Guardians of the Data | Navigating the Data Maze - Brian Cherry - Guardians of the Data

Navigating the Data Maze - Brian Cherry - Guardians of the Data - Episode # 43

May 21, 2026 / 47:15/E43

What data do you have, where does it live, and who has access to it?

These three questions sit at the heart of every data security challenge and according to Brian Cherry, most organizations still can't answer them.

In this episode, Brian, a Global Director of Information Security with over 20 years in cybersecurity, joins Ward to dig into the sprawling reality of data security: why data never stays where you think it does, how shadow IT and bad governance quietly create massive exposure, and why AI is raising the stakes on all of it.

Brian also shares how curiosity, mentorship, and asking the right questions shaped his entire career and why those same instincts are the most powerful tools any security professional can have.

Takeaways:

Know your data before you protect it. You can't secure what you can't find. Start by asking four foundational questions: What data needs protection? Where does it live? Have you truly looked everywhere? And who has access and how did they get it? These questions sound simple, but most organizations haven't fully answered any of them.
Act like an investigative journalist when talking to the business. Going into stakeholder conversations without pretending to have all the answers actually gets you further. When people feel like they're teaching you, they open up and that's when you learn where the real data risks are hiding.
Governance isn't sexy, but it's where the real power is. Red team exercises find problems, but governance is what actually prevents them. Policies, controls, and proper data classification programs are what keep businesses from accidentally creating their own worst security incidents.
AI is amplifying your existing data problems, not creating new ones. If sensitive data is scattered in shared directories, staging environments, or forgotten backups, any AI tool with access to it becomes a liability. Getting AI-ready means solving the fundamentals first classification, access control, and visibility.
Find a mentor, and be one. A mentor who pushes you to understand the business side of security, not just the technical side, can completely change your trajectory. And when you've made it, look back. The best investment you can make in the profession is helping someone else ask the next question.

Quote of the Show:

"If you don't ask questions, you're never going to know the answer. That's where my career started, and it's still the most powerful tool I have." - Brian Cherry

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