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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.
