The article addresses a common tension between product managers and risk management teams, particularly legal departments. It highlights how miscommunication can occur when product managers misunderstand the level of risk they can navigate. Legal teams often flag issues, which product managers interpret as outright rejections rather than cautionary advice. This misinterpretation leads to frustration on both sides, with legal appearing overly cautious and product teams feeling their decisions are second-guessed. To improve this dynamic, both roles need to adjust their approaches. Risk management professionals must not only provide technically sound advice but also consider how their guidance is received. If their input consistently comes across as a hard stop, they should refine how they communicate, emphasizing context and trade-offs to empower decision-makers. On the flip side, product managers should not accept “no” at face value. Instead, they should actively seek solutions, understand the underlying concerns, and work towards mitigating risks while balancing business needs with user interests. Ultimately, the goal is to avoid treating every flagged risk as a catastrophic issue. Organizations should cultivate the ability to navigate ambiguity, enabling them to make informed decisions about risks without stalling progress. Emphasizing a mindset of looking for possibilities instead of focusing solely on obstacles can lead to more effective outcomes.