How to plan a killer company offsite in just 8 weeks

Aug 17, 2022

As a company born at the beginning of the pandemic, PostHog has been fully-remote from its inception. Our team is 35+ people distributed across 11 countries; we have no central office, but we still value getting together in person.

We give employees social and co-working budgets to encourage meetups and in-person onboarding. But the main way we facilitate in-person collaboration is through offsites – small team offsites for focused work, and one all-company offsite per year for high-level strategic planning and cross-team interaction.

In large companies, offsite planning is centralized within the People & Ops teams, but this isn’t possible in many early-stage startups. This guide is for those small to medium startups who need a little help, and includes a few tips and tricks I’ve learned over a decade of organizing team retreats.

Grace McKenzie is the Finance & Ops Lead at PostHog. She tackles any and all back office projects that help build the scaffolding we need as our company scales. In her spare time, you can find her on the rugby pitch playing flanker or at her local billiards hall practicing her 8-ball breaks.

It starts with a really good checklist

Here’s one we made earlier – feel free to use it.

Seriously, a comprehensive checklist is a must for offsite planning. We made this list to help team leaders organize their small team offsites independently. Our three person “Plops” (that’s People & Operations) team help where possible, but with nine small teams all organizing one or more meetups a year, we need people to take ownership.

The checklist is structured as an eight-week timeline with items to check off at eight weeks, seven weeks and so on. It also includes post-offsite items for collecting feedback – we’ve learnt a lot about running offsites from gathering feedback on them!

Here are some key items to highlight:

• Centralizing flight booking is a huge headache, so don’t do it. We give all team members company cards for this reason – see our startup ops kit for more on this. This also means you don’t have to gather up lots of sensitive info (passport numbers etc.).

• Decide in advance who is going to record the notes from offsites sessions. It is really easy for post-offsite follow-up to fall through the cracks, which means a bunch of wasted time and effort.

• It’s good if the offsite organizer arrives a day early to prep for the team's arrival. Whether it’s grocery shopping or troubleshooting airport transfers, it just makes everyone’s experience smoother.

Choosing a location

Choosing where to host your offsite is one of the most subjective planning decisions you will make. When I’m thinking about where to host, I consider a few things:

• Timing: Depending on the season, you can have wildly different experiences. For example, hosting an offsite in Reykjavik during Icelandic winter, or at the height of forest fire season in central Washington, can mean a fairly uncomfortable few days for your team. Check what conditions will be like in a given location before locking in your dates, and consider that seasons in your part of the world may not match those in different hemispheres or climates.

• Novelty: Planning an offsite in an exciting or exotic location can really enhance the excitement factor for your event, but it’s important to take into consideration travel duration and jet lag. Even if you’re choosing somewhere less exotic, choosing a novel venue like a super cool AirBnB or a quirky hotel can spice things up without stretching your team too thin.

• Affordability: An ideal offsite location depends on the stage of the company – a realistic budget for a five-person company won’t be the same as one for 100. Work out how much you can spend per person on travel and accommodation for your chosen location as soon as possible. And don’t go to Switzerland – it will bankrupt you.

Planning your schedule

It’s tempting to maximize your time together by packing the itinerary full of brainstorming, planning, and breakout sessions. Don’t overdo this. In reality, having a good balance between sessions, free social time, and fun activities is important to avoid burning your team out.

In my experience, planning for a majority of unstructured time can lead to really amazing brainstorming and ideation. People will inevitably discuss their work anyway as it’s something that everyone has in common.

One mainstay event that we do at every all-company offsite is a 24-hour hackathon, where our team comes up with the most outlandish ideas possible, and self-organizes into interdisciplinary teams to produce an MVP by the following day. Some core features of our product, like the ability to view your users on a world map; and some seriously silly things, like a children’s book focused on product analytics, have been born from this highly-rated session.

Pro Tip: Encourage people to use their company-sponsored travel for a lower-cost vacation in an interesting locale. After our Iceland offsite, my teammate Neil and I rented a camper van and traveled around the iconic Ring Road for a week! Other team members arranged their own excursions together. It’s a great way to create social connections.

Budget

I won’t sugar coat it – offsites will be some of the larger single expenses you will incur as a company each year. However, in my experience, the benefits of hosting a well-organized offsite greatly outweigh the cons if you budget effectively and manage costs as you go.

Budgeting doesn’t need to be the first thing you consider, but it should definitely be on the earlier side. I recommend coming up with a draft budget about a month and a half out, and finalizing it after a gut check with your manager or another member of your team by the end of the following week.

Numbers can vary wildly depending on location, accommodations, activities, team size, and a multitude of other factors. In my experience, the following benchmarks can be useful in initial projections before you’ve finalized any of the above factors:

• Accommodations = $200/night/person
• Long haul airfare = $1,000/person
• Short haul airfare = $500/person
• Ground transportation = $50/day/person
• Food & drinks = $50/day/person
• Contingency = 10% of total budget

As a reference, we budget $1,500 per person for a small team offsite and $3,000-5,000 for an all-company offsite, depending on location.

Final thoughts

Offsite planning can often be some of the hardest, yet most rewarding work you can do in a startup. I hope the information above helps you along the way, but be sure to check out our open-source guide for planning offsites. It includes our comprehensive checklist and some public templates you can use to make the process as efficient as possible.