I have a fascinating conversation with Evan Campbell in this episode. Evan brings an unusually broad perspective to organizational transformation, drawing on a career that spans the U.S. Army Special Forces, telecommunications, software development, entrepreneurship, Lean consulting, and executive leadership. He is also the author of Adapt to Win, a book focused on helping organizations turn strategy into execution while developing the adaptability required to compete in a rapidly changing world.

Our conversation begins with a deceptively simple question: Why are so many organizations bad at executing their strategies? Companies spend millions developing sophisticated strategies, yet those strategies frequently fail to translate into meaningful changes in how work gets done. Evan argues that the problem often isn't the strategy itself; it's strategy deployment. By the time strategic intent travels from executives through layers of management to the people actually doing the work, the signal has often become distorted, fragmented, or lost entirely.

Evan also offers a useful test for whether an organization really has a strategy: Where do we play, and how do we win? If leaders across the organization provide dramatically different answers, or if the strategy consists entirely of statements nobody could reasonably disagree with, then the apparent alignment may be little more than superficial consensus. Real strategy requires choices, and choices necessarily mean deciding what the organization will not do.

We explore this through Evan's experiences inside large organizations, including an IT organization overwhelmed by more work than it could effectively process. Rather than confront excessive work in process and unstable delivery, leadership wanted to repair relationships with dissatisfied stakeholders. Evan uses the example to illustrate a recurring transformation failure: organizations often want consultants to address the symptoms of a broken system without changing the system producing those symptoms.

The conversation eventually turns toward AI and the latest wave of digital transformation. We see many of the same patterns that appeared during outsourcing, Agile, DevOps, and previous transformation movements. Organizations can easily mistake adopting a technology or creating a new department for actually transforming how they operate. AI may dramatically reduce the effort required to produce software, but that doesn't eliminate constraints. Understanding requirements, architecture, validation, strategic prioritization, and determining whether we're building the right thing become even more important.

Ultimately, this episode is about much more than strategy frameworks, OKRs, Lean, or AI. It's about building organizations capable of learning and adapting. Technology will continue to change, constraints will move, and today's transformation will eventually be replaced by another. The organizations most likely to thrive will be those that can understand their systems, make deliberate strategic choices, learn from results, and continuously adapt how they invest their limited resources.

Show Notes:

• Evan's book, Adapt to Win: https://adapttowin.co/ Also available on Amazon, Barnes & Noble, and other major retailers.
• Adaptivity Group (Evan's consulting firm): https://www.adaptivitygroup.com/
• Evan's YouTube Channel: https://www.youtube.com/@AdapttoWin-Book