Leadership doesn’t have to be complicated—even in complex times.
SIMPLER Leadership LLC was founded by Kai Degner, a former mayor, civic facilitator, and leadership educator who has spent over 20 years guiding individuals and teams through uncertainty, transition, and high-stakes conversations.
Kai's multi-sector experience in leadership roles also gives Kai an ability to understand the context, polarities, and constraints faced by many different types of organizations. He has served as mayor and councilmember, nonprofit executive director, nonprofit board member, small business owner, and higher education administrator. As of 2023, Kai is also a doctoral candidate in Strategic Leadership studies with an emphasis on organizational change, leadership development, and listening.
Drawing from a unique blend of civic experience, adult learning design, organizational change theory, and cutting-edge leadership research, Kai created the SIMPLER Leader/ship Frameworks to help leaders do what matters most: adapt with clarity, integrity, and impact.
Whether leading yourself, a team, a community, or an organization, SIMPLER Leadership equips you with practical tools and mindsets that make complexity feel manageable—and leadership feel possible.
SIMPLER Leadership specializes in:
Facilitating clarity and coordination in messy, urgent, or high-stakes moments
Designing energizing meetings and summits that mobilize people into aligned action
Teaching listening as a core leadership competency
Supporting emerging and experienced leaders through live masterminds, trainings, and coaching
If you’re navigating conflict, polarization, or transition—and want to lead with intention—we’ll help you grow your leadership capacity and move your work forward with confidence.
Kai Degner, M.B.A., has an extensive background in facilitating a range of events, from strategic planning, to team-building, to large-scale community summits.
Kai’s interest in facilitation developed when he founded The OrangeBand Initiative, a civil discourse nonprofit that hosted over 300 discussion events in the Harrisonburg/Rockingham area in 2003-2007. The effort connected him with the National Coalition for Dialogue and Deliberation, and exposed him to the many facilitation methods and frameworks cataloged in The Change Handbook: Group Methods for Shaping the Future (Holman et al., 2007).
His facilitation strengths include knowledge and experience with a broad array of facilitation methods and frameworks that are designed for problem identification, dialogue, ideation, prioritization, and reaching decisions. This allows him to match and combine tools to fit a specific group’s needs and constraints, rather than continuously applying the same approach for all clients.
Kai’s facilitation experience includes nonprofit, government, university, and small/medium business contexts.
Kai brings over a decade of experience designing and delivering transformative learning experiences for adult professionals. As a university instructor and director of professional development, he has taught graduate and noncredit leadership courses on topics including strategic communication, project management, systems thinking, and facilitation. His teaching style blends academic theory with hands-on learning, allowing participants to immediately apply insights to real-world contexts.
Kai holds an M.B.A., is a certified trainer in adult learning and instructional design, and integrates experiential learning methods into all of his workshops. Whether leading half-day trainings or semester-long courses, he specializes in helping professionals connect leadership concepts to their day-to-day challenges.
He has taught hundreds of students and led trainings for nonprofit staff, government teams, and community coalitions—always with an emphasis on clarity, curiosity, and action.
As a trained executive and leadership coach, Kai supports individuals navigating leadership transitions, burnout, interpersonal conflict, or the desire to grow into more adaptive, values-aligned leadership. His coaching draws from evidence-based practices in adult development, complexity leadership, and communication, including his original work on listening in leader-follower relationships.
Kai has coached mayors, nonprofit founders, community organizers, and early-career professionals alike. He helps clients clarify their priorities, build new leadership habits, and move forward with confidence—even in ambiguity. His coaching style is deeply empathetic, structured, and action-oriented.
Coaching is available as a stand-alone service, which blends small-group coaching with structured peer support and micro-trainings.