The Digital Dilemma: Tech, Risk & AI for Leaders
Monthly insights from The Digital Dilemma Podcast on cybersecurity, IT, and AI governance for business leaders. We translate complex technology and compliance decisions into clear moves that protect your data, your team, and your bottom line.
Lead the human side of AI change, not just the tech
Why Jennifer Santoso insists communication, coaching and real training beat secrecy — and how to do each one concretely.
The three fixes that make AI safe and useful at work
Nick Dreyfus on the data rules, skills, and ownership every business needs before they hand employees an AI login.
Copilot is a search engine on top of your secrets
Nick Dreyfus: turning on Copilot doesn't add risk — it makes 20 years of forgotten permissions readable in seconds.
The spreadsheet your agency read (and what to ask on Monday)
How a stray accounting file taught one company that vendor AI use — not your employees — is the bigger risk
Don't treat AI like an employee — treat it like a trainee
Why a model that's 'wrong 1 in 8 times' needs guardrails, a watcher, and a plan for where saved hours actually go.
The account that never died and the two kinds of IT problems
Why the riskiest things cost nothing to fix — and the seven questions every CEO should ask this week.
Who’s running AI on your data? The vendor you didn’t ask
Why a signed employee acknowledgment and four one-minute questions to vendors can stop data leakage — before the courts decide.
When an AI 'just kept trying': what CEOs must ask now
Nick Dreyfus on the OpenAI–Hugging Face incident, why persistence beats perimeter, and three questions your leaders should answer this week.
Why most AI projects never show up on the P&L
Nick Dreyfus explains the 98% vs 95% paradox, the one-sentence tripwire, and how to turn ‘saved hours’ into real revenue.
AI's True Role: Beyond the Hype and Headlines
Unpacking the 95% AI failure rate and finding real value
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