Cityblock Health’s GC Wendy Chow talks automating Q&A with Josef, AI adoption hacks, and more

Wendy Chow is General Counsel at Cityblock Health, a healthcare provider headquartered in New York City.

Recently, her team began creating AI Q&A tools on Josef to automate repetitive Q&A, and give the business instant access to legal knowledge as and when it’s needed.

Wendy sat down with Josef Co-founder Sam Flynn to talk about the tools, why successful tech adoption starts at hiring, her pragmatic take on AI, and more.

Watch the conversation above, listen on Apple Podcasts, Spotify or YouTube, or read our recap below.

4 problems that plague every GC

From Wendy’s perspective, every General Counsel faces the same fundamental challenges:

1. Understanding macro and micro environments: Assessing political, economic, and internal forces driving their business
2. Answering repetitive legal questions: Fielding questions that have often been answered before or are documented in existing policies
3. Managing throughput vs. burnout: Balancing team productivity with employee wellbeing under constrained budgets
4. Delivering value and showing that you’re delivering value: “You have to make sure that your team is both delivering value and you have to demonstrate that they’re delivering value,” Wendy explains. “And actually those two things are not the same.”

Deliver value then make it known!

Most legal teams focus on the first part but struggle with the second. Wendy’s solution?

First, solve problems, not just answer questions. “You’re trying to solve problems. In the course of solving problems, you are answering questions, but it cannot just be that transactional.” Instead, she says, “What is the thing that they’re trying to solve? You have to get inside of that.”

Second, speak the business’s language: numbers. “The business speaks in numbers. Finance absolutely speaks in numbers. That is their language. And you have to speak in their language in order to demonstrate value.”

The keys to tech adoption

“I hear all the time about GCs saying they have a vision for some idea or some tech, but the team’s really struggling with adoption,” Wendy says. Her solutions?

#1 Hiring

Successful adoption doesn’t start “when you’re convincing your team of a tool that you really like,” she says. “It starts at hiring!”

During interviews, Wendy makes it explicit that an open, growth mindset is core to being on her team: “We literally talk about this during the interview… this is what the culture is gonna be like.” By screening for adaptability early, change becomes much easier later down the line.

#2 Legal ops is not subservient to legal

“Legalops reports to me. They always have, and always will,” she says. Wendy’s reason? “I want to demonstrate that legalops is not subservient to Legal.”

By positioning legal operations as peers, not support staff, Wendy ensures they have authority to drive change, selecting and implementing tools alongside Legal, not beneath it.

#3 Choose the right tool!

“I’m really, really picky about the tools we adopt,” she says. “They need to be beautiful, easy to use and the implementation time needs to not be that much.”

Now, with Josef, Wendy says, “you can load in a solid policy and out of the gate, the answers the tool generates, even untrained, are pretty great!”

The business wants validation, not an answer

One of Wendy’s hottest takes: “Policies are literally self-service… But [employees] want legal to give them that answer so they feel 100% sure they’re not messing up.”

The business doesn’t just want information, they want confidence that comes from legal validation.

Tech democratizes access to the science of law, not the art

“AI is democratizing access to the science part of law,” Wendy explains. It helps people quickly get answers to questions like: “What does this contract say?” or “What does that law mean?”

For Wendy’s team, this means more time to focus on “the art”: solving problems and unblocking the business faster, instead of answering the same questions repeatedly.

“What is the EIN for one of our entities?”

Wendy jokes that one measure of Josef’s success will be “if anyone on my team has to keep answering what is the EIN for whatever entities.”

For her legal team, this means less busywork and more time for higher-value, strategic work.

For the business, it means speed and confidence: the company’s hundreds of staff will get instant access to answers sourced from Legal’s own trusted documentation.

Turn off that lizard brain

Beyond automation, Wendy points to prioritizing health and wellness as key to sustaining performance:

“It’s natural to feel like you should sacrifice your health for work… But that’s absolutely a short-term play. If you want to maximize the total hours you’re productive, focusing on mental and physical health is actually the path to that.”

Wendy’s advice? “Everybody should start meditating.”

That way, “you’re not just reactive and it’s not just your lizard brain that comes online first. You can be so much more creative in your solutions,” Wendy says.