In episode nine of Compliance Chronicles, we learn from Deb Sokol the importance of embracing the gray and look at the evolving nature of compliance. Deb shares her compliance journey and lessons she's learned along the way.

What we cover:

• Being open to new opportunities and volunteering for stretch assignments can unexpectedly launch a career in privacy and compliance
• Moving from a pure legal role into a compliance role requires a mindset shift toward controls, documentation, metrics, and disciplined, programmatic thinking
• Mature compliance programs are built on clearly defined controls, monitoring, testing, and consistent documentation
• Privacy and AI work often happens “in the gray,” where laws are incomplete or unclear, and professionals must use analogies, principles, and creativity
• Giving specific, actionable guidance to the business is challenging when statutes and regulations leave gaps or ambiguities
• Rotations or close work inside a compliance function help lawyers better understand operational realities and what “good” looks like on the ground
• Building a strong network and “phoning a friend” — peers, experts, and trade organizations — is critical when working in uncertain or novel areas
• Learning to be comfortable with ambiguity reduces anxiety and enables better decision-making in evolving regulatory landscapes
• Effective compliance planning starts with mapping principles and end goals, then designing a practical program around them
• When teams feel overwhelmed by a compliance plan, it helps to prioritize: start with what is highest risk or what must be done first to enable everything else
• Version one of a solution does not need to be perfect; a good-enough, law-compliant baseline can be iterated over time
• Risk-based prioritization allows teams to focus limited resources on changes with the greatest impact, while deferring lower-risk improvements
• Stepping outside your comfort zone is essential for growth in privacy and compliance, even when it feels uncomfortable
• Raising your hand and being known as someone willing to try new things expands opportunities and builds a deeper experience base
• Each new experience, even tangential ones, adds to your toolkit and confidence for future roles and challenges
• Curiosity is a superpower in a fast-changing field; asking follow-up questions and staying inquisitive keeps you adaptable and effective

If you enjoy this conversation, make sure to subscribe to Compliance Chronicles in your favorite podcast app and follow the show so you don’t miss future episodes on privacy, AI, internal audit, and real‑world compliance leadership.