Offsites this year are planned for Mid-March and Mid-September

Pre-Offsite Planning (Template)

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8 weeks out

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Choose dates

Try to avoid public holidays and be mindful of proximity to other offsites to minimize travel fatigue

School holidays are more difficult for people with children

Be mindful of the season of your chosen location, as this will dictate what activities you can plan

It is worth getting people to hold dates as early as possible, even before you've selected a location

Generally, we try to time OKR’s kick-offs + Off-sites around public holidays & School Holidays

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Choose location

Consider choosing a location that is relatively easy for most people to attend without having to travel outrageous distances or deal with difficult visa processes or COVID testing requirements

Transportation to the offsite is usually one of the larger budget line items, so do some research on the cost of flights or transportation from team locations before finalising a location.

Consider the cost of transportation to/from the airport, and around town, for when your team arrives at the offsite location.

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Announce to team

You can have fun with this and build excitement by progressively dropping hints and having folks try to guess the location

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Create an offsite Slack channel and invite team

This is super useful for making announcements and keeping the team updated throughout planning

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Draft

budget⁠

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These are the rough budgets we estimate for planning purposes:

Accommodations = $250/night/person

Ground transportation = $35/day/person

Food & drinks = $50/day/person

Activities, Events & Merch =$400

Total Budget Per Person = ~$1500-$1800

Contingency = 10% of total budget

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Secure accommodations

The ideal location will depend on the size of your team

I recommend booking a large AirBnB or 2 for teams under 25 people as this provides for a more casual atmosphere and can help control costs if you opt to have the team cook meals together

For larger teams, consider a centrally located hotel or glamping that has a bookable space with configurable furniture for different activities, an onsite restaurant or bar to simplify meals and provide a location for free social time, as well as amenities like a gym for those who like to stay active while they travel

7 weeks out

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Start flight booking process (or book transportation)

To simplify this process, we give all team members access to a company card, and we ask people to book their own flights

Encourage folks to buy flights early and with the option to refund if they are unable to attend to save on costs

In the event that a new team member will be attending an offsite, but has not started yet, please contact the Ops team to help coordinate. In these cases, the process is:

Preemptively create the new team member a Google account

Issue them a Airwallex card to their work email with a sufficiently high temporary balance to cover travel costs

Add them as a guest to any planning Slack channels and/or share any necessary itinerary information such as arrival dates/times and airports

Have the new team member book travel as usual

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Draft rough schedule

Building the schedule as a

separate Google Calendar⁠

that can eventually be

shared with the team⁠

will allow you to move sessions around as you finalise the itinerary flexibly

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Send

info gathering form⁠

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Use this form to collect important information like flight details, clothing sizes for merch, dietary restrictions, and preferences for things like sharing rooms

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Brainstorm merch/meeting room decorations

Having some branded merch to commemorate the offsite upon arrival is a great way to welcome people and get them excited for their time together (generally this is for whole team offsites only for budgetary reasons)

If you are staying in a hotel, decorating a meeting room makes it feel much more personal and less corporate

In the past, we've done shirts, hats, scarves, notebooks, stickers, pens, and water bottles -- feel free to get creative with it

6 weeks out

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Secure transportation

Book any group transportation like coaches or a rental car ahead of time

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Finalise team outings and book as needed

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Flights booking deadline

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Info gathering form deadline

5 weeks out

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Assign

rooms⁠

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Using preferences from the info gathering form regarding sharing rooms, assign them accordingly

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Review and finalise merch proofs

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Finalise itinerary

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Finalise budget

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Assign session leads & secretaries

Decide in advance who is going to record the notes from each session - it is really easy for post-offsite followup to fall through the cracks

With the schedule finalised, assign folks as session leads to design

session plans⁠

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4 weeks out

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Reserve restaurants for communal meals

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Book any remaining activities

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Order merchandise

Important to give yourself lots of lead time here, in case of production or shipping delays

Depending on how restrictive customs are for your destination, consider shipping merch to teammates and checking them as additional bags on flights to the offsite

3 weeks out

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Draft session plans/presentations due

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Draft

offsite guide package⁠

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Design and print

superlatives/awards⁠

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One activity we've found quite popular is giving out superlative awards to the team during the closing ceremonies

2 Weeks Out

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Review and finalize session plans/presentations

We recommend having the offsite lead connect with session leads to review their plans and offer feedback before finalizing them - you want to make the most out of your sync time together

1 Week Out

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Final plan review

The offsite lead should do a final, thorough review of the full plan and finalize any outstanding details - visually walk through the entire schedule and see if anything is missing

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Unveil the final offsite guide + pre-read to the team

1 day before

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We recommend that the offsite organizer consider arriving a day early to prep for the team's arrival

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Shop for any miscellaneous supplies and groceries (onsite)

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Print and organize a few paper copies of the itinerary (onsite)

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Create "Careless Whispers" envelopes (onsite)

This passive activity involves creating an envelope for every member of the team, posting them in a central location, and encouraging folks to write small notes to each other. These can be anything from retreat memories to compliments, and make a really nice memento to remember the offsite

Consider also making and posting envelopes for folks who cannot attend

1 week after

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Collect post-mortem feedback from the team

We generally do this as an open GitHub issue, but you can also create a Google form to facilitate this

Pre-Read

Before you go, I give the team pre-read. This gives them context to where the company is today and where it needs to be in the future. The team needs this in order to set relevant goals. In the pre-read I try to include…

Table of contents with how long to spend on each section.

Review last quarter’s goals, to get them thinking about their own performance.

Business recap for the last quarter, teaches them how to think about our business.

Remind them about the bigger vision of where we are going.

Remind them to re-read our values, culture and product principles.

Provide context to what matters in the up coming quarter

In general I want most of their time spent thinking about the future and what goals we need to set to get there.

Off-Site Agenda (Template)

Off-Site Agenda (Template)

Day

Day 1

Day 2

Day 3

Day 4

Day 5

Notes

Theme

Celebrate + Vent

Thinking Big + Planning

Culture + Kick-off

Hackathon

Bonding + Reflecting

Open

Morning

9:00am-9:15am:

Meet at Bus Location

9:30am-11:30am

Travel

11:30am-12:30pm

Settle In

8:00am-9:30am

Breakfast

9:30am-11:00am

Activity or Adventure

11:00am-1:00pm

Exercise: What are our biggest levers to grow 3-4x and hit our targets

8:00am-9:30am

Breakfast

9:30am-11:00am

Activity or Adventure with a form of accomplishment

11:00am-12:00pm

Cultural Topic brainstorm: Can be about anything, compensation, communication, processes. Bring notes from the first nights session.

8:00am-9:00am

Breakfast

9:00pm-12:00pm

Hacking

8:30am-10:00am

Breakfast

10:00am-11:00am

Packup

11:00am

Depart

Open

Afternoon

12:00pm-2:00pm

Lunch & Overview of the Week

2:00-2:30pm

Checkin

2:00pm-3:30pm

Icebreakers

Mission and Vision

Q&A with founders

3:30pm-5:00pm

Last Quarter Retro (Teams or Company Wide)

1:00pm-2:00pm

Lunch

2:00pm-4:00pm

OKR Planning Session 1

4:00pm-4:30pm

Break

12:00pm-1:30pm

Lunch

1:30pm-3:00pm

First most important cultural topic

3:00-4:30pm

Second most important cultural topic + 3rd if Time

4:30pm-5:00pm

Break

12:00pm-1:30pm

Lunch

1:30pm-6:00pm

Hacking

Open

Evening

5:00pm-5:30pm

Break

5:30pm-6:30pm

Each team shares their retro feedback and why they did/didn’t hit them. Shout out each teams individual hero moments.

6:30pm-7:30pm

Exercise: Break down what’s broken. Get stuff on the table they are frustrated about that we need to fix. Write these down to address.

7:30pm-10:00pm

Dinner

4:30pm-6:30pm

OKR Planning Session 2

6:30pm-7:30pm

OKR Presentation

7:30pm-9:30pm

Dinner

5:30pm-6:30pm

Company Awards

6:30pm-7:00pm

Hackathon Overview

7:00pm-8:30pm

Ideation Dinner

8:30pm-9:30pm

Pitch Session + Team Formation

9:30pm-Late

Hacking

6:00pm-7:30pm

Presentations

7:30pm-8:30pm

Dinner

8:30pm-late

Themed Party / Activity

Open

There are no rows in this table

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Off-site Exercises

These exercises come from Marc Barros (Founder of

Moment⁠

) Which is a hardware company specialising in photography, creatives that I’ve admired for a long time. Moment was Marcs second business.

Session – Review The Past

We have done this a few ways over the years. As the group has gotten larger we’ve moved from doing this company wide to doing this by teams and then recapping with the whole company.

Our general process is…

Review the goals. Here we go goal by goal. We score each goal from 0-1 depending on how much of it accomplished. With each goal we list a few why’s. This helps us learn how to set better goals.

Highs and Lows: Each person goes around and shares their personal highs and lose from the last four months. We now do this within teams but we used to do this company wide. It was very powerful as it pushed people to be open with others.

Props: Public acknowledgement matters. We have each person go around the room and give props to their teammates. You can see how body language changes immediately when this happens.

What’s important during this session is you take notes. You are looking for threads for things you need to fix. Working through these issues is very, very important.

Session – Think Big

People aren’t taught how to scale teams or revenue and so these exercises give the team a chance to learn how. I’ve run this exercise in terms of revenue and/or team growth.

You post a questions…How would we get to $X in revenue?

You have them for cross functional teams (4-7 people) and they get 20 minutes to do this exercise. After 20 minutes they will come back and present their brainstorm. Generally what you get are a list of tactics.

This is your chance to teach. First you let them know you only gave them 20 minutes on purpose which means there was no way to get into tactics. You were looking for the "how" which means they have to start at the highest level and then break down your path into smaller details…

Start with the most basic unit in your business. In ours, it’s customers.

Map out how many you need to get to answer the $X question.

Once you know how many customers break down what percent comes from new versus repeat.

Once you know the mix you need a framework for how you get there.

….a very efficient group can maybe get this far in 20 minutes.

You then send them back to do the exercise again this time having them come back with a framework for how. They return with something that’s closer on number of customers but the how goes back into tactics versus outlining a strategic framework for how.

You then would show them that in order to get growth you either need to go wide (more offerings to the same customer), go deeper (more customers with the same offering), or expand distribution. You send them back to better outline a framework for "how" they are going to get $X from new and $Y from existing customers.

After 20 minutes they are closer. They have made some assumptions about what would work in order to reach those customers.

Depending on how much time you have, you continue to repeat this process until they have a rough plan of how to get to $X in revenue.

In doing this kind of exercise you quickly realise that you need to understand the process in order to teach it. Secondarily you realise this kind of strategic thinking is not taught.

You can run this type of exercise at every off-site, you just increase the revenue scale of the initial question to make it harder.

Session – Role Playing

These sessions are my favourite. I’ve run different role playing scenarios to get the teams thinking about topics they would never expect. Generally I’m creating scenarios so they can see elements of a shitty culture. This helps them clarify what they want in our culture.

An example would be…I wanted to teach people how to quit. No one teaches this and whenever someone quits it’s terribly done, which leaves the existing team in a bad spot. Therefore while doing a team hike we had a 30 minute break to run this session.

I paired everyone up and gave them one of two cards.

Card one said you had to quit. Each card was a slightly different version of quitting. I had the passive aggressive quitter, the angry quitter, the I don’t give a shit quitter, the over apologetic quitter, etc.

Card two said you had to fire the person. I again came up with different versions of firing someone from passive aggressive to direct to excuse filled.

It doesn’t take too long for people to catch on to what is going on. They can somewhat overhear other teams, which makes it funnier. This ran for about 20 minutes and then I brought the whole group together and let them share what they liked and didn’t like about the person they interacted with.

In the end I was able to teach that what matters in the business world is your legacy. Therefore if you are quitting, here is how you do it.

If you get creative you can come up with all kinds of role playing scenarios like this. They are fun and give you a chance to teach something often missed in startups.

Pre-Offsite Planning (Template)

Off-Site Agenda (Template)

Off-site Exercises