Before I was a ghostwriter, I spent two decades running technology infrastructure and security for a major national retailer, plus years before that on SCADA systems, fraud detection, and the first disk defragmenter ever built. This series is what I learned in the server room. Real talk on cybersecurity, digital transformation, and the metaverse, from someone who did the work, not someone who read about it.
TechnologyMost digital transformation advice assumes you build software. I ran it for a retailer whose actual business was selling things, which is harder and different in ways the advice ignores, your transformation competes with the real business for money and…
TechnologyI ghostwrote three digital transformation books for executives, and it taught me what running transformations never did: each one did it completely differently, at Fortune 500 scale, agile and scrum where I had used waterfall, each with a methodology they…
TechnologyDo digital transformation in this order: people, process, technology. People first, always, asking what happens to each person, retrained, retired, moved where. Process next, where you often find the process is just broken and fixing it solves the problem with…
TechnologyThe hardest part of running technology was never the technology; it was that leadership spoke business while I spoke tech, and neither of us understood the other. I did not grasp how much that cost until the CEO of Trader…
TechnologyLegacy systems do not die because your roadmap wants them gone. I kept ancient ones alive for years, including a dead-vendor system on unmaintainable hardware with a database that existed nowhere else, no support, but it ran the business, so…
TechnologyMost digital transformations fail for an unglamorous reason: poor testing. Everyone checks whether the system works normally; almost nobody tests it under real load or watches what happens when it breaks. I saw systems go live with untuned queries that…
TechnologyDigital transformation is plumbing. The buzzword suggests a bold leap; the real work is infrastructure, one component at a time. I led enterprise transformations at a national retailer, and the method that worked was never a big bang, it was…
TechnologyI was never a CISO by title; my networking partner and I were both directors who, with a boss who was not security savvy, functioned as a de facto CISO together, setting the rules and getting them approved. The job…
TechnologyMost security tools are theater. I sat through endless vendor pitches for products with giant dashboards full of blinking widgets that looked impressive and did almost nothing. The attack surface is enormous, phones, laptops, servers, cloud, even charging cables, and…
TechnologyThe human layer is the biggest security weakness and the one people are least prepared for, because they do not expect the guy in the uniform, or the friendly caller, to be the attacker. You can harden every server and…
TechnologySecurity is mostly dull work nobody wants to do, patching, access reviews, backups, and it is also the entire job. Two decades in, the one time everything broke, it was backups that saved us, barely: a triple failure, snapped tapes,…
TechnologyAttackers rarely come through the firewall; if they do, you were sloppy, because the firewall is the easy part. The real vectors are social engineering and the insider, and the insider is the most common and most overlooked. Two decades…
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