205. Say What Sucks: Catalyzing Organizational Change with AI

2025-05-27

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A live SXSW panel on how employee complaints illuminate the path to organizational innovation.Wrong question: How can AI revolutionize productivity in my organization?Right question: What do my employees hate most about their jobs?For the Portland Trail Blazers, a winning game plan for AI implementation didn’t begin with a tech-first approach — it began with a talk-first one. “The whole concept was to talk about pain points," explains David Long, VP of Digital Innovation, describing the "Lunch and Launch" sessions where employees could openly share...

A live SXSW panel on how employee complaints illuminate the path to organizational innovation.

Wrong question: How can AI revolutionize productivity in my organization?

Right question: What do my employees hate most about their jobs?

For the Portland Trail Blazers, a winning game plan for AI implementation didn’t begin with a tech-first approach — it began with a talk-first one. “The whole concept was to talk about pain points," explains David Long, VP of Digital Innovation, describing the "Lunch and Launch" sessions where employees could openly share frustrations about their daily work. “People really enjoy talking about what they hate about their jobs,” says Christa Stout, Executive Vice President and Chief Strategy & Innovation Officer, and as they did, they illuminated opportunities for optimization. “By getting this insight across the whole company, it is already opening our eyes [to how] we can potentially transform the business more broadly,” Stout says.

In this special live episode of Think Fast, Talk Smart, recorded at SXSW, host Matt Abrahams leads a panel with Long, Stout, and Stanford colleague Jeremy Utley, exploring how "catharsis catalyzes change.” For any team wanting to implement new technology or rethink workflows, these experts reveal how creating space for complaints can catalyze meaningful innovation throughout an organization.

Episode Reference Links:

Jeremy Utley
David Long
Christa Stout
Ep.77 Quick Thinks: AI Has Entered The Chat – A "Conversation" with ChatGPT
Ep.134 How to Chat with Bots: The Secrets to Getting the Information You Need from AI

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Matt Abrahams >>> LinkedIn

Chapters:

(00:00) - Introduction
(04:53) - The Business Behind Basketball
(06:24) - Why AI and Why Now?
(07:32) - Collaborating with the Team
(08:50) - The Lunch & Launch Method
(11:22) - Branding AI Initiatives
(12:40) - David Detractor & Kelly Kindness
(16:11) - Human Connection through AI
(16:56) - Auditing for Brand Consistency
(19:04) - AI in National Parks
(21:47) - Making AI Personal
(23:09) - Using AI to Learn AI
(27:38) - Encouraging AI in the Workplace
(30:32) - Change Management: Iteration Over Perfection
(34:18) - Start with Curiosity and Empower Action
(38:01) - Communication Ingredients
(40:59) - Conclusion

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