Offsite Pack: Q2 Strategy + Working Agreements Reset
Produced by: running-offsites skill pack
Date generated: 2026-03-17
Step 1: Intake + Boundary Check
Context Snapshot
| Field | Value |
|---|---|
| Offsite type | Strategy + team reset (hybrid) |
| Team | 10-person product team, remote-first |
| Duration | 1 day (full day, ~8 hours on-site) |
| Location | NYC (in-person venue, all participants traveling in) |
| Budget | Moderate (~$3,000-5,000 total; covers venue, food, supplies, not flights/hotels) |
| Key goals | Decide Q2 priorities; reset working agreements |
| Work mode | Laptops-down whiteboard day |
Assumptions (labeled)
- A1: All 10 participants can attend in-person in NYC (no hybrid/remote attendees). If anyone is remote, a backup plan is included in Logistics.
- A2: The team lead / Head of Product is the primary decision-maker for final Q2 priority calls; the full team has input.
- A3: There is no severe trust or interpersonal conflict; the "reset working agreements" signals friction in ways-of-working, not deep relationship damage.
- A4: Moderate budget means we rent a dedicated offsite space (not the office) to create psychological separation from day-to-day, with catered lunch and snacks.
- A5: Q1 metrics, customer feedback, and a draft roadmap exist or can be assembled as prework.
- A6: Stakeholders not in the room (e.g., Engineering lead, CEO, Sales) will need a post-offsite summary.
Boundary Check: Is an Offsite Appropriate?
Yes. The request involves two goals that benefit from synchronous, in-room, focused time:
- Q2 priority decisions -- requires divergence, debate, and commitment that is hard to do async for a remote-first team.
- Working agreements reset -- requires candid conversation about norms, which benefits from face-to-face safety.
Elephants to monitor (safe level):
- The need to "reset" working agreements implies current agreements are broken or never existed. The facilitation plan names this directly and uses a structured "start/stop/continue" format (not forced vulnerability).
- Priority-setting may surface disagreements about team direction. The facilitation plan includes a disagreement-handling protocol.
No escalation needed: No indicators of HR-level conflict. If anything surfaces during the day, the facilitator will park it and follow up privately.
Step 2: Offsite Brief (1-Pager)
Offsite name: Q2 Strategy Sprint + Ways-of-Working Reset Date: TBD (recommend a Thursday to allow Friday for travel/recovery) Duration: 1 day (9:00 AM -- 5:30 PM ET) Location: Dedicated offsite venue, NYC (not the office) Work mode: In-person, laptops-down Participants: 10 (full product team) Decision-makers in room: Head of Product (final call on Q2 bets); full team (working agreements are collective)
Purpose (why are we doing this?)
- Why now: Q1 is ending; the team needs to commit to Q2 priorities before the quarter starts, and current working agreements are causing friction in a remote-first setup.
- We're here to: Align on Q2 strategic bets, make binding priority decisions, and establish working agreements the team commits to follow.
Target Outputs (5)
- Q2 Strategic Bets (3-5) -- Prioritized bets with rationale, anti-bets (what we are NOT doing), and owners.
- Decision Principles (5-7) -- Principles the team will use to make tradeoff decisions during Q2 without escalating everything.
- Working Agreements v2 -- Explicit norms for decision-making, communication, meeting cadence, and escalation for a remote-first team.
- Q2 Action Plan -- First 2-week actions for each bet, with owners, dates, and dependencies.
- Post-Offsite Comms -- Summary for stakeholders not in the room (Engineering, leadership, Sales).
Decisions In Scope
- Which 3-5 bets define Q2 (and which ideas we are explicitly NOT pursuing).
- Decision principles for making tradeoffs during Q2.
- Working agreements: meeting norms, async vs sync defaults, escalation paths, Slack/comms hygiene.
- Owners and first actions for each Q2 bet.
Decisions Out of Scope
- Org structure or role changes.
- Compensation, headcount, or hiring plans.
- Multi-quarter roadmap beyond Q2.
- Engineering architecture or technical debt prioritization (that's a separate session with Engineering).
Success Measures
Immediately after:
- Every participant can state the Q2 bets and their own first action without looking at notes.
- Working agreements are written and every person has said "I commit" (or raised a specific objection that was resolved).
- The post-offsite comms draft is ready to send.
2-4 weeks after:
- Q2 bets are in the tracking system with progress updates.
- Working agreements are visibly in use (e.g., meeting norms followed, escalation path used at least once).
- The 2-week checkpoint meeting happened and surfaced any drift.
Risks + Constraints
| Risk | Mitigation |
|---|---|
| Participants arrive cold (no prework done) | Prework is lightweight but mandatory; facilitator checks completion 2 days before |
| Priority debate becomes circular | Decision principles session runs first; facilitator uses criteria-based convergence |
| Working agreements discussion gets personal | Use "start/stop/continue" format (behavioral, not personal); park sensitive items |
| Key person absent (illness/travel) | Identify a proxy; defer their decisions to async follow-up within 48 hours |
| Energy crash after lunch | Schedule the most interactive session (working agreements) post-lunch; include a walk break |
Roles
| Role | Person |
|---|---|
| Facilitator | TBD (recommend: someone NOT the Head of Product, so the decision-maker can participate fully) |
| Timekeeper | TBD (rotate among team) |
| Scribe / decision logger | TBD (one designated person with laptop open; everyone else laptops down) |
| Logistics owner | TBD (handles venue, food, supplies, travel coordination) |
Step 3: Format Recommendation
Chosen Format: Laptops-Down Whiteboard Day
Why this format:
- 1-day constraint eliminates a retreat model.
- The work is strategic (Q2 bets) + normative (working agreements) -- both benefit from physical co-creation, not slides.
- Remote-first team rarely gets face time; maximize interactive whiteboard time.
- Moderate budget supports a dedicated venue with whiteboards and catering, not a multi-day hotel retreat.
Schedule skeleton:
| Block | Time | Energy Level | Type |
|---|---|---|---|
| Morning 1 | 9:00-10:30 | High | Connection + Context Alignment |
| Break | 10:30-10:45 | -- | -- |
| Morning 2 | 10:45-12:30 | Peak | Decision Principles + Q2 Bets (divergence) |
| Lunch | 12:30-1:30 | -- | Catered, informal |
| Afternoon 1 | 1:30-3:15 | Rebuilding | Working Agreements (interactive) |
| Break + Walk | 3:15-3:35 | -- | Outdoor walk if weather permits |
| Afternoon 2 | 3:35-5:00 | Moderate | Q2 Bets (convergence + commitment) + Action Plan |
| Close | 5:00-5:30 | Wind-down | Decisions review + checkpoint + close |
Cadence suggestion: If this goes well, consider establishing a quarterly 1-day burst cadence (next one at mid-Q2 for a check-in, or start of Q3 for the next planning cycle).
Step 4: Agenda + Session Output Map
| Time | Session | Goal | Format | Facilitator | Laptops | Prework/Input | Output Artifact |
|---|---|---|---|---|---|---|---|
| 9:00-9:15 | Opening + Norms | Set intent, rules, and energy | Plenary: facilitator speaks | Facilitator | Down | None | Norms poster (on wall) + outcomes list |
| 9:15-9:45 | Connection Round | Build trust before hard work | Pairs rotate (3x 10-min 1:1s); prompt: "What's one thing going well and one thing you're wrestling with?" | Facilitator | Down | None | Warmed-up room; psychological safety baseline |
| 9:45-10:30 | Context Alignment | Get everyone to the same starting line | Silent read of pre-read (10 min) then structured Q&A (20 min) then "what surprised you?" round (15 min) | Facilitator | Down (printed pre-read) | Pre-read packet (Q1 metrics, customer insights, draft roadmap) | Shared "current state" bullets + constraints list (on whiteboard) |
| 10:30-10:45 | Break | -- | -- | -- | -- | -- | -- |
| 10:45-11:30 | Decision Principles | Establish criteria for Q2 tradeoffs | Small groups (3-3-4) generate principles from real tradeoff examples (15 min) then merge + vote as full group (20 min) then stress-test against 2-3 scenarios (10 min) | Facilitator | Down | Prework: each person brings 1 tradeoff example from Q1 | 5-7 Decision Principles (written on wall + captured by scribe) |
| 11:30-12:30 | Q2 Bets: Divergence | Generate and debate candidate bets | Solo brainstorm on stickies (10 min) then affinity cluster (15 min) then pitch + challenge each cluster (35 min) | Facilitator | Down | Prework: each person submits top 3 bet candidates | Clustered candidate bets on whiteboard with pros/cons notes |
| 12:30-1:30 | Lunch | Refuel + informal connection | Catered at venue; no structured content | -- | Optional | -- | -- |
| 1:30-1:40 | Energizer + Reset | Rebuild energy post-lunch | Quick stand-up activity (e.g., "move to the corner that matches your Q2 mood: optimistic / cautious / fired up / uncertain") | Facilitator | Down | -- | Energy reset |
| 1:40-3:00 | Working Agreements v2 | Define team norms for remote-first work | Start/Stop/Continue: solo write (10 min) then share + cluster (20 min) then negotiate top agreements (40 min) then commitment round -- each person states "I commit to X" or raises objection (10 min) | Facilitator | Down | Prework: each person answers "What's one thing about how we work that you'd change?" | Working Agreements document (8-12 norms, written + captured by scribe) |
| 3:00-3:05 | Parking Lot Check | Surface anything parked | Quick review of parking lot items; assign owners or defer | Facilitator | Down | -- | Parking lot items with owners |
| 3:05-3:25 | Break + Walk | Reset energy; get outside | Outdoor walk (weather permitting) or stretch break | -- | -- | -- | -- |
| 3:25-4:30 | Q2 Bets: Convergence + Commitment | Select 3-5 bets; kill the rest | Apply decision principles to candidate bets (20 min) then dot-vote on top bets (10 min) then debate top 5 and commit to 3-5 (25 min) then define anti-bets explicitly (10 min) | Facilitator | Down | Candidate bets from morning session + decision principles | Q2 Bets list (3-5 bets with rationale + anti-bets) written on wall |
| 4:30-5:00 | Action Plan Sprint | Turn bets into first actions | Each bet owner drafts 2-week actions (10 min solo) then share-out + challenge (15 min) then capture dependencies (5 min) | Facilitator | Scribe only | Q2 Bets list | Q2 Action Plan (owners, first actions, dates, dependencies) |
| 5:00-5:30 | Close: Decisions + Commitments + Checkpoint | Lock in decisions; prevent Monday amnesia | Read back all decisions (scribe reads) then confirm owners and dates then schedule 2-week checkpoint then "one word" close: each person shares one word for how they feel leaving | Facilitator | Scribe only | All session artifacts | Final Decisions Log + Checkpoint date + Memory artifact plan |
Time allocation check
| Category | Minutes | % of Working Time (390 min) |
|---|---|---|
| Interactive / co-creation | 280 | 72% |
| Context / alignment (semi-interactive) | 45 | 12% |
| Opening / closing / transitions | 45 | 12% |
| Energizer / parking lot | 20 | 5% |
Result: 72% interactive -- exceeds the 60% minimum.
Step 5: Prework Pack
Message to Participants (Send 7 Business Days Before)
Subject: Q2 Strategy Offsite -- What to Prepare (action required by [DATE -2 days])
Team --
On [DATE] we're spending a full day together in NYC to decide our Q2 bets and reset how we work together. Here's what you need to do before you arrive.
The goal: Arrive ready to debate and decide, not to get caught up on context.
What to prepare (due [DATE - 2 days]):
-
Read the pre-read packet (attached / linked). It includes Q1 metrics, customer insight highlights, and the draft roadmap. Takes ~20 minutes.
-
Submit your Top 3 Q2 Bet Candidates via [shared doc / form]. For each, write 1-2 sentences: what it is and why it matters. No slides.
-
Answer these 5 prompts (add your responses to [shared doc]):
- What is the #1 decision we must make in the next 30 days?
- What are we pretending not to know about our current direction?
- Name one tradeoff from Q1 where we struggled to decide. What made it hard?
- What is one thing about how we work together (remote-first) that you would change starting tomorrow?
- What should we explicitly stop doing in Q2?
-
Bring one physical artifact that represents a Q1 win or learning (a sketch, a screenshot printout, a customer quote on paper). We'll use these in our opening.
What NOT to do:
- Don't build slides.
- Don't bring your laptop planning to use it during sessions. Laptops will be down except for our designated scribe.
- Don't prep a long presentation on your area. The pre-read covers context.
Logistics:
- Venue: [Venue name + address]. Arrive by 8:45 AM. Coffee and breakfast provided.
- Dress: Comfortable. We'll be standing at whiteboards and walking outside.
- Travel: [Link to travel/reimbursement policy if applicable].
- Dietary needs: Reply to this email by [DATE - 5 days] with any dietary restrictions.
See you there.
-- [Organizer name]
Pre-Read Packet (to be assembled by Logistics Owner)
| Document | Owner | Purpose |
|---|---|---|
| Q1 Metrics Dashboard (1-2 pages) | Data/Analytics lead | Shared fact base |
| Customer Insight Highlights (top 5 themes) | UX Research or PM | Voice of customer |
| Draft Q2 Roadmap (strawman, not final) | Head of Product | Starting point for bets discussion |
| Current Working Agreements (if they exist) | Team lead | Baseline for reset session |
| Open Strategic Questions (3-5 bullets) | Head of Product | Frame the decisions we need to make |
Prework Prompts (repeated from message above)
- What is the #1 decision we must make in the next 30 days?
- What are we pretending not to know about our current direction?
- Name one tradeoff from Q1 where we struggled to decide. What made it hard?
- What is one thing about how we work together (remote-first) that you would change starting tomorrow?
- What should we explicitly stop doing in Q2?
Assignments
| Owner | Deliverable | Due Date |
|---|---|---|
| Each participant | Top 3 Q2 bet candidates (1-2 sentences each) | [DATE - 2 days] |
| Each participant | Answers to 5 prework prompts | [DATE - 2 days] |
| Data/Analytics lead | Q1 Metrics Dashboard (1-2 pages) | [DATE - 3 days] |
| UX Research / PM | Customer Insight Highlights | [DATE - 3 days] |
| Head of Product | Draft Q2 Roadmap + Open Strategic Questions | [DATE - 3 days] |
| Logistics owner | Pre-read packet assembled and distributed | [DATE - 2 days] |
| Facilitator | Review all prework submissions; synthesize themes | [DATE - 1 day] |
Step 6: Facilitation Run-of-Show
Opening Script (9:00-9:15)
Facilitator stands at front. Norms poster is already on the wall.
"Good morning. We're here to do two things today: decide our Q2 bets and reset how we work together. By 5:30 PM, we will leave this room with:
- Three to five Q2 strategic bets with owners
- A set of decision principles for making tradeoffs
- Written working agreements we each commit to
- A 2-week action plan
- A summary ready to send to stakeholders
Norms for today:
- Laptops down. [Scribe name] is our designated scribe. Everyone else: phones on silent, in your bag.
- One conversation at a time. No side chats. If you disagree, say it to the room.
- Timeboxes are real. I will cut us off. We can always park items.
- Disagree in the room, commit when we leave. We use decision principles, not authority, to resolve disagreements. Once we decide, we all own it.
- Parking lot is on that whiteboard [point]. Anyone can add items. We review them at 3:00.
Questions on norms? [Pause.] Great. Let's start with connection."
Norms (posted on wall)
- Laptops down (scribe exception).
- One conversation; disagree openly.
- Timeboxes are real.
- Parking lot for tangents.
- Decide and document; commit when we leave.
- Breaks are mandatory, not optional.
Decision Capture Protocol
The scribe captures every decision using this format:
| Field | Description |
|---|---|
| Decision | Clear statement of what was decided |
| Rationale | Why we chose this over alternatives |
| Tradeoffs accepted | What we gave up or accepted as risk |
| Owner | Single person accountable |
| Next step + date | First concrete action and deadline |
| Review trigger/date | When we revisit (date or condition) |
Scribe reads back each decision aloud before moving on. The room confirms or corrects.
Session-by-Session Facilitator Notes
Connection Round (9:15-9:45)
- Pair people who don't work together daily.
- Rotation: 3 rounds of 10 minutes. Prompt: "What's one thing going well for you, and one thing you're wrestling with -- work or otherwise?"
- No share-out to the full group (keep it intimate). Just say: "Thank you. Now we've warmed up."
Context Alignment (9:45-10:30)
- Hand out printed pre-read packets (even if people read them before; the physical copy matters).
- Silent reading: 10 minutes. Set a timer.
- Q&A: Facilitator asks "What's the single most important thing you saw in the data?" Go around the room. Capture key themes on whiteboard.
- Close with: "Given what we just discussed, here are the constraints we're working within." Write constraints on the whiteboard.
Decision Principles (10:45-11:30)
- Small groups (3-3-4): "Using the tradeoff examples from your prework, extract 2-3 principles that would have helped you decide faster. Write each principle on a sticky note."
- Merge: Groups present principles. Facilitator clusters similar ones on the wall.
- Vote: Each person gets 5 dots. Vote on the principles that matter most.
- Stress-test: Take the top 5-7 and test them: "If [scenario X], does this principle help us decide? Does it give a clear answer?"
- Capture: Scribe writes the final 5-7 principles.
Q2 Bets: Divergence (11:30-12:30)
- Solo brainstorm: "Write each bet candidate on a separate sticky note. One idea per note. You have 10 minutes."
- Affinity clustering: Everyone places stickies on the wall. Facilitator groups them silently, then asks for adjustments.
- Pitch + challenge: Each cluster gets 3-5 minutes. The person(s) whose ideas are in the cluster pitch it. Others challenge: "What would have to be true for this to work? What's the risk?"
- No decision yet. This is divergence. Mark energy/enthusiasm levels informally.
Working Agreements v2 (1:40-3:00)
- Start/Stop/Continue: Each person silently writes stickies (10 min):
- GREEN: things we should start doing
- RED: things we should stop doing
- YELLOW: things we should continue doing
- Share + cluster: Place on wall. Facilitator clusters. Read themes aloud.
- Negotiate: For each top cluster, the facilitator asks: "What's the specific agreement? Can someone propose the exact wording?" Discuss and refine.
- Target: 8-12 working agreements covering:
- Meeting norms (cameras, agendas, async defaults)
- Communication (Slack response times, deep work blocks, escalation)
- Decision-making (who decides what; when to escalate)
- Feedback (how to give it; cadence)
- Commitment round: Go around the room. Each person says: "I commit to these agreements" or "I have a concern about [specific agreement]." Resolve concerns or note them for follow-up.
Q2 Bets: Convergence + Commitment (3:25-4:30)
- Apply decision principles: "For each candidate cluster from this morning, evaluate it against our principles. Does it pass? Write 'yes/no/maybe' on each."
- Dot vote: Each person gets 5 dots. Vote on the bets you believe we must pursue.
- Debate top 5: Facilitator leads discussion on the top-voted bets. Use a "2 minutes for, 2 minutes against" format for contested bets.
- Commit: Head of Product makes the final call on which 3-5 bets we pursue. State each bet aloud. Scribe captures.
- Anti-bets: "What are we explicitly NOT doing? Name 3-5 things we're saying no to." Capture these -- they're just as important.
Action Plan Sprint (4:30-5:00)
- Each bet owner takes 10 minutes to draft on paper:
- First 2-week action items
- Dependencies on others in the room
- Known blockers
- Share-out: Each owner has 2 minutes to present. Others add dependencies.
- Scribe captures the action plan.
Close (5:00-5:30)
- Scribe reads back ALL decisions (bets, principles, working agreements, action items). Room confirms.
- Confirm checkpoint: "We'll meet on [DATE + 2 weeks] to review progress. [Owner] will set up the calendar invite."
- Memory artifact: "I'll send the decisions summary, photos of the whiteboards, and the action plan within 24 hours."
- One-word close: Go around the room. "Share one word for how you're feeling right now."
- Thank the room. Done.
Handling Disagreement
If debate stalls on a bet or agreement:
- Name it: "We're stuck on [topic]. Let me restate what we agree on and where the disagreement is."
- Apply principles: "Which of our decision principles applies here? What does it tell us?"
- Timebox: "We have 5 more minutes on this. If we can't resolve it, I'm going to ask [Head of Product] to make the call, or we'll assign a 2-person working group to propose 2 options by [date]."
- If it gets personal: "Let's separate the idea from the person. What are the tradeoffs of Option A vs Option B? Let's write them on the board."
Parking Lot Protocol
- Physical whiteboard in the corner labeled "PARKING LOT."
- Anyone can add an item at any time (write it on a sticky, put it on the board).
- At 3:00 PM, facilitator reviews: assign an owner and a next step for each item, or explicitly defer it ("We're not handling this today; [Owner] will follow up by [date]").
Step 7: Logistics Plan + Checklist
Venue / Space
| Item | Details | Status |
|---|---|---|
| Venue type | Dedicated offsite space (NOT the office). NYC options: Breather, Convene, The Yard, or similar. | [ ] Book by [DATE - 3 weeks] |
| Room capacity | 12-15 people (buffer for comfort) | [ ] Confirm |
| Room setup | Large open room with movable tables. Cabaret/cluster seating for small groups, NOT boardroom rows. Space to stand at walls. | [ ] Confirm layout |
| Whiteboards | Minimum 2 large whiteboards or wall-mounted whiteboard film. If not available, bring large sticky easel pads (3 pads minimum). | [ ] Confirm or order |
| Breakout space | One additional small room or hallway nook for sidebar conversations. | [ ] Confirm |
| Accessibility | Wheelchair accessible entrance, elevator if not ground floor, accessible restroom. Ask team in advance for any specific needs. | [ ] Survey team; confirm venue |
| Natural light | Prefer rooms with windows. A windowless room drains energy fast. | [ ] Confirm |
Supplies
| Item | Quantity | Status |
|---|---|---|
| Sticky notes (3x3, assorted colors: green, red, yellow, blue) | 6 packs | [ ] Order/buy |
| Markers (thick, for whiteboards) | 12 (assorted colors) | [ ] Order/buy |
| Markers (thin, for stickies/paper) | 10 (black Sharpies) | [ ] Order/buy |
| Dot stickers (for voting) | 100 (5 colors) | [ ] Order/buy |
| Easel pads (large sticky-back) | 3 pads | [ ] Order/buy |
| Painter's tape (for hanging paper on walls) | 2 rolls | [ ] Order/buy |
| Printed pre-read packets | 10 copies | [ ] Print by [DATE - 1 day] |
| Printed agenda (1-page) | 10 copies | [ ] Print by [DATE - 1 day] |
| Name tags (if team doesn't all know each other well) | 10 | [ ] Optional |
| Timer (phone or physical) | 1 | [ ] Facilitator brings |
| Camera/phone for whiteboard photos | 1 | [ ] Scribe/logistics owner |
| Power strips / phone chargers | 2 strips | [ ] Bring |
| HDMI adapter + backup dongle | 1 set | [ ] Bring (emergency use only) |
Food + Breaks
| Meal/Snack | Time | Details | Status |
|---|---|---|---|
| Breakfast / coffee | 8:45-9:00 | Coffee, tea, pastries, fruit. Available as people arrive. | [ ] Order from venue or caterer |
| Morning snack | 10:30-10:45 | Refill coffee + light snacks (nuts, bars) | [ ] Include in catering order |
| Lunch | 12:30-1:30 | Catered lunch at venue. Family-style or boxed. Include vegetarian, vegan, and GF options by default. | [ ] Order by [DATE - 1 week]; collect dietary needs |
| Afternoon snack | 3:05-3:25 | Energy snacks (fruit, chocolate, trail mix) + water | [ ] Include in catering order |
| Water | All day | Pitchers or bottles in room. Refill at breaks. | [ ] Confirm with venue |
Dietary constraints: Collected via prework email. Default: include vegetarian, vegan, gluten-free, and nut-free options.
Estimated catering budget: $800-$1,200 for 10 people (NYC pricing).
Travel
| Item | Details | Status |
|---|---|---|
| Arrival | Ask all to arrive by 8:45 AM at venue. | [ ] Communicate in prework email |
| Departure | Offsite ends at 5:30 PM. Optional team dinner at 6:30 PM (see below). | [ ] Communicate |
| Hotels (if needed) | For those flying in: book within [budget per night] at a hotel near venue. Share a recommended hotel list. | [ ] Send hotel recs by [DATE - 2 weeks] |
| Flights (if needed) | Book per company travel policy. Arrive day before; depart day after (or evening of). | [ ] Remind team by [DATE - 3 weeks] |
| Local transport | Provide venue address + nearest subway/transit directions. Mention ride-share option. | [ ] Include in logistics email |
| Reimbursement | Link to company reimbursement policy / Expensify instructions. | [ ] Include in prework email |
Tech (Minimal -- This Is a Laptops-Down Day)
| Item | Details | Status |
|---|---|---|
| WiFi | Confirm venue has WiFi (for scribe and emergencies). Get password in advance. | [ ] Confirm |
| Shared doc | Set up a shared Google Doc or Notion page for the scribe to capture decisions in real-time. Share link with all participants. | [ ] Create by [DATE - 1 day] |
| Photo capture | Scribe or logistics owner photographs every whiteboard at end of each session. | [ ] Assign |
| Projector/screen | NOT needed by default (laptops down). Have adapter available in case of emergency. | [ ] Bring adapter |
| Comms break plan | Two 5-minute Slack/email check windows: 10:30 AM break and 3:05 PM break. Facilitator announces. | [ ] Build into agenda |
Contingencies
| Scenario | Plan |
|---|---|
| Key person is absent (illness/travel) | Identify a proxy for their decisions. Defer any decisions that absolutely require them; handle async within 48 hours. Do not cancel the offsite for one absence. |
| Venue falls through | Backup: book a large conference room at a coworking space (WeWork, Industrious) or use someone's apartment with a large living room. Have 1 backup venue identified. |
| Energy drops hard after lunch | Facilitator has 3 energizer options ready (stand-up activity, walk break, change of room configuration). The working agreements session is designed to be high-participation. |
| Debate gets heated or personal | Facilitator uses disagreement protocol (name it, apply principles, timebox, park if needed). If it involves interpersonal conflict, park it: "Let's take this offline. [Head of Product] and I will follow up with both of you this week." |
| Prework not done | Facilitator checks 2 days before. Send a direct reminder to anyone who hasn't submitted. On the day: extend context alignment by 15 minutes and compress lunch by 15 minutes. |
| AV/tech fails | We don't depend on AV. All work is analog (whiteboards, stickies, paper). The scribe's laptop is the only tech required. |
| Weather (outdoor walk) | If weather is bad, replace the walk break with an indoor stretch break and a room reconfiguration (move chairs, change seating). |
Optional: Team Dinner
| Item | Details |
|---|---|
| Time | 6:30 PM (1 hour after offsite ends; gives people time to decompress) |
| Venue | Restaurant near offsite venue. Book for 10. Moderate price point (~$60-80/person). |
| Vibe | Celebratory. No work talk required. This is connection time. |
| Budget | ~$700-$900 including drinks and tip. |
Budget Summary (Estimated)
| Category | Estimate |
|---|---|
| Venue rental (full day) | $1,000-$2,000 |
| Catering (breakfast, lunch, snacks) | $800-$1,200 |
| Supplies (stickies, markers, easel pads, etc.) | $100-$150 |
| Printing | $20-$30 |
| Optional: team dinner | $700-$900 |
| Total (without dinner) | $1,920-$3,380 |
| Total (with dinner) | $2,620-$4,280 |
Note: Travel and lodging are separate and depend on how many people are flying in.
Step 8: Post-Offsite Output Pack
Decisions Log (Template -- fill in during/after offsite)
| # | Decision | Rationale | Tradeoffs Accepted | Owner | Next Step + Date | Review Trigger/Date |
|---|---|---|---|---|---|---|
| D1 | Q2 Bet 1: [e.g., "Launch self-serve onboarding for SMB segment"] | [Why this bet; what data supports it] | [What we gave up: e.g., "Delaying enterprise features by 4 weeks"] | [Name] | [First action] by [Date] | Mid-Q2 check: [Date] |
| D2 | Q2 Bet 2: [TBD] | |||||
| D3 | Q2 Bet 3: [TBD] | |||||
| D4 | Anti-bet: [e.g., "We are NOT building a mobile app in Q2"] | [Why not] | [What we accept: customer requests will go unaddressed] | N/A | Communicate to Sales/CS | N/A |
| D5 | Decision Principle: [e.g., "When in doubt, optimize for activation over retention in Q2"] | [Rationale] | [What this means we deprioritize] | Team | Use in weekly prioritization | End of Q2 |
| D6 | Working Agreement: [e.g., "All meetings have agendas shared 24h in advance or the meeting is canceled"] | [Why this matters for remote-first] | [Overhead of writing agendas] | Team | Start enforcing [Monday after offsite] | 2-week checkpoint |
| D7-D12 | [Additional working agreements] |
Action Plan
| # | Action | Owner | Due Date | Dependencies | Status |
|---|---|---|---|---|---|
| A1 | Write Q2 Bet 1 brief (1-page problem/solution/metrics) | [Bet 1 owner] | [Date + 1 week] | Q1 metrics finalized | Not started |
| A2 | Write Q2 Bet 2 brief | [Bet 2 owner] | [Date + 1 week] | Customer research summary | Not started |
| A3 | Write Q2 Bet 3 brief | [Bet 3 owner] | [Date + 1 week] | Engineering capacity estimate | Not started |
| A4 | Send post-offsite comms to stakeholders | [Head of Product] | [Date + 1 day] | Decisions log finalized | Not started |
| A5 | Publish working agreements to team wiki/Notion | [Team lead] | [Date + 2 days] | Agreements finalized by scribe | Not started |
| A6 | Set up Q2 bets in tracking system (Linear/Jira/Notion) | [PM or TPM] | [Date + 3 days] | Bet briefs drafted | Not started |
| A7 | Schedule 2-week checkpoint meeting | [Facilitator] | [Date + 1 day] | Calendar availability | Not started |
| A8 | Publish memory artifact (photos + 1-page summary) | [Scribe / Logistics owner] | [Date + 2 days] | Whiteboard photos captured | Not started |
| A9 | Share anti-bets list with Sales/CS (so they know what's NOT happening) | [Head of Product] | [Date + 3 days] | Decisions log finalized | Not started |
| A10 | Follow up on parking lot items | [Assigned owners per item] | [Date + 1 week] | Parking lot captured | Not started |
Follow-Up Comms Draft
To: Product Team + Key Stakeholders (Engineering Lead, CEO, Sales Lead) Subject: Q2 Strategy Offsite -- Decisions, Bets, and Next Steps
Team --
On [DATE], the product team spent a full day together in NYC to align on Q2 and reset how we work. Here is what we decided.
Q2 Strategic Bets (what we're committing to):
- [Bet 1 name] -- [1-sentence description]. Owner: [Name].
- [Bet 2 name] -- [1-sentence description]. Owner: [Name].
- [Bet 3 name] -- [1-sentence description]. Owner: [Name].
What we're NOT doing (anti-bets):
- [Anti-bet 1]: [Why not, in 1 sentence].
- [Anti-bet 2]: [Why not].
Decision Principles for Q2: We established [5-7] principles to guide tradeoff decisions this quarter so we can move faster without escalating everything. [Link to full principles doc].
Working Agreements (effective immediately): We reset our team norms. Key changes: [list 2-3 most important new agreements]. Full list: [Link to working agreements doc].
What happens next:
- Bet briefs due by [Date + 1 week].
- Bets set up in [tracking tool] by [Date + 3 days].
- 2-week checkpoint: [Date + 2 weeks] to review progress on bets and working agreements.
Open questions (still being worked):
- [Open question 1]
- [Open question 2]
Full decisions log and whiteboard photos: [Link to shared doc].
If you have questions or concerns about any of these decisions, reach out to [Head of Product] by [Date + 3 days]. After that, we're moving forward.
-- [Head of Product / Facilitator name]
Memory Artifact Plan
Format chosen: Photos of whiteboards + 1-page narrative summary.
Contents:
- Photo of the "Current State + Constraints" whiteboard
- Photo of the "Decision Principles" wall
- Photo of the "Q2 Bets" whiteboard (with anti-bets)
- Photo of the "Working Agreements" wall
- 1-page narrative: "What we aligned on, what we chose, what we're doing next"
Published to: Team Notion/Wiki + Slack channel Published by: [Scribe / Logistics owner] Deadline: Within 24 hours of offsite
Review Checkpoints
| Checkpoint | Date | Purpose | Owner |
|---|---|---|---|
| 2-week check-in | [Date + 2 weeks] | Are bet briefs done? Are working agreements being followed? Any early blockers? | Facilitator |
| Mid-Q2 review | [Date + 6 weeks] | Are bets on track? Do we need to adjust? Are decision principles holding? | Head of Product |
| End-of-Q2 retro | [End of Q2] | Did we achieve what we set out to? What worked about the offsite format? Plan next one. | Team lead |
Risks, Open Questions, and Next Steps
Risks
| Risk | Likelihood | Impact | Mitigation |
|---|---|---|---|
| Prework not completed by majority of team | Medium | High -- wastes first 90 min of offsite on context | Facilitator checks 2 days before; sends direct reminders; extends context alignment if needed |
| Q2 bets debate becomes political (pet projects) | Medium | Medium -- weak bets chosen for wrong reasons | Decision principles session runs BEFORE bets; criteria-based convergence, not authority-based |
| Working agreements feel like "rules" and don't stick | Medium | High -- defeats purpose of reset | Commitment round requires each person to verbally commit; 2-week checkpoint reviews adherence |
| Head of Product dominates and team doesn't voice disagreement | Low-Medium | High -- false alignment | Facilitator ensures HoP speaks last in key rounds; small-group work before plenary |
| Post-offsite follow-through drops (Monday amnesia) | High | High -- entire offsite wasted | 24-hour comms deadline; 2-week checkpoint; memory artifact published to shared space |
Open Questions
- Who is the facilitator? Strongly recommend someone who is NOT the Head of Product, so the decision-maker can participate fully. Could be a senior PM, a Design lead, or an external facilitator.
- Exact date? Recommend a Thursday (Friday is recovery/travel day). Coordinate with the team's sprint cycle to avoid disrupting an active sprint.
- Which venue in NYC? Need to book 3+ weeks in advance. Suggest evaluating Breather, Convene, or The Yard for the right size and budget.
- Are there any team members who can't travel to NYC? If so, we need to decide: include them remotely (with significant facilitation overhead) or find a date when all 10 can attend.
- Are stakeholders (Engineering, CEO, Sales) expecting to give input on Q2 bets before the offsite? If so, add their input to the pre-read packet.
- Does the team have existing working agreements? If yes, include them in the pre-read as the baseline. If no, the session starts from scratch (which is fine but takes slightly longer).
Next Steps
| # | Action | Owner | Deadline |
|---|---|---|---|
| 1 | Confirm offsite date | Head of Product | ASAP |
| 2 | Assign facilitator, scribe, timekeeper, logistics owner | Head of Product | [Date - 4 weeks] |
| 3 | Book venue | Logistics owner | [Date - 3 weeks] |
| 4 | Send prework email to team | Facilitator / Logistics owner | [Date - 7 business days] |
| 5 | Collect dietary restrictions and accessibility needs | Logistics owner | [Date - 2 weeks] |
| 6 | Order catering | Logistics owner | [Date - 1 week] |
| 7 | Buy supplies (stickies, markers, easel pads, dot stickers) | Logistics owner | [Date - 3 days] |
| 8 | Print pre-read packets + agendas | Logistics owner | [Date - 1 day] |
| 9 | Assemble and distribute pre-read packet | Logistics owner + content owners | [Date - 7 business days] |
| 10 | Check prework completion; send reminders | Facilitator | [Date - 2 days] |
| 11 | Synthesize prework themes for facilitator prep | Facilitator | [Date - 1 day] |
| 12 | Run the offsite | Facilitator + full team | [Date] |
| 13 | Send post-offsite comms | Head of Product | [Date + 1 day] |
| 14 | Publish memory artifact | Scribe / Logistics owner | [Date + 2 days] |
| 15 | Schedule and run 2-week checkpoint | Facilitator | [Date + 2 weeks] |
Quality Gate: Self-Assessment
Checklist Verification
1) Offsite Brief checklist
- Purpose is a single sentence and includes "why now"
- Target outputs are 5 artifacts (not feelings)
- Decisions in scope are explicit; out-of-scope items are named
- Participants list includes decision makers
- Success measures include "immediately after" and "2-4 weeks after"
- Risks include team dynamics and missing inputs/data
2) Agenda checklist
- Every session has an output artifact
- 72% of time is interactive/co-creation (exceeds 60% minimum)
- "Laptops down" blocks are explicit (scribe exception defined)
- Breaks are scheduled (10:30, 12:30, 3:05)
- Day starts with connection (Connection Round) and ends with follow-through (Close)
3) Prework checklist
- Prework reduces context-setting time
- Prompts are specific and require thought
- Assignments have owners and due dates
- Sensitive topics are handled safely
4) Facilitation checklist
- Opening script names purpose, outputs, and norms
- Decision capture fields are defined (all 6 fields)
- Disagreement handling plan exists
- Parking lot mechanism exists with owner assignment during close
5) Logistics checklist
- Room setup supports whiteboards and breakouts
- Supplies are explicitly listed
- Accessibility needs are accounted for
- Contingency plan exists (7 scenarios covered)
6) Post-offsite follow-through checklist
- Decisions log is complete with owners + next steps
- Action plan has due dates and dependencies
- Follow-up comms draft is ready
- Checkpoint date is scheduled (2 weeks)
- Memory artifact is defined and publishable within 24 hours
Rubric Self-Score
| Criterion | Score | Rationale |
|---|---|---|
| 1) Scope + boundaries | 2 | Clear when to use/not use; conflict boundaries explicit; neighboring skills referenced |
| 2) Input contract | 2 | Minimum inputs explicit; missing info handled with 6 labeled assumptions |
| 3) Outputs are artifact-first | 2 | Every deliverable is concrete; output order defined; every session produces a named artifact |
| 4) Agenda quality | 2 | Timed agenda; 72% interactive; every block has output; breaks and connection included |
| 5) "Defrag the day" | 2 | Laptops down explicit in norms, script, and agenda; scribe pattern defined; physical tools; comms breaks defined |
| 6) Prework protects time | 2 | Pre-read, prompts, and assignments; participants arrive ready to decide |
| 7) Facilitation runnable | 2 | Full run-of-show with opening script, norms, decision capture, breakout instructions, disagreement handling |
| 8) Logistics frictionless | 2 | Complete checklist: venue, supplies, food, travel, tech, accessibility, 7 contingencies |
| 9) Memory + follow-through | 2 | Decisions log, action plan, comms draft, memory artifact, 3 checkpoint dates |
| 10) Safety + realism | 2 | No forced vulnerability; elephants named at safe level; escalation path defined; realistic about what offsite can fix |
| Total | 20/20 |
End of Offsite Pack.