Remote Meeting | Ian Kitajima and Tracie Foglia discuss the launch and impact of the Hawaii Leadership Academy

In this meeting, Ian Kitajima and Tracie Foglia discussed the launch and impact of the Hawaii Leadership Academy, aimed at developing senior leaders across various industries in Hawaii through experiential learning and fostering collaboration. Ian shared insights from his extensive technology and entrepreneurship background, emphasizing the importance of AI proficiency combined with human experience and the need for leaders to model AI adoption to cultivate adaptive organizational cultures. They also explored practical ways to leverage AI, innovate, and build partnerships within Hawaii’s unique community and business environment to drive positive change.

Meeting Summary:

Participants: Ian Kitajima, Tracie Foglia
Date: September 23, 2025
Format: Remote meeting

1. Personal and Professional Updates

  • Ian shared his experience of managing an overloaded schedule and his recent decision to limit meetings to four per day for better sanity and productivity.
  • Tracie discussed her experience creating a new division within the Hawaiian Players Council, describing it as a “startup” environment with no existing parameters, highlighting the nuances of neighbor island businesses versus O‘ahu.
  • Both expressed enthusiasm for their current work and a shared love for continuous learning and leadership development.

2. Hawaii Leadership Academy Launch

  • Tracie introduced the Hawaii Leadership Academy (HLA), launched in partnership with Hawaii Business Magazine.
  • The academy targets senior leaders (director level and above) from diverse industries across Hawaii’s islands, focusing on growing leadership capacity, fostering community-oriented mindsets, and encouraging collaboration rather than competition for resources.
  • The inaugural cohort includes 27 leaders from various sectors, with workshops and guest leaders providing frameworks and sparking dialogue rather than traditional curriculum.
  • Ian noted parallels to his own experiences with leadership and organizational silos, emphasizing the importance of leaders bridging gaps across sectors.
  • The cohort will continue with alumni engagement and leadership opportunities, including moderating panels at future conferences, where Ian will be a featured speaker.

3. Ian’s Background and Current Work

  • Ian recounted his journey from Kaneohe public schools through community college and University of Hawaii at Manoa, highlighting his early passion for learning and his ventures in technology businesses in the U.S. and Finland.
  • Emphasized his role in transitions from typewriter to personal computing and participation in early mobile phone innovations, including a startup in Helsinki focused on mobile virtual communities.
  • Returned to Hawaii around 2000 to join Oceanit, dedicating over 20 years there before retiring three years ago.
  • Currently leading activities at Picture, a nonprofit incubator that supports both Japanese and Hawaiian startups entering the U.S. government market.
  • Launched Hawaii Wave, an incubator for Hawaii-based companies aiming to enter government sectors, alongside continuous workshops on AI for nonprofits and corporate clients.

4. Leadership and AI Integration

  • Ian and Tracie discussed AI as the “Fifth Industrial Revolution,” focusing on its rapid impact on work and leadership.
  • Ian emphasized critical leadership mindsets for successful AI adoption:
    • Continuous learning and personal AI proficiency.
    • Combining deep experience with AI to become “superhuman” in problem-solving.
    • Visioneering: the ability to suspend reality constraints to innovate and dream big while managing risk realistically.
  • Training and empowering teams to use AI tools in their everyday work is crucial for organizational agility and adapting to AI-driven changes.
  • Leaders must model AI learning and usage to foster a culture of experimentation and openness.
  • The role of non-technical leaders as translators between technical teams and broader organization was identified as vital.
  • Ian predicts a new category of workers—“visioneers”—who blend visionary thinking with hands-on AI application skills.
  • Emphasized the importance of young professionals gaining diverse experiences and learning continuously to stay relevant, while older leaders must avoid being constrained by experience that discourages innovation.

5. Building AI-Enabled Organizational Culture

  • Culture was described as intangible, transmitted through leader behaviors and interpersonal interactions rather than formal messaging.
  • AI adoption depends on grassroots education supported by leadership demonstrating its use.
  • Sharing AI learnings organization-wide via regular gatherings or collaborative groups is key to scaling proficiency.
  • Organically building in-house AI expertise by empowering individuals tackles AI challenges pragmatically.
  • Encouraged leveraging AI to automate mundane tasks, freeing leadership to focus on strategy and reflection.
  • Ian shared personal success stories of rapid project completions made possible by AI tools.
  • Both agreed on the value of intentional time for reflection and thinking amidst busy schedules.

6. Future Initiatives and Collaboration

  • Discussion about expanding AI “vibe coding” workshops (hands-on AI application building) to the Big Island in partnership with local leaders.
  • Tracie is organizing cohort groupings using AI matchmaking tools based on work preferences.
  • Ian highlighted his use of AI for complex matching tasks, illustrating practical AI applications.
  • Ian to send Tracie the video recording, transcription, and summaries from the session.
  • They expressed gratitude for each other’s support and commitment to advancing leadership and innovation in Hawaii.

7. Closing Remarks

  • Both acknowledged the exciting era for leadership and entrepreneurship fueled by AI.
  • Ian shared upcoming business trips and expressed hope for moments of joy amid busy schedules.
  • Strong mutual appreciation was expressed, emphasizing ongoing collaboration to uplift Hawaii’s leadership and technology ecosystem.

Key Takeaways

  • Leadership in the AI era requires continuous learning, visionary thinking, and modeling technology adoption.
  • Building a supportive, adaptive organizational culture is critical for embracing AI-driven transformation.
  • Collaboration and shared learning enhance AI readiness and leadership impact across diverse Hawaiian communities.
  • Hawaii’s unique island-specific nuances and neighbor island talent must be recognized and leveraged to foster equitable growth.
  • Ian and Tracie’s partnership reflects a dynamic synergy supporting leadership development and AI integration in Hawaii’s business and nonprofit sectors.

This meeting emphasized the significance of leadership mindset shifts and practical organizational strategies to fully harness AI capabilities, particularly within the unique context of Hawaiian business and nonprofit ecosystems.

Listen to the meeting here.