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In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias take on one of the most pivotal—and often overlooked—challenges in association innovation: getting your board on board with AI. Drawing from Amith's personal boardroom experience and Mallory’s deep dive into board psychology, they break down how to navigate internal politics, craft compelling AI use cases, and turn skeptical board members into innovation allies. From emotional storytelling to small pilot wins, this episode is your roadmap to aligning AI ambition with boardroom approval.
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CDS Global https://www.cds-global.com/
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🛠 AI Tools and Resources Mentioned in This Episode:
ChatGPT ➡ https://openai.com/chatgpt
Claude ➡ https://www.anthropic.com
HeyGen ➡ https://www.heygen.com
NotebookLM ➡ https://notebooklm.google
Chapters:
00:00 - Welcome to Sidecar Sync
01:00 - Setting the Stage: Why Board Buy-In Matters
06:55 - What Motivates Board Decisions in Associations?
10:15 - Volunteerism, Ego, and Career Goals
13:55 - Navigating Volunteerism, Legacy, and Tradition
25:37 - How Can You Build an Irresistible AI Use Case?
27:21 - Selecting the Right Pilot Project
32:59 - The Role of Demos and Emotional Buy-In
37:19 - Is an AI Data Platform the Right Starting Point?
40:34 - What’s the Pathway to Getting Board Approval?
42:53 - Building Support and Presenting With Impact
51:14 - Closing Thoughts and Next Steps

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Amith Nagarajan is the Chairman of Blue Cypress https://BlueCypress.io, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.
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Mallory Mejias is the Manager at Sidecar, and she's passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space.
📣 Follow Mallory:
https://linkedin.com/mallorymejias