Weird Ways to Become a Better In-House Lawyer

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Deep Dive

You probably haven’t heard this advice before . . .

A lot of advice about how to succeed in-house, including some of the advice I give, feels logical and intuitive once you’ve heard it. It’s useful to hear or read since you didn’t actually think of it until someone else said it, but when you hear it, you go “oohhh, right. Of course.”

This newsletter issue is not that.

This is full of advice you may need to sit with to believe. Some of the tips you may ponder for a while before you ever consider implementing. Others, many of you will outright reject as not for you—though a few will try them to great success.

So here goes. These are some weird ways to be more successful in-house, from me- an in-house lawyer whose career has been anything but typical

1. Dedicate time to an activity societally deemed “lower prestige”

Lawyers are told, far too often in my opinion, that we are special. As a group, we are highly educated, well-paid, and like to believe we are thought of as successful (even if not always well liked). But none of that means any of us is any better than anyone else. Doing an activity society deems to carry less prestige is a powerful reminder of that.

Knowing you are no better than others is, obviously, an important part of being a good person. But it also teachers you to look for opportunities to learn from, work with, and appreciate, everyone you meet. That makes you a better lawyer.

In my own life, I’ve been a teacher, bartender, and coach. I spent years working behind the counter of my own juice bar. Plus, I’ve volunteered for all sorts of (literally) dirty jobs like cleaning up a local river and picking up trash from local beaches.

Try it. Volunteer as a trash picker, work a few shifts as an Uber driver or bartender.

Experiencing these things firsthand will remind you that hard work looks different in different contexts, that intelligence isn't measured by letters after your name, and that the people who make your daily life possible are doing vital work whether or not LinkedIn celebrates it.

Key point: don't tell anyone you're a lawyer while you're doing it. Let people see you as just another person doing the work.

This perspective makes you better at collaborating across all levels of an organization. It also makes you a more pleasant human, which matters more than most of us want to admit.

2. Talk to, or consume content created by, people who think that lawyers are the problem

Lawyer jokes are everywhere, so as much as lawyers like to think we're special (see point 1 above), we also know our profession isn't exactly beloved. Understanding why that is can be invaluable in helping you become the type of in-house lawyer that colleagues are excited to work with, rather than dread.

This doesn't mean wallowing in self-loathing or accepting unfair criticism. It means genuinely listening to perspectives that see legal as an obstacle rather than a partner. What do engineers say when legal isn't in the room? What do salespeople actually think about contract redlines? What do product managers wish lawyers understood?

You can seek this out in real conversations—ask a colleague in another department what frustrates them most about working with legal, and then listen without getting defensive. Or consume content that challenges the legal worldview entirely.

If you want to read a whole book with this perspective, I'm currently listening to Breakneck: China's Quest to Engineer the Future. It's full of comparisons between the U.S. and China and blames nearly every American problem on our being a "lawyerly society" that can't get anything done, as opposed to China's "engineering society" of builders. You don't have to agree with the thesis to learn from understanding it. The discomfort is the point.

3. Dedicate as much time to learning business as learning law

To be an effective in-house lawyer, you need to know relevant law. Obviously. But you also need to know and understand business generally, as well as the specific business of your company and the industry it operates in.

Here's the shift: approach learning business with the same intentionality and time commitment you bring to learning law. Most in-house lawyers already have a strong foundation in legal principles. What separates good in-house lawyers from great ones isn't usually deeper legal knowledge—it's business fluency. When you understand how your company makes money, what drives customer decisions, how your competitors operate, and what keeps your CEO up at night, you can give advice that goes beyond legally sound. You can give advice that actively drives the business forward.

Read your company's board materials. Listen to earnings calls. Take a finance or business strategy course. Ask your colleagues in sales, product, and operations to teach you their world. Learn to read a P&L. Understand your company's unit economics. The law will still be there when you get back, but your ability to apply it strategically will be transformed.

4. Dedicate time to studying how people think and make decisions: psychology, persuasion, sales, etc.—even if that means less time studying the business or the law

Learning how people think is great for negotiating with counterparties or navigating disputes, but it's equally useful for how you work with your own colleagues. Because here's an awkward truth: most of your job as an in-house lawyer isn't about knowing the right answer. It's about getting people to listen to you, trust you, and act on what you're telling them. You can have perfect legal analysis, but if you can't persuade the VP of Sales to change course, or if the CEO tunes you out because of how you frame risk, your expertise is useless.

This is why studying human behavior and decision-making can be more valuable than your next CLE. Learn about cognitive biases and how people assess risk. Study negotiation tactics and what actually persuades people to say yes. Read about sales methodologies—salespeople are professional persuaders, and you're essentially selling "let's do this the legally sound way" every single day. Understanding loss aversion will help you frame legal advice more effectively than understanding another regulatory nuance ever will.

Start with books like Influence by Robert Cialdini, The 48 Laws of Power by Robert Greene, or Never Split the Difference by Chris Voss. Take a sales training course. Learn how therapists build trust and manage difficult conversations. Watch how the best communicators in your company deliver bad news or drive change. The law you already know will become exponentially more powerful when you understand how to deliver it in ways that humans can actually hear and act on.

5. Openly talk with colleagues about silly or unique things that bring you joy

This one sounds trivial until you realize how many in-house lawyers are terrified of being seen as anything other than Serious Legal Professional. We worry that if we admit we're ranked in the top 500 globally in Candy Crush, that we're writing Regency-era fan fiction, or that we spent Saturday building a 6,020-piece Lego Hogwarts Castle alone because our kids lost interest after the first turret but we were hooked, we'll somehow be taken less seriously. So we keep conversations surface-level and wonder why we feel disconnected from our colleagues.

Here's what actually happens when you share the quirky things that light you up: people remember you're human. They relax around you. They start to trust you more, because you've signaled that you're a real person with a life beyond redlining contracts. The product manager who learns you're both into vintage video games will think of you differently the next time they need legal advice. You become someone they want to work with, not just someone they have to work with.

This doesn't mean oversharing or making everything about your hobbies. It means letting people see that you have enthusiasms, that you're more than your job title. Talk about the concert you went to, your backyard chickens, your terrible golf game, the novel you can't put down. Be specific and genuine—"I'm really into urban foraging right now" is more memorable and connectable than "I like nature."

The lawyers who build the strongest relationships at work aren't always the ones with the best legal skills. They're the ones people actually know and like. And it's hard to like someone who you only ever see as a walking legal department. So let people see what brings you joy, even if—especially if—it's a little silly. You'll be amazed how much it changes the way people work with you.

This is part 1 of 2

I have five more tips like these coming next week—equally out there and equally worth considering.

You don't need to try all of these. You might not try any of them. But if even one of these ideas gets you thinking differently about what it means to be successful in-house, that's a potential win for you as you work to build a career on your own terms. The unconventional path isn't for everyone, but it's available to anyone willing to take it.