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# Lessons from Jonathan Brill
- URL: https://www.antoinebuteau.com/lessons-from-jonathan-brill/
- Published: 2026-03-12T02:56:01.000Z
- Updated: 2026-07-18T22:07:35.000Z
- Description: Jonathan Brill is a strategist and futurist who helps organizations navigate radical change, using economics, psychology, and technology to show how collisions among unpredictable trends, or “rogue waves,” can become sources of competitive advantage.
- Author: Antoine Buteau
- Tags: Profile, Strategy, Leadership & Management Thinkers Profiles

Jonathan Brill is a world-renowned strategist and futurist, formerly the Global Futurist at Hewlett-Packard, who specializes in helping organizations navigate radical change and systemic disruption. By synthesizing insights from economics, psychology, and technology, Brill provides a pragmatic framework for turning "rogue waves"—the collision of unpredictable trends—into competitive advantages.

![Visual summary of operating lessons from Jonathan Brill.](https://www.antoinebuteau.com/content/images/2026/07/image-11-optimized.webp)

### Part 1: Strategic Foresight & The Five-Year Horizon

1. **On Strategic Planning:** "Traditional three-to-five-year plans are often obsolete before the ink dries; leaders must instead focus on real-world constraints to build flexibility for the future." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
2. **On The Five-Year Window:** "The next five years are the critical strategic sweet spot: close enough for actionable planning, yet distant enough for significant strategic pivots." — [*Source: BigSpeak Speakers Bureau*](https://www.bigspeak.com/speakers/jonathan-brill/?ref=antoinebuteau.com)
3. **On Converging Trends:** "Rogue waves in business are not single events but the result of technological, geopolitical, and social trends colliding at once." — [*Source: Clear Purpose*](https://clearpurpose.media/rogue-waves/?ref=antoinebuteau.com)
4. **On Future-Proofing:** "Success in an uncertain future is less about predicting specific events and more about building adaptable frameworks to embrace disruption." — [*Source: Talent Bureau*](https://talentbureau.com/speakers/jonathan-brill/?ref=antoinebuteau.com)
5. **On Systematic Intuition:** "Companies that develop systematic intuition consistently outperform their peers by making better decisions during high-velocity change." — [*Source: Jonathan Brill Official Website*](https://www.jonathanbrill.com/?ref=antoinebuteau.com)
6. **On The Reality Test:** "The first step in foresight is a reality test: deeply understanding your current state before attempting to model the future." — [*Source: YouExec - Rogue Waves Summary*](https://youexec.com/book-summaries/rogue-waves-by-jonathan-brill?ref=antoinebuteau.com)
7. **On Modeling Systems:** "Modeling systems and performing simulations is the best way to correct the cognitive biases that lead to poor strategic decisions." — [*Source: Medium - Lessons from Rogue Waves*](https://medium.com/@anton.korobkin/lessons-from-the-book-rogue-waves-by-jonathan-brill-e9c1c4966952?ref=antoinebuteau.com)
8. **On Underlying Forces:** "Even if specific futures cannot be seen, many of the underlying forces that determine them are obvious and reliable if you look for the undercurrents." — [*Source: Medium - Lessons from Rogue Waves*](https://medium.com/@anton.korobkin/lessons-from-the-book-rogue-waves-by-jonathan-brill-e9c1c4966952?ref=antoinebuteau.com)
9. **On Anticipating Disruption:** "If a company doesn’t know why it has to change, it won’t; awareness is the prerequisite for survival." — [*Source: Jonathan Brill HBR Article - HP Case Study*](https://www.jonathanbrill.com/writing/how-hp-turns-business-catastrophes-to-their-advantage/?ref=antoinebuteau.com)
10. **On Trend Intersections:** "Major shocks hit U.S. companies an average of four times per year; the question isn't if they happen, but how they intersect." — [*Source: Jonathan Brill HBR Article - HP Case Study*](https://www.jonathanbrill.com/writing/how-hp-turns-business-catastrophes-to-their-advantage/?ref=antoinebuteau.com)

### Part 2: Navigating Rogue Waves & Managing Risk

1. **On Rogue Wave Definition:** "In the ocean, rogue waves routinely sink ships; in business, they are the cumulative likelihood of unlikely events occurring simultaneously." — [*Source: Jonathan Brill HBR Article - HP Case Study*](https://www.jonathanbrill.com/writing/how-hp-turns-business-catastrophes-to-their-advantage/?ref=antoinebuteau.com)
2. **On Resilience as Strategy:** "Traditional efficiency models eliminate the very redundancies required for survival; resilience is the new growth strategy." — [*Source: Inside Personal Growth Podcast*](https://insidepersonalgrowth.com/rogue-waves-future-proof-your-business-to-survive-and-profit-from-radical-change-with-jonathan-brill/?ref=antoinebuteau.com)
3. **On Competitor Weakness:** "If your competitor cannot ride out the next wave and you can, you win by default." — [*Source: Jonathan Brill Official Website*](https://www.jonathanbrill.com/?ref=antoinebuteau.com)
4. **On Categorizing Problems:** "We create unnecessary risk by assuming all problems are the same, failing to distinguish between manageable risks and systemic threats." — [*Source: Medium - Lessons from Rogue Waves*](https://medium.com/@anton.korobkin/lessons-from-the-book-rogue-waves-by-jonathan-brill-e9c1c4966952?ref=antoinebuteau.com)
5. **On The ROGUE Framework:** "Transforming systemic threats into opportunities requires five steps: Reality test, Organize forces, Generate futures, Uncouple opportunities, and Experiment." — [*Source: YouExec - Rogue Waves Summary*](https://youexec.com/book-summaries/rogue-waves-by-jonathan-brill?ref=antoinebuteau.com)
6. **On Risk Mitigation:** "Leaders often write off rogue waves as improbable, but the cumulative likelihood of unlikely events is actually quite high." — [*Source: Jonathan Brill HBR Article - HP Case Study*](https://www.jonathanbrill.com/writing/how-hp-turns-business-catastrophes-to-their-advantage/?ref=antoinebuteau.com)
7. **On Uncoupling Threats:** "To survive, you must uncouple the opportunity from the threat—finding where you can intervene to change the outcome." — [*Source: YouExec - Rogue Waves Summary*](https://youexec.com/book-summaries/rogue-waves-by-jonathan-brill?ref=antoinebuteau.com)
8. **On System Stability:** "You must model the forces that maintain your current system's stability to understand how a rogue wave will break them." — [*Source: YouExec - Rogue Waves Summary*](https://youexec.com/book-summaries/rogue-waves-by-jonathan-brill?ref=antoinebuteau.com)
9. **On Economic Undercurrents:** "Rogue waves are powered by deep-seated economic and social undercurrents that have been building for decades." — [*Source: Clear Purpose*](https://clearpurpose.media/rogue-waves/?ref=antoinebuteau.com)
10. **On Strategic Fragility:** "The more efficient a system becomes, the more fragile it is to external shocks." — [*Source: Blinkist - Rogue Waves Summary*](https://www.blinkist.com/en/books/rogue-waves-en?ref=antoinebuteau.com)

### Part 3: Innovation as Resilience

1. **On Innovation Velocity:** "If you double the number of experiments you do per year, you double your organizational inventiveness." — [*Source: Medium - Lessons from Rogue Waves*](https://medium.com/@anton.korobkin/lessons-from-the-book-rogue-waves-by-jonathan-brill-e9c1c4966952?ref=antoinebuteau.com)
2. **On The Value of Failure:** "The main value of an experiment is the gained experience; an unsuccessful experiment still reveals a mistake at low cost." — [*Source: Medium - Lessons from Rogue Waves*](https://medium.com/@anton.korobkin/lessons-from-the-book-rogue-waves-by-jonathan-brill-e9c1c4966952?ref=antoinebuteau.com)
3. **On Innovation and Risk:** "The most valuable innovations often stem from effectively removing major risks from the user experience or business model." — [*Source: Singularity University*](https://su.org/blog/author/jonathan-brill/?ref=antoinebuteau.com)
4. **On Operational Innovation:** "Change how you work, not just what you make; operational innovation consistently beats strategic prediction." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
5. **On Experiment Portfolios:** "Build a portfolio of experiments to maximize success, ensuring you have multiple paths forward when the landscape shifts." — [*Source: YouExec - Rogue Waves Summary*](https://youexec.com/book-summaries/rogue-waves-by-jonathan-brill?ref=antoinebuteau.com)
6. **On Adapting Primitives:** "In times of radical change, utilize platform-native primitives to build new solutions quickly rather than over-engineering." — [*Source: Inside Outside Innovation Podcast*](https://insideoutside.io/podcast/ep-254-jonathan-brill-author-of-rogue-waves/?ref=antoinebuteau.com)
7. **On Systematic Experimentation:** "Innovation is not a spark of genius but a systematic process of trial, error, and rapid feedback loops." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
8. **On Responding to Uncertainty:** "Innovation in a vacuum is useless; it must be tied to the specific risks identified in your foresight process." — [*Source: YouExec - Rogue Waves Summary*](https://youexec.com/book-summaries/rogue-waves-by-jonathan-brill?ref=antoinebuteau.com)
9. **On The Cost of Caution:** "The greatest risk is not doing too many experiments, but doing too few and having no backup when the core business fails." — [*Source: Medium - Lessons from Rogue Waves*](https://medium.com/@anton.korobkin/lessons-from-the-book-rogue-waves-by-jonathan-brill-e9c1c4966952?ref=antoinebuteau.com)
10. **On Future Capabilities:** "We are moving from a world of 'buying' innovation to a world of 'architecting' the future through continuous experimentation." — [*Source: Speakers Corner UK*](https://www.speakerscorner.co.uk/speaker/jonathan-brill?ref=antoinebuteau.com)

### Part 4: The Octopus Organization & Distributed Intelligence

1. **On Distributed Intelligence:** "The octopus has a distributed mind where each tentacle can operate independently; organizations must push decisions to the edge similarly." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
2. **On The Ammonite Model:** "Traditional hierarchical organizations are like ammonites: rigid shells that failed to adapt and went extinct." — [*Source: James Taylor Show - YouTube*](https://www.youtube.com/watch?v=S3UonmU5h%5FU&ref=antoinebuteau.com)
3. **On Local Autonomy:** "In the Octopus Organization, local autonomy and bottom-up coordination replace the 'big brain' at the top of the pyramid." — [*Source: James Taylor Show - YouTube*](https://www.youtube.com/watch?v=S3UonmU5h%5FU&ref=antoinebuteau.com)
4. **On The Neural Necklace:** "AI acts as a 'neural necklace' that connects and synchronizes the distributed intelligence of the entire firm." — [*Source: The CIO Magazine*](https://theciomagazine.com/ai-and-the-octopus-organization-building-the-superintelligent-firm/?ref=antoinebuteau.com)
5. **On Fluid Architectures:** "The future belongs to fluid, intelligent architectures that can respond faster to market changes than any hierarchy." — [*Source: Speakers Connect*](https://www.speakersconnect.com/jonathan-brill-ai-and-the-octopus-organization/?ref=antoinebuteau.com)
6. **On Changing the OS:** "The octopus doesn't change its DNA; it changes its operating system—its RNA—to adapt to the environment." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
7. **On Coordination vs. Control:** "The future of leadership is not control; it is the coordination of highly autonomous, intelligent agents." — [*Source: PR Newswire*](https://www.prnewswire.com/news-releases/jonathan-brill-and-stephen-wunker-launch-ai-and-the-octopus-the-definitive-guide-for-the-future-of-the-firm-302111111.html?ref=antoinebuteau.com)
8. **On Empowering the Edge:** "AI gives all nodes in an organization the ability to monitor what is happening across the entire system simultaneously." — [*Source: Leadership in Change*](https://leadershipinchange.com/the-octopus-organization/?ref=antoinebuteau.com)
9. **On The End of Command:** "The 19th-century model of command and control is fundamentally incompatible with the speed of an AI-driven world." — [*Source: James Taylor Show - YouTube*](https://www.youtube.com/watch?v=S3UonmU5h%5FU&ref=antoinebuteau.com)

### Part 5: Artificial Intelligence as a Cultural Force

1. **On AI as an X-Ray:** "AI is an X-ray for culture; it reveals underlying organizational dysfunctions rather than fixing them." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
2. **On Accelerating Dysfunction:** "If you deploy AI into a dysfunctional system, all it does is make those dysfunctions happen faster." — [*Source: PR Newswire*](https://www.prnewswire.com/news-releases/jonathan-brill-and-stephen-wunker-launch-ai-and-the-octopus-the-definitive-guide-for-the-future-of-the-firm-302111111.html?ref=antoinebuteau.com)
3. **On Junior Empowerment:** "AI empowers junior employees to perform at the level of senior experts, requiring a shift from supervision to agency." — [*Source: James Taylor Show - YouTube*](https://www.youtube.com/watch?v=S3UonmU5h%5FU&ref=antoinebuteau.com)
4. **On Cognitive Collaboration:** "The goal of AI integration is cognitive collaboration—designing systems where humans and machines augment each other's strengths." — [*Source: Speakers Connect*](https://www.speakersconnect.com/jonathan-brill-ai-and-the-octopus-organization/?ref=antoinebuteau.com)
5. **On The Diamond-Shaped Org:** "AI is turning organizations into diamond shapes, where a robust middle layer manages the exceptions that AI cannot handle." — [*Source: James Taylor Show - YouTube*](https://www.youtube.com/watch?v=S3UonmU5h%5FU&ref=antoinebuteau.com)
6. **On Data-Driven Culture:** "AI initiatives fail not because of the tech, but because the culture refuses to yield decision-making power to data." — [*Source: PR Newswire*](https://www.prnewswire.com/news-releases/jonathan-brill-and-stephen-wunker-launch-ai-and-the-octopus-the-definitive-guide-for-the-future-of-the-firm-302111111.html?ref=antoinebuteau.com)
7. **On The Army of Einsteins:** "We now have an army of Einsteins inside our organizations thanks to AI, but we are still treating them like they need to be told what to do." — [*Source: James Taylor Show - YouTube*](https://www.youtube.com/watch?v=S3UonmU5h%5FU&ref=antoinebuteau.com)
8. **On Rapid-Response Specialists:** "In the AI era, middle managers must become rapid-response specialists who identify and escalate unusual situations." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
9. **On AI Governance:** "Governance in the Octopus Organization is about setting parameters for autonomous nodes rather than micromanaging their steps." — [*Source: The CIO Magazine*](https://theciomagazine.com/ai-and-the-octopus-organization-building-the-superintelligent-firm/?ref=antoinebuteau.com)

### Part 6: Leadership, Luck, and Decision Making

1. **On Luck as Choice:** "Luck isn’t chance; it’s a choice made through specific behaviors that position you to benefit from the unexpected." — [*Source: Premium Speakers Bureau*](https://premium-speakers.com/en/speaker/jonathan-brill/?ref=antoinebuteau.com)
2. **On The LUCK Framework:** "Exceptional leaders use the LUCK framework: Leverage help, Use diverse connections, Control chaos, and Know what’s missing." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
3. **On First Principles:** "To control chaos, you must go back to first principles—stripping a problem down to its fundamental truths." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
4. **On Counterfactual Questions:** "Know what’s missing by asking counterfactual questions: 'What if the opposite were true?'" — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
5. **On Crisis Leadership:** "Your value as an executive is determined by how you handle the crisis; no one pays much attention when things run smoothly." — [*Source: Medium - Lessons from Rogue Waves*](https://medium.com/@anton.korobkin/lessons-from-the-book-rogue-waves-by-jonathan-brill-e9c1c4966952?ref=antoinebuteau.com)
6. **On Assumptions:** "Our worst decisions are often the ones we don’t even notice we make because they are built on unexamined assumptions." — [*Source: Jonathan Brill HBR Article - Career Risk*](https://www.jonathanbrill.com/writing/identify-and-mitigate-risks-to-your-career/?ref=antoinebuteau.com)
7. **On The Power of Peers:** "Leveraging help from peers is the most underutilized tool in a leader's arsenal during a systemic shock." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
8. **On Decision Velocity:** "In a rogue wave, the cost of a slow decision is often higher than the cost of a slightly imperfect one." — [*Source: Blinkist - Rogue Waves Summary*](https://www.blinkist.com/en/books/rogue-waves-en?ref=antoinebuteau.com)
9. **On Diverse Connections:** "Diverse connections act as an early-warning system, alerting you to trends outside your immediate industry." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)

### Part 7: Organizational Culture & Behavior Change

1. **On The ABCs of Growth:** "Resilient growth requires three pillars: Awareness of trends, Behavior change to respond, and Culture change to sustain." — [*Source: Adam Mendler - Lessons in Leadership*](https://www.adammendler.com/blog/leadership-lessons-with-jonathan-brill?ref=antoinebuteau.com)
2. **On Psychological Safety:** "Psychological safety is the fuel for organizational learning; without it, employees will hide the very risks you need to see." — [*Source: Apple Podcasts - The James Taylor Show*](https://podcasts.apple.com/us/podcast/ai-and-the-octopus-organization-with-jonathan-brill/id1112390823?i=1000652755581&ref=antoinebuteau.com)
3. **On Embedding Skills:** "Companies must embed the skills to exploit the unexpected, making agility a standard operating procedure rather than an emergency response." — [*Source: Adam Mendler - Lessons in Leadership*](https://www.adammendler.com/blog/leadership-lessons-with-jonathan-brill?ref=antoinebuteau.com)
4. **On Process Design:** "Culture follows design; if your processes reward efficiency over resilience, your people will choose efficiency every time." — [*Source: Clear Purpose*](https://clearpurpose.media/rogue-waves/?ref=antoinebuteau.com)
5. **On The Resistance to Change:** "If a company doesn't understand the 'why' of a threat, its culture will naturally resist any 'how' of a solution." — [*Source: Jonathan Brill HBR Article - HP Case Study*](https://www.jonathanbrill.com/writing/how-hp-turns-business-catastrophes-to-their-advantage/?ref=antoinebuteau.com)
6. **On Cultural Inertia:** "The old ways of working will not build a new reality; you must change the incentives to drive resilient growth." — [*Source: Adam Mendler - Lessons in Leadership*](https://www.adammendler.com/blog/leadership-lessons-with-jonathan-brill?ref=antoinebuteau.com)
7. **On Managing Fear:** "Fear of the future is a lack of tools; when you give people a framework like ROGUE, you replace fear with empowerment." — [*Source: Tiffany Vora - Future Proofing*](https://tiffanyvora.com/jonathan-brill-rogue-waves/?ref=antoinebuteau.com)
8. **On Continuous Transformation:** "Transformation is not a one-time project but a continuous state of being for the modern organization." — [*Source: Speakers Corner UK*](https://www.speakerscorner.co.uk/speaker/jonathan-brill?ref=antoinebuteau.com)
9. **On Systems Thinking:** "Organizations are systems; changing a single part without understanding the forces that maintain stability is a recipe for failure." — [*Source: YouExec - Rogue Waves Summary*](https://youexec.com/book-summaries/rogue-waves-by-jonathan-brill?ref=antoinebuteau.com)

### Part 8: Personal Growth & Career Durability

1. **On Career Planning Risks:** "When career planning, we unintentionally focus only on optimistic scenarios, ignoring the risks that could threaten our vision." — [*Source: Jonathan Brill HBR Article - Career Risk*](https://www.jonathanbrill.com/writing/identify-and-mitigate-risks-to-your-career/?ref=antoinebuteau.com)
2. **On Identifying Blind Spots:** "Envision your ideal career, then work backwards to imagine everything that could go wrong to illuminate your blind spots." — [*Source: Jonathan Brill HBR Article - Career Risk*](https://www.jonathanbrill.com/writing/identify-and-mitigate-risks-to-your-career/?ref=antoinebuteau.com)
3. **On Skill Buffers:** "Developing connections and skills unconnected to your primary field serves as a buffer against industry-wide disruption." — [*Source: Jonathan Brill HBR Article - Career Risk*](https://www.jonathanbrill.com/writing/identify-and-mitigate-risks-to-your-career/?ref=antoinebuteau.com)
4. **On Career as Investment:** "Your career is a long-term investment; proactively looking at possible futures ensures your efforts today yield better returns tomorrow." — [*Source: Jonathan Brill HBR Article - Career Risk*](https://www.jonathanbrill.com/writing/identify-and-mitigate-risks-to-your-career/?ref=antoinebuteau.com)
5. **On Personal Mastery:** "Mastering decision-making under uncertainty is the single most important skill for the next decade of professional life." — [*Source: Premium Speakers Bureau*](https://premium-speakers.com/en/speaker/jonathan-brill/?ref=antoinebuteau.com)
6. **On Domain Expertise:** "Despite the rise of AI, deep domain expertise remains crucial for making the sense-making decisions that machines cannot." — [*Source: James Taylor Show - YouTube*](https://www.youtube.com/watch?v=S3UonmU5h%5FU&ref=antoinebuteau.com)
7. **On Human Value:** "Human value in the age of AI shifts from 'doing' to 'deciding' and 'coordinating' complex systems." — [*Source: PR Newswire*](https://www.prnewswire.com/news-releases/jonathan-brill-and-stephen-wunker-launch-ai-and-the-octopus-the-definitive-guide-for-the-future-of-the-firm-302111111.html?ref=antoinebuteau.com)
8. **On Managing Stress:** "Resilience is not just an organizational trait but a personal one; it is the ability to maintain cognitive function during a rogue wave." — [*Source: Blinkist - Rogue Waves Summary*](https://www.blinkist.com/en/books/rogue-waves-en?ref=antoinebuteau.com)
9. **On The Future Self:** "The person you need to be in five years is likely a radical departure from who you are today; start the experiment now." — [*Source: BigSpeak Speakers Bureau*](https://www.bigspeak.com/speakers/jonathan-brill/?ref=antoinebuteau.com)