What General Counsel Actually Want From Outside Counsel
There’s a lot of guessing in the legal industry about what general counsel want from outside counsel.
More client alerts.
More CLEs.
More follow-up emails.
More credentials.
But when we sat down with Jessica Nguyen — Deputy General Counsel of AI Innovation and Trust at DocuSign and head of Contract Nerds — the answer was much simpler. General counsel want trust. They want relevance. And they want you to actually be helpful. Not theoretically helpful. Actually helpful.
Trust is doing what you say you’ll do
Jessica said something during our conversation that stuck with us:
Trust is doing what you say you’ll do.
Not “trust us.” Not “we value relationships.” Trust is built when you listen to what someone needs and then deliver on it.
That sounds obvious, but it’s surprisingly rare. Especially right now, when so many conversations in legal are wrapped around AI. Clients are still asking whether AI tools are accurate, secure, and responsible with data. The firms and companies that stand out are the ones that are clear about what they’re doing — and then actually follow through.
Most law firm marketing still misses the mark
Jessica was also refreshingly candid about law firm marketing. The formula hasn’t changed much:
sponsor an event
host a CLE
present a slide deck
hope people remember you
Meanwhile, half the room is answering emails and the other half is there for the CLE credit. That doesn’t mean CLEs or client alerts don’t matter. They do. But they only work when the content is relevant and useful. The issue isn’t the format. The issue is whether the audience actually wants what you’re sharing.
The content people want is the content that works
Contract Nerds is proof of that. Jessica shared that their webinars regularly draw more than 1,700 registrants, and some topics reach over 2,000. Anyone who works in legal marketing knows those numbers are wild.
But it’s not magic. It’s community. The topics are based on what the audience actually wants to learn. For law firms, the takeaway is simple: Less “here’s what we want to say.” More “here’s what our audience actually needs.”
What impressed this General Counsel most about outside counsel
When we asked Jessica if a law firm had ever really impressed her, the answer had nothing to do with credentials or legal analysis.
It was about a partner who understood her business. When she was GC of a startup, one of her outside lawyers took the time to understand that growth mattered most. He didn’t just provide legal advice — he offered introductions to other general counsel who could help the company grow. That’s what stood out. Not a pitch. Not a deck. Just someone adding real value.
The best business development question
Jessica shared one question that outside counsel should ask more often: “What’s keeping you up at night right now, and how can I support you?” That question opens the door to a real conversation. You don’t have to know everything in advance. You just have to listen and be willing to help.
The takeaway
If you’re trying to stand out with general counsel, the answer isn’t more noise.
It’s better relationships.
Be curious.
Be relevant.
Be useful.
And most importantly — do what you say you’ll do.
That’s what builds trust. And that’s what clients remember.
Want more conversations like this on legal marketing, business development, client experience, and what actually moves the needle for lawyers? Reach out to stage at info@stage.guide
