From Vision to Reality: How We Built a Company Retreat With Purpose

Crete, Greece – where the sea is impossibly blue, the mountains rise like stone guardians, and time slows just enough for clarity to catch up. It’s here, between the cobbled streets of Rethymno and the sun-warmed shores of Plakias, that for five days, the LearnWorlds team traded remote work for real connection, retreating not to escape their mission but to deepen it.

Idyllic picture, right? But how did we make it real? Let’s rewind a bit.

Done right, company retreats are more than just a change of scenery. They’re a strategic tool – a way to strengthen alignment, spark creativity, and reset team dynamics. But they don’t happen by accident. Retreats require structure, intention, and tradeoffs.

Here’s the approach we used to plan our most recent LearnWorlds retreat in Crete. If you’re thinking of doing something similar, these are the decisions that matter most – and the sequence we think works.

The Seven Decisions That Shape a Retreat

1. Set your goals.
   What do you want the retreat to achieve and how do you want it to feel, and why? This should drive every other decision.
2. In-house or outsourced?
   Decide early. In-house gives you more control and authenticity, but it also means more complexity and much more work. Outsourcing saves time but can dilute the experience.
3. Choose your location.
   This should follow from step 2. The right location supports your goals. If you’re going in-house, pick somewhere you or your team have deep local knowledge and network.
4. Lock your timeline.
   Start nine months out. Six is doable, but only just. Later than that and you risk higher costs, lower attendance, and more last-minute compromises.
5. Assign clear roles.
   If you’re managing it internally, define who’s doing what early. Appoint a local “ground crew” if you have connections in the area. Build a predictable planning cadence. Communicate clearly and often.
6. Design the rhythm.
   Your retreat needs a pulse. Blend strategic sessions with time for rest and discovery. Make space for unscheduled time (this can be the most profound and memorable) – but nothing should feel accidental.
7. Build internal comms early.
   Create clarity and excitement through various means & channels. This keeps energy high and anxiety low.

How That Worked in Practice

It’s one thing to write down 7 steps and it’s another to make a successful retreat in practice for a 135-person team while work continues as usual. Let’s go through it step by step.

The 3 main goals that guided us through:

1. Strengthen Cultural Cohesion Across a Distributed Team.
   At the time we were a fully remote company with 140+ people across 18 countries. A retreat like this creates the kind of shared context, emotional resonance, and informal trust that remote tools can’t replicate. This was about investing in real interpersonal bonds, psychological safety, and cross-functional familiarity.
2. Align the Team Around Strategy and Values During a Period of Change.
   We aimed to reflect on the company’s operational and cultural challenges, share the vision and values for what comes next and set a tone of honesty, clarity, and realism in the face of growth. Creating a shared narrative: Where are we going, what matters, and how do we navigate change together?
3. Rebuild Momentum and Energy for the Year Ahead.
   Renew motivation and belief in the mission, spark creativity through unstructured encounters and leave people feeling proud to be part of LearnWorlds. Especially in a fully remote setup, this kind of emotional and energetic reset helps avoid drift and helps people return to their work with clarity, connection, and commitment.

A hybrid approach to organizing the retreat.

Because we had a deep local connection to Crete – our CTO and People Ops Manager are based there – we were able to be personally involved in every aspect, from scouting hotels and restaurants to selecting venues that felt authentic and welcoming. This gave us full control over the tone and quality of the experience, while allowing us to reflect LearnWorlds’ values through every detail.

At the same time, we brought in a local operations team to support us on the ground once we arrived – helping with last-minute logistics, activity coordination, transfers, and on-site setup. This hybrid approach gave us both ownership and flexibility, without overstretching the internal team during the retreat itself.

We chose Crete

Not just because we had team members there – though that gave us a major head start – but because it embodies the kind of retreat experience we wanted to create: warm, grounded, culturally rich, and logistically accessible.

Being based in Greece is a real advantage when planning offsites; the country offers an unbeatable combination of hospitality, natural beauty, local character, and infrastructure that can handle teams of all sizes. Crete, in particular, let us blend historic towns with rugged landscapes, calm beaches with adventurous hikes – all within a few hours’ reach. It felt authentic, not corporate. And it reminded us how lucky we are to be building a global company from a place that’s made for connection.

Locked our timeline 6 months in advance

We started planning the retreat about six months out. In hindsight, we made it work, but it left little room for error. With 135 teammates flying in from 18 countries, the logistics were intense: we booked dozens of flights, coordinated group transfers from five Greek airports, secured four separate hotels across two towns, and handled restaurant reservations, activity signups, swag preparation, and micro-requests – all in parallel with the day-to-day.

Our People team was in daily motion: building roommate lists, printing luggage tags, assigning buses, managing changes, and fielding hundreds of Slack DMs. At one point, our People Ops Manager was juggling hotel contracts, transfer routes, airport escort instructions, last-minute payment reconciliations and many more.

Started with clear ownership and then expanded into shared execution

Our management team – and founders in our case – played a key role in shaping vision, budget, and cultural direction. Their involvement set the expectations, ensured alignment, and gave the retreat its strategic backbone.

Our People Ops Manager led all things logistics: budgeting, contracts, flights, hotels, transfers, and payments. Our People Experience Manager handled the orchestration layer – designing the master tracking sheet, creating and sending forms, shaping policies with Legal, and fielding a steady stream of Slack questions. The People Director set the operational rhythm and ensured everything stayed aligned to purpose, while also arriving on-site early to oversee final setup before the team landed.

Meanwhile, our Creative and Web Design teams built the retreat website, logo, banners and swag kits. Our Brand & Social team directed on-site video capture with future storytelling in mind.

The local “ground crew,” guided by our Crete-based CTO, played a key role in scouting restaurants, venues, and activities. We started with bi-weekly meetings, switched to weekly two months out, and moved to three syncs per week in the final stretch. In the end, it was a cross-team effort – structured, collaborative, and always moving toward a shared goal.

Once everyone was finally there and we pressed play, the People team didn’t press pause. Eyes on the ball and hearts in the game, we were everywhere – coordinating, organizing, herding, preparing, energizing, and cheering everyone on. From last-minute logistics to emotional support, from holding the mic to holding the line, we kept the engine running behind the scenes. Tirelessly. Joyfully. Purposefully.

We split the retreat into two distinct phases: focus first, then flow

The first two days were work-centered – Day 1 opened with an all-hands led by our founders, setting the strategic tone, sharing our challenges and defining our culture, while Day 2 was dedicated to hands-on workshops where teams explored feedback, collaboration, and ways of working. From Day 3 onward, we shifted gears into full experience mode: hikes, boat cruises, distillery visits, beach games, parties and shared meals. The mix kept things intentional – every moment had a purpose, but no part of it felt forced.

We treated internal comms as part of the retreat experience – not just logistics

To get people involved from the start, we ran a company-wide vote on the most-used custom Slack emojis and phrases – which we then turned into stickers for the swag bags. Clear, human, and just the right amount of weird.

From there, we launched a dedicated retreat microsite as the single source of truth, featuring the schedule, maps, activity options, packing tips, policies. We also hosted a pre-retreat all-hands to walk through the plan, answer live questions, and ease any remaining concerns.

Closer to departure, we used our HRIS to create a new “retreat” section in every team member’s profile, uploading personalized details like flights, hotel allocations, and bus transfers. Weekly Slack posts helped build momentum, and once on-site, we launched a real-time Slack group to coordinate and mainly excite!

What We’d Repeat – What We’d Rethink

✅ Local knowledge made the difference. Without dedicated people on the ground, costs and friction would have risen fast.
✅ Clear internal roles kept momentum. One lead for logistics. One for experience. One for comms.
✅ Transparency mattered. Letting the team know how and why decisions were made helped them engage more fully.

If we did it again:

• We’d start a month earlier. It makes all the difference in overall management esp. bookings and organising team sanity and workload.
• We’d simplify how activities were selected and create more space for free time.
• We’d budget more time post-retreat for structured feedback while memories are fresh.

Final Thought

Planning a retreat is operationally complex. But it’s also a culture-building opportunity you can’t get any other way. Start with your goals. Make tradeoffs with intent. Communicate clearly. Reflect on the outcome.

And treat the retreat not as a reward, but as a rhythm – part of how you build alignment, trust, and momentum in a distributed remote team.