The 5 Layers of Business Literacy Every HR Leader Must Master, with Jeff Diana, former CPO of Calendly

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Recorded10 Jul 2025

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For today's essential Heretics 101 feature, Kelli and Nolan examine the persistent challenge of HR professionals becoming genuine business leaders. Jeff Diana Investor/Entrepreneur, and former CPO of Calendly, join in to dissect tactical strategies for developing business acumen, moving beyond traditional people operations to drive meaningful organizational impact through financial literacy and strategic thinking.*Email us your questions or topics for Kelli & Nolan: [email protected] coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Planful empowers teams just like yours to unlock the secrets of successful workforce planning. Use data-driven insights to develop accurate forecasts, close hiring gaps, and adjust talent acquisition plans collaboratively based on costs today and into the future. ✍️ Go to https://planful.com/heretics to see how you can transform your HR strategy.Metaview is the AI assistant for interviewing. Metaview completely removes the need for recruiters and hiring managers to take notes during interviews—because their AI is designed to take world-class interview notes for you. Team builders at companies like Brex, Hellofresh, and Quora say Metaview has changed the game—see the magic for yourself: https://www.metaview.ai/hereticsKEEP UP WITH JEFF, NOLAN + KELLI ON LINKEDINJeff: https://www.linkedin.com/in/jeff-diana-a1906212/Nolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(01:21) The Frustration: Why "HR at the Table" Still Doesn't Work(02:13) Jeff's Do's and Don'ts Framework for Business Leadership(04:26) KD's C-Suite Litmus Test(05:50) The Controversial Take: Understanding Founder Irrationality(06:49) Jeff's "Layers of the Cake" Business Metrics(08:35) Sponsors: Planful | MetaView (11:35) Synthesizing Learning for Your Team(12:14) Being the Best-Run Function Strategy(13:43) Career Mobility Benefits(14:10) The SuccessFactors Sales Kickoff Story(15:33) Wrap This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hrheretics.substack.com

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