From HP Chief of Staff to Emotion-based Leadership Revolution: How Kathy Eastwood Built a Purpose-Driven Leadership Development Boutique

An exclusive interview with Kathy Eastwood, Founder & CEO of E Equals Why, by Roy Perlson, founder of Jobago.ai digital outplacement, on Kathy's journey from corporate accounting to transforming leadership across organizations. 

 Kathy Eastwood, Founder & CEO of E Equals Why.

Q: Kathy, you've had quite a remarkable journey - from starting as a CPA at Ernst and Young to becoming the Founder and CEO of E Equals Why. What was the pivotal moment that made you realize you needed to leave the corporate world and start your own leadership development company? 

Kathy Eastwood: You know, Roy, it really came down to witnessing too many talented teams being held back by poor management. I spent over 25 years in corporate roles - from Chief People Officer at Data Intensity to Chief of Staff at Hewlett Packard Enterprise - and I kept seeing the same pattern: brilliant people working in environments where toxic leadership prevented them from reaching their potential. The breaking point came when I realized I had experienced that toxic leadership myself, and I knew there had to be a better way. I took a year off to realign my values with my goals, and that's when E Equals Why was born in October 2019. 

Q: That's fascinating. You mentioned the E3 Leadership Code - Express, Engage, Execute, powered by Emotional Qualities. Can you walk us through how you developed this framework? 

Kathy Eastwood: The E3 Leadership Code came from my realization that only 8% of organizations actually achieve their goals, while people-first strategies can increase profitability by 23%. I needed a repeatable system that leaders could actually use. Express means defining your vision and purpose with clarity and transparency - where are we going and why? Engage is about connecting authentically with the people you need to influence, creating shared ownership. Execute focuses on discipline and rhythm, ensuring accountability and progress. But here's the key - all three are powered by emotional intelligence, the emotional qualities that make leadership human, not mechanical. 

Q: You're also a Board Member of Conscious Capitalism NYC. How does conscious capitalism intersect with your leadership philosophy? 

Kathy Eastwood: Conscious Capitalism is about building businesses that are both profitable and purposeful. It’s a global movement that started about 20 years ago and continues to expand. At its core, it’s about considering all stakeholders — employees, customers, communities, and investors — not just shareholders. That aligns perfectly with my philosophy that leadership must be people-first, especially as we move into an AI-first future. When leaders take a stakeholder view and lead with compassion, you create a virtuous cycle: engaged people, loyal customers, and stronger business results.  

Q: Speaking of AI's impact on leadership, you mentioned that the future will be "AI-first, which means leadership must be people-first." Can you elaborate on this paradox? 

Kathy Eastwood: It's not really a paradox when you think about it. As AI handles more of the technical, repetitive tasks, what becomes invaluable is the uniquely human elements of leadership - emotional intelligence, authentic connection, purpose-driven decision making. The leaders who will thrive are those who can lift others as they climb, who can navigate disruption with compassion, and who understand that engaged, empowered employees are the foundation of profitability and customer retention. 

Q: You've mentioned that your company name comes from both your family name and a formula. Can you explain the "E Equals Why" connection? 

Kathy Eastwood: Absolutely! It's a play on both Eastwood - my family name - and our core formula. E represents Express plus Engage plus Execute, all powered by Emotional Qualities, and that E, Equals Why leaders succeed. Leadership is fundamentally about winning the hearts of others to take the action you need them to take. When you understand the emotional component of leadership and combine it with clear vision, authentic engagement, and disciplined execution, you get results. 

Building Leadership Excellence: Practical Applications and Real-World Impact 

Q: In your work with clients, what are the most common leadership challenges you encounter, and how does the E3 framework address these specific pain points? 

Kathy Eastwood: The most frequent issues we see are strategic initiatives stalling because daily demands hijack progress, silos creating friction where competing priorities and poor handoffs erode trust, and inconsistent processes blocking scaling efforts. Leaders often rely on workarounds and heroic efforts, which makes growth painful. What I find particularly troubling is how many managers are ill-equipped - they simply don't have the training or frameworks to align teams, drive accountability, and deliver results. The E3 Leaders Code addresses this systematically. When leaders Express clearly, teams know exactly where they're going and why it matters. When they Engage authentically, those silos break down because people feel heard and valued. And when they Execute with discipline, you eliminate those workarounds because everyone knows their role and how it contributes to the bigger picture. 

Q: Can you share a specific example of how the E3 Leadership Bootcamp has transformed a team or organization? 

Kathy Eastwood: I love sharing Aileen Allkins' story from YNV Group. She told us, "With E Equals Why, our executive team has achieved remarkable progress in understanding and collaborating, setting higher benchmarks for excellence and accountability that have distinctly elevated our performance." What happened there was classic - they had brilliant individual contributors, but they weren't functioning as a cohesive leadership team. Through the bootcamp, they learned to Express their collective vision, not just individual departmental goals. They discovered how to Engage across silos, creating shared ownership of company-wide objectives. Most importantly, they Execute now with a rhythm that keeps everyone accountable to results, not just activities. 

Q: You mentioned that you take a people-first lens because that’s what drives profit.. How do you balance these seemingly competing priorities? 

Kathy Eastwood: This is where people often misunderstand the people-first approach. It's not about being soft or avoiding difficult decisions - it's about recognizing that engaged, productive employees are your path to profitability and creating a virtuous cycle. The data backs this up completely. When employees are disengaged, productivity drops — in fact, 67% of the workforce ends up negatively impacting output. That creates friction across the business and ultimately shows up in the customer experience, with disengaged organizations seeing a 32% decrease in customer retention. When people leave, the cost is steep — on average, 33% of their annual salary just to replace them. But when you flip that cycle and invest in people, everything changes. Teams are more engaged, customers stay longer, and the business thrives — including up to a 23% increase in profitability. When you invest in people through authentic leadership development, you're making the smartest business decision possible. It's not people versus profit - it's people creating profit. 

Q: Your E3 Leadership Profile helps individuals map their values, purpose, and leadership style. How has this tool evolved since you launched it, and what impact have you seen? 

Kathy Eastwood: The E3 Leadership Profile has become our secret weapon for career transitions and team alignment. Initially, it was just a framework I used in coaching, but clients kept asking for something they could reference and share. Now it's a practical tool that helps people tell their leadership story on one page - whether they're stepping into a new role, preparing for interviews, or aligning with their team. What I love about it is how it forces people to get clear on their non-negotiables - their values - and then connect that to the impact they want to create. Too many leaders drift without this clarity, and the best ones find their way back to these fundamentals when challenges arise. 

Q: As someone who's navigated both corporate politics and entrepreneurial challenges, what advice would you give to leaders who are feeling stuck or overwhelmed in their current roles? 

Kathy Eastwood: First, recognize that feeling stuck often means you're not aligned with your values or you've lost sight of your purpose. Start with the fundamentals - map out what truly matters to you and the impact you want to create. Then, look at your current situation through the E3 lens. Are you Expressing your vision clearly enough that people understand and buy into it? Are you truly Engaging with your team, or are you just managing tasks? Are you Executing with the right rhythm and accountability measures? Often, leaders feel overwhelmed because they're trying to control everything instead of empowering others. Remember, leadership is about winning hearts to drive action - if you're doing all the work yourself, you're not leading effectively. 

Q: What's been the most challenging aspect of building E Equals Why, and how has your corporate background helped you navigate entrepreneurship? 

Kathy Eastwood: The biggest challenge was transitioning from being someone who could rely on established corporate systems to building everything from scratch. But my corporate experience, especially my time as Chief People Officer, taught me that people-first strategies work. I learned that when teams thrive, business results follow. This wasn't just theory - I saw it in action when engaged employees led to better customer retention and profitability. That knowledge gave me confidence that our approach would work for other organizations too. 

Q: You've successfully built E Equals Why from a solo venture into a thriving team over five years. What's your vision for the next phase of growth? 

Kathy Eastwood: We have three major initiatives ahead. First, we're developing the E3 Leadership Seal of Approval - a comprehensive, universal certification platform that will help organizations identify and hire leaders who truly inspire and enable team success. Second, I'm completing a book that will give leaders the tools to achieve what I call the "top 8% edge." Finally, we're scaling our E3 Leadership Bootcamp to reach leaders globally, because the need for authentic, effective leadership has never been greater. 

Q: For leaders who are struggling with team alignment or facing the kind of toxic dynamics you experienced, what's your first piece of advice? 

Kathy Eastwood: Start with yourself. Use our E3 Leadership Profile to map your values - what matters most to you and your non-negotiables. Then define your purpose - the impact you want to create. Finally, clarify your leadership style - how you show up for others. This gives you a one-page leadership story that you can use whether you're stepping into a new role, preparing for interviews, or aligning with your team. Purpose is the anchor that fuels resilience, clarity, and results. When you align who you are with how you lead, you can help others do the same. 

Key Takeaways 

• The 8% Success Gap: Only 8% of organizations achieve their goals, but people-first leadership strategies can increase profitability by 23% 

• AI Amplifies Human Leadership: As artificial intelligence handles technical tasks, emotional intelligence and authentic human connection become more valuable than ever 

• The E3 Framework: Express your vision clearly, Engage people authentically, Execute with discipline - all powered by emotional qualities 

• Purpose-Driven Leadership: Aligning personal values with leadership style creates a foundation for sustainable success and team engagement 

• Conscious Capitalism Connection: Considering all stakeholders while driving profit creates the "virtuous cycle" of happy people, happy customers, and happy results 

• Leadership Development ROI: Investment in proper leadership training pays dividends through improved employee retention, customer satisfaction, and organizational profits 

• Breaking Down Silos: Effective leadership eliminates organizational friction by creating shared ownership and clear accountability structures 

• Values-Based Decision Making: Leaders who map their non-negotiables and purpose create consistency that teams can trust and follow 

Kathy Eastwood is the Founder & CEO of E Equals Why, a New York City-based leadership development company that empowers individuals, teams, and organizations through their proven E3 Leadership Code methodology. 

Connect with Kathy Eastwood: 

• Website: www.eequalswhy.com 

• LinkedIn: linkedin.com/in/kathyeastwood 

• Voices of Leadership Series - YouTube