Maximizing Your Offsite: A Case Study in Strategic Gathering Design
Offsites are more than just meetings in a different location. They are high-stakes moments where company culture is on display, team engagement is tested, and leadership credibility is on the line. The difference between a good offsite and a great one lies in its design—shifting from a logistical event to a strategically crafted experience that achieves a clear, desired effect.
At The Gathering Effect, I specialize in helping organizations influence groups through strategic gathering design. This case study, featuring Beth Portesi, Lead Executive Assistant at Fivetran, illustrates how applying The Gathering Effect methodology transformed a routine legal team offsite into a high-impact experience.
The Challenge: Moving Beyond Logistics
Beth was tasked with organizing an offsite for Fivetran’s legal team following a turbulent period of layoffs and low engagement. While she could handle the tactical aspects of planning, she wanted the gathering to be truly effective—ensuring the team left feeling more connected and aligned.
“I didn’t want our offsite to be just ‘good,’” Beth shared. “I wanted it to be great. I needed help from someone who specializes in the strategy of how to get the most out of in-person time.”
The Approach: Three Key Strategies
Through our collaboration, we applied three essential principles to elevate the offsite’s impact:
1. Clarify the Desired Effect
When Beth first came to me, she had a detailed list of what she and her Executive wanted the offsite to accomplish. But before diving into the agenda and sessions, we first worked to define the offsite’s desired effect. Rather than simply listing topics, we asked key stakeholders:
What do we want to be different because of this offsite?
What would this change mean for the business?
If we looked through a camera lens, what would we see people doing afterward?
What do we need from the people we’re trying to affect? Why?
How will we know we’ve succeeded? Can we tell a before and after story?
After conducting stakeholder interviews, we aligned on three core objectives:
Understand our team’s strategy and goals.
Learn how individual contributions support the company’s maturation.
Leave embodying “one team, one dream”—ready to tackle challenges together.
Clarifying your desired effect helps to co-create the agenda so the gathering is done with others, not at them. It also helps avoid ‘the kitchen sink mentality,’ where an offsite lacks effectiveness in trying to be everything to everyone.
2. Create a Structure, Not Just an Agenda
Attendees want to know where you’re taking them. A structure instead of a list of topics or sessions helps increase certainty and clarity.
Typical agendas look like the agenda on the left. They highlight the content you are sharing. This makes it easier for people to tune out when the section isn’t relevant to them, especially virtually.
Instead of crafting an agenda slide based on topics or content, Fivetran prepared their agenda slide based on the effect (the right). Not only that, but they communicated the ‘effect agenda’ before and after the gathering to increase clarity and retention. Doing so makes it very explicit what employees will walk away with and what will be different because of their time together.
Many offsites fall into the trap of being an endless stream of presentations. Instead, we designed the agenda to facilitate engagement and action, grouping sessions into a structured journey:
I (Individual Focus): Sessions designed for self-reflection and personal insights.
We (Sub-team Focus): Activities to build alignment within functional groups.
All (Full-team Focus): Collective experiences reinforcing shared goals.
For example, instead of a traditional keynote, we introduced a celebrity interview format with the Chief Legal Officer, turning a passive presentation into an interactive conversation.
3. Land the Plane
Many gatherings fail to drive lasting change because they don’t close the loop between learning and application.
Use debriefs, thoughtful reflection, and application to help close the gap between the utility of the information and the participant’s ability to do something with it.
Ask participants to name takeaways at the close of your gathering.
Clarify action items, if applicable.
Have employees teach back or teach each other what they learned. What are a-ha’s and takeaways?
Close the gap: Clarify or ask what could get in the way of the content sticking.
To ensure the offsite had a lasting impact, we built in structured reflection:
At the start, participants wrote what they hoped to gain from the offsite.
On the final day, they revisited their notes and reflected on their takeaways.
Discussions centered on how to integrate learnings into daily work.
The difference between an informed versus engaged offsite is often this lack of reflection. I call it education without implementation.
The Results: Measurable Impact
Following the offsite, a post-event survey showed unanimous positive feedback:
100% of respondents felt the offsite objectives were clear and well-communicated.
100% left with a clear understanding of the team’s strategy and goals.
100% better understood how their work contributed to company success.
100% felt aligned with the “one team, one dream” mission.
Beth reflected, “My biggest takeaway from working with Lindsey was to hone in on the desired effect. That’s your north star. Everything you do should be structured around that.”
A well-designed offsite doesn’t just inform—it transforms. When you take the time to define the desired effect, structure the experience for engagement, and ensure lasting impact through reflection, your offsite becomes more than an event. It becomes a catalyst for alignment, motivation, and action.
Lindsey Caplan is a screenwriter turned organizational psychologist who helps HR & business leaders create experiences that boost motivation, engagement, and performance