Planning a team offsite? Read this first.

I've planned at least a hundred offsites , for teams small and large.

They're an amazing tool for building bonds and strategic thinking more but if poorly planned, they can feel like a big waste of time.

At my current startup, Hoop , we're a remotely distributed team that gets together a few times a year. We believe strongly in purpose driven, infrequent get togethers and face time to build psychological safety and group cohesion. The rest of the time, we're remote and mostly async.

We're planning our first offsite of the year, so I thought it might be useful to share how we think about offsites, largely modeled after how we ran offsites when we previously worked at Trello :

1. Purpose - Before even choosing a location, it's important to categorize the purpose of an offsite because that should drive many of the planning decisions.

Is the goal mostly to forge deeper connections with the team? Is it a strategic offsite? Is it a working offsite?

Taking a step back to consider the goal will save a lot of time in the future when you're putting the schedule together.

2. Logistics - This is the most annoying part, and I like to use ChatGPT to help . Once I get everyone's availability in a Google Form, I figure out the guidelines for what type of location we want. We have people across the country so we tend to pick not super expensive cities in the middle of the US.

3. Organization - Once we've picked the location, we give the team members parameters for booking their own travel and putting the info into a Notion page. Self-organization is key to maintaining sanity when you're planning offsites at a startup. We document everything related to our offsites in Notion- from planning to session notes, to things we want to change for the future. Documentation is key.

4. Content- We'll start planning content about a month in advance, casually. Because of our early stage, most of our offsites tend to be strategic, so there's a lot we want to cover. The team will suggest sessions, and each one will have a designated driver to plan what we do and develop a goal for the session. Two weeks out we finalize the schedule.

5. Pre-Work- One of the keys to a successful offsite is pre-work. Each session driver comes up with relevant pre-work ahead of the offsite, giving everyone an opportunity to think about topics in advance and write down ideas.

Research shows that ideating independently and coming together to collaborate drives better outcomes, and people have different interaction styles. Pre-work gives everyone the gift of time to think and also showing up and knowing exactly what we're doing.

If you're interested in seeing what our pre-work looks like, there are examples here.

Offsites benefit from clear thinking, good planning, and self-serve documentation so everyone can find the info they need.

Don't forget to leave time for fun! That's often the most valuable part that people end up remembering.

#remotework #offsites #teamwork #teambuilding #futureofwork