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By Phase By Day Calendar
Empathize Define Ideate Prototype Test/Present
Empathize
Participants will ground the retreat in direct human-centered inquiry by interviewing fellow leaders about real pivot points, stress patterns, and decision contexts. They will produce evidence-based empathy artifacts that surface non-obvious needs and assumptions, creating a rigorous foundation for defining meaningful leadership challenges in the next phase.
Day 1
πŸŒ… Villa Welcome & Essential Question Circle
Launch 120m
🎧 Leadership Interview Lab
Knowledge/Skill Building 90m
🌿 Peer Leadership Interviews in Nature
Research 180m
πŸ—ΊοΈ Empathy Map & Journey Synthesis
Deliverable 90m
No activities have been added to this phase yet.

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Define
Participants will synthesize their peer leadership interviews and reflection data into a clearly framed, evidence-based leadership pivot problem statement. Through structured clustering, dialogue, and peer critique, they will produce a rigorous How Might We statement and rationale that anchors the next phase of ideation in real human need rather than assumption.
Day 2
🧠 Affinity Mapping Leadership Patterns
Knowledge/Skill Building 120m
🎯 Crafting the HMW Leadership Pivot
Deliverable 150m
πŸ” Evidence Check Peer Critique
Assessment 120m
πŸͺž Reflective Journal: Reframing My Leadership Challenge
Deliverable 90m
No activities have been added to this phase yet.

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Ideate
Participants will generate a wide range of human-centered leadership practice concepts grounded in peer interview evidence, then converge on 2–3 high-potential solutions for prototyping. Through structured divergence, analogy, and evidence-based decision-making, they will create annotated concept sketches that clearly link design features to documented user needs and retreat insights.
Day 3
πŸ’‘ Leadership Practice Idea Sprint
Deliverable 480m
No activities have been added to this phase yet.

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Prototype
Participants will translate their defined leadership pivot challenges into tangible, testable prototypes; gather structured feedback from real users and peers; and iterate their designs to better align with documented user needs, core values, and strategic priorities.
Day 4
πŸ›  Rapid Leadership Practice Prototypes
Deliverable 240m
πŸ” Iteration Log & Refined Prototype
Deliverable 240m
No activities have been added to this phase yet.

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Test/Present
Participants will conduct a final live validation of their cohort leadership prototype with new users, synthesize feedback into last refinements, and present their full design journeyβ€”from empathy research to iterationβ€”to an authentic audience during the closing evening circle.
Day 5
πŸ” Final Prototype Test with New Leaders
Assessment 240m
πŸ›  Iteration Log & Portfolio Finalization
Deliverable 120m
πŸŒ… Closing Circle: Design Journey & Transformation
Assessment 120m
No activities have been added to this phase yet.

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Empathize Days 1–1
Day 1
πŸŒ… Villa Welcome & Essential Question Circle
Launch 120m
🎧 Leadership Interview Lab
Knowledge/Skill Building 90m
🌿 Peer Leadership Interviews in Nature
Research 180m
πŸ—ΊοΈ Empathy Map & Journey Synthesis
Deliverable 90m
Define Days 2–2
Day 2
🧠 Affinity Mapping Leadership Patterns
Knowledge/Skill Building 120m
🎯 Crafting the HMW Leadership Pivot
Deliverable 150m
πŸ” Evidence Check Peer Critique
Assessment 120m
πŸͺž Reflective Journal: Reframing My Leadership Challenge
Deliverable 90m
Ideate Days 3–3
Day 3
πŸ’‘ Leadership Practice Idea Sprint
Deliverable 480m
Prototype Days 4–4
Day 4
πŸ›  Rapid Leadership Practice Prototypes
Deliverable 240m
πŸ” Iteration Log & Refined Prototype
Deliverable 240m
Test/Present Days 5–5
Day 5
πŸ” Final Prototype Test with New Leaders
Assessment 240m
πŸ›  Iteration Log & Portfolio Finalization
Deliverable 120m
πŸŒ… Closing Circle: Design Journey & Transformation
Assessment 120m

July 2026

Mon
Tue
Wed
Thu
Fri
27 Day 1
Empathize
πŸŒ… Villa Welcome & Essential Question Circle πŸŒ… Villa Welcome & Essential Question Circle
🎧 Leadership Interview Lab 🎧 Leadership Interview Lab
🌿 Peer Leadership Interviews in Nature 🌿 Peer Leadership Interviews in Nature
πŸ—ΊοΈ Empathy Map & Journey Synthesis πŸ—ΊοΈ Empathy Map & Journey Synthesis
28 Day 2
Define
🧠 Affinity Mapping Leadership Patterns 🧠 Affinity Mapping Leadership Patterns
🎯 Crafting the HMW Leadership Pivot 🎯 Crafting the HMW Leadership Pivot
πŸ” Evidence Check Peer Critique πŸ” Evidence Check Peer Critique
πŸͺž Reflective Journal: Reframing My Leadership Challenge πŸͺž Reflective Journal: Reframing My Leadership Challenge
29 Day 3
Ideate
πŸ’‘ Leadership Practice Idea Sprint πŸ’‘ Leadership Practice Idea Sprint
30 Day 4
Prototype
πŸ›  Rapid Leadership Practice Prototypes πŸ›  Rapid Leadership Practice Prototypes
πŸ” Iteration Log & Refined Prototype πŸ” Iteration Log & Refined Prototype
31 Day 5
Test/Present
πŸ” Final Prototype Test with New Leaders πŸ” Final Prototype Test with New Leaders
πŸ›  Iteration Log & Portfolio Finalization πŸ›  Iteration Log & Portfolio Finalization
πŸŒ… Closing Circle: Design Journey & Transformation πŸŒ… Closing Circle: Design Journey & Transformation
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