Barbara Wittman: Lost in Transformation

In this episode, Eric talks with Barbara Wittmann, founder of the Digital Wisdom Collective, about why digital transformation so often fails despite good intentions, smart leaders, and expensive technology.

Barbara argues that most change initiatives don’t collapse at the top or the bottom of organizations. They collapse in what she calls “the juicy middle” — the layer where strategy meets execution, where quiet experts carry institutional knowledge, and where complexity actually gets absorbed or resisted.

Drawing on more than 25 years in enterprise technology and transformation work, including time at SAP, Barbara explains why transformation is rarely a technology problem and almost always an orientation problem. Leaders add tools, frameworks, and methodologies, but fail to upgrade the human capacity for judgment, sense-making, and collective intelligence.

The conversation explores why consultants often surface knowledge that already exists inside organizations, why the most valuable contributors are frequently overlooked or burned out, and how change accelerates when leaders identify and empower the right people rather than rolling out one-size-fits-all programs.

Eric and Barbara also discuss trust, diversity, and community, drawing connections to Putnam’s research on social capital and to How We Talk Can Change the Way We Work. They examine why complaints often signal care rather than resistance, how reading the room is a critical leadership skill, and why transformation is better understood as evolution rather than a project.

This is a grounded, experience-driven conversation for leaders navigating digital change, AI adoption, and organizational complexity — especially those who sense that progress depends less on new tools and more on how people think and work together.

Topics Covered