Strategic planning is a pivotal process for organizations seeking to evolve their mission and achieve long-term goals.
Recently, FarWell facilitated a collaborative strategic planning session for a Madison-based organization aiming to develop a new 2–3-year roadmap to support its evolving mission and mark a significant organizational milestone. The goal was not simply to generate ideas, but to help a diverse group of stakeholders align on priorities and translate strategic intent into a clear, actionable path forward.
Navigating Diverse Perspectives
The session brought together almost 20 participants—board members and employees—each with unique roles, perspectives, and power dynamics. Employees tended to be more reserved, while board members approached discussions from a strategic standpoint. Although board members often hold decision-making authority in their professional roles, this session was designed to be purely collaborative.
Managing Time Constraints
With only seven hours available, the challenge was to align a large and diverse group on priorities, generate ideas, and build a strategic roadmap. Such a compressed schedule required efficient facilitation to ensure all voices were heard and key topics were thoroughly addressed.
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With limited time and a lot to accomplish, we used a visual example of what we aimed to complete by the end of the day. It illustrated the level of detail we were looking for and helped everyone quickly understand the expectations. As we began building the roadmap, we kept the visual displayed so the team could reference it and use it as a template.
Addressing Risks and Constraints
Strategic planning must balance bold, forward-looking initiatives with realistic constraints and macro-level risks. The session required clarity about the future, while also acknowledging uncertainties that could impact what was achievable.
FarWell’s Approach: Structured and Inclusive Collaboration
To maximize engagement and effectiveness, FarWell conducted a pre-session survey to gather input on key topics, sharing a summary as a pre-read to ensure every perspective shaped the agenda. During the session, structured breakout groups encouraged balanced participation, creating space for all voices and fostering a collaborative environment.
By the conclusion of the session, we had identified two to three high impact strategies and initiatives to drive sustained growth over the next two to three years. We also co created a clear, actionable timeline and calendar to guide execution moving forward.
Key Takeaways for Organizations
There are a few things that we feel are important to understand as organizations head into Strategic Planning:
- Preparation is essential: Pre-session surveys and agenda sharing promote inclusivity and focus.
- Structure drives engagement: Breakout groups and clear facilitation techniques help balance power dynamics and encourage participation.
- Realism leads to actionable plans: Addressing risks and constraints upfront ensures strategic plans are both bold and achievable.
By combining thoughtful preparation with structured collaboration, organizations can transform strategic planning sessions into powerful catalysts for future success.
Ready to elevate your organization’s strategic planning?
Connect with FarWell to learn how expert facilitation and proven frameworks can help your team build a roadmap for lasting impact. Start your journey from strategy to execution today!



