“HR Heretics” | How CPOs, CHROs, Founders, and Boards Build High Performing Companies

Sally Thornton, founder of Forshay and expert in fractional executive roles, discusses the evolving landscape of fractional work. She highlights the essential skills needed for success, including consultative abilities and trust-building. Sally unpacks common misconceptions surrounding fractional roles, particularly in tech, and drives home the significance of transparent compensation structures. Additionally, she emphasizes the importance of resilience and collaboration in both career management and the fractional hiring process.

Kelli and Nolan dive into the nuances of punctuality in professional settings. They discuss the balance between establishing personal boundaries and extending grace to those who are late. The hosts share anecdotes about how workplace cultures influence attitudes toward tardiness and emphasize the importance of clear communication. They also touch on the dynamics of accountability and social etiquette, particularly how power influences perceptions of time. Insights into unwritten rules of meeting conduct add depth to their engaging conversation.

Jared Kleinert, founder of Offsite.com, specializes in planning transformative team retreats for remote and hybrid teams. He highlights how strategic offsites elevate organizational alignment and build trust among team members. Kleinert shares insights on the shift towards meaningful retreats post-pandemic, emphasizing their role in enhancing company culture and engagement. He also discusses the importance of intentional planning to ensure these gatherings provide measurable business value and foster team cohesion.

Nolan and Kelli unveil the hidden risks of equity compensation, sharing tales like Nolan’s missed $8 million opportunity with DoorDash. They emphasize that understanding share counts and strike prices is crucial for maximizing startup wealth. With practical advice, they equip listeners to navigate the complexities of equity offers and negotiate job terms effectively. The conversation also introduces innovative tools enhancing workforce management, underlining the need for self-education in the intricate world of equity grants.

In this installment of AI Corner, Siadhal Magos, the CEO of Metaview, and Nolan Church explore the emerging trend of "CEO AI mandates" from the likes of Tobias Lütke and Aaron Levie at Box.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor coaching and advising inquire at https://kellidragovich.com/HR Heretics is a podcast from Turpentine.Support HR Heretics Sponsors:Thatch makes it easy to give your team great healthcare. Save ~$1620 per employee yearly while giving them customizable plans. Visit https://thatch.AI/HR for a demo and receive a $100 gift card.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 SIADHAL, NOLAN + KELLI ON LINKEDINSiadhal: https://www.linkedin.com/in/siadhalNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro(00:33) The CEO AI Mandate Trend(01:22) Siadhal's Take on AI Mandates(02:35) AI Orchestration as a Career Necessity(03:00) Headcount Management in the AI Era(04:04) AI Leverage vs. Team Size(06:03) Sponsors: Thatch | Planful(08:13) AI Upskilling and Education(09:21) Personal AI Tuition in Organizations(10:18) The Reflexive AI Problem-Solving Approach(11:27) Show and Tell: Learning from Power Users(12:00) Knowing What's Possible as Motivation(13:22) Carrot vs. Stick: Recognizing AI Adoption(14:38) Beyond AI as a Metric: Performance is the Goal(15:34) Wrap(15:58) Sponsor: Metaview 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

In this week's 'Dear Heretics' segment, Kelli and Nolan unpacks the intricacies of 360 reviews from a management perspective, offering pragmatic approaches to synthesizing overwhelming feedback data. They contrast methodical theme-based analysis with modern AI-assisted solutions, emphasizing that meaningful feedback isn't an annual crucible but a continuous conversation peppered with five compliments per criticism.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor 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 NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/—TIMESTAMPS:(00:00) Intro (00:36) Dear Heretics - 360 Reviews Question (00:52) Good vs Bad 360 Reviews (06:34) Sponsors - Planful | Metaview (09:34) Using AI for 360 Reviews (11:38) On Using AI Tools (13:27) Sports Analogy Break (14:45) Getting the Ball Rolling (15:22) Continuous Feedback Approach (17:21) 5:1 Positive Ratio (17:59) Explaining the Why in Feedback (19:20) Making Feedback Enjoyable (19:26) 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

Troy Sultan, CEO and founder of Guide, shares his journey from Google to revolutionizing recruitment with AI. He tackles the outdated assumptions of traditional hiring, advocating for speed and transparency. Sultan discusses the importance of empowering candidates with self-service options, transforming their experience. He also emphasizes the cultural shift towards automation in hiring processes and the need for HR leaders to adapt. With insights on improving candidate experiences, Troy invites a rethinking of power dynamics in recruitment.

Kelli and Nolan recap their experience at the recent Sapphire People Leader Retreat focused on the evolving role of CPOs in 2025, covering executive alignment, moral boundaries, burnout prevention, and peer networks. They also share a case of corporate identity theft targeting job candidates, highlighting emerging recruitment security challenges.*Email us your questions or topics for Kelli & Nolan: hrheretics@turpentine.coFor 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 NOLAN + KELLI ON LINKEDINNolan: https://www.linkedin.com/in/nolan-church/Kelli: https://www.linkedin.com/in/kellidragovich/TIMESTAMPS:(00:00) Intro(02:10) The Role of CPO in 2025(02:20) Corporate Deep Fake Fraud Story(03:30) How the Deep Fake Was Discovered(04:00) FBI Involvement & Next Wave of Fraud(05:10) Pelion VC Domain Fraud Case(05:50) Value of Raw Conversations at Retreat(06:10) No One-Size-Fits-All CPO Role(07:00) Executive Alignment Importance(08:30) Sussing Out Cultural Fit(10:10) Moral Boundaries vs. Running Experiments(12:00) Learning from Radical Ideas at Carta(12:30) "Care a Little Less" Philosophy(14:14) Sponsors: Planful | Metaview(17:14) Avoiding People Leader Burnout(19:20) Building Your Peer Network(21:10) Tactical Work vs. Strategic Leadership(22:20) 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

Annie Wickman, Head of People at Character AI and former Googler, shares her unique journey from being the first non-founder at Humu to leading talent strategies at Character AI. She discusses the essential balance between product-market fit and company culture, and how this interplay affects internal dynamics. Annie also dives into her experiences with Google’s strategic deals and offers insights into rebuilding organizational trust. Additionally, she touches on the emotional challenges of leadership in venture capital and maintaining a strong team culture during transitions.

Explore the ethical tightrope that startups walk, where personal values clash with innovative ambition. Hear advice on whether to align with ethically questionable founders or gracefully step away. Delve into the importance of integrity in leadership and the signs of workplace toxicity. Discover insights on building supportive networks amid personal crises. Plus, learn about innovative tools that enhance workforce management, like AI-powered solutions that revolutionize recruitment processes.