Legal boundaries, when approached creatively, can lead to smarter, more innovative solutions.
The post Start With ‘Yes, If’: How I Help Teams Innovate Without Fear appeared first on Above the Law.
“No.” It’s the word that strikes dread into product teams when they hear it from legal counsel. It signals roadblocks, delays, and shelved ideas. Early in my career, I saw this play out again and again. Saying “no” felt like the safest choice, but it often killed momentum — and trust.
Then I started shifting my approach. Instead of leading with “No, we can’t,” I began framing my feedback as “Yes, if we …” This subtle change unlocked collaboration and innovation while still keeping the company on solid legal ground. Here’s how this mindset has transformed how I work with product teams — and how it can work for you.
Understand The ‘Why’ Before You Respond
Before shutting down an idea, ask why it’s on the table in the first place. What problem is the team solving? What’s the goal behind the feature or campaign?
Once, a team wanted to scrape publicly available data for an AI project. Instead of saying, “That’s too risky,” I asked, “What’s the outcome we’re trying to achieve?” Together, we explored alternatives like licensing agreements or using open datasets. The team still hit their goal, but without the legal headaches.
The takeaway? Understanding the “why” shifts the conversation from risk avoidance to goal achievement.
Frame Risks As Design Challenges
Every risk is also a design opportunity. Legal boundaries, when approached creatively, can lead to smarter, more innovative solutions.
For example, when a rewards program risked violating state lottery laws, I didn’t say no outright. Instead, I suggested tweaks to the structure — like skill-based competitions — that met legal exceptions. The final program was not only compliant but also more engaging for users.
What I’ve learned is simple: legal constraints don’t have to stifle creativity. They can inspire it.
Always Offer A Path Forward
Teams need solutions, not just red flags. If you spot a problem, pair it with a way to move forward.
For instance, a startup team wanted to use customer testimonials in ads. Saying “That’s risky — it could be misleading” would have shut the idea down. Instead, I said, “Yes, if we verify the claims and include disclaimers to meet advertising laws.” The team got their campaign, and the company stayed compliant.
A “Yes, if we …” approach builds momentum instead of stopping it cold.
Weigh The Risk Versus The Reward
Not every risk is worth taking, but not every risk is a deal-breaker, either. Legal counsel adds value by helping teams evaluate which risks are worth it.
When a team wanted to launch a feature that might invite regulatory scrutiny, I didn’t veto it outright. Instead, we analyzed the potential rewards — customer loyalty and competitive advantage — and paired them with a mitigation plan. The result? A bold move that paid off.
Balancing risk and reward is key to helping teams innovate responsibly.
Break Big Risks Into Small Steps
When a project feels overwhelming, propose incremental progress instead of an all-or-nothing approach.
For example, a team launching a complex subscription model faced tricky tax regulations. Instead of delaying the entire rollout, I suggested starting with simpler regions to test and adapt. Breaking it into smaller steps minimized risk and kept the momentum going.
Small wins build confidence — and trust.
Be A Partner, Not A Referee
The earlier legal is involved, the better the outcomes. By joining brainstorms or design sessions early, you can shape ideas into legally viable solutions before they become problems.
When I sat down with engineers to co-design a compliance-heavy feature, we avoided costly rewrites later. Similarly, being part of marketing discussions helped guide bold campaigns while keeping them safe from legal pitfalls.
Collaboration is how you turn legal from a roadblock into a trusted ally.
Celebrate Wins
When your guidance leads to a success, make sure to celebrate it. This reinforces your value as a partner and builds trust for future collaboration.
For example, when our privacy-first data strategy became a customer favorite, I made sure the team recognized how legal had contributed. Wins like these make teams eager to involve legal in their next big idea.
The Bottom Line
Starting with “Yes, if …” isn’t about ignoring risks. It’s about showing your team that you’re invested in making their ideas work. By focusing on solutions and being a partner in the process, you can help teams innovate with confidence — and without losing sleep.
For more strategies on how to balance innovation and risk as a product lawyer, check out my book, “Product Counsel: Advise, Innovate, and Inspire.” It’s filled with practical insights and real-world examples to help you lead with solutions and become a trusted partner to your teams.
Have you tried a “Yes, if we …” approach? I’d love to hear your experiences — let’s keep the conversation going.
Olga V. Mack is a Fellow at CodeX, The Stanford Center for Legal Informatics, and a Generative AI Editor at law.MIT. Olga embraces legal innovation and had dedicated her career to improving and shaping the future of law. She is convinced that the legal profession will emerge even stronger, more resilient, and more inclusive than before by embracing technology. Olga is also an award-winning general counsel, operations professional, startup advisor, public speaker, adjunct professor, and entrepreneur. She authored Get on Board: Earning Your Ticket to a Corporate Board Seat, Fundamentals of Smart Contract Security, and Blockchain Value: Transforming Business Models, Society, and Communities. She is working on three books: Visual IQ for Lawyers (ABA 2024), The Rise of Product Lawyers: An Analytical Framework to Systematically Advise Your Clients Throughout the Product Lifecycle (Globe Law and Business 2024), and Legal Operations in the Age of AI and Data (Globe Law and Business 2024). You can follow Olga on LinkedIn and Twitter @olgavmack.
