Offsites

While we have set up the company to work asynchronously as much as possible, there's a very real benefit in getting together in real life. We've learned that our best ideas come from working together.

We understand organizing travel can be a challenge when you have personal/family commitments to manage, so we try to take a balanced approach to meetups:

• Once a year: all-company offsite
• Once a year: Small Team offsite (app and platform teams do this as a single combined offsite)
• Occasionally: in-person onboarding
• Whenever you like: in-person meetups

All-company offsites

Once a year, the entire company will get together somewhere in the world for a week. Usually we'll all fly on Sunday, have an opening dinner, spend the week doing a mix of hard work, strategy, culture and fun activities and we then all fly back home on Friday. Our past offsites have been in Italy, Portugal and Iceland.

These are organized by the Ops & People team, and we budget up to $3,000 per person in total for these.

We filmed a video in Porto in August 2021 which should give you a taste for how these run!

Typical agenda:

• A couple of structured social events
• Team dinners
• 24hr Hackathon
• All-hands strategic sessions and workshops
• All-hands culture exercises
• A small amount of downtime so people can explore

Small team offsites

We want to try to encourage small teams to get together once each year. These are more focused on work and on creating strong bonds within teams. Ideally they are spaced appropriately through the year in relation to the all-company offsite.

Some guidelines:

• These are more focused on work than the all-company offsite, but it's still worth organizing a fun activity, do some sightseeing and in general spend time together.
• You should default to picking a city that one or more of your team members already live in, and a place that minimizes travel time/expenses for everyone else.
• Outside of your small team, you should only invite people who actually need to attend to make the offsite a success - if it would be 'nice to have' them attend, they shouldn't be going.
• We'd encourage you to get an AirBnB for everyone not living in the city, as you automatically get a space you can work from and there's less organizing involved.
• These offsites don't happen very often and involve a lot of travel, so make sure you make the most out of it by having an agenda and an idea of what you want to achieve before the start of the trip.

Ideas for the agenda:

• A spoken README session early in the week to share "Who am I/How I work best"
• Planning session. What does the team want to achieve in the next month/quarter/year?
• Look at the team page - what needs to be updated?
• 360 degree feedback session - these are more effective at small team offsites
  • This can work better over a shared cooked meal or takeaway in the accommodation rather than a noisy restaurant. Particularly for people who might be anxious about the format or the feedback.
• Hackathon - try to leave 2 days for this

The budget for these trips is up to $1,500 per person in total. We ask team members to use their best judgement for these and try to be thrifty where possible - these should be enjoyable, but not feel like a holiday.

You should assign someone on the small team to be responsible for planning the offsite (doesn't have to be the lead), and they will be supported by the Ops & People team to ensure a successful experience.

Hedge House

PostHog runs the Hedge House, in Cambridge, UK. It's a place designed for small teams to run their offsites and for in-person onboarding. We'd recommend using the Hedge House for small team offsites for cost and convenience reasons if you are in Europe.

Anyone at PostHog is welcome to use it as much as they like. See the full Hedge House docs.

Travel insurance

Many of our company offsites involve team members traveling abroad, and although we hope that these trips are uneventful and safe for all, in the event of an accident or medical emergency, we carry travel insurance through as well as general & auto liability policies through our partner Embroker.

In the event of an emergency, please cover any related expenses (ideally on your company card) and keep receipts, and then reach out to either Charles or Grace as soon as possible. We will assist with making a claim based on our policy binders.

How to plan an offsite in 8 weeks - a checklist

Below is a rough timeline for planning your next offsite, as well as links to templates and resources that you can repurpose and customize as needed. To use any of the templates, create a copy to your own drive and edit as you see fit.

8 weeks out

• 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
• 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 from team locations before finalizing a location.
  • Consider the cost of transportation to/from the airport, and around town, for when your team arrives at the offsite location.
  • Be mindful that people who take long flights won't appreciate a 2hr journey from the airport to accommodation!
• Announce to team
  • You can have fun with this and build excitement by progressively dropping hints and having folks try to guess the location
• Create an offsite Slack channel and invite team
  • This is super useful for making announcements and keeping the team updated throughout planning

7 weeks out

• Secure accommodations
  • The ideal location will depend on the size of your team
  • We recommend booking a large AirBnB for teams under 20 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 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
• Start flight booking process
  • To simplify this process, we give all team members access to a company card, and we ask people to book their own flights
  • We strongly recommend this approach as centralizing flight booking can be a huge headache for offsite lead, and this allows team members to accurately enter their personal information including airline frequent flier and trusted traveller numbers
  • 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:
    1. Preemptively create the new team member a Google account
    2. Issue them a Brex card to their work email with a sufficiently high temporary balance to cover travel costs
    3. Add them as a guest to any planning Slack channels and/or share any necessary itinerary information such as arrival dates/times and airports
    4. Have the new team member book travel as usual
• Draft rough schedule
  • Building the schedule as a separate Google Calendar that can eventually be shared with the team will allow you to flexibly move sessions around as you finalize the itinerary
• Send info gathering form
  • Use this form to collect important information like flight details, clothing sizes for merch, dietary restriction, and preferences for things like sharing rooms
• 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

• Draft budget
  • Using the tentative schedule, you can begin to estimate a rough budget to guide planning. Here are some benchmarks to use, however these will vary a lot based on location, size of team, and how cost-constrained you are:
    • Accommodations = $200/night/person
    • Intercontinental airfare = $1000/person; intracontinental airfare = $500/person
    • Ground transportation = $50/day/person
    • Food & drinks = $50/day/person
    • Contingency = 10% of total budget
• Secure transportation
  • Book any group transportation like coaches or a rental car ahead of time
• Finalize team outings and book as needed
• Flights booking deadline
• Info gathering form deadline

5 weeks out

• Assign rooms
  • Using preferences from the info gathering form regarding sharing rooms, assign accordingly
• Secure visas where necessary
• Review and finalize merch proofs
• Finalize itinerary
• Finalize budget
• 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 finalized, assign folks as session leads to design session plans

4 weeks out

• Reserve restaurants for communal meals
• Book any remaining activities
• 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

• Draft session plans/presentations due
• Draft offsite guide package
• Design and print superlatives/awards
  • One activity we've found quite popular is giving out superlative awards to the team during the closing ceremonies

2 Weeks Out

• 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

• 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
• Unveil the final offsite guide to the team

1 day before

• We recommend that the offsite organizer consider arriving a day early to prep for the team's arrival
• Shop for any miscellaneous supplies and groceries (onsite)
• Print and organize a few paper copies of the itinerary (onsite)
• 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

• 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

All company offsite hackathon

The hackathon is always a highlight of the offsite. We tend to run them like this:

Session 1: ideation dinner The day before the start of the hackathon we do a casual 'ideation' dinner where we encourage people to chat about ideas

Session 2: hackathon kick-off The hackathon kick off is 1.5 hours at the end of the day. Ideally we do this in a conference room with beers and wine.

• Everyone writes down their ideas on multiple post-it notes in about 10 minutes.
• People come up to the front one-by-one, and they get 30 seconds to pitch all their ideas.
• Everyone gets three votes to put on whichever ideas they like most. Just do this as a tally. You can't vote on your own idea
• We dismiss all ideas with zero votes, and sort all the other ideas from top to bottom based on the number of votes.
• Everyone writes their name on the other side of the sticky bit of a small piece of post-it note, then add their name to the idea they want to work on. Every group should have at least two people in it, and ideally 3.
• Once groups are formed, everyone can go off and ideate or hack.

Session 3: presentations

This should be the last work related session of the offsite. Again ideally in a conference center with beer and wine provided.

Each group gets 5 minutes to demo and present their idea.

2 weeks after

• Compile post-mortem feedback and share with team
• Host post-mortem meeting to discuss any outstanding issues (optional)