Why Teams Lose Their Way at Scale with Randy Silver

Matt is joined by product and leadership consultant Randy Silver to unpack one of the most frustrating problems in product organizations: everyone knows where they want to go, but no one knows how to actually get there. Together they explore what causes this breakdown in execution, how companies drift from product strategy to dysfunction, and what strong leadership really looks like at scale. Key Discussion Points Why strategy is easy—execution is the problem Why in-shitification happens The three organizational dysfunctions Randy sees most Why autonomy without alignment fails The real root of dysfunction: unclear product strategy What leaders can do right now to fix the mess Resources & Links Randy Silver’s consulting work Follow Randy on LinkedIn Randy Silver Good Strategy Bad Strategy by Richard Rumelt Link to Book

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Why Teams Lose Their Way at Scale with Randy Silver is an episode from Startup Hustle - Startups, Entrepreneurship, Business and Making Money are Hard! by Startup Hustle.

This episode is 31:34 long.

This episode was published on Jan 8, 2026.

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