LeadingAgile

I’ve spent the last 25 years trying to answer one question: how do you actually get a large, complex organization to deliver software predictably? The question hasn’t changed. The technology has changed. The buzzwords have changed. The funding model has changed. But the underlying problem has been the same one the whole time, and right now it’s wearing a new...

In my last article, Why Most App Modernizations Fail, I made the case that organizations know they need to modernize but are lacking a framework that remo...

Most Fortune 100 companies aren’t struggling with AI because they lack the right tools or models. They’re struggling because AI fails at the organizational level: fragmented data, misaligned incentives, no clear ownership of outcomes, and legacy systems that weren’t designed to feed production AI. It’s these issues that stop promising pilots from scaling int...

Application modernization continues to be at the forefront of organizations’ concerns as they struggle to respond to the undeniable acceleration of digital transformation and the ability to respond to rapid changes in the market. According to an October 2025 MarketsandMarkets [1] research report, spending on legacy application modernization is expected to gr...

Twenty-five years of change in the cost structure of technology created a minefield of risk as executives fund software application development, regardless of whether the software is sold or leased to customers or developed for internal use. Conflicting pressures lead to one breakthrough solution: Stop arguing about CapEx versus OpEx. Fund the ne...