Organized Chaos

In this episode, I talk with Barbara Wittmann, founder of Digital Wisdom Collective, about why so many digital and AI initiatives quietly fail, and what it really takes to make transformation stick. We go beyond tools and platforms to explore the deeper system of people, structures, and culture that Barbara calls “human infrastructure”, and why this matters even more in startups where the pace is fast and the margin for error is thin. Main Topics We CoverWhy Digital Transformation Fails (Even with Great Tech): How organizations keep treating transformation as an IT project, and the recurring people and structure patterns behind failure.Human Infrastructure as a Strategic Asset: What “human infrastructure” actually means—mindsets, capabilities, relationships, and learning rhythms—and why it should show up as its own budget line item.The Real Role of Middle Management: Why change “starts in the middle,” how middle managers become the load-bearing walls of any transformation, and what happens when they’re bypassed or underpowered.AI Without the Hype (and Without Panic): The difference between responsible AI adoption and shiny-object chaos, including the reality that some roles will disappear—mostly the ones that never fully leveraged human capability—and how this is an opportunity to double down on work humans do best.HR and IT as the New Power Couple: HR and IT must operate as true partners in startups, co-owning outcomes, roadmaps, and the design of how people and technology evolve together.What Startups and HR Leaders Need to Do Differently: Concrete guidance for founders and HR leaders on aligning tech choices with business outcomes, building human infrastructure early, and avoiding “transformation theater.”LinksConnect with Barbara on LinkedInLearn more about Digital Wisdom CollectiveConnectVisit organizedchaos.fyi and subscribe to the newsletter for more conversations and exclusive content. Have thoughts or questions about this episode? Connect with me on LinkedInReach out by email