Lead Change with Kindness: Insights from

Timshel Tarbet
Sep 1, 2025
3 min read

Updated: Oct 8, 2025

In a world where business leadership often prizes efficiency over empathy, Red Helicopter by James Rhee offers a refreshing alternative. This parable emphasizes leading with humanity, clarity, and purpose. Rhee shares his unlikely journey—from a Harvard-educated private equity investor to the CEO of a twice-bankrupt retailer. His story is anchored in kindness, blended with a little math. It invites leaders to redefine success through goodwill, intentional action, and values-driven strategy.

Why This Book Matters

Rhee’s story is deeply human. It begins with a childhood act of generosity, symbolized by a toy red helicopter. This evolves into a profound leadership philosophy. As a Harvard graduate, Rhee chose to lead Ashley Stewart—an iconic brand that serves largely Black women. He emerged as an unlikely CEO who rebuilt its fortunes with empathy, rigor, and operational clarity. The book quickly became a national bestseller, praised for its balance of feel-good storytelling and practical business wisdom.

Library Journal described it as “a well-crafted narrative with a genuine and heartfelt approach.” This positions Rhee alongside influential leadership thinkers like Simon Sinek and Brené Brown.

Lessons That Resonate With Organizational Leadership

1. Human-Centered Leadership Can Drive Results

Rhee’s anecdote about receiving a red helicopter as a child serves as a powerful reminder. Leadership rooted in kindness is not sentimental—it’s strategic. Aligning values with operations is how organizations like Providence or SCAN create culture-driven outcomes. This approach fosters an environment where everyone feels valued and motivated.

2. Goodwill as a Business Asset

Rhee introduces the concept of “measuring goodwill” as a key business metric. It’s not just about feeling good; it drives loyalty, culture, and long-term value. When organizations prioritize goodwill, they cultivate stronger relationships with their stakeholders.

3. Small Acts—Big Impact

The red helicopter symbolizes the power of small, meaningful gestures. These actions can lead to systemic shifts. For instance, equipping 90% of staff with equity training or refining patient/member experiences can significantly improve CMS star ratings. It’s about making every interaction count.

4. Kindness and Math—Together

Rhee’s formula for change combines quantifiable strategy—“a little math”—with deep empathy. This dual approach mirrors our own experiences. Transforming risk models, building culture, and optimizing operations requires a balance of both elements. We cannot ignore one for the other.

5. Resilience Amid Uncertainty

Rhee’s leadership at Ashley Stewart was high-risk yet rooted in values and discipline. This combination of clarity and courage is foundational to sustainable transformation. Whether in health systems, nonprofits, or enterprises, resilience is key to navigating challenges.

Why You Should Read Red Helicopter

Red Helicopter is more than just a business memoir. It serves as a playbook for values-centered leadership. Whether you're steering change in healthcare, HR, risk, or transformation, this book offers a framework rooted in humanity. It’s rare to find leadership literature that blends storytelling, business insight, and emotional wisdom so elegantly. If you’re ready to lead with intention—and impact—this book will resonate long after you close the cover.

Final Thoughts from My Journey

I’ve led transformations that protected $120M in revenue, fueled 17% membership growth, and earned national accolades for ethics and risk. Time and again, the leaders who leave a lasting impact are those who, like Rhee, understand that business is deeply human. Red Helicopter doesn’t just say that—it shows it.

Implementing the Lessons

Creating a Culture of Kindness

To bring the lessons of Red Helicopter into your organization, we must start by fostering a culture of kindness. This involves:

Encouraging Open Communication: Create an environment where team members feel safe to express their thoughts and ideas.
Recognizing Contributions: Celebrate small wins and acknowledge the efforts of individuals. This builds morale and strengthens relationships.
Investing in Training: Equip staff with the skills they need to succeed. This includes equity training and professional development opportunities.

Measuring Goodwill

Next, we should focus on measuring goodwill. This can be achieved by:

Conducting Surveys: Regularly gather feedback from employees and stakeholders to assess their feelings about the organization.
Tracking Engagement Metrics: Monitor participation in company initiatives and community outreach programs.
Evaluating Customer Loyalty: Analyze retention rates and customer satisfaction scores to gauge the impact of goodwill on business performance.

Embracing Resilience

Finally, embracing resilience is crucial. To do this, we can:

Develop Contingency Plans: Prepare for potential challenges by having strategies in place to address them.
Foster a Growth Mindset: Encourage a culture where mistakes are viewed as learning opportunities rather than failures.
Prioritize Well-being: Support the mental and emotional health of team members to ensure they can navigate uncertainty effectively.

Conclusion

Ready to bring the lessons of Red Helicopter into your organization? Let’s discuss how combining values, strategy, and small actions can elevate your leadership—and your results.

Stay inspired. Stay intentional. Fly your own red helicopter. ***[Schedule a Consultation
] or Join Our Newsletter for More Insights.

Sources: