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 hadn’t ever met in person. Then our second goal was to make a few big decisions so that we were all headed in the same direction.

#2. Any time is the right time

Teams change. People leave and new members join. Team regeneration is great for disrupting both thought and behaviour patterns. But even with the best luck, your “once a year strategic development / team dynamics offsite” can’t possibly be timed to accommodate all the changes.
[source: Melissa Rosenthal, Executive Coach]

#3. Don’t overload the agenda

Offsite agendas are often full of “the things we don’t have time or headspace for in our day-to-day work”. So as a solution we shove them into a tightly packed agenda where each critically important topic gets allocated an hour or 2 to be “solved”.
[source: Melissa Rosenthal, Executive Coach]

Housing logistics

Consider these three tips for what sort of venue to book.

#1. Optimize for connection

Whether you have a group of 3, 30 or 300, your group should occupy the entire space. Size your venue so that you can rent the whole thing. A three-person team takes a regular house. A thirty-person team occupies a retreat. A 300-person team buys out an entire hotel or co-working space. What’s key is that anyone can walk up to anyone else at that venue and strike up a conversation, knowing they’re part of the same group. I cannot over stress the importance of this point. It changes the dynamic entirely to have strangers in the group. Everyone at the space must be a part of the event.
[source: Chris Beasley, Automattic]

#2. Small teams

We all live under the same roof. We all wake up around the same time, we cook together, eat together, work together, and then when it’s time to unwind at the end of the night, we can do that together as well. Not to mention, it’s also an affordable and convenient way to travel with 5–10 people.
[source: Drew Austin, Wade and Wendy]

#3. Large teams

Call hotels directly to inquire if they rent out the entire property. Boutique hotels like the Ace Hotel, Jupiter Hotel and The Freehand are ideal for 150–300 person teams and have locations in Portland, Seattle, Palm Spring, Chicago and New York. The Ace in Palm Springs, for example, offers small and medium-sized meeting rooms, two pools and a covered lounge area. Some rooms offer private patios which people used to host smaller groups.
[source: Chris Beasley, Automattic]

Online retreats.

For cost, and certainly during the COVID pandemic, companies are experimenting with virtual online retreats. Both Coinbase and Whisk made use of Gather so that the offsite wouldn’t feel like yes more video chats. But they also made creative use of their normal tools, for example:

For the icebreaker, in each small group we created a Google Slides presentation, asked everyone to join anonymously (incognito tab), then (1) draw a picture of themselves; (2) share a fun fact; (3) create a nickname. After all the slides were in, we went around the room and guessed who was who. This led to lots of laughs and an ever-enduring record of our bad artistic abilities.
[source: Coinbase]

Ground rules & codes of conduct

An offsite is a new context that may require some ground rules that aren’t necessary in day-to-day work. Consider refreshing or highlighting ground rules that are specific to your offsite.

One common suggestion is to create a safe space.

It’s a good idea — and may be comforting to your team — to set ground rules. Make sure everyone knows that the offsite should be a safe space where people can speak up and constructively challenge one another (and you) without any fear of reprisal. It’s also helpful to pledge confidentiality within the meeting space. What is said at the offsite is for you and your team alone, and will not be shared with others in the office — unless the team reaches a consensus about authorizing specific messages or information to be communicated externally.
[source: Dan Schoenbaum Managing Partner, Hightide Advisors]

But these ground rules don’t need to feel stodgy.

Injecting some creativity into setting and reinforcing ground rules can be helpful. For example, one of my clients uses the term ‘devil’s avocado’ to inject a little humour and make people more relaxed about challenging the consensus.
[source: Dave Bailey, CEO Coach]

A third is to highlight expectations around time, for example:

Time-box Everything. When you are basically conducting a work Iron Man, where time is not a discussion and nobody even knows what day it is, it’s important to not get stuck on one task too long. Timebox everything. Timebox the things you like doing, timebox the things you don’t. This will enable you to maintain the feeling of urgency of time constraints, although it may feel like you have all the time in the world.
[source: Drew Austin, Wade and Wendy]

A fourth is around downtime:

Initially, the introverts on the team were nervous that the house would mean they could never get away to recharge, but the opposite ended up being true. They can go back to their rooms and when they felt up to being social again, all they have to do was walk out of their door to find the team.
[source: Chris Beasley, Automattic]

A fifth is encouraging participation from everyone, perhaps by using the Round Robin meeting technique:

Ensuring everyone is listened — especially the voices of quiet people — will increase participation. Senior executives, loud people, and men, in particular, tend to be more outspoken and inhibit or influence other participants’ thoughts.
[source: Gustavo Razzetti, Author of “Remote, Not Distant”]

Circling back to downtime to underline how important downtime is:

Whilst you’re out of the office, don’t just replicate the stiff culture of your office. Build in generous breaks, and if you’re somewhere where the best time of day to enjoy the outside is the afternoon, don’t wait till sunset to build that into the schedule. I’ve found those unstructured moments are where the relationships get built and sometimes genuine break-throughs happen, either in relationships or personal creativity.
[source: Nathan Waterhouse, consultant]

Schedule & structure

Dave Bailey, CEO Coach recommends thinking in phases.

  1. Setup is the organization, expectation setting and homework that happens before the event.
  2. Connection is the opening of the event where people connect, get to know each other, and bond.
  3. If there is work to be done, follow a brainstorming model with clearly demarcated time for divergent thinking first, followed by convergent thinking after.
  4. Then make commitments.
  5. Then celebrate.

A good way to finish each day is to hold a ten minute reflection on the day so far and to zoom out and review the plan for the rest of the offsite. You can ask a simple question like ‘what’s become clearer after today?’ or ‘what did you learn today?’ This is a good opportunity to review the plan for the rest of the week and review priorities. Be ready to ditch less important items on the agenda and add new topics.
[source: Nathan Waterhouse, IDEO]

Intros & connections.

There are a lot of good exercises to help people connect and get to know each other. Here are some suggestions:

‘One-question ice-breakers’: Effective questions are ones that allow people to share something about themselves, such as ‘What past event are you most proud of?’, ‘What’s something funny we might not know about you?’ or ‘What’s a significant event that helped you grow as a person?’. Everyone could answer the same question, or pick one out of a hat.
[source: Dave Bailey, CEO Coach]

We kicked it off with everyone going around the room talking about their accomplishments for the year, things they’re proud of their department or the company as a whole for getting done, and what they hope to get out of the next two days.
[source: Kyle Racki, CEO]

Personal Histories Exercise
Go around the table and have everyone answer three questions about themselves:

Where did you grow up?

How many siblings do you have and where do you fall in that order?

Describe a unique or interesting challenge or experience from your childhood
[source: Sarah Hodges, VC]

Learn personalities: If you have team disfunction or poor collaboration across your team, I highly recommend exercises to learn about team personalities and working styles. Explore performing a Myers-Briggs assessment, a DiSC analysis, or other psychometric personality analysis. This can help your team understand one another’s personality and working style. It can help highlight employees who will collaborate best with each other, might surface and improve chances of potential conflict, and more — all very valuable insights to strengthening your team and the bonds within it.
[source: Dan Schoenbaum, CEO]

There are, of course, more involved options. The Carted team organized a scavenger hunt. Or you could try cooking a meal together.

Building Your Agenda

One common way is to put the agenda in the hands of the attendees. See Elizabeth Hunt’s A Simple Process for Co-Creating a Team Retreat Agenda.

Your offsite can be a chance for skill building. For example, Carted included a design thinking exercise.

Your offsite is also often a good chance to step back and articulate your team values. Eric Friedman, executive coach, offers this offsite values exercise.

Wishlist Topics

I’d like to fill in gaps in this post, especially around the following topics. If you write something about these on Medium, please let me know.

  • What expectations to set around alcohol.
  • Real world budget breakdowns
  • Experiences using an agency to plan your offsite.
  • Reviews of locations like AutoCamp.
  • More on goal setting and ROI