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Claire's Offsite Toolkit

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Claire's Offsite Toolkit

The Stripe COO's handbook for running offsites that work.
This toolkit is meant to be copied and customized for your team.
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Ask someone who's worked with me about my leadership style, and one of the first things they'll mention is offsites. I'm a firm believer in the power of offsites to help teams solve problems, make decisions, and work through goals and strategies. They're where you lay down the common groundwork and vocabulary, share your working styles, and determine who you want to be as a team.
Over time, I've developed a unique approach to offsite design and facilitation—one I'm frequently asked to share. I worked with the Coda team to develop a comprehensive offsite toolkit you can copy and use with your own team.
But before we jump into logistics, make sure to reflect on the state of your team. As powerful as they can be, offsites aren't always the answer. You need to be confident that it's a wise use of your team's time.

Why have an offsite?

Offsites generally have three objectives, and most offsites are a mix of all three:
Move a set of people from being a ‘work group’ to becoming a ‘team’
Evaluate progress while planning future priorities and goals
Engender long-term strategic thinking

Although one could argue you can do all of these things within a typical work rhythm, research (like that on and the function of ) indicates that taking people out of their day to day has a powerful imprint on their ability to focus and think differently. And it's not just about the ice breakers. If your team is geographically dispersed, planning together is particularly powerful for enabling the team to work separately.

Which type of offsite is most appropriate?

Just because a group has come together in service of a goal or task doesn’t necessarily mean they are a team.
Building a team is conscious, active, on-going work. Ultimately, the goal for anyone aspiring to build a high-performing team is to consider the needs of the task and the team simultaneously. Focus too much on the task, and the team suffers (dictatorial mode); focus too much on the team, and the task suffers (country club mode); neither are sustainable. Your first order of business is to determine how balanced your team currently is on this dynamic.
A successful offsite most likely has both influences, but it’s up to you to determine the weighting of each. Here are some examples to further illustrate task versus team activities:
💡 Tip: poll your team on which elements your next offsite should focus on.



Setting or reviewing metrics
Planning, setting goals, assigning DRIs
Retrospectives on completed work product
Getting to know you / team building
Team breakfast, lunch, dinner
Defining team norms

What is your team's development stage?

Another helpful lens to consider is your team’s stage of development. As it turns out, teams go through somewhat predictable stages of group development, and you can use 's model to support your agenda structure.
Tuckman was one of the first researchers/writers in the space, and the phases of development he puts forth are: forming, storming, norming, and performing. Psychological safety is a core underpinning of teams progressing, defined as an individual being able to take interpersonal risks (e.g., asking questions, offering a dissenting opinion, discussing a failure, expressing vulnerability) without fear of negative consequence to their identity or inclusion in the team.
Your team’s phase provides insight into how you should structure the agenda to help support them move forward (note that there isn’t a standardized length of time a team will stay in a particular phase).
Goals, roles, and processes are ill-defined
Reliance on the manager to direct
Little psychological safety, so not much risk taking or confrontation
Overt politeness / agreement
Expect to be more directive
Expect and work with silence in response to questions
Provide extra support, direction, and modeling in activities
Actively work to build psych safety by setting up collaborative/supportive team norms
Boundaries around goals, roles, and processes still not 100% // toe-stepping
Increased psych safety allows conflict to emerge
Frame the conflict as a healthy step // don’t try to squelch it; work with it
Work toward cleaning up the goals, roles, and processes
Share this theory to help teams understand that it’s normal (and that every member is part of the progression)
Goals, roles, and processes are clearer
The manager begins to become more consultative
Increased commitment and collaboration
Decision making is cleaner
Celebrate getting through storming
Continue to hone how the team gets work done
With the team getting in stride, continue the urgency and focus toward the goal
The team is in flow
Healthy debate and decision making
Smooth conflict resolution
Continue to button up norms
Continue to increase the rate of challenge
Know that this phase is not permanent // change is most likely just around the corner
There are no rows in this table

If, for example, your team is in
mode and has just come together, you might index on creating clarity around the team’s goals, roles, and processes. If the team is in full
mode, perhaps spend more time in building relationships and team identity. Actively work to increase and secure psychological safety in each phase.

A toolkit to plan your offsite.

After you've settled on the type of offsite you want to run, it's time to begin planning. Typically at this point, I start creating artifacts ー an array of agendas, budget spreadsheets, checklists, and slide decks. One of the main benefits of Coda is that it houses everything in a single doc. Planning your offsite in one doc also provides helpful documentation for future offsites—a place you can come back on to reflect on what worked and what didn't.

...and run your offsite.

Some people enjoy meetings more than others. A doc is a helpful forcing function to ensure you get the best, most thoughtful information from everyone in the room. They also have a number of other benefits:
Inclusivity: Docs provide a safe place for others to convey ideas without the pressure to debate in the room.
Anchoring effect: By writing your core objectives together and presenting them in a shared doc, you anchor the conversation.
Pre-work: One of the more obvious reasons for a doc, pre-work creates a shared mental space for a group.

Make a copy and get started!

This doc is meant to be used as a full toolkit - just
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If you would like to try this technique and need help implementing it, the Coda team has graciously offered to help. Click this button to get assistance:
Here's an outline of the different parts of this toolkit:

Plan your offsite

: So you don't miss anything
for your offsite
for each of your session leads
to get the wheels turning

Day of the offsite

set context & agenda for attendees

Some extra behind-the-scenes.

Want to see how this doc was made? Watch me and former colleague Shishir in this episode of .

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