Team Retreat Itinerary Planning

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?

I spoke with the new CEO of a national non-profit who was kicking off their first major strategic planning cycle. They're a smart, inspiring leader who has inherited a strong organization. But they're feeling the weight of needing to put their stamp on things while not breaking what already works. Here's some of what I've learned about strategic planning over the years. - Most leaders already have a prior strategy to learn from, a planning rhythm, and deep institutional knowledge. The work is usually about sharpening direction and focus, not reinventing the organization. - The leverage comes from looking at three things in parallel. What's already working and deserves to be strengthened. What's stuck or not landing despite real effort. And what partners, customers, or communities keep asking for that you're not yet built to do. Those signals point more clearly to the future than any blank-page brainstorm. - Frame your work in terms of causes and consequences. Upstream: what structural forces create the problem you exist to solve? Downstream: what happens to real people if it stays unsolved? Organizations waste months debating whether to own a solution they should obviously partner on, simply because they hadn't mapped this clearly. - Strategies that last do three things at once. They make the core excellent enough that you can stop worrying about it. They build what's coming around the corner. And they protect space for experiments that could shift the system if they work. - Process matters as much as content. Good work starts in small, honest conversations, not big workshops. Input processes typically over-index on the usual voices. Intentionally seek partners who want more from you but aren't getting it, frontline staff who see daily friction, and people at the edges of your work who see things core staff might miss. The real strategic insights often sit in conversations you haven't been having. - Synthesize first in a small group (then use AI to summarize). Use larger sessions with staff and board to validate alignment, surface the few real trade-offs needing decisions, and turn priorities into concrete initiatives. - Strategic planning surfaces anxiety about what we're not doing well. That discomfort is the work, not a sign you're doing it wrong. - The best strategies are memorable enough that people can recite the priorities without opening the deck. If your plan doesn't make it easier for someone on the front line to answer "What matters most this year?" you're not done yet. - Strategic planning is talent assessment in disguise. How people show up in strategic work tells you who can think at system level and who excels in focused execution. Who asks about trade-offs versus who defends their turf. Who can hold paradox versus who needs binary choices. To everyone kicking off strategic planning: may your core become excellent enough to run itself, your experiments be bold, and your trade-offs be explicit rather than accidental.

Last week I had the opportunity to lead a strategic planning session at a law firm retreat. Using our Commercial Maturity Matrix, we structured a candid conversation around several key issues, including billing confidence, cross-selling, succession planning, AI, generational differences, and expansion. I am seeing these same themes surface across many firms right now. A few observations stood out: • Client feedback shaped the dialogue in a meaningful way. Many lawyers were genuinely surprised, both by the positive praise and the constructive themes. External perspective has a way of cutting through internal assumptions. • Like many firms, this one was simultaneously optimistic and uncertain. There is confidence about the future, paired with real questions about what that future will look like. That tension is healthy. It signals awareness and a willingness to confront change rather than ignore it. • When given space to reflect, partners did not always gravitate toward the issues leadership expected. Priorities did not align neatly with tenure, practice group, or personality. In the right environment, people reveal what actually matters to them. • An important theme emerged around billing confidence. Partners are exceptional at negotiating on behalf of clients. They are less comfortable negotiating fees with those same clients. The gap is not tactical. It is psychological. • Associates were grateful to be included and added real value. They were especially engaged around talent development and technology strategy. Inclusion signals seriousness about the future. Strategic planning only works when firms are willing to have an honest dialogue, and hear what they did not expect to hear. The five year strategic plan is no longer a strategy. The firms that will thrive over the next decade will operate in tighter strategic cadences, regularly confronting uncomfortable truths as markets, clients, and technology evolve. What key themes are emerging from your strategic discussions so far this year?

A sexy location won't save a bad offsite. BUT a clear "why" will. Most team offsites fail before anyone walks in the room. They might have a strong agenda, and even a scenic venue. But where leaders trip up is by treating offsites like just another (very long) meeting. Great offsites don't happen by accident. They require clear purpose, intentional preparation, and smart follow-through. Here's how to lead an offsite that actually has a lasting impact: 1️⃣ Know the purpose: ↳ Every great offsite does three things ⬇️ 1 - Resets the vision 2 - Strengthens trust and alignment. 3 - Leaves people with energy, ownership, and clear next steps. If you're not clear on the goal of the retreat, you won't be successful. 2️⃣ Be prepared: ↳ Before anyone arrives, get clear about the kind of experience you want to create. Mindset Check: • Who do I need to be? • How do I need to behave? • What do I need to believe? Preparation Game Plan: • Define why you're meeting and ideal outcomes. • Share your thoughts early so people are ready to contribute. • Build an agenda with time to think, talk, and make decisions. • Make sure the agenda includes everyone. • Handle logistics so everyone can focus on the work. 3️⃣ Facilitate for impact: ↳ Your job is to create a space for problem-solving and decision-making. Not to tell people what needs to be done.   → Track the group's energy and pace. → Make room for everyone to speak. → Encourage respectful, honest discussion. → Stay steady when things get tense. → End each session with clear decisions or agreement. 4️⃣ Post retreat, make the effects last: ↳ This is where the offsite earns its value. → Share a short recap within 48 hours. → Turn key points into specific actions or goals. → Hold a follow-up meeting within two weeks to check progress. → Keep themes visible in team meetings and updates. → Recognize what's already improving. 5️⃣ Common pitfalls: ↳ Avoid the traps that make an offsite feel like another meeting. ❌ Too packed: No time to breathe or talk. ❌ No real purpose: Everyone's busy, but no one knows why. ❌ Avoiding conflict: Skipping the hard but necessary conversations. ❌ No follow-up: Big energy in the room, then nothing happens. When you get your offsite right, your team will walk away with clarity, motivation, and enthusiasm about their work. If you're planning how to make your offsites and leadership more effective, my 2-minute quiz will help you assess what your team needs from you: bit.ly/ExecutiveQuiz What do you think is most important when it comes to offsites? ➕ For daily advice on business and leadership, follow Ben Sands. ♻️ Repost this to help other leaders you know.

I led a $350M org through a strategic planning session - after just 2 hrs the CEO called it a "walk-off home run". Here's my exact framework for creating rapid alignment and vision: 1. The Trust Foundation (20 mins) First, let the room breathe. Watch. Listen. Then, ask each leader to share one childhood challenge they overcame. Why? Because vulnerability creates humanity, and humanity creates trust. When someone shares about their parents' divorce or getting cut from a team, defenses drop naturally. 2. The Vision Journey (30 mins) Create space for deep thinking: - Dim the lights - Play soft instrumental music (I use Dwell on Spotify) - Guide them through a day-in-the-life meditation set 5 years in the future Pro tip: Most leadership teams spend 95% of their time in the daily battle. Few step back to truly envision the future. At $350M scale, this vision gap costs millions. 3. Personal Expression (60 mins) Transform thoughts into tangible vision: - Silent journaling period - Create visual representations on flip charts - Share personal stories of their envisioned future 4. Collective Alignment (10 mins) Bring it home: - Synthesize individual visions - Craft collective bullet points - Write a unified vision paragraph - - - By the end, the team didn’t just have a vision. They had their vision, one that was personal, connected, and inspiring. For the first time, the company’s future wasn’t just a business strategy. It was a shared journey everyone felt deeply invested in. 🔑 The Magic Ingredient: It's not just about the business vision. By connecting personal futures with company direction, you create authentic alignment that drives real change. 💡 Key Learning: Most strategic planning fails because it jumps straight to strategy. But vision without trust is just words on a page. Trust without vision is just a nice conversation. Magic happens when you build both!

"We need a retreat!" I hear this all the time from the teams I work with—and especially now as we head into the end of the year when organizations start looking back and looking forward. December and January feel very "retreaty" times for a lot of organizations. But here's what I've learned: sometimes what looks like a retreat need is actually just a focus problem. In this week's Facilitation Fundamentals post, I'm sharing how I help organizations decide between retreats and extended "deep dive" meetings—because they serve very different purposes. I recommend a retreat when we need to: 🎯 Think bigger about mission, vision, or strategic direction 🌟 Honor significant transitions 🤝🏾 Rebuild relationships and team dynamics I suggest an extended meeting when we need to: 🔎 Go deep on one specific topic 🏁 Finally finish that stalled project ✅ Create a concrete deliverable without day-to-day distractions Last year, I worked with a library leadership team that was functioning fine operationally but was weighed down with fatigue. They hadn't checked in with each other in over a year, were finishing a major capital project, and key leaders were transitioning out. They needed a retreat. Recently, I facilitated an extended meeting for a board that needed to clarify their conflict of interest policy and board member expectations. In 2.5 focused hours, we created new documents for both and updated their meeting calendar. A retreat would have been overkill—they just needed dedicated time. The difference? Retreats require 4+ hours (often 1-3 days) and work well offsite. Extended meetings are 2-3 hours max and can happen anywhere—as long as we protect that time from routine updates and distractions. I've included a decision tree in the full post to help you choose the right format for your next gathering. What's your experience? Have you ever planned a retreat when an extended meeting would have done the trick—or vice versa? Read more: https://lnkd.in/gtXRxXmX #FacilitationFundamentals #NonprofitLeadership #StrategicPlanning #TeamDevelopment #BoardDevelopment

Dear Office of the CEO: a bad C-suite retreat can cost you upwards of $100,000 in wasted time, poor decisions and leadership distrust. Here are 7 steps to plan, design and execute highly engaging leadership retreats for your C-suite: 𝟭. 𝗦𝗲𝘁 𝗰𝗹𝗲𝗮𝗿 𝗴𝗼𝗮𝗹𝘀 Set clear retreat goals and expectations to make sure you are getting maximum value out of high stakes retreats. For example, are you looking for better team collaboration or improved strategy? 𝟮. 𝗜𝗱𝗲𝗻𝘁𝗶𝗳𝘆 𝘀𝘁𝗮𝗸𝗲𝗵𝗼𝗹𝗱𝗲𝗿𝘀 Reduce the amount of stakeholders to keep the retreat at an intimate level. Consider inviting star performers or external advisors for guest appearances on focused topics like increasing emotional intelligence or incorporating AI into the workplace. 𝟯. 𝗖𝗼𝗺𝗽𝗹𝗲𝘁𝗲 𝗹𝗼𝗴𝗶𝘀𝘁𝗶𝗰𝘀 Assess your C-suite team’s preferences on retreat location and lodging. Make sure to book the venue and secure travel plans months in advance. You do not want to scramble the week before. 𝟰. 𝗖𝗿𝗲𝗮𝘁𝗲 𝗮 𝗺𝗮𝘀𝘁𝗲𝗿 𝘀𝗰𝗵𝗲𝗱𝘂𝗹𝗲 Source session ideas from your C-suite team. Create a master schedule with agendas and session goals. Break up intense working sessions with team bonding sessions, meals and special activities. If you do too many back to back workshops, your C-suite team might doze off. 𝟱. 𝗙𝗮𝗰𝗶𝗹𝗶𝘁𝗮𝘁𝗲 𝘀𝗲𝘀𝘀𝗶𝗼𝗻𝘀 Appoint a trusted facilitator or hire one to help you run these high stakes retreats. If not, assign meeting minutes and action tracking to your Chief of Staff or Executive Assistant. 𝟲. 𝗖𝗼𝗺𝗽𝗹𝗲𝘁𝗲 𝗳𝗼𝗹𝗹𝗼𝘄 𝘂𝗽 After the retreat has concluded, send a copy of all notes and actions to the group, as well as a  feedback survey. Your Chief of Staff or the Executive Assistant can follow up with individual C-suite leaders for complete accountability. 𝟳. 𝗥𝗲𝗽𝗼𝗿𝘁 𝗼𝘂𝘁𝗰𝗼𝗺𝗲𝘀 Did you hit your retreat goals? Share the results of your retreats with your C-suite team and selectively share headlines with your entire company. Make adjustments as necessary for future retreats. That’s it. Follow these 7 steps to deliver amazing retreats that boost C-suite collaboration and improve company strategy. === Like this post if it will help you plan and execute amazing C-suite retreats. Comment below with other leadership retreat best practices that you've used. Follow me, Mackenzie Lee, for more Office of the CEO content and an upcoming, industry-defining Office of the CEO Playbook.

40 people walked into a room with 40 different versions of the future in their heads. By the end of the day, they were building one. This month I facilitated a Vision and Growth Planning Summit for Westside Waldorf School. The morning opened with 40 voices. By afternoon, a working group of 20 got into the specifics. The day closed with a two-hour board session where decisions got made. The group got smaller as the work got sharper. By design. What made it work? Here's what I've learned, and what you can steal for your next strategy and planning session. 1. Listen before you enter the room. Stakeholder conversations are where the real agenda gets built. Depending on the project, that might mean a few weeks of conversations or several months. Talk to the decision-makers and the people closest to the work. 2. Co-design the session with the key leaders. Collaborate on the structure, the flow, the goals. It takes more time and iteration, it's almost always more effective. When leaders help shape the day, they show up as champions, not just participants. 3. Invite people to state their intention. There's science behind this. Set the context first: the vision, the stakes, what this day is for. Invite each person to share their intention. It shifts the room from a group of individuals into a community with shared purpose. Every time. 4. Name the common ground before you explore the differences. Surface the shared goals first. Name them. Let the group refine them. When people know what they agree on, they can disagree productively on everything else. 5. Create a home for every idea, issue, offer, and ask. Designate space on the wall for the key themes. Direct people to write and post. The quiet thinkers and the big talkers contribute in roughly equal measure. Nothing gets lost. The room stays on track. 6. Don't leave without next steps. A beautiful conversation that ends without clarity is a missed opportunity. Use dot voting, round-robins, or ranked choices. Build the action plan together, in the room, before anyone leaves. 7. Communicate out, or the good ideas die. Two things need to happen. First, a warm message back to all participants capturing the highlights. This isn't just documentation. It's fuel. It keeps momentum alive. Second, a full report to key leaders: the specific ideas generated, the priorities surfaced, the action steps, the 90-day plan. Together, they help turn a great day into a lasting shift. I'm so fortunate to get to work with committed, intentional, inspired leaders like Evan Horowitz and Anjum Mir. Strategy and planning sessions are one of the highest-leverage investments a leader can make. Done well, they don't just create a roadmap. They create belief in the vision, in each other, in what's possible. If you're preparing for a planning retreat, a leadership summit, or an organizational pivot and want to think through your approach, let's connect. #StrategicPlanning #Leadership #OrganizationalTransformation

Please, do us all a favor: Do NOT start your next leadership offsite with strategy. You're putting limitations in front of your Ambition. Which is fine if you want to limit your Ambition. Just back in the office after a couple of weeks on the road. But the teams I was working with made the same mistakes - across industries and geographies. When we bring a leadership team together to reset and accelerate their performance (for each client we will do this two to three times a year), I tell teams I do not want to hear a single word about strategy for the first two days. I know: This probably sounds completely counter to conventional wisdom and what you're doing during your leadership "offsites" or "retreats" - or whatever you call them. But here is the reality: if you lead with strategy, it instantly becomes a filtering function. The moment you open the slide deck, the conversation devolves into constraints: "We don't have the resources," "We don't have the market share," or "We don't have the time." Organizations will invest millions (hard dollars and time) in strategic planning while entirely lacking the conviction to execute it, the audacity to depart from convention, and the energy to pull others along. So, before you figure out how you are going to get there, you have to build absolute, unwavering Conviction about where you are going. Conviction is the non-negotiable foundation. To build that conviction, you have to do the hard work first: ★ Deliberately create the conditions for genuine conversations: You have to build the team chemistry where individuals can be honest and call out the elephants in the room. ★ Avoid the "Goldilocks" trap: Without honest dialogue, you end up with superficial conversations. You settle for the strategy that feels "just right"—safe, incremental, and comfortable. But safe doesn't move the needle. You think your competitors are sitting around having "safe" conversations? Your business needs something bolder. ★ Be kind, not nice: I hear it constantly in executive coaching: "My team isn't moving at the pace I want." You have to find the courage to say the hard things. Avoiding decisive action because you want to be a "nice boss" is actually cruel. Being decisive (even when uncomfortable) is kind because it provides clarity and enables high performance. Make it about the problem, not the person. No one wants another strategy deck. No one wants to sit through another offsite that just talks about strategy. ⚡️They want to talk about where you are going. ⚡️They want a destination that matters. Build that conviction deeply first - because that is what will actually propel you forward. The bigger thinking. The unconstrained imagining. The strategy to get there will follow. Cheers. ~~~ 🤝 Hi, I'm Russell  ★ I work with teams to get ambitious results at speed. ★ Connect with me, follow me, let's meet. The Ambition Company

🎯 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.