Legacy systems run more of the world than anyone admits, and replacing them is rarely as simple as buying something new. These articles cover maintaining, modernizing, and reasoning about the old systems businesses still depend on.
Change ManagementJuly 4, 2026
Nobody in the room called it digital transformation, because the term did not exist. We had a retailer running accounting, HR, and payroll on paper, a mandate to computerize all of it, and years later the industry invented a name…
Digital TransformationJuly 4, 2026
Friday we were on the old platform. Monday we were on the new one, and it was buckling. We stood at the edge of a rollback with the whole company standing on a system that could not carry the load,…
Change ManagementJuly 4, 2026
The system that worked yesterday would not come up today, and there were no logs to explain why, because the failure was the logging. We spent three days awake hunting an earthquake. The cause was a punctuation mark, and the…
Digital TransformationJuly 4, 2026
The migration budget covered the conversion, the cutover, the infrastructure, the testing. The real bill arrived afterward, by invoice: hundreds of SQL queries that had to be re-optimized for the new platform, by six specialist DBAs, over six months, on…
Digital TransformationJuly 4, 2026
We were hunting for a machine during a disaster recovery effort. Systems were talking to it, work depended on it, and it was not in the server room. We found it under a user's desk in accounting, running decade-old software,…
Change ManagementJuly 4, 2026
People ask what our transformation covered, and the honest answer sounds like bravado: everything. Accounting to SAP, HR and payroll to SaaS, merchandising to a real system. The completeness was the hardest-won property of the program, and the point of…
Business ContinuityJuly 4, 2026
The consultant's heroics got the disks back. Then came the part the first article only promised: bringing up applications that had been written on the assumption they would never stop. No restart procedures, no known states, dependencies documented in nobody's…
Digital TransformationMay 27, 2026
In 1980 a snow-locked water district faced a problem the era's technology could not solve: pumping stations cut off from central command for weeks each winter, with the water still needing to flow. The team built autonomous controllers in Pascal…
Executive GhostwritingApril 30, 2026
The technology executive's career is a real story almost nobody captures: the arc from writing code to running the whole operation, the disasters survived, the political fights to fund critical work, the teams built and led. I lived that arc,…
Digital TransformationApril 16, 2026
Most 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…
Change ManagementApril 2, 2026
Do 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…
Digital TransformationMarch 26, 2026
The 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…
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