My first project as Chief of Staff at Gather was running our upcoming, weeklong company retreat. For our small team, this event would be a critical launching pad for our next phase of growth. 

So, I dove in headfirst. I spoke to fellow retreat planners, researched goal-setting frameworks, and drafted a few dozen agendas before getting it right. I learned that putting together an outstanding retreat would take more than a crash course in event planning — it demanded careful thought and strategy. 

But planning was just the first step. Actually running the event — and having it drive momentum for months to come — was the biggest challenge.

Here are my five biggest takeaways from organizing my first-ever Gather retreat: 

1. Delegate.

You can’t do it all — and at the best retreats, you shouldn’t have to. 

Offering ownership of events to individual team members encourages participation and makes your team feel like the retreat is truly theirs (because it is!).

Ari, a software engineer, designed what ended up being one of our favorite activities: a city-wide scavenger hunt culminating at the iconic Cleveland script sign. 

2. Invite your customers.

‍(inspired by the team at Close!)

It’s not everyday your engineering and operations folks get to have facetime with customers. So we spent a day interviewing our users to inform an exciting new part of our product.

Understanding their goals and challenges not only gave us valuable product insight, but also served as a reminder of why we do what we do — to empower those working hard to put people first in the workplace. 

3. Manage time wisely.

Retreats are the one time of year we get to hash out ideas live, without the buffer of screens and Slack messages.

To make the most of it, we traded in our digital tools for Post-its and Sharpies. We focused our retreat on teamwide goal-setting and building out a comprehensive product roadmap. 

In order to be a successful remote-first team for the rest of the year, we knew we’d need to sweat the details in person at the retreat. 

4. Don’t forget your roots.

‍Reflection is often a big focus at retreats — but how often do you think back to the very beginning?

During an afternoon of service at a local farm, we reflected on why we started Gather in Cleveland in the first place. The choice fulfilled a vision of a more equitable future of work, where great ideas can thrive outside of traditional tech hubs. 

Giving back to the city Gather calls home revitalized our core belief that the future of work is anywhere. 

5. Don’t forget to have fun — really.

‍The most common piece of feedback I got was that people wanted more unstructured time to spend with each other. Not team bonding exercises, not going out to dinners — just time to hang out.

Sure, retreats are a prime time for team alignment. But we realized how important it is to carve out time to get to know each other as people, not just co-workers.

At the end of the day, I’m proud of all that we accomplished. 

We reflected on our wins and challenges, got to know each other on a deeper level, and built a ton of momentum around the future of Gather we’re creating together. I'm excited to see how this energy carries us into our next chapter. 

And I’m already looking forward to using everything we learned to make the next retreat even better.