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As we approach year-end, it's time to talk about a powerful tools for any business owner:

The Annual Offsite

Today, I’m breaking down the essentials of planning an offsite that sets your team up for a strong, aligned year. From getting the right people in the room to nailing the agenda, a well run and intentional offsite sharpens focus and helps you drive results.

Let’s dive into how to nail your annual planning.

In Today’s Post

• 🚨 Tomorrow: An AMA with Brent Beshore of Permanent Equity

• 🏆 Nail Your Annual Planning Offsite: A Playbook for Success

• 📆 Upcoming Events

• ⏰ In Case You Missed It

With the end of the year in sight, it’s time to start thinking about annual planning.

This is your opportunity to step back, reflect on what’s worked (and what hasn’t), and set a sharp vision for 2025. It’s about getting the most out of your team — and giving them a clear path forward.

Annual planning allows you to take stock of your business and decide where you’re headed next. It’s a chance to zoom out, see the big picture, and make the strategic decisions that will shape the coming year — and beyond. Done right, it brings clarity, focus, and direction to your team.

For us, annual planning boils down to three essential components:

1. The Plan: Revising your strategy based on your mission, vision, and past performance. What are your goals for the year ahead, and what adjustments need to be made?

2. The Budget: How will you fund this plan and meet your financial goals? Budgeting ensures resources are allocated where they’ll make the biggest impact.

3. The KPIs: What key performance indicators will track your progress? KPIs help you monitor execution, know when to pivot, and determine where to double down.

An effective offsite ties these elements together.

It’s where you align your team around the plan, budget, and KPIs — ensuring everyone understands where you’re headed, how you’ll get there, and how you’ll measure success.

Why Offsites Are Essential

Offsites aren’t just fancy meetings in nice locations.

They’re a critical part of the planning process. Offsites allow your leadership team to step away from daily operations and have the deep, strategic conversations that are often hard to fit into a typical workday.

When done right, offsites are powerful tools for alignment and strategy.

I learned this the hard way early in my career. My first offsite at a startup had no real agenda — I thought time and space would be enough to get us on the same page. Instead, it turned into a mess of unfocused discussions, and we left with more questions than answers.

Since then, I’ve realized that successful offsites are all about balance — structure where it matters, and flexibility to let the best ideas emerge.

The Core Goals of an Offsite

1. Alignment: Your team should leave the offsite aligned on the company’s direction and their role in it. Everyone needs to be on the same page about where the business is headed and how they’ll contribute.

2. Clear Next Steps: Discussions are valuable, but they need to translate into action. Make sure there’s a clear action plan with ownership for every key initiative.

3. Trust & Connection: Offsites build trust. When your team understands each other — how they think, work, and what drives them — it improves collaboration. Strong trust leads to faster, more effective execution.

Offsite Logistics

• When to Do It

  The end of the year is a natural time to hold an offsite, but any time you need to recalibrate or pivot is a great opportunity. Choose a time when your team can focus without distractions, avoiding peak busy periods.

• Where to Do It

  Get out of the office. The environment plays a huge role in how your team engages. It doesn’t need to be extravagant — even a nearby retreat can open up new thinking. The key is finding a place where your team won’t be interrupted and can focus.

• Who Should Be There

  Keep the group small and focused. Your leadership team and key decision-makers should be at the table. This isn’t a company-wide event. You want people who can make decisions and drive action. Too many voices can dilute the conversation.

• How Much to Spend

  Offsites don’t have to be lavish. While it’s tempting to plan an extravagant getaway, it’s not essential. Focus on creating the right environment for meaningful conversation. Save the big splurges for when the company has had a standout year.

Balancing Structure & Flexibility

The key to a great offsite is balance. You need structure to ensure the essential topics are covered, but you also need flexibility to let organic, valuable discussions happen.

• Structured Sessions:

  These are for the critical discussions. What’s the long-term vision? What worked this year? What didn’t? Have a clear agenda to guide these sessions, so nothing important slips through the cracks.

• Unstructured Time:

  This is where the magic often happens. The dinner after a day’s session, a casual hike, or a relaxed chat around a fire. These moments build trust, spark new ideas, and strengthen the team’s bond. Make room for them.

Sample Offsite Agenda

Pre-Work

• An offsite isn’t where planning starts — it’s where everything comes together.

  The pre-work sets the stage: share key reports, provide pre-reading to focus thinking, and set clear expectations so everyone arrives prepared. This groundwork ensures your offsite is strategic, efficient, and productive.

Day 1: Reflect & Analyze

• Morning: Arrival, Breakfast & Welcome Session

  Casual start with an overview of the offsite’s goals and agenda.

• Midday: Performance Review & Data Analysis

  Deep dive into last year’s performance, focusing on key metrics, trends, and insights. Assess current KPIs to identify necessary adjustments.

• Afternoon: SWOT Analysis & Department Breakouts

  Break into teams to conduct a SWOT analysis. Regroup to share findings and pinpoint common themes.

• Evening: Group Dinner with Structured Conversation

  Host a dinner with guided prompts like “What surprised you most this year?” to encourage open dialogue.

Day 2: Vision, Strategy & Collaboration

• Morning: Long-Term Vision & Strategic Planning

  Revisit the company’s mission, vision, and 10-year goals. Focus on strategic priorities for the next year.

• Midday: Strategy Workshops on Key Initiatives

  Break into teams to develop strategies around 3-5 key initiatives, informed by Day 1 insights.

• Afternoon: Cross-Functional Collaboration Sessions

  Mix people from different departments to identify areas for synergy and improved collaboration.

• Evening: Team Dinner & Open Conversations

  Relaxed setting for open conversation, reflection, and building deeper connections.

Day 3: Action Planning & Next Steps

• Morning: Action Plan & Accountability Session

  Create a clear roadmap for the year. Assign owners, actions, and deadlines for each initiative.

• Midday: Setting Future KPIs & Performance Metrics

  Define KPIs for the year, ensuring each initiative has clear metrics. Discuss ongoing performance tracking.

• Afternoon: Wrap-Up & Key Takeaways

  Summarize key outcomes, set follow-up actions, and outline how results will be communicated.

• Late Afternoon: Departures

Decada’s Approach to Annual Planning

At Decada, annual planning is more than a routine — it’s how we set the foundation for the year ahead. It’s a holistic approach, looking beyond budgets to assess where we’ve been, where we’re going, and how to get there.

Our process kicks off each September, as operators of each of our companies draft their preliminary plans for the upcoming year. It’s a collaborative effort, ensuring each operator’s vision aligns with Decada’s broader goals.

From initial drafts to final approvals, our planning unfolds across several key phases. Each stage sharpens strategies, builds clarity, and aligns the team.

Initial Planning Phase (September): Operators draft a preliminary plan outlining strategy, budget, KPIs, and goals. This phase lays the groundwork, helping us see upcoming opportunities and challenges.

Review & Refinement (October): Decada’s leadership reviews and refines these plans, offering feedback and adjustments. It’s not just about numbers — it’s a chance to discuss what’s working, what’s not, and how to improve. Performance reviews are a key part, helping us set a stronger course for the year ahead.

Strategy Offsite (November): The offsite brings everything together. It’s where we finalize direction, align on strategy, and confirm key initiatives. We reflect on the past year, discuss vision, and ensure our plans and resources are set for success.

Final Plan Approval (December): After the offsite, leadership locks in the plan, budget, and KPIs. Every detail is approved, and tracking systems are set, ensuring smooth execution. The outcome is a clear, actionable roadmap for the new year.

Annual Kick Off Summit (January): Our planning wraps with the January kick-off, where operators present the finalized plan. It’s about energizing the team, aligning on the vision, and setting the tone for execution. Every leader leaves knowing their role and responsibilities.

Why does this process matter? Because it drives alignment and sets clear expectations. It’s about building trust, ensuring every team member is equipped, aligned, and ready to hit the ground running. Annual planning gives us the chance to reflect, strategize, and prepare to execute seamlessly.

10 Final Tips to Nail Your Offsite

1. Get Out of the Office: Even if you stay local, a new environment gets the team thinking differently. It helps shake off the day-to-day mindset and opens space for new ideas.

2. Location Matters: Tie the location to performance. If the team crushed it this year, reward them with a cool spot. If not, maybe keep it closer to home. The setting can set the tone.

3. Details Matter: Don’t skimp on food or wine. Print the agendas. Make it feel structured but enjoyable. The little details make a big difference and make the team feel valued.

4. Assign Pre-Work: Send some pre-reading or reflection questions. It helps everyone show up prepared to contribute meaningfully from the start.

5. Be Intentional About Structure: Have a clear agenda to cover the big topics, but also leave flexibility to pivot if needed. A balance of structure and adaptability keeps things flowing.

6. Prioritize Trust-Building: Encourage vulnerability. Open, honest conversations build trust, and strong trust strengthens collaboration and alignment.

7. Incorporate Fun: Build in some team-building activities. A hike or casual dinner is a great way to build connections outside the boardroom.

8. Use a “Parking Lot”: Create a “parking lot” for off-topic issues that come up. It keeps the conversation focused without dismissing important topics that can be revisited later.

9. Wrap with Accountability: Ensure every attendee leaves knowing their responsibilities for the year. Clarity is key to execution, and accountability turns plans into action.

10. Follow Up: After the offsite, send a summary and action plan. Keeping the momentum going is critical to success. Don’t let the energy from the offsite fade away.

Final Thoughts

Annual planning is more than just a yearly routine — it’s the foundation for everything your business will accomplish next year. A well-executed offsite makes it easier to align, focus, and connect without the daily distractions.

It’s about more than goals and budgets. It’s making sure your team understands the mission, knows what they’re working toward, and trusts each other to get it done.

If you’re new to offsites, start simple. Focus on a few elements to improve your planning — use a “parking lot” to keep discussions on track, or schedule more open-ended conversations.

And remember, you don’t need to wait for the end of the year. Offsites are just as powerful when there

⏰ In Case You Missed It

Earlier this year, I kicked off The Leadership Series: An Operator’s Guide on Local Legends.

This series is my way of sharing what I’ve learned about the qualities that make or break a great leader — the kind of lessons I wish I’d had earlier in my career. So far in this series, I’ve covered two essential topics:

In this kickoff post, I dig into why strong leadership is the backbone of any enduring business and what separates the greats from the rest.

The best leaders focus on what truly matters. This post explores how to prioritize with purpose, staying out of the weeds and keeping the team focused on what counts.

More is on the way as we dive into critical topics like decision-making, culture, and resilience. This series is for operators aiming to sharpen their skills and build something lasting.