Navigating AI Leadership with Cynefin
In the previous post, we explored how AI is making it possible for everyone to be a CEO, by lowering the barriers to execution and putting powerful tools in the hands of individuals. This newfound agency creates a more dynamic and unpredictable landscape. To navigate this, leaders need new sense-making tools.
AI leadership needs Cynefin's sensemaking discipline to decide when to experiment, when to codify, and when to get out of the way. Wardley Mapping explains how components evolve along the value chain, but leaders still have to choose the right play for the terrain in front of them. Cynefin complements Wardley Mapping by framing how decision-making should adapt when the landscape is obvious, complicated, complex, or chaotic—exactly the challenge AI agents introduce.
How this post fits the series
- Anchors the series in a shared sensemaking language after the opening essay on AI-enabled agency.
- Sets up the need for continuous map governance so Cynefin decisions rest on live data instead of static diagrams.
- Prepares the ground for autonomous strategy execution, where that governance becomes executable doctrine.