Professional Development Workshops

Last week I shared how AI helped analyze our retreat feedback survey data in minutes. Today, I want to highlight the three elements that our team rated most impactful from our recent company retreat in Ireland... - [New addition] "Connection Court": We created a dedicated space in the castle with games, snacks, and comfy seating that was open throughout the day and late into the night. This gave people a relaxed place to connect in case of bad weather and removed the pressure to drink or socialize in high-energy environments. This was great for introverts and those who don't enjoy the bar scene and provided more inclusive evening activities that worked for everyone. - Doist Build (our company hackathon) hit different this year: We surveyed the team for "hack-worthy" topics ahead of the retreat, pre-selected the top 10 we felt could make an impact on the company, and revealed them the day before so people could start brainstorming. Morning of, it was first-come-first-serve with limited seats per topic, which created some incredible energy to start the day. Best part? The winning team's project was implemented right there at the retreat and immediately improved our onboarding metrics 🚀 - "Choose your own adventure" itinerary structure: Instead of forcing everyone into the same activities, we offered parallel options during free time. We balanced physical activities (hiking, sports), cultural experiences (castle tours, local music), and team building events (escape rooms, group games). This approach let people naturally form smaller groups around common interests, creating deeper connections through shared experiences. After organizing multiple retreats over the years, one principle stands out: create a flexible structure and trust your team to find meaningful ways to connect. When people have the freedom to choose activities that align with their interests and energy levels, authentic relationships naturally develop. Hope this is helpful and I'd love to hear what's working for other teams as well 👇

How I'm Structuring Our Core Team Retreat to Prepare for 2026 In a few weeks time, I'm taking our five-person core team at e27 (Optimatic) off-site for 2.5 days. Not a typical team bonding exercise, this is strategic preparation work. Thaddeus Jit Siong Koh, Christine Galolo, Justin C., Hung N.: I haven't shared the pre-treated handbook yet but here's a sneak peak of the process. The Philosophy Most leaders underestimate the power of undistracted, collective thinking time. When you remove Slack notifications and daily firefighting, something shifts. People get vulnerable. They think deeper. They connect dots they'd never see in a conference room between meetings. This retreat isn't about trust falls. It's about creating a structured environment where we honestly assess our year, confront our failures, and align on what 2026 demands from us. The Structure 80% structured sessions, 20% informal time. Key sessions I'm facilitating (learned through coaching): - Getting Naked: Vulnerability exercises - Gratitude: Acknowledging what worked - Self-Reflection: Individual introspection - Full Year Visualization: Projecting into December 2026 The Pre-Work Matters Here's what most retreat planning gets wrong: people show up unprepared and spend the first day thinking through basics. I'm requiring significant pre-work. Everyone comes with their thinking done. At the retreat, we're examining thought processes, challenging assumptions, and making decisions, not doing the initial thinking. Dissecting Our Misses One session focuses on what we failed at this year. For each miss, we're categorizing: - Execution/reactor issues? (We knew what to do, didn't do it well) - People issues? (Wrong team, roles, capabilities) - Market/timing? (Right idea, wrong moment) - Strategic misalignment? (Shouldn't have done this at all) This framework prevents the trap of "let's just work harder" when the real issue is strategic. The AI Question We're dedicating serious time to AI's impact on our business model. Not surface-level discussions but deep strategic conversations about how AI reshapes media, events, and community building in our space. Why Every Voice Matters I'm facilitating, but this isn't my retreat, it's ours. Five people, equal voices. In small teams, hierarchy can't hide dysfunction. Everyone sees everything. So everyone needs to be part of solving everything. What Success Looks Like Two dimensions: 1. Qualitative: How does each person feel about our direction? 2. Quantitative: Do we leave with clear decisions and concrete plans? Feelings without plans are therapy. Plans without emotional buy-in gather dust. We need both. For Fellow Founders The best retreats I've experienced weren't the most fun, they were the most uncomfortable. They forced hard conversations we'd been avoiding. That's what separates a retreat from a holiday. When's the last time you gave your core team uninterrupted time to think together? Not plan. Not execute. Just... think?

Summer Assignment: Create Space for Deep Thinking A few years ago, I had a CEO client whose company had a unicorn valuation and was entering a critical moment of growth. My client, who hadn’t taken a day off in six years, was running on fumes. To give him space to step back and see the future more clearly, I encouraged him to get out of his office and take a long weekend—a thinking retreat. Thinking retreats are a habit of every single high-impact leader I've ever worked for and with. - Bill Gates’s "think weeks" are now folklore at Microsoft. Twice a year, he would identify some big questions and retreat solo with a curated reading list. These sessions helped shape Microsoft’s internet strategy, cybersecurity pivots, and product vision. - Jeff Bezos credits his quarterly thinking retreats with generating ideas like Amazon Web Services (AWS) and Prime, which became key strategic initiatives. - Eric Schmidt, former Google CEO, used travel downtime to reframe challenges and unlock insight. He described it as “pulling up above the trees to finally see the forest.” The common thread here: Creating time for reflection isn’t a break from leadership. It’s core to it. Time away from routine boosts divergent thinking, the foundation of creativity and strategic insight. And research has found that leaders who take vacations are 30% more productive and make significantly better decisions when they return. Once you find the time for a thinking retreat, how can you ensure you’re using it wisely? The CEO I was coaching called me on his first day off in a full panic asking: "How will I know if I'm doing this right?" He was not the first, nor the last, leader to ask for this guidance. I recommend my clients channel what psychologist Graham Wallas identified as the four-stage creative process: 1- Preparation: Before your thinking retreat, set a clear intention. What problem do you want to solve? Be as specific as possible. 2- Incubation: Deliberately set aside time to allow your mind to wander in new and inspiring environments. Don't force anything. 3- Illumination: Seize on the aha moments that emerged during the incubation phase and capture your thoughts in a notebook. Don’t edit—simply write down your unfiltered ideas. 4- Verification: When you return home, synthesize your top ideas. What are the connective ideas or insights that can inspire new action? Share at least one actionable insight with your leadership team and commit to revisiting your notebook regularly to glean more. I've seen incredible insights result from this seemingly simple process! I'd love to hear your aha moments that result! Please share them here. (Above is a shortened version of my post last week for Harvard Business School "Executive Agenda" newsletter in collaboration with Adi Ignatius. Subscribe at HBR for the full version and essential leadership content delivered weekly to your inbox!)

A lot of leadership development arrives too late. By the time people get access to serious coaching, reflective space, or good developmental design, they are senior enough to have learned the hard way. They have absorbed the habits, compromises, over-functioning, and secret self-betrayals that complex work tends to reward. The people who often need the space earlier are precisely the ones least likely to get it. Early-career professionals. New managers. High-potential contributors. People carrying more complexity than their title admits. People not yet “senior enough” for executive development, but already old enough in the system to be shaped by it. That is why I have a lot of time for what the PaperFrame7 team are building. I joined their Founding Edition retreat and was impressed by the seriousness of the design. Perhaps cynically, I had been half-expecting wellness theatre. It wasn't that at all. Nor was it another beautifully photographed escape from work, where the inbox waits patiently at the airport for your return. The aspproach is sharper and larger. Seven days of slowing down. Separating facts from stories. Testing possible futures. Turning reflection into a concrete plan. They also iterate. BAsed on the feedback from the Founding Edition, the next version of their program has become more structurally intelligent. It helps participants ask a deceptively important question: Where does the friction actually live? It then pushes them to reflect: - Is this a self question? - Is it a role question? - Is it a system question? Not every struggle should be turned into a personal growth project. Sometimes the answer is not “reframe yourself.” Sometimes it is redesign the role, renegotiate the work, change the context, or recognise that the system is asking too much from you at too little cost to itself. They approach the digital revolution in a way that moves beyond “screen addiction” or doom-scrolling. For many people, the screen is a small part fo the problem. Tthe deeper issue is that the phone has become a work anchor. It keeps them permanently reachable, even when they have physically left the workplace. The anxiety that accompanies that is palpable. Most importantly, they balance the opprtunity for solitary reflection with a social mirror in the retreat. This offers vital opprtunities for peer reflection that helps people recognise that some things they are interpreting as “personal failures” are actually shared conditions taht they are coping with far bettere than they might have previously thought. I’m sharing this because I think there is a real gap here. Many people are crying out for a properly designed space to pause, think, name what is happening, and make better choices before the system quietly trains them out of themselves. PaperFrame·7 is doing that work with care. Worth a look if you, your team, or someone you care about is carrying more than their title can explain. Photos all from the retreat location.

🎯 Thinking About Hosting a Retreat? Here’s What Smart Planners Do Differently (with real-world examples + proven ROI). In Part One, we explored what actually matters when planning a corporate or influencer retreat. Now let’s go deeper. Because when done right, a retreat isn’t just “a cool experience.” 👉 It’s a high-ROI move for team performance, brand growth, and strategic alignment. ✅ 1. Start with Purpose, Not a Location Don’t ask: “Where should we go?” Ask: “What do I want attendees to feel, learn, or change?” Harvard Business Review found that retreats with a clear learning or connection goal deliver a 26% boost in team alignment. 🧠 2. Design for Experience, Not Just Aesthetics People don’t remember the venue—they remember the transformation. ✔️ Small group discussions ✔️ Wellness sessions ✔️ Unstructured time for creativity ✔️ Hands-on learning and team building Memory retention increases by 65% when tied to emotional or experiential learning. (Forbes Council) 🔍 3. Real-World Examples of Smart Retreats 🎧 Spotify’s “Band Retreats” Global teams meet for strategy, wellness, and connection Focus: psychological safety, creativity, and human-first design Result: +21% employee satisfaction, +18% collaboration (Spotify Internal Data) “When people gather intentionally, it amplifies trust, clarity, and creativity.” —Katarina Berg, CHRO, Spotify 🛠️ Shopify’s Remote Retreats Built for remote team alignment Prioritize workshops + personal connection Improved internal communication + post-retreat performance metrics 🌿 Create & Cultivate Retreats (Influencer & Entrepreneur-Focused) Wellness + strategy + brand activations Highly curated, Instagrammable—but never superficial Result: High attendee engagement + strong brand partnerships 💸 4. Budget Smarter, Not Bigger You don’t need a 5-star resort to impress. Some of the most impactful retreats happen at: Boutique villas during shoulder season Unique Airbnb estates with indoor/outdoor flow Local offsites with intentional programming Brands save up to 50% on retreat costs by choosing location-flexible formats—without sacrificing comfort or vibe. 📸 5. Make It Shareable (Without Forcing It) Design scenic, relaxed moments that naturally invite content creation. People share what makes them feel seen, inspired, or connected—not what feels overly curated. Brands that prioritize organic experiences get 50% more social shares (Sprout Social) 💬 Ready to Plan One That Works? 📩 DM me and let’s make your retreat both meaningful and smart.