From Forced Upgrades to Agentic AI: Rethinking ERP, Innovation, and Leadership | DisrupTV Ep. 428

Beating the Odds in an AI Era: Leadership, Probability Hacking, and the Power of Kindness

On the latest episode of DisrupTV, co-hosts Vala Afshar and R "Ray" Wang sat down with:

• Seth Ravin, CEO of Rimini Street

• Elizabeth Weingarten, author of How to Fall in Love with Questions

• James Taylor, author of SuperCreativity

Together, they explored how agentic AI is changing enterprise software strategy, leadership behavior, and even how organizations approach creativity.

ERP Isn’t Going Away—But the Old Model Is

For decades, enterprises were locked into vendor-driven ERP roadmaps—forced upgrades, rigid timelines, and rising maintenance costs that didn’t always align with business outcomes.

Today, that model is breaking down.

ERP environments are increasingly becoming modular and composable, allowing CIOs and CFOs to mix best-of-breed capabilities across finance, CRM, supply chain, and operations. Instead of ripping out core systems, many organizations are layering agentic AI on top of legacy ERP to:

• Adapt workflows to regulatory or market changes in real time

• Reduce costly custom code changes

• Improve agility without destabilizing core infrastructure

In short: modernization no longer has to mean migration.

Agentic AI Is Becoming a Structural Necessity

AI isn’t just a productivity boost—it’s becoming essential infrastructure.

With labor costs rising and global talent shortages accelerating due to aging populations and declining birth rates, enterprises must find ways to maintain performance without scaling headcount. Agentic AI can help organizations:

• Reduce labor required per unit of output

• Maintain service levels and compliance

• Preserve margins under increasing competitive pressure

For CIOs already juggling multiple vendor AI roadmaps, the challenge isn’t adopting AI—it’s deciding which initiatives actually support enterprise strategy versus supplier agendas.

Leadership in the AI Era Requires Better Questions

While infrastructure matters, leadership mindset may matter more.

Elizabeth Weingarten emphasized that in an AI-rich environment—where answers are abundant—the real competitive advantage lies in asking better questions. Leaders who default to speed over reflection risk shallow thinking, confirmation bias, and diminished critical reasoning.

Developing a “questions practice” helps leaders:

• Navigate uncertainty more effectively

• Align decisions with organizational values

• Open new strategic possibilities instead of narrowing prematurely

In the age of generative AI, curiosity becomes a leadership skill—not just a personality trait.

The Rise of Human-AI “SuperCreativity”

James Taylor introduced the concept of SuperCreativity: human creativity amplified by AI collaboration.

AI can now assist with:

• Audience analysis before key presentations

• Predicting stakeholder objections

• Matching innovation ideas with collaborators across the enterprise

Rather than replacing creative work, AI is making human insight more targeted, effective, and scalable—helping surface “backstage heroes” and democratize innovation across teams.

As routine cognitive tasks become automated, creativity is rapidly emerging as one of the most valuable enterprise skills.

Key Takeaways

• Modernization ≠ migration: Agentic AI can extend legacy ERP without disruptive upgrades.

• Autonomy matters: Enterprises must align technology roadmaps to business outcomes—not vendor timelines.

• AI addresses labor realities: Automation is becoming necessary to offset workforce constraints.

• Questions are strategic assets: Better inquiry leads to better decisions in uncertain environments.

• Creativity is scalable: Human-AI collaboration can unlock innovation across the organization—not just in R&D.

Final Thoughts

Agentic AI won’t just change how software works—it will reshape how enterprises make decisions, allocate resources, and compete.

The organizations that succeed in this next era will be those that:

• Reclaim autonomy from vendor-driven roadmaps

• Encourage leaders to ask better strategic questions

• Treat creativity as a core organizational capability

In a world of infinite AI-generated answers, competitive advantage may ultimately belong to leaders who chart their own direction—and remain curious enough to question it along the way.

Related Episodes

If you found Episode 428 valuable, here are a few others that align in theme or extend similar conversations:

• Beating the Odds: AI Leadership, Enterprise Advantage, and Probability Hacking | DisrupTV Ep. 427
• Why AI Pilots Fail, Why 2026 Matters, and How Entrepreneurs Win in the Age of Agents | DisrupTV Ep. 425
• AI, Critical Thinking, and Geopolitical Risk: Inside DisrupTV’s Deep Dive on Gemini, Multimodal AI, and Global Resilience | DisrupTV Ep. 426