Being Intrepid: Navigating the Future of Learning with Sam Herring

A large government agency took 18 months to onboard one high-risk role, and the average person left around month 18. Workflow analysis and a digital coach on day one cut the path to full independence to six months. 

Bob Mosher, Founding Partner and Chief Learning Evangelist at APPLY Synergies and co-creator of the Five Moments of Need, joins Sam Herring to explain why AI fails when technology gets ahead of method. 

In this episode: 

• How task-level workflow analysis shows which tasks to automate, augment with a human in the loop, or keep away from AI 
• How a government agency cut onboarding from 18 months to six by starting with workflow analysis and a digital coach 
• Why L&D should stop building training first 
• What skills L&D needs to master to earn a seat in AI workflow decisions 

Guest: Bob Mosher, Founding Partner and Chief Learning Evangelist, APPLY Synergies 

Catch more Being Intrepid Podcast episodes at https://www.intrepidlearning.com/category/podcasts/ 

Member needs in healthcare shift constantly, the regulatory environment changes quickly, and the workforce has to keep pace. Kristine Ellis, Senior Director of Talent Development and Management at GuideWell/Florida Blue, has built her award-winning team to keep pace with constant change, and AI has become the operating engine that enables their speed. 

Kristine joins Sam Herring to talk about how her team moved from early AI uncertainty to full-on advocacy, why the Prompting Lab and Critical Thinking class are so foundational to AI upskilling at Florida Blue, and why she sees AI simulation as critical to moving from knowledge assessment to skill application. 

In this episode: 

• Why speed to capability, not AI adoption, is the defining pressure for her team right now 
• How GuideWell deployed 26 courses in two months using their internal LLM 
• What a Prompting Lab and a Critical Thinking class each do, and why the pairing matters 
• How to coach an AI-anxious team member into expanded, higher-value contribution 
• Why AI simulation moves learning from knowledge assessment to skill application, and what “N of 1” learning means for employees

Guest: Kristine Ellis, Senior Director, Talent Development and Management, GuideWell / Florida Blue 

Half of all L&D professionals aspire to a senior learning leadership role. Less than 1% hold the title. And many who think they want the job have never really examined what it requires. 

Amy DuVernet, VP of Learning Products at Training Industry, joins Sam Herring to unpack what it takes to develop the career of the person who develops everyone else. Drawing on TI's research across 250,000 L&D professionals, Amy shares what separates those who reach the CLO level and what holds most aspiring leaders back. 

In this episode: 

• The three competencies that define CLO readiness — enterprise perspective, executive presence, and business leadership — and why they require more than a course to develop 
• Why executive presence is trainable, and how the Training Industry Senior Leaders Program uses Intrepid to bring together AI-enabled practice, peer learning, and expert-led sessions in a structured development experience
• The supply-side reality: how to assess whether the CLO role is actually the right fit, and what adjacent paths are worth taking seriously 
• The highest-leverage skill most L&D professionals overlook (hint: it's not instructional design) 
• How to pitch the CFO and the question that reframes the conversation 

Guest: Amy DuVernet, VP of Learning Products, Training Industry

The L&D field has spent a decade on skills — frameworks, taxonomies, skills-based organizations. But as AI commoditizes skill execution, what actually develops a leader? 

Brian Miller, founder of Win With Talent and former head of talent at Levi Strauss, Adobe, Impossible Foods, and Gilead, argues the answer is experience: the judgment, discernment, and believability built through high-stakes situations that no model update can replicate. 

In this episode: 

• Why skills are what you can do — but not what you’ve navigated or who you've become 
• How experience architecture works: sequencing experiences to build capability velocity 
• The CFO question that reorients L&D investment from programs to prioritized roles 
• Why the magic in simulation is in the debrief — not the exercise itself 
• The succession frame that changes everything: "Who's been tested enough?" 

Guest: Brian Miller, Founder, Win With Talent 

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Catch more Being Intrepid Podcast episodes at https://www.intrepidlearning.com/category/podcasts/ 

Traditional change management models were built for a different era.

Today's leaders face complexity that's faster, messier, and less predictable than any framework anticipated.

Recorded live at ATD26, Sam Herring spoke with Karie Willyerd, Head of Strategic Engagements at GP Strategies, about what it takes to prepare leaders for AI-driven change.They explore practical strategies for helping leaders unlearn outdated assumptions, build adaptability, and lead with confidence when there's no clear playbook.

About Our Guest, Karie Willyerd: Karie Willyerd is a former 6-time Chief Learning Officer, including at Visa and Sun Microsystems. She is a best-selling author and advisor to organizations on the future of work. Karie has written for multiple magazines, including HBR, and is currently a columnist for Training Magazine. She works with start-ups and Fortune 500s to shape strategy at the intersection of people and technology. She was honored with the 2017 ATD Distinguished Contribution Award and has led two organizations to ATD #1.

Catch more Being Intrepid podcast episodes at: https://www.intrepidlearning.com/category/podcasts/

Learning budgets are usually the first to get cut when business gets tight. That's not inevitable — it's a symptom of a CLO who's playing defense instead of connecting their work to the income statement. 

Ted Forbes — author of Making HR Matter (with co-author David Alsop), former CLO at Capital One, and CHRO at Cotopaxi and Backcountry — joins Sam Herring to talk about what makes HR and learning credible to a CEO: income statement thinking, a sharper framework for identifying high potentials, and the wisdom that AI won’t replace. 

In this episode: 

• Why connecting learning to the income statement is more useful than proving ROI 
• The doom cycle that keeps HR functions trapped in low-expectations, low-performance loops 
• A reframed 9-box that replaces performance/potential with culture and economic performance 
• Insight and wisdom — the pattern recognition and persuasion capability that separates advisors from administrators 

Guest: Ted Forbes, Author, Making HR Matter 

Catch more Being Intrepid Podcast episodes at https://www.intrepidlearning.com/category/podcasts/

When organizations kick off AI and agentic transformation — redesigning workflows, reimagining roles — business and technology leaders run the work. Learning leaders are rarely in the room. By the time L&D gets called, the decisions are made and the upskilling need is already behind. 

Yulia Barnakova, AI Innovation and Learning Advisor at Accenture and faculty in Accenture's AI Academy for Business Leaders, joins Sam Herring to make the case for why that has to change — and what learning leaders can do about it now. 

In this episode: 

• Why 95% of AI workflow redesign conversations happen without learning leaders — and what that absence costs organizations  
• How to position L&D as a strategic partner to business and technology leaders, not downstream upskilling fulfillment 
• A spectrum framework for AI-based practice design: when text is enough, when voice helps, and when avatar fidelity actually matters 
• How to make technology decisions in a market where the options keep improving — without getting paralyzed 
• Why personal upskilling is a team readiness strategy, even when organizational tool access is restricted 

Guest: Yulia Barnakova, AI Innovation and Learning Advisor, Accenture 

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At ServiceNow, the speed at which customers and partners can be certified is a real constraint on the company’s commercial growth. That makes learning a true strategic enabler — and it changes what L&D is accountable for. 

Shellie Grieve, Director of Learning Innovation and Emerging Technology at ServiceNow, joins Sam Herring to discuss how cohort learning became the architecture for skills development across 28,000 employees, millions of platform users, and a global partner ecosystem. She shares the design discipline behind 18 Academy programs, a 75% reduction in admin time, and skill growth that shows up in week one. 

In this episode: 

• Why the design question “what does completion actually prove?” changes everything about how you build a program 
• How milestone-badge architecture lets delivery teams manage at scale without losing sight of individual progress 
• Where AI is being used across the L&D stack at ServiceNow — and how to tell the difference between a point solution and a real workflow shift 
• How to get started with AI when the space is moving faster than any organization can keep up with 

Guest: Shellie Grieve, Director, Learning Innovation & Emerging Technology, ServiceNow

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Catch more Being Intrepid Podcast episodes at https://www.intrepidlearning.com/category/podcasts/ 

Physicians are trained to have the right answer under pressure. But when a doctor becomes a CEO, that expertise can become a ceiling. The real work is an identity shift, from expert to enterprise leader. 

Raj Ramachandran, Senior Partner for Leadership Advisory at WittKieffer, joins Sam Herring to unpack how he develops senior healthcare leaders through executive coaching, stoic philosophy, and structured reflection. 

In this episode: 

• Why the shift from problem-solving to "holding complexity" catches new executives off guard 
• How the stoic framework E + R = O helps leaders focus on how they respond  
• The TFAL method, "Think for a Living," and why blocking time without an intention doesn't work 
• Why a dyad coaching model (leadership coach + physician mentor) works for healthcare executive development 
• Where AI coaching shows promise and why it falls short with executives 

Guest: Raj Ramachandran, Senior Partner, Leadership Advisory, WittKieffer

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Catch more Being Intrepid Podcast episodes at https://www.intrepidlearning.com/category/podcasts/

Most enterprise AI investments are funded backwards—93% to technology, 7% to people—and the ROI is falling short as a result.

In this episode, Sam Herring sits down with Matt Stevens, Managing Director for Human Performance and Learning at Deloitte Consulting, to explore what it actually takes to move AI from fragmented pilots to enterprise-wide adoption. 

Matt draws on client work across financial services, healthcare, and beyond to make the case that learning isn't a support function for AI strategy. It is the strategy. 

In this episode: 

• Why organizations are underinvesting in workforce readiness and what it's costing them in AI ROI 
• How one client's AI Academy started with a CEO workshop and cascaded across the organization 
• The difference between building AI technical skills and the human skills that complement them—curiosity, critical thinking, judgment 
• What L&D leaders must shift: from content production to experience design 
• A practical starting point for AI in L&D without a massive budget 

Guest: Matt Stevens | Managing Director and Market Offering Leader, Human Performance and Learning | Deloitte Consulting