Previously, we wrote about an event planning checklist we used for organizing our company offsite. Now, as our team retreat is over, we’re sharing a behind-the-scenes look into how it went.

When Gable raised our Series A, we knew organizing a team retreat was at the top of our to-do list. It was high time for our global team to meet after two years of working together and experience the special bond we have virtually, but this time in person.

The team had many interesting destinations to propose (including tropical getaways!) but we ended up deciding on New York City as the offsite location, for various reasons.

Firstly, we don't have team members living in NYC, so everyone had to travel to get there - making the experience equitable. And on top of that, we felt NYC's hustle-bustle and contagious energy would provide a great backdrop to our team finally being in one place.

We didn't have a specific agenda in sight right away, but we did know one thing: our offsite was not going to try and replicate the office experience. The last thing we wanted was for our team to fly halfway around the world just to sit at desks, headphones in, and work in solitude.

The north star of our offsite planning was to design an agenda that maximizes the impact of the time we'll spend together. Our primary focus was on fostering meaningful connections and collaborations, sparking fresh ideas, and having fun together.

So, let's dive into how we made our first-ever company offsite a roaring success!

Offsite planning, logistics, and support

As we embarked on the planning phase for our offsite, we knew attention to logistics and support would be crucial to ensure a smooth experience. Breaking down the planning process into manageable components allowed us to focus on supporting every employee individually.

To recap, here's what our planning process was like:

• Visa assistance: Some of our employees needed US visas, so we made sure to provide paperwork support and supply everyone with invitation letters
• Flights and accommodations: We prioritized employee comfort and personal schedules, including family commitments, when booking flights and accommodations
• Support for working parents: Our team facilitated employees who were coming to New York with their children and family members
• Post-offsite exploration: We ensured team members who wished to stay and explore NYC after the offsite could do so by encouraging PTO requests and approving them before the offsite

If you know anything about Gable by now, it's that we are fans of looking at things holistically. In this case, that meant providing every employee with the support they individually need - as that was the key element in making our offsite event successful. So the support doesn't stop at flight tickets and hotel rooms - it takes into account the different personal needs of our team.

Work sessions at our offsite

Continuing in the spirit of Gable's holistic approach to work, our offsite was designed to focus on our mission and vision. As our base for the offsite, we chose Studio by Tishman Speyer, one of the most loved spaces on our platform, which offered the perfect setting for our team, as we had access to both the common space and several conference rooms of different setups and sizes.

Need help choosing an offsite location and workspace? Read our guide to planning a company offsite with Gable >>>

While to some it may sound counterintuitive, our offsite meeting agenda prioritized interactive and team-oriented activities over solo desk work. The primary goal was to bring the team even closer together and further align with our shared mission and goals. To achieve this, we planned sessions and workshops to foster collaboration and growth, including:

• Investor Q&A sessions: We held two insightful Q&A sessions with our investors, who highlighted the unique strengths of our team and offered valuable perspectives on our journey.
• Cross-team workshops: To address potential roadblocks, we organized workshops in small groups that encouraged open discussions on topics that could hinder us from reaching our goals. These sessions allowed team members to brainstorm, share ideas, and collaborate on problem-solving.
• Leadership presentation: Our founders and leadership team led a presentation outlining the company's goals for the year, ensuring everyone was on the same page and working towards a common purpose.

For us, the goal of the offsite was twofold: build relationships and teamwork that will benefit the whole team as we continue to work together, and provide every team member with a clear vision of how they contribute to the company culture, growth, and continued success.

We believe that by opting out of solo work and choosing a workshop-based approach for the offsite agenda we achieved both goals.

Organize unforgettable team get-togethers using Gable’s events feature. Here’s how >>>

High-impact workshop

The single most impactful session during our offsite was our communication workshop, which definitely deserves its own section.

The topic of this 3-hour workshop was effective team communication in a distributed, remote team like ours. Before the offsite, we sent out a detailed survey for our whole team to fill out, so we could narrow down the specific topics of the workshop and tailor it to the challenges we are facing.

Led by an expert in communication, the session delved into essential topics for day-to-day work, such as conflict resolution, understanding different communication styles, and mastering both synchronous and asynchronous communication in a remote work environment.

Throughout the workshop, we identified areas where our communication was and wasn't working, setting clear and actionable goals and an action plan for improvement post-offsite.

A particularly inspiring part of the session was the one-minute slots where we expressed appreciations for our teammates. We wrote all of these down, and our teammates now have their appreciations printed out and visible in their home offices, so they can always see them.

This powerful workshop gave us valuable insights and strategies for effective communication - most of which we have already implemented - but it also proved to be a moving experience that left a lasting impact on our entire team.

Team building activities

At Gable, we practice what we preach - and that's what makes it vital for us to balance the workshops and sessions with fun, relaxation, and bonding time. Based on our team's interests, we opted for several team activities that helped us foster relationships and create fun memories together. Here's what we chose:

• Icebreaker sessions: On our first day, the kick-off event was icebreaker sessions, with our Employee experience manager as a facilitator.
• Yoga session: Our team often does yoga together virtually, so we gave it a shot to do some stretching together in person
• Cooking class: One of the highlights of the offsite was a cooking class where we made pasta from scratch. This hands-on activity not only allowed us to bond over a delicious meal but also kickstarted some friendly competition among the team.
• Cocktail happy hour: We couldn't miss heading to an NYC rooftop for cocktails and finger food, so we used that chance to mingle and soak in the views in a relaxed atmosphere
• Team dinner: Having dinner together was the perfect time to get dressed up, enjoy a meal, and have a laugh...or several. There’s nothing like a large group dinner to set the atmosphere.

Get inspired with our ideas for impactful offsite activities >>>

There's one additional element to our team bonding, and it's not an event - company swag.

We're maybe a little biased when we say our company goods are the coolest thing ever, but it's truly how we feel. Our branded hoodies, stickers, and personalized cards were not just a great addition to our collection - they helped us instantly feel closer and increased our sense of belonging.

Planning for unstructured time

In planning our offsite meeting, we recognized the importance of allocating unstructured time. This allowed everyone the freedom to engage in spontaneous conversations, forge deeper connections, and decompress from the sessions and activities.

During our last evening and afternoon, we intentionally left the agenda open. Similarly, our final morning together had minimal planned activities. This unstructured time created opportunities for serendipitous chats and encouraged team members to grab each other for coffee, lunch, dinner, or drinks at their own pace.

We were mindful of the diverse personalities within our team, as some of our colleagues are introverts who benefit from this flexibility. Unstructured time and spontaneous gatherings provided a more comfortable environment for people to connect and engage with others in a way that feels natural to them.

Another crucial aspect to consider was in-person exhaustion. Company retreats can be particularly intense, especially after years of remote work. By planning for downtime and rest, we ensured that our team members could recharge and make the most of their offsite experience without feeling overwhelmed.

Feedback: What our team said

While we’re still analyzing and processing the details of our offsite feedback forms, the preliminary results show what we all hoped for:

• Our entire team feels more connected to each other
• Everyone feels more aligned with the shared mission, vision, and goals
• We’re more engaged and trust each other more as a team

Gathering specific and detailed feedback is as important as all the activities you’re planning, if not more. For us, it was essential to get a pulse on how our team felt post-event, especially since it was our first team gathering.

We’re big fans of feedback and iteration, so we’re already thinking about our next in-person gathering and how we can improve on it with the feedback we got on this one. One thing is for sure: we enjoy working remotely and leveraging all the benefits of being distributed - but nothing can replace being with each other in the same room. That’s all the more reason to plan our offsites with connection as the primary focus.

The perfect balance of remote work and in-person connections

To sum it up: our first-ever company offsite was a resounding success. We firmly believe the time we spent together will yield returns in the months to come, with long-lasting relationships, the trust we built, and improved communication.

At Gable, the way we work balances the best of both worlds. For 51 weeks every year, we embrace the benefits of remote work and async communication and work efficiently from all corners of the globe as a virtual team. But we also recognize the value in setting aside a week each year to focus on human connections, camaraderie, and having a great time together.

By striking this balance, we're able to fill in the gaps of connection and build a workplace that's optimized for the future: global, flexible, and connected.