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Sample Leadership Retreat Agendas

Use these as starting points. Your leadership objectives shape the content — Firefly supports the environment and flow at either Paradise (conversation-first intimacy) or Rock Springs (multi-zone momentum and scale).

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How to Use These Agendas

These structures are designed to create momentum without burnout. Each agenda includes:

  • A clear opening to align expectations

  • Working blocks that alternate between plenary and breakouts

  • Built-in reset time to protect decision quality

  • An evening “continuation window” where the best conversations happen

  • A closing block that converts decisions into ownership and next steps

2-Day Strategy Sprint-Paradise Only

Best for leadership teams who need rapid alignment on priorities, decisions, and execution — without taking a full week away from the business.
*Two-day strategy sessions include a one-night stay with required early arrival and late departure extensions to support a full program experience. A per-person extension fee applies.

Day 1 — Align & Decide

Early Arrival
• Lunch

Context
• Welcome and retreat objectives
• Current-state briefing (what’s true right now)
• Define top priorities to solve

Working Blocks
• Plenary strategy session
• Breakout groups: options, risks, tradeoffs
• Reconvene for decision points

Evening Continuation
• Hosted dinner
• Informal conversation window (no slides, high candor)

Day 2 — Own & Execute

Decision Consolidation
• Confirm final decisions
• Clarify what changes immediately

Ownership & Accountability
• Assign clear owners
• Define timelines and dependencies
• Confirm decision rights

Execution Plan
• 30/60/90-day roadmap
• Communication plan for broader team

Close
• Final alignment check
• Next-step commitments

Late Departure
• Lunch

Plan Your Retreat
Download the Planning Guide
Schedule a Call

3-Day Annual Planning Retreat

Best for annual planning, long-range strategy, and cross-functional alignment when leadership needs depth and pacing across multiple days.

Day 1 — Vision & Direction

Arrival & Context Setting
• Welcome and retreat objectives
• Year-in-review: what worked, what didn’t
• Market landscape and external realities

Strategic Direction
• Define annual priorities
• Clarify what will NOT be pursued
• Align on long-term positioning

Priority Framing
• Identify top 3–5 enterprise initiatives
• Define decision criteria
• Surface early risks and constraints

Evening Continuation
• Hosted dinner
• Informal reflection and relationship building

Day 2 — Functional Alignment & Tradeoffs

Department Breakouts
• Functional strategy refinement
• Resource needs and constraints
• Risk identification

Cross-Functional Sessions
• Interdependency mapping
• Budget and capacity discussions
• Resolve friction in real time

Decision Integration
• Reconvene as full group
• Confirm enterprise priorities
• Adjust sequencing and scope

Evening Continuation
• Fireside or patio conversations
• Open dialogue on unresolved tensions

Day 3 — Execution & Commitment

Execution Planning
• Convert priorities into a roadmap
• Define 30/60/90-day milestones
• Confirm key metrics

Ownership & Governance
• Assign executive owners
• Confirm reporting cadence
• Clarify decision rights

Communication & Rollout
• Plan internal messaging
• Define launch timeline
• Align leadership messaging

Close
• Final alignment check
• Confirm next leadership touchpoint
• Departure

Plan Your Retreat
Download the Planning Guide
Schedule a Call

Private Leadership (Weekend Agenda)

Best for ownership groups, founders, or senior leadership teams who want strategic conversation with lighter formal structure and deeper relationship space.

Friday — Arrival & Reconnection

Arrival & Orientation
• Arrival window and welcome reception
• Light framing of weekend objectives
• No formal presentations

Hosted Dinner
• Shared meal in private environment
• Open-ended conversation
• Relationship reconnection

Evening Continuation
• Fireside or patio discussion
• Space for candid dialogue

Saturday — Strategic Focus

Morning Strategy Block
• 1–2 focused strategic topics
• High-candor discussion
• Clarify decision themes

Midday Reset
• Walking conversations
• Optional light activity
• Informal small-group dialogue

Afternoon Alignment Session
• Surface unresolved tensions
• Identify major directional agreements

Evening Gathering
• Hosted dinner
• Relationship-first conversation

Sunday — Alignment & Commitment

Morning Alignment
• Confirm decisions and directional agreements
• Clarify what changes next week

Ownership & Follow-Through
• Assign accountability
• Confirm next leadership meeting

Close
• Reflection round
• Departure

Plan Your Retreat
Download the Planning Guide
Schedule a Call

Which Environment Fits Your Agenda?

Paradise by Firefly

Best for executive teams prioritizing proximity, candor, and layered conversation environments.

Paradise by Firefly-46 Acres

Rock Springs by Firefly

Best for larger leadership groups requiring multi-building separation, movement, and energy pacing.

Rock Springs by Firefly- 200 Acres