How to Become a Better In-House Lawyer (by doing things differently)

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Deep Dive

This is not the same old advice . . .

There's a lot of great advice out there for in-house lawyers. It’s so good that everyone agrees it's good and repeats it constantly.

Like the five tips I shared last week, the ideas in this newsletter are not that advice. This is part two of the weirder approaches that have worked for me and my friends as we build in-house careers we love.

So here are five more unconventional tips for in-house success—starting with one that might seem a little out there.

If you're new or missed last week's ideas, you can view the full issue here.

6. Create and maintain a “legal but stupid” list

Just because you can, doesn't mean you should.

While I'm a big fan of in-house lawyers doing what they can to avoid becoming known as the "department of no," there are times when we should tell our companies not to do things, even when they're legally permissible. Things like enforcing a contract right that destroys a long-term relationship over a small amount of money. Launching a product feature that's technically compliant but feels exploitative to vulnerable users. Filing a lawsuit against a sympathetic defendant that will make your company look like a bully even if you win.

The problem is that many in-house lawyers struggle to articulate why something feels wrong when it's not actually illegal. We default to legal analysis because that's our training, but sometimes the issue isn't actually legal risk—it's reputational risk, ethical murkiness, or just plain bad judgment.

Start a simple document. Every time someone proposes something that's technically allowed but makes you uneasy for non-legal reasons, write it down. Document what happened, why it felt wrong, and whether the company did it anyway. Over time, you'll start to see patterns in the gap between "legal" and "right."

This practice does two things. First, it helps you get comfortable speaking up about business judgment, not just legal compliance. You'll start saying things like "That's legal, but here's why I think it's a terrible idea" with more confidence. Second, it trains you to spot the situations where your value goes beyond legal expertise—where you're the person willing to ask "just because we can do this, should we?" And you'll become the trusted advisor who catches these issues before they become PR nightmares.

We're hired to help our companies do the legal thing. We're most effective (and sleep best at night) when we also help them do the right thing.

7. Make a habit of talking to leadership about other people’s wins

Professional trust and credibility are built step by step, one action at a time. Sharing other people's wins is one of the simplest and most effective ways to build both.

When you tell leadership about a colleague's great work, three things happen. The person whose win you share looks great without having to self-promote. Leadership learns that good work is happening across the organization. And you become known as someone who lifts others up and pays attention to what's working.

Plus, the person you talked about remembers. They know you have their back. That matters more than almost anything else when it comes to building real professional relationships.

And also, talking up a colleague who did good work just feels great.

Win-win-win.

8. Embrace the idea of professional seasons

Your career doesn't have to look the same every year, or even every month. And pretending it should is exhausting. Because life changes, and so should your career.

As a 20-something BigLaw associate, I rarely left the office before 8PM and almost always ate dinner at my desk. But my late evenings were predictable—unexpected client calls were rare, and I could plan my life around the grind. As a 40-something General Counsel, I rarely work through dinner, but I'm often on my phone evenings, weekends, and on vacation because the business doesn't stop. When I was running my own business, life and work were completely indistinguishable, and eating smoothies for breakfast, lunch, and dinner while taking back-to-back calls was just Tuesday.

There have been seasons when I leaned all the way into my career—80-hour weeks, work as identity, every ounce of energy aimed at professional achievement. And there have been seasons when my job was just one small but important part of who I am, what I do, and how I view myself.

By embracing the idea that my career will look different at different times, I've built a richer, more fulfilling life than I ever could have with a steadier, more "consistent" approach. Some years you sprint. Some years you coast. Some years you explore completely new terrain. All of it counts. All of it builds the career that's actually yours.

Instead of trying to sustain the same pace and intensity forever, give yourself permission to have seasons.

9. Keep a “graveyard” list of deals that died and projects that went nowhere.

When was the last time you studied a deal that fell apart?

Most lawyers know the importance of studying our wins. We save the big contracts, celebrate the closed deals, reference the successful projects in performance reviews. But we rarely examine our failures with the same rigor, even though that's where some of the best learning lives.

Start keeping a graveyard list. Every time a deal falls apart, a project gets killed, or an initiative you worked on goes nowhere, write it down. Note what happened, why it died, and what you learned. Was it a valuation gap? A culture clash during diligence? A product the market didn't want? A regulatory hurdle no one saw coming? Leadership cold feet?

Over time, you'll start to see patterns. You'll notice which types of deals your company actually closes versus which ones leadership gets excited about but never pulls the trigger on. You'll learn to spot the early warning signs of a doomed project. You'll get better at asking the questions that reveal fatal flaws before you've invested weeks of work.

This practice also builds resilience. When you've documented twenty deals that died for reasons that had nothing to do with the quality of your legal work, the twenty-first one stings less. You stop taking it personally when things fall apart, because you can see it's just part of the process. And when you contributed to some of them failing, and realize it, you can avoid making the same mistake twice.

The graveyard may seem depressing, but it's one of your most valuable teaching tools. Failed deals teach you what your business actually values, what risks it won't take, and where the real decision-making power sits. Pay as much attention to what dies as to what survives.

10. Build a relationship with a challenging stakeholder

You know who I'm talking about. The executive who constantly pushes back on your advice. The founder who treats legal like an annoying speed bump. The sales leader who thinks every contract negotiation is you killing deals.

Most lawyers avoid these people. We deal with them when we have to, keep interactions transactional, and complain about them to our friends. That's a mistake.

Pick your most challenging stakeholder and deliberately invest in that relationship. Before you need anything and before a crisis arises.

Take them to coffee. Ask them about their goals, their frustrations, what keeps them up at night. Learn what success looks like in their world. Find out what they think legal doesn't understand about their job. And then—this is the hard part—actually listen without getting defensive.

You don't have to agree with their perspective or change how you do your job. But understanding why they see you as an obstacle instead of a partner gives you information you can't get any other way.

If you do this, something surprising might happen. That challenging relationship might become one of your most valuable ones. The stakeholder who used to fight you on everything starts coming to you earlier. They begin to trust that you're trying to help them succeed, not just protect the company. And when a real crisis hits, you have relationship capital to draw on.

That’s a wrap on part 2

You don't need to do all of these. In fact, you probably shouldn't—some of them simply won't make sense for you, your role, or your company. But if one or two stick with you, if they change how you think about success or how you show up at work, that's a win.

One of the most important realizations I've had moving along in my in-house career is that some people succeed by following the standard playbook. But a lot of us didn't. We succeeded by figuring out what works for us specifically, even when it looks weird to everyone else.

Your turn. Pick one tip from this list and try it this week.