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Most AI rollouts skip the one step that makes everything else work: redesigning the work itself. This episode puts your questions on the record — about AI strategy, your CHRO seat, and whether leadership development is actually doing anything.
Jackson Lynch and Scott Morris answer alongside Rihanna Barr, a two-time Chief People Officer now fractional CHRO at Pinnacle Peak HR. She's been in the seat. She knows when an answer is complete and when it just sounds that way.
What You'll Learn
- Why starting with vendors before mapping your work is the single biggest AI rollout mistake — and what to do first instead.
- How to reframe the AI headcount conversation with your CFO before it becomes a pure cost-out exercise.
- Why "strategic HR" has become a self-description and what real CHRO influence looks like instead.
- What separates CHROs who get pulled into decisions early from those briefed after the fact.
- Why "accountability" as a frame suppresses your best performers — and what to use instead.
Key Quotes
- "Strategic has become a self-description and a posture. How the hell do you measure it?"
- "Authority follows demonstrated impact on the business — not an org chart fight. It's about usefulness."
- "Your best performers are auditing your culture every day. When they go quiet, they're self-censoring judgment while maintaining effort."
Sources for Statistics Cited
- ~5% of AI implementations show positive ROI (Jackson stated this inversely — the actual MIT finding: 95% fail) — MIT GenAI Divide Report 2025
- Less than 5% of 2025 layoffs were AI-driven — Challenger, Gray & Christmas 2025 Year-End Report
- 55% of companies regret their AI-driven layoffs — Forrester via HR Executive
- 47% of the working population can't confirm they know what's expected — Gallup
- ~50% of HR people don't see their business as a force for good (Marc Effron / Talent Strategy Group) — Source not independently verified
- Companies benefiting from AI focus on growth, not cost-cutting — a16z Big Ideas 2026 (specific article referenced not located)
Support the show
If this episode landed, the next move is yours.
Coaching is where it closes fastest — Jackson has developed CHROs from both sides of the table, as their leader and as their coach. The CHRO Ascent Academy, Private Coaching, Mandate Protocol, CHRO Chronicles, and the best-selling Substack are there too.
All at mytalentsherpa.com.
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In private equity: Propulsion AI surfaces workforce risk before the close and translates strategy into individual accountability after it. Before AI automation - drive outcome clarity with digital teammates to do the work fast and at scale.
All at getpropulsion.ai.
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CHRO podcast, CEO Podcast, Business, Management
CHRO strategy, HR strategy, talent management, leadership development, talent management podcast, human capital strategy, mandate clarity, peacetime wartime leadership, talent hat framework, leadership pipeline, senior leadership, people strategy