Executive Offsite Agenda with AI

Category: Academy · Stage: Alignment

By Max Beech, Head of Content

Updated 12 July 2025 · Expert review: [PLACEHOLDER: Chief of Staff, Chaos Council]

Why it matters: Executive offsites cost days of leadership attention. PwC’s 2024 CEO Survey shows almost 40% of CEOs have pushed into new sectors in the past five years, yet only 7% of revenue comes from newly created businesses.^[1]^ An executive offsite agenda that embraces agentic prep can turn that gap into a plan instead of another deck.

TL;DR

      - Begin with unsolved tensions rather than department updates; let agents assemble the facts so humans focus on choices.

      - Structure the executive offsite agenda into divergent, convergent, and commitment phases to avoid endless debate.

      - Leave with a published narrative and follow-up rituals so the plan survives contact with the calendar.

    

  
  
    Jump to:
    1. How do you design an executive offsite agenda that creates movement?
    2. How do you equip the executive offsite agenda with insight?
    3. Where do executive offsite agendas fail?
    4. Summary and next steps
  
  

Chaos queues pre-work reminders so executives arrive primed for decision-making rather than status updates.

How do you design an executive offsite agenda that creates movement?

Start with three tension statements (“We invest heavily in X but growth comes from Y”). Build each session around a decision, not a presentation. The executive offsite agenda should alternate between divergence (expanding possibilities) and convergence (selecting commitments) before ending with a “write the press release” exercise. Document the expected artefact for every slot—strategy doc updates, hiring plan revisions, or a go/no-go verdict—so nobody leaves with fuzzy action.

    - Use the meeting notes workflow to capture pre-reads and keep them searchable during the retreat.

    - Borrow energy resets from our neurospicy weekend reset so long agenda blocks stay humane.

    - Close each day with a recorded reflection the team can revisit during the Sunday reset check-in.

  

  
    Executive offsite agenda skeleton
    
      
        Phase
        Purpose
        Inputs
        Outputs
      
    
    
      
        Day 1 AM (Diverge)
        Surface assumptions, explore scenarios
        Market trend packs, customer recordings
        Updated opportunity map
      
      
        Day 1 PM (Converge)
        Rank bets, draft guardrails
        Scoring matrices, financial envelopes
        Prioritised bet list
      
      
        Day 2 (Commit)
        Assign accountability, craft narrative
        Owner matrix, change story prompts
        Press release draft, 30-60-90 actions
      
    
  
  

How do you equip the executive offsite agenda with insight?

Feed agentic research packs in advance. Chaos can assemble a dossier with customer sentiment, competitor launches, and macro shifts. PwC reports 56% of CEOs already see generative AI freeing employee time, and one-third see revenue gains.^[2]^ Use that liberated time to run mini “premortems” the week before: what could make this offsite a waste? Bake the answers into your agenda.

An executive offsite agenda dashboard shows decisions, owners, and blockers in one place.

What does a successful executive offsite agenda sound like?

Mini case story: At social impact studio North Star, we piloted this executive offsite agenda over two days in Devon. Chaos agents compiled regulatory briefs, while the team used analogue whiteboards for divergent thinking. By the closing “press release”, they retired two vanity OKRs, ringfenced two innovation bets, and agreed to publish a quarterly investor note—decisions that stuck because owners and dates were assigned on the spot.

Where do executive offsite agendas fail?

Three traps: skipping dissent, skipping logistics, and skipping follow-up. If the executive offsite agenda doesn’t invite contrarian voices early, you’ll waste time litigating decisions later. If travel and sensory needs aren’t considered, you burn energy before strategy discussions begin—borrow accommodations from our sensory-friendly workday template. Finally, if nothing hits the calendar within 48 hours, the offsite becomes a memory. Book a post-retreat “decision audit” while everyone is still in the room.

Key takeaways

      - Anchor every executive offsite agenda block to a decision, not a status update.

      - Prime the room with agentic research so humans can focus on debate and commitment.

      - Publish decisions as narratives with owners within 48 hours to protect momentum.

    

  
  
    

Summary

An executive offsite agenda that respects neurodiversity, agentic insight, and operational rigour turns strategy retreats into shippable roadmaps. Use human time for debate; let AI do the compiling and cross-referencing.

Next steps

      - Draft three tension statements and run them past the board chair to validate priority.

      - Ask Chaos to compile a risk dossier and align it with our EU AI Act operations briefing.

      - Schedule a 30-day post-offsite review to compare commitments against the focus scoreboard you’ll set up next.

    

  
  
    

About the author

Max Beech facilitates Chaos’ quarterly leadership labs and writes battle-tested facilitation kits that respect different thinking styles.

Expert review: [PLACEHOLDER: Chief of Staff, Chaos Council] · Compliance check: Completed 10 July 2025.

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