By Tatiana Dominguez
What really makes a retreat work?
Everyone talks about the outcomes of a great retreat—connection, clarity, momentum. But what about the invisible labor that makes that magic possible? From the snacks on the table to the flow of the agenda to the heat transfer station you set up at midnight, the smallest decisions can make the biggest difference. This behind-the-scenes peek pulls back the curtain on what it really takes to pull off a powerful offsite.
If you’re the one making the retreat actually happen—planning the details, prepping the space, worrying about what’s in the room and on the table—this is for you. Think of it as your unofficial checklist, born from years of real-life retreats and “please never do that again” moments.
Don’t sleep on the power of teacher resources. I often start at classroom supply stores for fun, functional materials—things like dot stickers, foam dice, timers, mini whiteboards, and Sharpies in every color. For facilitator kits? I swear by makeup organizers. They're portable, visual, and hold everything from markers to masking tape. A great offsite lives in the details—and often in a rolling cart.
Snacks aren’t just fuel—they’re facilitation tools. I think about snacks as emotional cues: do people feel cared for? Are we giving them the energy to stay present? I always aim for variety—protein bars, cut fruit, trail mix, dark chocolate, gluten-free treats—because no one wants to feel like an afterthought.
Pro tip: Put snacks out early and keep them accessible. Hungry brains don’t collaborate well.
Swag isn't about logos. It’s about supporting the experience. If we’re outdoors around a fire, I’ll get cozy blankets. If we’re moving between breakout spaces, branded backpacks or fanny packs for workshop supplies. One year, we gave everyone new laptop bags—and as a surprise opening activity, we set up a heat transfer station so people could decorate their bags with icons and affirmations. Did it take planning? Yes. Was it worth it? Absolutely.
Prizes aren’t just for fun (though they should be fun)—they’re an easy way to reinforce your values. I love choosing unique, usable items people can bring back to their desks or homes. Think: highlighters shaped like crystals, Bluetooth clickers, desktop diffusers, color-coded planning pads. Prizes that say, “I see how you work, and I want to support it.”
I design agendas like energy arcs: warm up, rise, reflect. Start light and connective. Build into focused strategy. End with appreciation and intention. And always—always—build in white space. People need time to walk, rest, think, or call their kids. That’s not downtime—it’s integration.
A handwritten note. A playlist that matches the moment. A phone charger taped under every table. These are the things people remember. I once saw someone tear up because their snack bag included their name, a kind note, and the exact trail mix they love. That’s not swag—that’s strategy.
Retreats aren’t made by accident. They’re built through intention, insight, and a thousand tiny decisions no one claps for. If you're the one behind the curtain, you are the heartbeat of the experience. Build for focus. Build for joy. Build for the people you’re gathering—and they’ll feel it.
Need support designing a retreat that works? Explore our podcast and planning resources, or reach out for customized help.
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Tatiana Dominguez is an executive producer and systems strategist who helps leaders bring clarity, creativity, and structure to transformative team experiences.