Unforgettable Offsites: Why Your Team Gatherings Are Failing (And How to Fix Them) with Tom Goulooze
with Tom Goulooze, Designer, Facilitator & Founder at Tomfoolery
Most company offsites fail because leaders design for themselves, not their teams. Tom Goulooze shares how listening-first facilitation transforms gatherings.
Most company offsites are expensive Zoom meetings with better catering. Someone flies 50 people to a hotel, puts them in a room, and then one person stands at the front talking at them for three hours like it’s a Monday standup. Tom Goulooze has made it his mission to prove there’s a better way.
Tom is the founder of Tomfoolery, an Amsterdam-based facilitation practice that helps companies design team gatherings that actually give people what they need. He joined Tine on the Love Not Fear podcast to talk about why most offsites miss the mark, what brave leadership really looks like, and a deceptively simple chair game that reveals everything about your team dynamics.
Why Your Offsite Feels Like a Waste of Time
Tom’s frustration is simple and specific. Companies spend enormous budgets uprooting teams and flying them to the same location, then fill the agenda with long presentations, polished leadership speeches, and maybe a cocktail workshop nobody asked for. The people who plan these events are usually leadership — people who talk to other leaders, share the same vocabulary, and nod in agreement when someone suggests “let’s go over our goals for Q3.”
The problem is that leadership is not the audience. The team is. And nobody asked the team what they actually need from those precious hours together in the same room. Tom’s approach is disarmingly straightforward: before designing anything, he talks to the people who will be in that room. One-on-one interviews, honest questions, sometimes a survey. What does a great gathering look like to you? What would make this time worthwhile? The insights that come back almost always point in a different direction than the original plan.
Give the People What They Need, Not What Looks Professional
Tom draws an unexpected analogy: planning an offsite is like picking a karaoke song. You can show up with a seven-minute Celine Dion ballad pre-rehearsed, or you can read the room first and pick something that lands. Company offsites work the same way. A bespoke experience designed around what the team actually says they need will always outperform the professionally adequate agenda that offends no one and inspires no one either.
This extends to how leaders show up. Tom has watched executives agonize over politically perfect messages filled with words like “leverage” and “revolution” that mean absolutely nothing. The leaders people remember years later — the ones who actually shape culture — are the ones who are human, real, and willing to make mistakes in front of their teams. One WeTransfer co-founder once plastered an ugly ad across the entire office facade to make a point about brand integrity. People hated it. He had to apologize. And it became a defining cultural moment.
The Chair Game and the Power of Discomfort
One of Tom’s favorite facilitation tools is something he calls the chair game, picked up at a teen camp for emotionally struggling teenagers. Everyone gets hidden instructions about what to do with a set of chairs — some people arrange them in a circle, others steal chairs away, some just high-five strangers. Nobody is allowed to talk. Chaos follows quickly.
The genius is in the debrief. How you behaved with the chairs mirrors how you behave in your team. Did you get dominant? Did you give up and check out? Did someone take your chair and you said nothing? It strips away the blame game and creates a shared mirror for the group to reflect on their real patterns. Tom’s advice for facilitators: let the discomfort sit a little longer than feels comfortable. That’s where the learning lives.
The Real Secret to Culture Transformation
Tom’s biggest insight comes from his days as an OKR coach: lead with the benefit first. Most change initiatives point to a promised land eight months away and ask everyone to work hard to get there. Nobody buys it. Instead, find the pocket of the organization that is already experiencing the benefit you want to spread. Show people what’s already working, right here, right now. Then help it grow outward in small, incremental steps. Don’t call it change. Don’t build a seven-month roadmap. Just move in the right direction, one gathering at a time.
Listen and Connect
Tom Goulooze runs Tomfoolery, helping companies design team gatherings and offsites that people actually remember. You can find him in Amsterdam, probably picking the perfect karaoke song for your next leadership retreat.
For more conversations like this, visit lovenotfear.com and subscribe to the Love Not Fear Podcast wherever you listen.