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Lessons from a trip creator: How to run an offsite

Thinking of running an offsite this year? Elina Rueda from The Coworker Experience shares her advice on how to make it great.

By Anisah Osman Britton

Elisa Rueda

When we asked Twitter a while ago who ran great offsites, Elisa Rueda’s name popped up. She is the founder of The Cowork Experience — a company that creates and manages team offsites and provides online programmes for team growth and development. She’s been trusted by the likes of open source platform GitLab, investor platform and jobs board AngelList and consultancy Capgemini. She’s taken teams everywhere from Hawaii to Bali. For our Startup Life newsletter we got her top tips for running an effective offsite for your team.

Determine how long you need

A lot depends on the size of your team: a company-wide offsite for 100 to 150 people normally lasts three days and three nights. When you’re hauling so many people around, you need to plan in logistics time. If your company is smaller or you’re taking out a group (a particular department or the executive suite), a shorter stay can be just as effective.

Run offsites more often

Prior to the pandemic, offsites gathered multiple offices of the same company in one place to meet. So once a year was probably enough. With remote-first companies, extra coworking time is valuable for team building, morale and team mental health — so a cadence of once a quarter may be better. The more you have, the more variety you need to make them fun and not feel like a chore. Maybe the first is a longer stay, the second only a night; one at the beach, one in the mountains, etc.

Choose a location that meets your needs

Budget: go somewhere that gives your team an exceptional experience. If you have a smaller budget, choose an offsite location in your country to be able to do that. Safety: this is not just a holiday. You are responsible for your team so select somewhere that meets your health and safety, accessibility and code of conduct requirements. Time zone: part of the team will need to work so choose somewhere that works for the regions you are serving (and that has good wifi!).

“Your goal is to team build; if people are stressed about tasks not done or they’re too drained from back to back activities, you’ll miss people coming together naturally”

Plan in work time and downtime

Your goal is to team build; if people are stressed about tasks not done or they’re too drained from back to back activities, you’ll miss people coming together naturally — which is what this is all for. So figure out how many hours people need to be working. Be explicit about the time you’re setting aside for it. Also, plan times where nothing is planned. Let them sit around, have a cup of coffee, relax and digest what they’ve been doing… meaningful conversations will happen in these moments. They will be the most valued times, not the most expensive activity.

Set varied activities

You need to have choices in your agenda for all different types of personalities and interests. Forced fun is no fun. People need to feel comfortable for an offsite to be valuable. We always have: something with a wellness angle like yoga or meditation; a workout; a high impact sport; an intentional team activity — for example, on one offsite there was a cart building exercise; something fun and different like team Olympics; a big brain problem like a critical thinking maze. You’ll have already met many interests by providing one activity from each of these groups.

Reassign what you’d spend on an office on offsites

Most offsite budgets are planned per person. If the location is farther away and flights required to get there are more expensive, you could be looking at $300 per person per day over three days. If you’re in the same country, $150 per person per day could do it.

Anisah Osman Britton is coauthor of Sifted’s Startup Life newsletter, which comes out weekly on Wednesdays. Sign up here.

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