AI Watching AI
At scale, humans can't review every agent interaction. The case for guardian agents — and why AI overseeing AI is uncomfortable but probably inevitable.
Tag: CTO Leadership
23 articles tagged with "CTO Leadership"
Time to Hello World
Vibe coding made getting to a first API call table stakes. The harder question: was your documentation written for the agent reading it for a user?
Built Secure, Deployed Dangerous
An agent built correctly can still drift into dangerous territory through misconfiguration. Most organizations have no way to detect it until something breaks.
Not Every Decision Needs a Human... But Some Do
Most AI agents run at whatever autonomy level was easiest to implement, not the one that reflects actual risk. Here's how to tell the difference.
The Agent Can Think. It Just Can't Get to the Data.
The biggest barrier to real AI automation isn't the model. It's connectivity. And the protocol solving it is creating your next governance problem.
Your Digital Workforce Has a Landlord
Thousands of AI agent workflows disrupted overnight — not because agents broke, but because a vendor changed its billing. That's a governance failure.
Every Agent Needs a Badge
Most organizations badge their contractors, track their access, and revoke it when they leave. They don't do any of it for AI agents. That gap is closing fast.
Your AI Strategy Is Only as Strong as Your Inventory
You can't govern, defend, or prove value from AI systems you can't account for. Why inventory is the first place enterprise AI governance gets real.
Who Owns the Outcome? Governing the Age of AI Sprawl
AI agent sprawl is outpacing enterprise governance. Here's why that's a leadership problem — and what the governance stack actually needs to look like.
AI Questions Every Leader Should Be Asking
Most AI initiatives fail not because the technology is immature, but because leaders never asked the right questions. Ten worth asking now.
The Rise of Artificial Confidence
AI delivers answers with total certainty, even when it's wrong. How artificial confidence is quietly eroding critical thinking in technical teams.
The CTO’s Edge: Demo-First Leadership in the Era of AI
Slide decks don’t win executive buy-in for AI investments. Why demo-first leadership closes the gap between technical vision and board-level confidence.
The CTO’s Edge: Leading Through Constraints
The best technology leadership lessons come from working within real constraints. How resourcefulness under pressure builds the skills that matter most.
The CTO’s Edge: From Technical Leader to Technology Executive
Technical skill gets you noticed. Business thinking gets you the executive role. What actually changes when you move from managing delivery to leading strategy.
The CTO’s Edge: Rethinking Build, Buy, Partner in the Age of AI
“AI changed the build-buy-partner calculus. A practical framework for deciding when to build custom AI, buy off-the-shelf, or partner for capabilities.”
The AI Hype Trap: Why You Should Be Skeptical of Overnight Success Stories
“Most AI success stories collapse under basic business scrutiny. How to separate real product-market fit from tech theater and weekend demos.”
The CTO’s Edge: Technical Leadership Isn’t Just Architecture… It’s Organizational Design
Most “technical” decisions aren’t technical. They’re organizational choices masquerading as system design. They may feel technical, but in reality...
The Real AI Transformation Starts When You Stop Talking About AI
The companies getting real value from AI have stopped talking about it. What post-hype AI adoption looks like when it's embedded in actual workflows.
The CTO’s Edge: Why Empathy, Learning, Accountability, and Quiet Influence Matter More Than Ever
We talk extensively about tools, architectures, frameworks, and roadmaps in tech. However, when it comes to leadership, especially at the executive level...
The Developer Paradox: Why Technology Innovation and AI Keep Creating More Dev Jobs
Every productivity tool was supposed to reduce demand for developers. Instead, the industry grew from under 1M to 27M. Why AI will likely do the same.
What It Means to Be Data Intentional
Most organizations collect far more data than they use. A data intentionality strategy focuses collection on what matters and turns it into decisions.
What It Means to Be Data Intentional
Most organizations collect far more data than they use. A data intentionality strategy focuses collection on what matters and turns it into decisions.
Overcoming flat data to unlock business insight and productivity
Flat data trapped in documents, PDFs, and forms costs businesses time and money. Contextual data extraction turns isolated information into actionable insight.