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Hi there! It’s Heather Stevenson.

Happy Wednesday and thanks for being here! Here’s what’s covered in today’s issue:

  • A word from today’s sponsor, Wispr Flow. I started using Wispr earlier this year, and it has been an absolute game changer. Whether I'm drafting emails that it cleans up and makes professional but still in my voice, or using it for long prompts, it makes me more efficient and my life easier.

  • Why your legal advice may not be landing, and a three-step framework for delivering the same guidance in a way your colleagues will actually hear and act on.

  • Links you’ll love;

  • And More.

Let’s dive in.

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Deep Dive

When Being Right Isn’t Enough

Early in my career, I learned something that reframed the way I think about delivering legal advice. Rather than learning from a mentor or a book, I learned this particular concept from watching my own words fall totally and completely flat in a conference room.

I was working on a contract with meaningful supply chain exposure. Our performance depended on a number of smaller vendors — and if any one of them missed a delivery window, we'd be late on our own obligations. The contract gave the counterparty immediate termination rights at that point, plus damages, after we'd already put in significant time and spend.

My first attempt at flagging it was technically correct: "This opens us up to breach of contract risk and is unbalanced."

Crickets. Polite nods. Zero traction.

So after a few minutes of discussion on other aspects of the deal, I tried again — same risk, different words: "If any of our small vendors don't perform, it could cost us several people's work over two weeks and thousands of dollars — and we could lose the contract entirely."

Suddenly everyone was glad I'd raised it. We agreed to push for, and ultimately got, the change.

The advice didn't change. The framing did. I've seen that same gap play out dozens of times since.

Why “Communicate Differently” Isn’t What You Think

When lawyers hear "communicate differently," our instinct is to get defensive. We aren't going to soften our advice to make people comfortable. We're fine with not being liked, and we won't downplay risk for the sake of it.

But that defensiveness misreads the direction. Communicating differently doesn't mean softening your guidance. It means reframing it — recentering it on the business.

"Breach of contract risk" is a legal conclusion. It's accurate, and it means almost nothing to a business colleague who didn't go to law school and isn't thinking in those terms. "You could lose the contract and eat the costs after two weeks of your team's time" is a business outcome — one they can picture, one they can feel, one that connects to something they actually care about.

Your colleagues weren't ignoring the risk in that first version. They just didn’t really see it, or its importance. The abstraction got in the way.

This matters because the risk police reputation doesn't usually come from lawyers who are wrong. It comes from lawyers who are right but sound like they're speaking a different language — one that signals "slow down" without ever explaining why, or what to do about it. Over time, that pattern teaches people to route around you rather than to you.

The goal is to be heard. And to do that, the move is translation — keeping the integrity of the advice while delivering it in the language of whoever needs to act on it.

The Structure I Come Back To

Once you've made the mindset shift, you need a repeatable structure. Here's the one I come back to, in three steps.

Start with the business goal. Before you say anything about risk, anchor yourself out loud in what your colleagues are trying to accomplish. This proactively signals that you understand the context and you're working toward the same outcome. "I know we want to close this deal as soon as possible" or "I understand we need this vendor locked in before Q3" tells the room you're a participant in the business goal, not just a checkpoint they have to clear.

Name the risk in outcomes, rather than categories. This is the translation step. Swap the legal conclusion for the business consequence. Not "this creates indemnification exposure" but "if something goes wrong on their end, we're on the hook for their costs too." Not "the IP assignment is ambiguous" but "we might not actually own what we're building." The test is simple: could your CFO or your head of sales picture what you're describing just as easily as your outside counsel could? If not, you haven't translated yet.

End on the path forward. This is the one lawyers skip most often. We flag the issue, explain the risk, and then stop. But the people in that room need to know what to do next. Give them the move: what changes in the contract, what the ask is, what a reasonable middle ground looks like. You don't have to solve every scenario. You just can't leave them sitting with a problem and no direction. Advice that ends at "this is risky" is only half-delivered.

Going back to that contract: the version that worked hit all three. It acknowledged what we were trying to accomplish, named the risk in terms the team could feel — time, money, the deal itself — and pointed directly at what needed to change. That's what business-minded legal advice and partnership requires.

Same Advice, Different Landing

The "department of no" and risk police labels don't stick because lawyers care too much about risk. Caring about risk is part of the job, and a good thing. The labels stick because the advice arrives in a language that feels like friction, which is something to push back on or route around, rather than information people can use.

You don't have to choose between rigorous advice and a seat at the table. The lawyers who lose that seat aren't usually the ones who said no too often. They're the ones who made it hard for anyone to understand what they were actually saying, or to understand how to move forward.

Give the same advice. But deliver it in the language of the business. That's the whole move.

Try it this week. Pick one conversation where you'd normally lead with the legal framing and flip the order. Start with the goal, translate the risk, end with the path forward. See what changes.

That’s it for today.

But before you go, here are a few links I think you will enjoy.

Each week, I share content from across the web that will help make your life as an in-house lawyer better. Let me know your favorite.

Thanks for reading! Look out for the next issue in your inbox next Wednesday morning.

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