On this page
Guest Bio
Sheryl Raphael Whitaker is a seasoned learning and talent development executive with over 20 years of experience. She has led transformative learning strategies for major organizations like USAA, AIG, and State Farm Insurance. She is also the founder of Eden Anthony Elite Talent Solutions. Sheryl brings a unique blend of humour, insight, and experience to the world of L&D, championing human interaction and experiential learning as keys to meaningful growth.
Breaking the Ice: A Hypnotic Introduction
Sheryl opens with a hilarious tale from early in her career when, at a claims leadership conference, she volunteered to be hypnotized. While under, she “fell asleep” on the shoulder of a very senior executive—awkward and unforgettable. The moment highlights Sheryl’s willingness to laugh at herself and embrace vulnerability, key qualities she brings into her leadership approach.
Transforming Learning in the Digital Age
Sheryl’s pivotal success came during her tenure as Global Head of Claims Learning at AIG. Faced with the inefficiency of in-person training, her team spearheaded a digital transformation by creating Claims University. This shift enabled scalable, global learning without travel, allowed integration of gamification and leaderboards, and connected training directly to business KPIs. The lessons learned at AIG would later shape similar initiatives at USAA, where she led the creation of digital learning and onboarding platforms.
Engagement Strategies for Learning Programs
Sheryl emphasizes that digital doesn’t mean dull. Success requires appealing visual design, gamified elements like badges and leaderboards, and storytelling to create relevance. Even skeptics became advocates once they experienced the fun and recognition these systems offered.
The Importance of Human Interaction in Learning
While Sheryl values digital transformation, she champions the 70-20-10 learning model:
- 70% from experience
- 20% from relationships
- 10% from formal learning
She implemented “skills circles”—cohorts where learners asynchronously study skills (e.g., storytelling with data), apply them in real work, and reconvene for facilitated discussions. These communities foster collaboration and practical application.
Learning from Mistakes and Embracing Failure
Sheryl shares a story about a promising digital maturity program that was derailed by leadership changes. While the enterprise-wide rollout never happened, individual teams embraced the content, and the team members developed new creative muscles. Her philosophy celebrates failure as a path to growth, advocating for safe spaces where mistakes fuel innovation and resilience.
Advice for Future Learning Leaders
Reflecting on her journey, Sheryl urges leaders to focus on the collective power of teamwork. Her mantra:
“One plus one equals three. That’s when the magic happens.”
She believes in prioritizing people over process, fostering environments where authenticity and collaboration thrive, and embracing change as the only constant. To Sheryl, it’s the journey and relationships—not just the outcomes—that define leadership success.
Ready to Push Boundaries?
Sheryl’s journey is a compelling example of transformative leadership in learning and development. Her story demonstrates how innovation, resilience, and human-centered design can shape impactful learning cultures. Listen to the full episode for more insights.
Episode Summary
In this lively and heartfelt episode, Sheryl Whitaker shares her journey from hypnotic mishaps to pioneering digital transformation in L&D. She breaks down the 70-20-10 model in practice, shares creative strategies to boost engagement, and reminds us why human interaction is still at the heart of learning. Her insights are essential for any learning leader navigating today’s evolving workplace.
Resources
- Learn more about Sheryl Raphael Whitaker
- Connect with Growthspace
Key Takeaways
- Lead with Humour and Vulnerability: Don’t be afraid to share your awkward moments.
- Digital is Powerful—if Done Right: Use gamification and design to make learning irresistible.
- Human Connection is Essential: Learning is social. Prioritize interaction.
- Failure is Fertile Ground: Embrace missteps as part of innovation.
- Focus on the 70-20-10 Model: Experience and collaboration matter more than content alone.
- Change is Inevitable: Adapt quickly and model resilience.
- Teamwork Multiplies Impact: Great things happen when people work together.
Chapters
00:00 – Introduction and Humorous Anecdote: Sheryl shares a hilarious story about being hypnotized at a leadership conference.
02:53 – Transforming Learning in the Digital Age: How Sheryl digitized global training at AIG with Claims University.
05:58 – Engagement Strategies for Learning Programs: Making training exciting with gamification and great design.
09:10 – The Importance of Human Interaction in Learning: Using the 70-20-10 model and skill circles to foster collaboration.
12:01 – Learning from Mistakes and Embracing Failure: A digital program that failed to launch but still created growth.
15:02 – Advice for Future Learning Leaders: Why teamwork, authenticity, and adaptability are the keys to leadership success.
Watch the full conversation here:
For a deeper dive into the conversation, listen to the full episode here:
