flag trends. Flag competitive issues. Help them see the deal in a larger context. Help them understand why a particular point may be important to the other side. Clients come to lawyers when they have to. They come back when you make them better at their job. Even as a junior attorney, you've probably seen more of these deals than your clients have. Share that perspective. Help them understand the patterns, the risks, and the opportunities that come from having a broader view. You get your foot in the door because your clients have to call their lawyer. You get welcomed back and become a trusted advisor because you made them smarter.