running-offsites

What this skill does

# Running Offsites

## Scope

**Covers**
- Designing an offsite that produces **durable alignment + decisions + momentum** (not “good vibes”)
- Choosing the right format: **1-day whiteboard sprint**, multi-day retreat, or remote-first **quarterly bursts**
- Creating conditions for deep work: **laptops down**, physical collaboration, and “out of day-to-day” space
- Building human connection **before** hard strategy work (so the room can disagree productively)
- Ending with clear artifacts: decisions, action plan, and follow-up communication that prevents backsliding

**When to use**
- “Plan a team offsite / retreat with a concrete agenda and outputs.”
- “Design a strategy offsite that results in decisions and owners.”
- “We’re remote-first—create a quarterly in-person ‘burst’ plan.”
- “Create the offsite prework + facilitation guide + logistics checklist.”
- “Turn our offsite into a documented plan and follow-up comms.”

**When NOT to use**
- You’re trying to fix deep interpersonal conflict with a workshop (“storytelling” won’t fix trust); do conflict repair first (or involve HR/leadership).
- You don’t know what you’re trying to achieve (use problem definition or product vision first).
- You need a large-scale event with complex vendor/contracting needs (use professional event planning support; this skill focuses on team-level offsites).
- The request is HR/legal/compliance-sensitive (escalate to humans and follow company policy).

## Inputs

**Minimum required**
- Offsite type: strategy / planning / retro / team reset / “burst”
- Outcomes: 3–7 desired outputs (decisions, plans, relationship goals)
- Participants (count, roles, time zones) + who must be in the room for decisions
- Constraints: dates, duration, budget band, location constraints, accessibility needs
- Current state: what’s broken today + any known tensions/elephants-in-the-room

**Missing-info strategy**
- Ask up to 5 questions from [references/INTAKE.md](references/INTAKE.md) (3–5 at a time).
- If details are missing, proceed with explicit assumptions and offer 2–3 format options.
- Do not request secrets; use anonymized/redacted context.

## Outputs (deliverables)

Produce an **Offsite Pack** (Markdown in-chat; or files if requested) in this order:
1) **Offsite Brief (1-pager)** (purpose, outcomes, decisions-in-scope, attendees, constraints, success measures)
2) **Agenda (timed) + Session Output Map** (each block has an explicit artifact output)
3) **Prework Pack** (pre-read + prompts + assignments + data/inputs to bring)
4) **Facilitation Run-of-Show** (scripts, norms, “laptops down” rules, decision capture method)
5) **Logistics Plan + Checklist** (venue/rooms/materials/food/tech/accessibility + backup plan)
6) **Post-Offsite Output Pack** (notes, decisions, action plan, follow-up comms, review checkpoints)
7) **Risks / Open questions / Next steps** (always included)

Templates: [references/TEMPLATES.md](references/TEMPLATES.md)  
Expanded guidance: [references/WORKFLOW.md](references/WORKFLOW.md)

## Workflow (8 steps)

### 1) Intake + boundary check (don’t design the wrong offsite)
- **Inputs:** user context; [references/INTAKE.md](references/INTAKE.md).
- **Actions:** Confirm: offsite type, desired outputs, constraints, and whether there’s underlying conflict/trust debt that must be handled first.
- **Outputs:** Context snapshot + assumptions/unknowns list + “offsite is appropriate” decision.
- **Checks:** You can name the “elephants” (at a safe level) and decide whether to address them directly, defer them, or escalate.

### 2) Define outcomes and decisions (artifact-first)
- **Inputs:** goals; constraints; stakeholder/participant roles.
- **Actions:** Convert goals into 3–7 concrete outputs (decisions, plans, principles, team norms). Define what must be decided **in the room** vs prepared in advance.
- **Outputs:** Offsite Brief sections: outcomes, decisions-in-scope, non-goals, success measures.
- **Checks:** Each outcome has an owner and a clear “done” definition.

### 3) Choose the right format (burst vs retreat vs whiteboard day)
- **Inputs:** outcomes; time available; work mode (remote/hybrid/on-site).
- **Actions:** Pick an offsite shape:
  - **Whiteboard day** for deep strategic work (“defrag the day”, laptops down).
  - **Retreat** (1.5–3 days) for reset + strategy + team bonding.
  - **Burst cadence** (quarterly) for remote-first high-velocity creative work.
- **Outputs:** Format recommendation + draft schedule skeleton (day blocks) + cadence suggestion.
- **Checks:** The format matches the work (creative/strategic/relationship) and the energy budget (no 8 hours of talks).

### 4) Design the agenda as a sequence of outputs
- **Inputs:** outcomes; session library in [references/WORKFLOW.md](references/WORKFLOW.md).
- **Actions:** Build a timed agenda where every session produces an artifact (decision log entry, principles list, strategy bets, roadmap slice, working agreements). Add breaks and “connection first” time.
- **Outputs:** Agenda + Session Output Map.
- **Checks:** At least 60% of time is interactive/co-creation; sessions have explicit facilitators and outputs.

### 5) Build prework that protects the offsite (remove day-to-day)
- **Inputs:** topics; data needed; participant availability.
- **Actions:** Create a prework pack that gathers inputs asynchronously and reduces meeting time wasted on context. Explicitly set “out of routine” expectations (no email/Slack during blocks, if feasible).
- **Outputs:** Prework Pack (pre-read + prompts + assignments).
- **Checks:** Participants can arrive ready to decide (not just “get informed”).

### 6) Write the facilitation run-of-show (make it runnable)
- **Inputs:** agenda; team norms; facilitation constraints.
- **Actions:** Draft the facilitation script: opening framing, norms, “laptops down” rule, whiteboard usage, breakout instructions, decision capture, and how to handle disagreement safely.
- **Outputs:** Facilitation Run-of-Show.
- **Checks:** A facilitator could run the day with minimal additional context; decision capture is defined.

### 7) Logistics + infrastructure (make it frictionless)
- **Inputs:** format; location; budget band; accessibility needs.
- **Actions:** Create a logistics plan and checklist (venue/rooms, supplies, food, travel, tech, accessibility, contingency plans). For bursts: define a repeatable booking/logistics process.
- **Outputs:** Logistics Plan + Checklist.
- **Checks:** Known failure modes are covered (no markers, bad room setup, no breaks, travel chaos, AV issues).

### 8) Close with memory + follow-through (prevent “Monday amnesia”)
- **Inputs:** notes/outputs; owners; timelines.
- **Actions:** Produce a post-offsite pack: decisions, action plan with owners/dates, follow-up comms, and review checkpoints. Add a “memory artifact” (1-page narrative, principles, or photo of boards + summary).
- **Outputs:** Post-Offsite Output Pack + comms draft + review plan.
- **Checks:** Every decision has an owner and next step; stakeholders not in the room receive a crisp summary.

## Quality gate (required)
- Run [references/CHECKLISTS.md](references/CHECKLISTS.md) and score with [references/RUBRIC.md](references/RUBRIC.md).
- Always include: **Risks**, **Open questions**, **Next steps**.

## Examples

**Example 1 (strategy offsite):** “Plan a 1-day strategy offsite for a 10-person product team (remote-first). Output the offsite brief, agenda + run-of-show, prework, logistics checklist, and post-offsite decision/action templates.”  
Expected: Offsite Pack with laptops-down whiteboard blocks + clear decision capture.

**Example 2 (quarterly bursts):** “Design a quarterly 2-day in-person burst cadence for a distributed team (PST/EST/UK). Include repeatable logistics, prework, and a default agenda that balances connection and deep work.”  
Expected: Burst program plan + default burst agenda + ops checklist.

**Boundary example:** “Run a storytelling workshop to fix our leadership team’s distrust