How to Plan a Company Offsite

Learn based on the best articles on Medium.

Tony Stubblebine
9 min readNov 24, 2022


This is an experiment to pick a single topic, Company Offsites and Retreats, and then curate and organize the best Medium articles on that topic. Help me keep it up to date by leaving feedback. What did you learn? Are there any Medium articles that you would recommend for this topic? What sub-topics do you wish were covered?

Company offsites can be meetings of the entire company, divisions, or just individual teams. They are chances to build connections, solve problems, and plan strategies. With so many companies moving to fully remote work, offsites are now one of the only times coworkers meet face to face.

Topics Below

  • TLDR; Best Articles.
  • Initial Planning
  • Housing logistics
  • Online retreats
  • Ground rules & codes of conduct
  • Schedule & structure
Best for a full company offsite: 
Team offsite events that even an introvert can love
(Chris Beasley, Automattic)
Runner up (and good for all variants of offsites):
How to design an effective strategy offsite
(Dave Bailey, CEO Coach)
Best for online offsites:
How Coinbase ran its first 100 person online offsite
Runner up for online offsites:
Our annual company retreat turned virtual this year
(Nick Holzherr, CEO of
Best for early stage startups:
How to crush a startup offsite
(Drew Austin, Wade and Wendy)
Best for VC offsites:
Our approach at Foundry Group
(Brad Feld)

Initial planning

#1. Goals and benefits.

Start your decision by setting some goals and target benefits. As one organizer put it:

We reflect on what we have learned, gain clarity as to where we are going, have uninterrupted product development time, and build strong bonds that are hard to achieve when sitting with headphones on in an office.
[source article by Drew Austin, Wade and Wendy]

When we ran our offsite with the Medium team, the first goal was to connect. Most of us…