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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.

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.