17-Jul-2023 by Allison McMillan

Read Time: Approx. 5 minutes

Nurturing Connections in Casual Gatherings

With businesses increasingly going remote or hybrid, the power of in-person gatherings to forge and fortify connections within teams is vital. Offsites can range from meticulously planned marathons of back-to-back sessions to free-flowing encounters, which on the surface seem laissez-faire but are often assumed to be catalysts for serendipitous collaboration and 'watercooler' brainstorming. They focus on the idea that to plan nothing allows for something to happen; that when you get smart, collaborative, kind people in the room together, magic is bound to occur. The assumption that people will get to know one another and they'll walk away from the experience with a greater understanding of who everyone is on a more personal level, they'll have had some interesting informal conversations, and that tangents or ad-hoc watercooler "wouldn't it be cool if" brainstorms will fuel the next unknown amount of time until the group can get together again.

While the latter promises an inviting mix of travel, leisure, and informal conversations, it often unwittingly favours extroverts, leaders, and those who know each other already, thereby leaving others on the periphery. Moreover, measuring the success of such offsites is nebulous both for the organizers and the attendees. Have people made new, meaningful connections? Have they delved beyond small talk? Was the offsite worth their time? Here are some suggestions about how to make your hangout offsite truly inclusive, engaging, and impactful without losing its laid-back vibes.

1. Set expectations and understandings beforehand.

Even with a gathering that is more of a hangout, pre-offsite communications are important. Here, you might include suggestions for questions to ask or ways for folks to engage with one another. You might ask people to come with a certain mindset or ask folks to think about ways in which they can connect with others authentically as opposed to just working from a different location for that week. Helping to frame the mindset for the week is really important to determine how people show up.

2. Build in ways for people to meet others they might not otherwise interact with.

One of my favorite ways to do this is through a short unconf. An unconference is a participant-driven time where the agenda is created by the attendees at the beginning of the meeting. Unlike the structured format of a typical conference, an unconference encourages spontaneous and interactive discussion. This can be a brilliant way to make your offsite more engaging.

At the start of the time, invite your team members to propose topics they're passionate about or challenges they're facing that they believe others could benefit from discussing. You can decide if you want to limit the topics to ideas that are work-related or open it up to anything people want to talk about! Vote to determine the ideas the most folks are interested in. Then, create a schedule based on these suggestions and let the organic conversations unfold. This not only encourages active participation but also brings to the fore diverse thoughts and ideas that might not surface in a typical team setting. It allows folks to get to know one another differently.

There are a variety of ways to add in similar aspects to a low-key offsite including pairing folks, having people sit next to different people for every meal, creating rotating walking buddies for breaks, and more. The goal here is to allow folks to interact with people they may not normally interact with AND go deeper than surface level conversation. Remember, you can always make some of these things optional as well.

3. Do one session that's all together and don't let that session be a solely frontal presentation.

Most teams or companies that get together do at least one session with everyone together... if not, it seems like a missed opportunity! But these sessions are frequently a "state of the company" or a usual all-hands that just happens to be happening in person. But what can you do in person that you can't do virtually? Don't miss the opportunity to have folks engage and interact with the material being discussed to really digest it. And no, i'm not talking about a Q&A. I'm talking about a small group discussion after the fact, or a big, but brief brainstorm about next steps, or even fun appreciations or an excitement/fear post-it exercise that enables folks to see what others are thinking and allows leadership to get a better sense of where their team is at. This doesn't have to take a lot of time, or be long and arduous, but if you don't want to miss our on the opportunity to talk to everyone together, in one space, then you definitely don't want to miss out on the opportunity to make it a lasting experience that will stick with people beyond the offsite.

As the businesses navigate hybrid and remote landscapes, thinking critically about how to connect individuals in ways that energize them and make the company more productive as a whole, it's crucial to reconstruct the idea of an informal hangout as a transformative, communal experience. By incorporating participant-driven activities like unconf, fostering deeper conversations, and capitalizing on the opportunities presented by being physically present, we can shape offsites that cater to a wider range of personalities and preferences. These enhanced offsites, while maintaining their relaxed atmosphere, can forge profound connections among team members, bringing about heightened understanding, empathy, and, ultimately, a more productive and cohesive team. The success of such an offsite then becomes a shared, palpable experience, far removed from the intangible benefits of past gatherings, setting the stage for a new age of team building and collaboration.


Need help leveling up your offsite? Book a free consultation today or check out my offsites service


people getting together around a fire getting to know each other

Ready to chat?

Join my mailing list

* indicates required

Set up a free call

phone icon