AI, modernized — written for the people who run the business.
No jargon. Just clear, practical guidance on deploying AI, managing risk, and modernizing your technology — most of it straight from The Digital Dilemma podcast.
The Account That Never Died: Two Kinds of IT Risk
Some technology risks cost nothing to fix. Others require planning and investment. Learn how leaders can identify and manage both.
Treat Business AI Like a Trainee, Not an Employee
AI can work quickly and confidently while still being wrong. Learn how guardrails, review, and clear ownership make business automation safer.
Is a Vendor Running AI on Your Company Data?
Your agencies, bookkeepers, and consultants may already use AI on company information. Four questions can reveal and reduce that risk.
When AI Keeps Trying: What Leaders Must Control
AI persistence creates value and risk. Learn how access limits, recovery testing, and human approval keep autonomous systems under control.
Why Most AI Projects Never Reach the P&L
Saved time is not automatically ROI. Learn how to choose measurable AI projects, set a 90-day tripwire, and turn capacity into revenue.
15 Minutes or 4 Hours: Why AI Should Do 80% of Your Team's Busywork
Your highest-paid people spend half their day on grunt work a machine should handle. Here is the data, the real ROI, and how to deploy AI the right way.
Secure AI, or Explain the Breach to Your Board?
Nearly 35% of what employees paste into ChatGPT is sensitive data. Here is the real risk profile of every major AI tool — and how to deploy AI securely.
Shadow AI Is Already Inside Your Business — IBM's 2025 Numbers
IBM's 2025 data: 1 in 5 organizations breached through shadow AI, $670K in added cost, 247 days to detect. The risk, the Amazon story, and 4 steps to take this week.
What Is Shadow AI — and How to Find It in Your Business
Shadow AI is the unsanctioned AI tools your team already uses at work. Here is what it is, why it is risky, and a practical way to find it.
AI in the Boardroom: 5 Questions You Must Answer
Your board is about to ask about AI. The five questions they're really asking — ROI, moat, risk, talent, accountability — and the answers that build confidence.
AI Readiness Is Not an IT Project
AI isn't software you hand to IT — it's a leadership decision. The real readiness gap is data quality, process ownership, and decision rights — not the tool.
The Illusion of Privacy: Are You Really in Control of Your Data?
Anonymized isn't anonymous. Incognito isn't private. The real stories — Netflix, Acxiom, Apple vs. Facebook — and practical steps to take back control of your data.
The Replacement Myth: AI Isn't Coming for Your Best People
The headlines say AI is replacing the workforce. The data from Goldman Sachs, Harvard, and the Dallas Fed says something very different. Why judgment is the moat.
Cloud Smart, Not Cloud Costly: Is Migration Worth It?
The cloud promises savings and scale — but hidden fees, sprawl, and security gaps catch businesses off guard. How to build a cloud strategy that actually pays off.
Untangling the Web: Is Your IT Network Too Complex?
Over-complex networks quietly kill productivity and reliability. Three questions to tell if your IT is holding your business back — and how to simplify it.
Why Cybersecurity and Compliance Feel Impossible as You Grow
Ten reasons security and compliance overwhelm growing companies — outgrown tools, human error, shifting regulations — and how to turn each one into a strength.
How AI Is Actually Transforming Businesses Today
Six ways AI is already changing how businesses run — from automation to security — and the practical place a smaller company should actually start.
Why Your Cyber Insurance Might Not Pay When You Need It
Seven reasons cyber insurers deny claims — vague definitions, missed deadlines, "failure to maintain" exclusions — and how to make sure your policy pays out.
The IT Maturity Journey: Why Your IT Provider Matters
The 5 levels of IT maturity, from chaotic to strategic — and the one-year test for whether your IT provider is moving you up or just keeping the lights on.
Zero Trust: Lessons from the Halliburton Cyberattack
Cyberattacks on Halliburton and the Port of Seattle show why critical infrastructure needs zero trust. A practical security audit, segmentation, and response plan.