running-offsites

SKILL.md

Framework-based guidance for planning and running productive team offsites.

Draws on five product leader frameworks covering purpose clarification, team readiness assessment, structure design, and logistics

Emphasizes removing teams from day-to-day routines, using physical collaboration tools like whiteboards, and balancing strategy work with social connection

Flags common pitfalls including overpacked agendas, soft skills training that masks underlying conflicts, and infrequent in-person gatherings for remote teams

Recommends quarterly "bursts" for remote-first companies and collaborative plan-building rather than presentation-focused sessions

Running Offsites

Help the user plan and run effective team offsites using frameworks from 5 product leaders.

How to Help

When the user asks for help with offsites:

Clarify the purpose - Ask what outcome they want from the offsite (strategy, connection, planning)

Assess readiness - Determine if there are underlying team issues that need addressing first

Design the structure - Help them balance work sessions with social connection

Remove friction - Guide them on logistics that make offsites productive

Core Principles

Use "bursts" for remote teams

Brandon Chu: "We've actually instituted with something we call bursts. So bursts at Shopify are the ability for your team generally maybe once a quarter or whatnot, to just come together to do really high velocity creative work together, to hang out together." Remote-first companies should schedule quarterly in-person sessions for high-velocity creative work that's difficult to do asynchronously.