Structure Before Features with Evan J. Schwartz

There’s a particular kind of exhaustion that hits when you’re building with AI. You’ve got the license. You’ve got the pilot. You’ve got a chat window that generates whatever you ask for. But then comes the wall—the workflow that almost works, the dependency that loops back on itself, victories that only come when you quietly move the goalposts. In this episode, we talk about how to get around the wall.

Evan J. Schwartz, Chief Innovation Officer at AMCS Group and an adjunct professor teaching AI stewardship, argues the real shift isn’t “AI does the work.” It’s that humans stop owning the full vertical of doing and start owning outcomes—while AI takes more of the output. That sounds abstract until he gets specific: if you ask a model for a feature before you describe actors, containment envelopes, and dependency policy, you’ll get something that passes the demo and fights you every time you try to change it.

Josh Tyson and Robb Wilson push on the organizational version of the same mistake—automating fifty-five use cases exactly as humans do them today, then acting surprised when nothing compounds. Evan’s answer is a two-step path that respects how messy humans actually are: first compress low-value work into AI for a confidence-building lift; then rethink the whole iterative cycle for asymmetric returns.

Also, learn why “no change without pain” isn’t cynicism, why POCs love moving goalposts, why big enterprises optimize one segment and break the connective tissue upstream, and why the scarcest resource won’t be another prompt library—it’ll be people who can think about constraints.

We cover: AI stewardship and the inverse-pyramid skill set, outcome vs output, structure-before-feature development, the two-step adoption path, risk-averse vs innovator cultures, SMB speed vs mid-market discipline vs enterprise battleships, critical vs non-critical systems, and why cutting headcount first is how you donate your newly trained stewards to your competitor.

Guest: Evan J. Schwartz, Chief Innovation Officer, AMCS Group; Adjunct Professor, Jacksonville University

Hosts: Josh Tyson, Robb Wilson

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