As companies grow, something unexpected happens. The challenge is no longer coming up with great ideas (every team has them), but making sure all of those ideas move in the same direction.
That is why, a few times each year, Holafly’s leadership team steps away from its day-to-day responsibilities and gathers in the same room. On paper, it’s a leadership offsite with presentations, workshops and discussions. In reality, it’s one of the few opportunities where people who spend most of the year solving completely different problems stop thinking only about their own department and begin looking at the company through someone else’s eyes.
A discussion about customer feedback quickly becomes a conversation about product priorities, a technical challenge raises questions about brand perception, and a marketing campaign uncovers operational dependencies that nobody had considered before. The further the conversations go, the more departmental boundaries begin to disappear, replaced by a shared objective: making better decisions that ultimately bring peace of mind to millions of travellers around the world.
For Alfonso Mata, Head of Strategy at Holafly, alignment starts by answering a much simpler question: What’s the ONE thing that matters most right now? “In a company growing as quickly as Holafly, being clear on our top priority is what allows every team to move in the same direction. Alignment isn’t about getting everyone to agree on everything. It’s about making sure every team understands where the company is heading, why certain decisions are being made, and how their work contributes to the bigger picture.” Those conversations may only last two days, but the priorities, decisions and relationships built during them continue shaping the company long after the meeting ends.
Perhaps the biggest impact isn’t on the projects themselves, but on the way people work together once they return home. Future conversations become easier because people understand each other’s priorities, challenges and constraints. Teams stop handing work from one department to another and start solving problems together, and collaboration becomes less about processes and more about trust.
That idea became especially clear during one of the activities organised as part of the offsite. Instead of discussing strategy, the team was asked to build with LEGO. Each group was responsible for a different stage of the customer journey to build a 10 out of 10 experience. It quickly stopped being about LEGO and became a lesson in how modern organisations work and how we all collaborate towards bringing peace of mind.
For Eileen Gregory, Head of People, that is exactly how culture is built. “The strongest cultures aren’t created through presentations or company values written on a wall. They’re created when people spend time understanding each other’s perspectives, challenge ideas respectfully, and realise they’re all working towards the same goal.” Moments like these create relationships that make collaboration feel natural long after the meeting has ended.
Carrier Operations Director César Serrano has experienced the value of that collaboration firsthand. Whether solving a complex connectivity issue, launching a new capability or improving the traveller experience, the biggest challenges never belong to a single department. They require Product, Engineering, Customer Experience, Brand and Operations to contribute different pieces of the puzzle before the solution finally comes together.
By the end of the two days, the presentations have finished, laptops are closed, and everyone returns to their day-to-day responsibilities. But they don’t return with the same perspective. They leave with a better understanding of the people behind the Slack messages, the decisions shaping other teams, and the shared responsibility they all have in delivering a better experience for travellers.
Because sometimes the most valuable outcome of a leadership meeting isn’t a new strategy or a finished roadmap, but creating the alignment, trust and collaboration that allow hundreds of people to move in the same direction long after everyone has left the room.
