Chief Change Officer Podcast Summary

Episode #336: Waverly Doidge – Coaching the Logical, Leading with Love
Release Date: May 1, 2025
Host: Vince Chan
Guest: Waverly Doidge

Introduction

In episode #336 of Chief Change Officer, host Vince Chan welcomes Waverly Doidge, a seasoned coach and former professor at Chicago Booth, to delve into the intricate balance between love and logic in coaching entrepreneurs and business professionals. This episode is the second installment of a three-part series titled "Love and Logic."

A Journey Through Chicago Booth

Waverly Doidge opens by reflecting on her 22-year tenure at Chicago Booth, where she taught and coached a diverse group of students—from undergraduates to seasoned executives. She highlights the distinct challenges faced by different cohorts:

• Undergraduates: Represented by raw innovation and an idealistic view of the corporate world. Waverly notes, “[Undergraduates] don't know what's possible, they don't know what's impossible, they don't have the foundation for a lot of that logic” (06:49).

• Executive MBAs: Often come with a strong corporate background, leading to ideas that are incremental rather than disruptive. She observes, “The ideas often lack innovation and lack creativity, are incremental to the way things are being done” (06:49).

Waverly emphasizes the importance of balancing passion with a logical process, defining entrepreneurship as “a process of taking an idea or identifying an opportunity and turning it into an organization” (06:49).

Overcoming Common Challenges

The conversation shifts to the common hurdles her students face and how she leverages her experiences to guide them. Vince probes whether Waverly leans more towards emotional support or calculated strategies in her coaching.

Waverly's Approach: She explains that her approach varies based on the individuals she mentors. For instance, with executive MBAs, she often works to temper overconfident projections by introducing realistic assessments of resource allocation and return on investment. Conversely, with younger entrepreneurs, she focuses on grounding their exuberant ideas with logical steps and practical examples.

Illustrative Example: Caitlin Smith of Simple Mills Waverly shares a poignant example involving Caitlin Smith, founder of Simple Mills. Initially hesitant about scaling her business beyond health food stores, Waverly encouraged Caitlin to envision a larger impact akin to Betty Crocker. This exercise led Caitlin to pursue venture capital, ultimately growing Simple Mills into a billion-dollar company available nationwide. Waverly notes, “By opening up just the completely low-risk experiment of just pitching it as a big business, it enabled her to bring her heart and head together” (10:59).

Transition to Independent Coaching

Vince transitions the discussion to Waverly's shift from a structured academic environment to independent coaching. He highlights the broader and more diverse client base she now engages with, encompassing various ages, cultures, and educational backgrounds.

Adapting Coaching Methods: Waverly discusses how her extensive experience with highly intelligent individuals at Chicago Booth has shaped her current coaching strategies. She acknowledges the challenge of working with clients who may not share the same level of academic or business acumen and underscores the importance of active listening and adapting her communication style to meet each client's unique needs. “I have to find out where they are and match them and meet them where they are” (22:17).

The Role of AI in Coaching

A significant portion of the episode is dedicated to exploring the impact of artificial intelligence on coaching. Vince poses a thought-provoking question about AI's potential to compete with human coaches, especially in the context of balancing logic (AI) and love (human coaches).

Waverly's Perspective on AI: Waverly asserts that while AI can enhance certain aspects of coaching, such as creating polished pitch decks or providing data-driven insights, it cannot replicate the human connection essential for building trust and fostering meaningful business relationships. She likens business-building to dating, emphasizing that “AI is never going to be able to build those kinds of human relationships” (30:10).

She further explains that AI should serve as a partner rather than a replacement, assisting in tasks that enhance human capabilities. “AI is going to write my resume… but an interview with the hiring manager is where the human element truly shines” (30:47). Waverly believes that the essence of entrepreneurship—customer acquisition, stakeholder management, and relationship building—remains inherently human and irreplaceable by AI.

Insights and Conclusions

Throughout the episode, Waverly underscores the irreplaceable value of human intuition, emotional intelligence, and personal connections in the entrepreneurial journey. She contends that while AI can provide logical support and streamline processes, the core of successful business ventures lies in human relationships and the ability to inspire and connect with others.

Key Takeaways:

• Balancing Logic and Love: Effective coaching requires a blend of analytical strategies and emotional support tailored to individual needs.
• Adaptability: Coaches must adjust their methods to accommodate the diverse backgrounds and intelligence levels of their clients.
• Human-Centric Business: Despite technological advancements, building and maintaining human relationships remains central to business success.
• AI as a Tool, Not a Replacement: AI can augment coaching by handling logical tasks, but it cannot replace the nuanced human interactions essential for personal and professional growth.

Conclusion and Next Steps

Vince wraps up the episode by summarizing the key discussions and highlighting the enduring importance of human connection in business, even as technology evolves. He teases the next episode in the series, which will focus on Waverly's journey as an entrepreneur, blending her coaching experiences with her ventures.

Final Thoughts from Vince: “We already seeing a new wave of tech products called AI agents. So what will happen with this new norm? … As Waverly argues, building a business is fundamentally about building human relationships” (37:21).

Vince encourages listeners to subscribe, follow the podcast on various platforms, and stay tuned for the concluding episode of the series.

Notable Quotes

• Waverly Doidge (06:49): “Undergraduates don't know what's possible, they don't know what's impossible, they don't have the foundation for a lot of that logic.”
• Waverly Doidge (10:59): “By opening up just the completely low-risk experiment of just pitching it as a big business, it enabled her to bring her heart and head together.”
• Waverly Doidge (30:47): “AI is never going to be able to build those kinds of human relationships.”
• Waverly Doidge (30:10): “Smart people in AI are starting to talk about AI human partnership… generative AI needs to be a human partner, not a human replacement.”

This summary captures the essence of episode #336, providing listeners with a comprehensive overview of the discussions and insights shared by Vince Chan and Waverly Doidge.