Executive Interview Series: Enterprise Agility with Jim Highsmith, Independent and Thought Leader

Featuring Jim Highsmith, and Lenka Pincot - June 15, 2026

Overview

In this conversation, agile pioneer and Agile Manifesto co-author Jim Highsmith reflects on the evolution of agility from software development to the enterprise level. He argues that enterprise agility is not simply about responding to change but also about shaping it, requiring organizations to develop strong sensing capabilities, embrace continuous learning and build leadership judgment. To achieve it, organizations must move from a mindset of control toward one of learning and adaptation. He also explores the role of AI as both a driver of disruption and an enabler of faster learning, while stressing that human judgment remains essential in navigating uncertainty and leading transformation.

Learning Objectives

Explain the shift from viewing agility as a delivery approach to viewing it as a strategic capability for navigating disruption and uncertainty.

Identify the leadership capabilities that enable organizations to build adaptability, alignment, and learning at scale.

Describe how AI can support enterprise agility while understanding the continuing importance of human judgment and decision-making.

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