Leading With Empathy

The Preeminent Leadership Training Program

Aloha! My name is Kit Kanohoaloha Wynkoop, and I’m the lead teacher and curator of the Leading with Empathy executive training program.

In today’s world, we need optimistic, purpose-driven leaders—leaders who foster meaningful connections, operate with clarity and integrity, and believe in their ability to create positive change within their organizations and society. Research shows that leaders are at their best when they lead with empathy and compassion, prioritizing both personal and collective well-being—especially in times of uncertainty and adversity.

This program is not just about leadership principles—it’s an experiential journey into leading from an awakened mind. In modern terms, we call this leading mindfully with empathy. But here in Hawai‘i, according to beloved wisdom keepers Aunty Pilahi Paki, Aunty Morrnah Nālamakū Simeona, and Aunty Nānā Veary, it's called living ALOHA.

This is the foundation of true leadership—one that cultivates trust, resilience, and lasting impact.

Neil deGrasse Tyson

Accomplished astrophysicist, author, and science communicator known for popularizing science. His books and TV appearances have helped millions understand the universe. 
“Humans aren't as good as we should be in our capacity to empathize with feelings and thoughts of others, be they humans or other animals on Earth. So maybe part of our formal education should be training in empathy. Imagine how different the world would be if, in fact, [formal education included] reading, writing, arithmetic, & empathy.”

Empathy: The Key to Thriving Teams in a Changing Workplace

Today’s workplace is evolving faster than ever. With rising burnout, disengagement, and distrust, employees are searching for something deeper—a work environment where they feel valued, connected, and motivated. Leaders who cultivate empathic leadership are uniquely positioned to meet these challenges head-on.

From high attrition rates to the complexities of hybrid and remote work, organizations are struggling to maintain strong connections among teams. When employees feel isolated, they naturally start looking for a way forward—sometimes by seeking new opportunities elsewhere. But the solution isn’t just about better perks or policies. It’s about leadership that prioritizes genuine human connection.

Companies like EY (Ernst & Young) recognize this shift. In a recent episode of The Happy At Work Podcast, EY Vice Chair of Talent Management, Ginnie Carlier, shared how the company is embracing empathic leadership as a core strategy. By fostering an environment where employees feel seen and supported, EY empowers both individuals and teams to take ownership of their well-being while ensuring leaders have the tools to guide with empathy and clarity.

When leaders develop the ability to listen deeply, communicate openly, and lead with presence, they create a workplace culture that isn’t just productive—it’s resilient, engaged, and thriving. Empathic leadership isn’t just a trend; it’s the foundation of sustainable success in the modern workplace.

Stephen R. Covey

American educator, author, businessman, and speaker. His most popular book is The 7 Habits of Highly Effective People.
“Leadership is communicating to people their worth and potential so clearly that they come to see it in themselves.”
Empathic Leadership Starts with Self-Awareness

For companies to truly integrate empathic leadership, it cannot be treated as an “add-on” training or reduced to a communication technique. Empathy is not something leaders learn—it’s something they remember.

As human beings, empathy is our natural state, but over time, unhelpful conditioned thinking has overwritten this innate ability. Reconnecting with empathy requires self-awareness—the ability to observe and understand one’s own thoughts, emotions, words, and actions in real time. It also requires body awareness, as physical stress is often a sign that we are operating from old, reactive patterns rather than a place of clarity.

Mindfulness is the key. By intentionally paying attention—without judgment—leaders can build the self-awareness muscle needed to recognize when they are operating from stress and conditioned habits rather than presence and clarity.

When a leader understands how their body responds under pressure, they can catch themselves in the moment—whether handling a difficult conversation with an employee or responding to an angry customer. Instead of reacting from habit, they respond with calm, clarity, and confidence—qualities that inspire trust and create a more resilient, engaged workplace.

Empathic leadership isn’t about following a script—it’s about leading with awareness, authenticity, and presence.

Morrnah Nālamakū Simeona

Teacher, Author, Native Hawaiian Wisdom Keeper, and Founder of the Foundation of "I."
“If we can accept that we are the sum total of all past thoughts, emotions, words, deeds, and actions, and that our present lives and choices are colored or shaded by this memory bank of the past, then we begin to see how a process of correcting or setting aright can change our lives, our families, and our society.”
Reclaiming Your Original Self: The Key to Leading With Empathy

When we were born, we came into the world with a natural state of presence—fully aware, curious, confident, and open-hearted. We had an unconditioned mind, free from fear, doubt, and limitation. This was our original self, the foundation from which we naturally learned, connected, and experienced life.

But over time, that changed.

Around the age of four, we began developing what most people today call the “logical” or “thinking” mind—what psychology and neuroscience might refer to as the conditioned or ego mind. This mind doesn’t generate new awareness; instead, it pulls from past experiences, shaping our beliefs, reactions, and perceptions based on what we’ve been exposed to. By the time we reach 25, this conditioned mind becomes our default way of operating. It’s what we rely on to navigate life—but at a cost.

In Western culture, we’ve become so dependent on this conditioned mind that we’ve lost touch with our original self. We overanalyze, overthink, and react instead of experiencing life directly. As a result, stress, anxiety, depression, and emotional reactivity have skyrocketed, not just in individuals, but across entire societies.

But here’s the good news: You are not your conditioned mind. You can reconnect with the clarity, peace, and presence of your original self—and when you do, you’ll discover a way of living that’s free from struggle, reactive emotions, and suffering.

Sadhguru Jaggi Vasudev  

Teacher, Author, and Founder of the Isha Foundation
“Integrity, insight, and inclusiveness are the three essential qualities of leadership.”
Empathic Leadership Starts from Within

True leadership isn’t about mastering a set of scripted behaviors—it’s about embodying authenticity. The foundation of empathic leadership is self-awareness: the willingness to recognize and release conditioned thoughts, emotions, words, and actions that no longer serve us or those around us.

When leaders do this inner work, they naturally reconnect with their original self—a state of clarity, presence, and ALOHA. From this foundation, leadership becomes less about managing and more about inspiring. People feel seen, heard, and valued—not because of carefully chosen words, but because of the leader’s genuine presence.

This kind of leadership isn’t optional in today’s world—it’s essential. Across industries, organizations thrive when leaders cultivate trust, transparency, and collaboration. Empathic interactions—rooted in active listening and speaking truth—build that trust. Teams become more engaged, workplace dynamics improve, and communication barriers dissolve.

Empathic leadership isn’t about avoiding difficult conversations—it’s about transforming them. When leaders operate from their original self, they bring confidence and clarity to any situation, knowing they can find fresh, effective solutions. Rather than sidestepping challenges, they navigate them with ease, fostering a culture where employees feel safe, motivated, and empowered.

At its core, this is simply the result of mindfulness and awareness—leading not from habit, but from presence.

Dame Jacinda Ardern

New Zealand Politician, 40th New Zealand Prime Minister and Leader of the Labour Party from 2017 to 2023.
"One of the criticisms I've faced over the years is that I'm not aggressive enough or assertive enough, or maybe somehow, because I'm empathetic, it means I'm weak. I totally rebel against that. I refuse to believe that you cannot be both compassionate and strong."
It has been observed by researchers that, if applied in daily life, mindfulness & awareness lead to:
  • Emotional regulation 
  • Empathy & understanding
  • Reduced reactivity
  • Enhanced coping skills
  • Improved problem-solving
  • Acceptance of imperfections
  • Enhanced self-awareness
  • Better focus & concentration
  • Pain management
  • Stress reduction 
  • Enhanced bonding & communication
  • Reduced anxiety & depression
  • Increased resilience
  • Overall well-being

Thao N. Le & Pono Shim

Co-Authors of the Paper Called Mindfulness and the Aloha Response
“We propose that [Buddhist] mindfulness meditation…facilitates the discovery, recovery, and uncovery of the Aloha response leading to the experiential awareness and embodiment of Aloha.”
The Foundation of Leading with Empathy

The Leading with Empathy program is built on a foundation of time-tested secular wisdom and modern science. It integrates insights from Buddhist mindfulness-awareness practices, Tibetan psychology and philosophy, the Shambhala teachings, Hawaiian culture and ALOHA, indigenous wisdom traditions, non-dualism, and quantum mechanics.

At the heart of these teachings is a simple yet profound truth: there is an innate source of wisdom, courage, and goodness within each of us—what Hawaiʻi calls ALOHA. The ancient Shambhala teachings refer to this as the way of the warrior—not in terms of conflict, but as a path of fearlessness, presence, and deep inner strength.

Through the practice of true meditation—which can be done anywhere, at any time—we learn to reconnect with this natural state. When leaders cultivate this presence within themselves, they are able to bring more clarity, harmony, and resilience into their lives, their teams, and their organizations.

Simon Sinek

English-Born American Author and Inspirational Speaker on Business Leadership
"Empathy is being concerned about the
human being, not just their output."

Empathy in Business is a Win-Win for All

Employees that experience empathy from their leaders are known to experience less burnout, more motivation, and increased work-life balance. A Catalyst survey of nearly 900 employees also found that empathy is an important driver of innovation, engagement, and inclusion. Here are some of the survey’s most impactful findings:

Higher Employee Engagement. 76% of employees with highly empathic leaders report they are often or always engaged, compared to only 32% of employees with less empathic leaders.

Increased Innovation. 61% of employees with highly empathic leaders report they are more innovative at work compared to only 13% with less empathic leaders.

Higher Retention. Data shows that practicing empathy increases women’s sense that their individual life circumstances are valued and respected has downstream consequences for attrition, significantly increasing women’s intentions to stay at their job

Increased Inclusivity. 50% of people with highly empathic leaders report often or always experiencing inclusion at work, compared to only 17% of those with less empathic leadership.

Better work-life balance. 86% of employees who feel that their leaders are more empathetic report being much more able to balance work obligations with family and personal obligations, compared to 60% with less empathic leaders.

These findings show how critical empathetic leadership is in building a healthier, engaged, and motivated workforce. Genuine empathy allows leaders to connect with their people on a deeper level to understand their values and motivators. This enables leaders to create the right work environment needed for their happiness, productivity, and performance.

Barack Obama

American Lawyer and Politician who Served as the 44th President of the United States from 2009 to 2017. 
"Learning to stand in somebody else's shoes, to see through their eyes, that's how peace begins. And
it's up to you to make that happen. Empathy is a quality of character that can change the world."

Key Benefits of the Leading with ALOHA Training Program:

  • Develop mindfulness & authenticity to build trust, create engagement, and promote productivity
  • Identify what holds you back from embodying your real values
  • Learn how subtle outdated habitual patterns of thinking influence your actions as a leader
  • Practice the frameworks, tools, and strategies to step into your true power as a leader
  • Achieve higher levels of trust in yourself and others toward creating improved communication, team-building, and strategic planning
  • Gain the clarity, confidence, and courage to lead as your true and best self
  • Discover your team’s authentic strengths
  • Keep the material you learn alive by connecting online with the broader community of trainees for further discussions, review, & socializing.
  • Ask questions and/or share experiences with the teacher in a group setting during weekly live online sessions
  • Access the teacher for one-to-one guidance, help, and insight when needed
  • Repeat any of the material you finish as often as you wish
  • Continue the journey of leadership training with further material at no additional cost

Gustave M. Gilbert

American psychologist best known for his writings containing observations of high-ranking Nazi leaders during the Nuremberg trials.
“I've come close to defining [the nature of evil]: A lack of empathy. It's the one characteristic that connects all the defendants: A genuine incapacity to feel with their fellow man.”

Who Should Attend?

• Senior- to mid-level professionals who are committed to implementing creative strategies and practices to position their organizations at the forefront of innovation

• Engaged leaders who are committed to developing their management skills and approaches to optimize team performance

• Enterprising professionals who wish to collaborate with other self-motivated individuals and value an exchange of diverse perspectives, to drive change

• Emerging leaders who want to up-level their career trajectory and master the foundations of impactful leadership

What Sets This Program Apart?

High-Touch Learning Model

A flexible blend of independent and group-based work, dynamic engagement with faculty and peers in live sessions, and personalized 1:1 feedback from the teacher will keep you engaged and empowered to apply what you learn!

Design Your Learning Journey

Start with the foundation program then additional levels as desired to build the skill set
you need to reach your personal and professional goals.

Lifelong Community

Join the community of hundreds of participants who are in or have completed the program with exclusive invitations to speaker sessions and special events that bring people who Lead with Empathy together even after the program ends.

Course Teacher & Curator

After a 30-year career as a Project Manager, Kit Kanohoaloha Wynkoop shifted his focus to a lifelong passion: guiding others on the path of awakened leadership and mindful living. Today, he is a recognized teacher of world belief systems, indigenous wisdom traditions, Buddhist psychology, and non-dual philosophy—as well as a dedicated meditation mentor and a living embodiment of ALOHA.

For over 50 years, Kit has explored, studied, and, in many cases, been initiated into some of the world’s most profound spiritual and philosophical traditions. Drawing from this deep well of experience, he now teaches meditation as a practical and transformative path to reconnect with one’s original self—leading with clarity, presence, and ALOHA in all areas of life.

Program Details

Per person program fee: $525
21 weekly pre-recorded on-demand classes.
Each pre-recorded class lasts approximately 60-minutes.
Following each class, find recommended study materials and practice guidelines.
Ask questions of or share realizations with the teacher weekly during live online group gatherings.
Connect directly with the broader community of trainees for further discussions, review, & socializing.
Repeat the classes that you complete as many times as you wish at no additional cost.
Attend a week-long meditation retreat with other trainees at an additional cost.
Access the teacher for one-to-one guidance, help, and insight when needed.
Continue your training with further material at no additional cost.