In this episode, Ward Balcerzak sits down with former CISO Todd Covert, who brings over 25 years of experience across healthcare, insurance, and fintech to unpack why data security still hasn't been solved. Todd breaks down the human side of the problem, from employees just trying to do their jobs without clear guardrails, to the challenge of protecting data whose sensitivity changes by the hour, to how AI tools have made it easier than ever to put information at risk without meaning to. The conversation moves from the technical to the deeply practical, covering how security leaders can build influence, communicate across different audiences, and turn their toughest critics into advocates.
Takeaways:
Most employees aren’t trying to misuse data, they’re trying to do their jobs, and often security hasn’t given them a clear, easy path to do it safely.
Data sensitivity isn’t fixed. A document can be highly confidential today and public tomorrow, and organizations still haven’t solved how to manage that shifting risk.
AI tools have made it dramatically easier to expose sensitive data, often without any bad intent involved, which raises the stakes on getting guardrails right.
Winning adoption for a security process means identifying your toughest critics early and working to turn them into advocates, rather than avoiding them.
Communication style matters as much as the message itself. Data driven leaders, emotionally driven leaders, and different departments all need to be approached differently to build real buy in.
"If I can take my toughest critics and turn them into advocates, that's where I can have that success." - Todd Covert
Connect with Todd:
LinkedIn: https://www.linkedin.com/in/toddcovert/
Ways to Tune In:
Transistor: https://podcast.guardiansofthedata.show/
Spotify: https://open.spotify.com/show/5gZXInkb12Qrs2Lyv0hstQ
Apple Podcasts: https://podcasts.apple.com/us/podcast/guardians-of-the-data/id1826819323
Amazon Music: https://music.amazon.com/podcasts/0754cdde-f1c4-4f6c-92a2-e263f7840eb8/guardians-of-the-data
iHeart Radio: https://www.iheart.com/podcast/269-guardians-of-the-data-285972170/