Generative AI Readiness with Justin Trombold

Definitely, Maybe Agile

Definitely, Maybe Agile
Generative AI Readiness with Justin Trombold
Nov 20, 2025 Season 3 Episode 200
Peter Maddison and Dave Sharrock

In this episode, Peter Maddison and Dave Sharrock welcome Justin Trombold, President and Founder of Antison Advisors, to discuss the parallels between agile transformation and generative AI adoption in organizations.

Justin shares insights from his work helping companies navigate generative AI readiness, revealing that the biggest challenges aren't technical; they're organizational. From end-user proficiency to cross-functional collaboration, the conversation explores why companies struggle to move beyond "toy apps" to create real business value with AI.

Key topics covered:
• Why organizations need an AI strategy before investing in tools
• The critical importance of end-user proficiency with LLMs
• How cross-functional collaboration enables AI success
• Why annual planning cycles may be holding your AI initiatives back
• The parallels between agile adoption and AI transformation
• Moving from efficiency gains to true value creation

Whether you're leading AI initiatives, managing agile transformations, or wondering why your organization's AI investments aren't paying off, this conversation offers practical frameworks for thinking about organizational readiness in the age of generative AI.

THREE KEY TAKEAWAYS:

1. End-user proficiency is everything. 
2. Define the sandbox before choosing the toys.
3. Innovation in planning matters as much as innovation in products. 

Contact us: feedback@definitelymaybeagile.com

#GenerativeAI #AgileTransformation #OrganizationalChange #AIReadiness #DigitalTransformation #LLM #CrossFunctionalTeams #Innovation

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