Stop obsessing over AI tools. The real win is reshaping your org so humans and machines decide faster together — like an octopus, not a rigid shell.
Body of Work: AI
LeadershipNOW: Lessons from the Octopus About Leading AI Transformation
The most successful leaders don’t treat AI as just another technology implementation. Instead, they recognize it as a catalyst for fundamental organizational redesign.
Jonathan Brill on the Profiles in Leadership Podcast
Jonathan Brill, Octopus Organizations Built for Speed, Resilience and Radical Adaptability In a recent episode of Profiles in Leadership, host Dr. Steve Anderson sits down with Jonathan Brill to explore how organizations must evolve to thrive in an AI-driven world. In...
Jonathan Brill on the Bringing Data & AI to Life Podcast
The AI Investment Strategies You Need to Know: Eye-Opening Insights from Jonathan Brill Placing bets is always a risky game, and yet, everyone’s looking to do it with AI. So, how can you make the best possible bet? In the latest episode of Informatica's podcast...
Keynote: Luxembourg Confederation Members’ Night 2025
Jonathan Brill provided the keynote address to the Luxembourg Confederation Members' Night 2025. His presentation “Leading When AI Joins the Leadership Team” offered valuable insights into the integration of artificial intelligence into decision-making and the...
AWS: Beyond the technology: Workforce changes for AI
An excerpt from the AWS blog post by Taimur Rashid highlighting Jonathan Brill's whitepaper The AI-First Enterprise: The New Rules of Jobs and Organizational Design. Workplaces are increasingly integrating AI tools into daily operations, with AI assistants supporting...
Jonathan Brill on the Thinkroom Podcast
The management system running most organizations today was designed for railroads in the 1850s—and AI just made it obsolete. In this revealing conversation with Johan Grönstedt on the Thinkroom Podcast, Jonathan Brill explains why the assumptions baked into our org...
Psychology Today: Humans + AI = Superintelligent Teams
Make faster, better calls together.
CIO: The Elephant Problem: Why you can’t see AI opportunities
You’re not missing AI’s potential because it’s hiding — it’s because you’re looking too closely. Step back and see the whole system, not just the tasks.
Blueprints for an AEC AI-First Built World
How AI is democratizing BIM and project management tools for AEC firms of all sizes.
Keynote: Navigating Rogue Waves and an AI Future in the Legal Sector
In this keynote presentation to 700 partners at a law firm, Jonathan Brill discusses the concept of 'rogue waves' in business, emphasizing the importance of recognizing and leveraging change, particularly in the context of the legal sector and the impact of AI. He...
CIO Magazine Interviews Jonathan Brill
An excerpt from the CIO Magazine interview "Building the Superintelligent Organization" wherein Jonathan explains why many AI projects fail not because of technology, but because they’re implemented in rigid, outdated systems. Brill outlines how leaders can transform...