Your Annual Planning Process Is Killing Innovation | Episode 36 episode artwork

EPISODE · Jun 1, 2026 · 44 MIN

Your Annual Planning Process Is Killing Innovation | Episode 36

from The Insurgent Mindset · host The Insurgent Mindset

Every year, leadership teams and boards invest significant time and resources into strategy offsites, planning sessions, and executive retreats. Yet many of these workshops produce little more than incremental improvements, recycled assumptions, and plans that struggle to keep pace with a rapidly changing market.In this episode of The Insurgent Mindset, Matt and Rondo challenge conventional thinking around strategic planning and leadership offsites. They explore why most organizations focus too heavily on resource allocation and execution while neglecting the deeper work of questioning assumptions, widening perspectives, confronting uncertainty, and identifying emerging opportunities. From AI disruption and scenario planning to customer involvement and board engagement, this conversation offers practical insights for leaders who want to move beyond annual planning exercises and build more adaptive, resilient, and insurgent organizations.--Hosted by seasoned strategy consultants Matt Tice and Rondo Moses, with a combined 50 years of experience, this podcast will challenge you to transcend the status quo and reshape how you think about and approach competing in the business marketplace.  Learn more at www.insurgencegroup.com.  Subscribe to “The Insurgent Mindset” on Apple Podcasts, Spotify Podcasts or Youtube, and visit us as www.insurgencegroup.com to learn more.  Have questions or topics you’d like us to cover in a future episode? Email us at [email protected]. This podcast is hosted by Matt Tice & Rondo MosesProduced by Faith MoavenzadehOriginal Music by Caius Tice

Every year, leadership teams and boards invest significant time and resources into strategy offsites, planning sessions, and executive retreats. Yet many of these workshops produce little more than incremental improvements, recycled assumptions, and plans that struggle to keep pace with a rapidly changing market.In this episode of The Insurgent Mindset, Matt and Rondo challenge conventional thinking around strategic planning and leadership offsites. They explore why most organizations focus too heavily on resource allocation and execution while neglecting the deeper work of questioning assumptions, widening perspectives, confronting uncertainty, and identifying emerging opportunities. From AI disruption and scenario planning to customer involvement and board engagement, this conversation offers practical insights for leaders who want to move beyond annual planning exercises and build more adaptive, resilient, and insurgent organizations.--Hosted by seasoned strategy consultants Matt Tice and Rondo Moses, with a combined 50 years of experience, this podcast will challenge you to transcend the status quo and reshape how you think about and approach competing in the business marketplace.  Learn more at www.insurgencegroup.com.  Subscribe to “The Insurgent Mindset” on Apple Podcasts, Spotify Podcasts or Youtube, and visit us as www.insurgencegroup.com to learn more.  Have questions or topics you’d like us to cover in a future episode? Email us at [email protected]. This podcast is hosted by Matt Tice & Rondo MosesProduced by Faith MoavenzadehOriginal Music by Caius Tice

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Your Annual Planning Process Is Killing Innovation | Episode 36

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Every year, leadership teams and boards invest significant time and resources into strategy offsites, planning sessions, and executive retreats. Yet many of these workshops produce little more than incremental improvements, recycled assumptions, and...

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