I have worked alongside enterprise technology for more than 30 years and watched AI evolve from a lab experiment into the modern boardroom’s core focus. However, the last few years of implementing AI alongside our customers have delivered our most profound reality checks. The initial hype has faded, leaving CIOs to drive real enterprise value.…
DetailsPredicting an outage is tricky business, but CIOs might want to circle Oct. 11, 2026, through Jan. 11, 2027, for likely trouble of a potentially widespread and puzzling nature. That’s because a relatively trivial update to DNSSEC on Oct. 11, one that will take full effect by Jan. 11, is likely to deliver a series…
DetailsFor years, I have been saying that cybersecurity is no longer a technology problem. It has become a business leadership challenge. Yet, despite record levels of spending, ever-growing security teams, increasingly sophisticated technologies and a constant stream of new regulations, organizations continue to suffer major cyber incidents with alarming regularity. Every week seems to bring…
DetailsLate in a large enterprise SAP transformation, the strategic governance conversations began to drift. Instead of executive decisions, we found ourselves debating whether the program needed dedicated testing, whether cutover required a full weekend, whether twenty Agile teams really needed coordination support and whether offshore resources were adding value at all. The questions were not…
DetailsGoogle CEO Sundar Pichai has sought to allay concerns over the delayed release of the Gemini 3.5 Pro large language model. He dodged questions about it in Google’s quarterly earnings call on Wednesday by focusing on the company’s next frontier AI model, Gemini 4, and plans to release subsequent LLMs at an almost monthly cadence.…
DetailsOpenAI has launched Presence, an enterprise service for deploying voice and chat agents that can resolve customer and employee requests, potentially automating some work now handled by frontline support teams. The agents can answer questions and operate IT systems, and enterprises can decide what actions the agents may take and when they should seek human…
DetailsCloudflare recently beat Q1 2026 earnings. Revenue up 34% year over year. EPS ahead of consensus. Full-year guidance raised. Then, in the same breath, they announced 1,100 layoffs, 20% of the company. CEO Matthew Prince’s explanation: “The way we work at Cloudflare has fundamentally changed.” Block did the same thing. Beat guidance, raised outlook, cut…
DetailsThe traditional methods of measuring success no longer tell the full story. Here’s what should replace them — and why. In brief: AI is transforming software as a service (SaaS), and the old ways of keeping score no longer apply. Smart companies are evolving new metrics that provide deeper insight into how AI-native software is…
DetailsOver the past few years, I have learned that basic prompts produce inconsistent, hallucination-prone results that no executive would trust in production. What turned the tide was my move to advanced prompting techniques. These weren’t theoretical experiments; they became a practical foundation for reliable, measurable outcomes. I want to share the techniques that consistently delivered…
DetailsI haven’t slept much in the past few weeks. Not because of some theoretical cyber risk that keeps many executives awake, but because reality just delivered a real wake-up call to our industry — a call that every executive must answer, now. Imagine this: A major global enterprise, a company most of us interact with…
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