Podcast: Get the Most from Your Next Board Retreat or Strategic Planning Session
- Tom Iselin
- Oct 24, 2023
- 3 min read
Updated: Dec 17, 2025
Get the most from your next strategic planning session
Listen in as Tom walks through a 17-point checklist of essential attributes you can use to plan an exceptional board retreat or strategic planning session.
A high-quality board retreat or planning session plays a critical role in shaping board culture, strengthening alignment, and setting the direction of the organization. These gatherings require a significant investment of time, money, and energy, so it’s essential that the day truly delivers the goods.
Unfortunately, many board members approach retreats with skepticism—or outright dread.
Why Board Members Dislike Retreats and Planning Sessions
Board retreats often get a bad reputation for good reason. Too many are poorly designed, poorly facilitated, and poorly executed.
Common complaints include:
Sessions that are boring or overly long
Speakers who drone on without engaging the group
Content that feels generic or irrelevant
Conversations that lead nowhere
Great ideas that never get implemented
When retreats miss the mark, board members leave frustrated, disengaged, and wondering why they bothered showing up.
The Difference Between a Forgettable Retreat and a High-Impact One
The most successful retreats don’t happen by accident. They are thoughtfully designed, carefully prepared, and led by a skilled facilitator who knows how to engage a room and drive meaningful outcomes.
A high-value retreat is:
Intentional in design
Relevant to the organization’s real challenges
Interactive and engaging
Focused on outcomes and implementation
Energizing, not draining
When done right, retreats can be productive and fun—and board members will talk about them long after the day ends.
Learn How to Design a Retreat That Actually Works
In the podcast “Get the Most from Your Next Strategic Planning Session and Board Retreat,” Tom shares practical tips, tactics, and insights to help you design a retreat that creates clarity, alignment, and momentum.
You’ll learn how to:
Avoid common retreat mistakes
Keep board members engaged and energized
Design a day that leads to real action
Create outcomes that don’t sit on a shelf
Takeaways
If you want a retreat that people actually look forward to—and one that produces lasting results:
Be intentional about design and facilitation
Focus on relevance, engagement, and outcomes
Choose quality over convenience
Plan for implementation, not just conversation
A well-designed retreat can transform how your board works together.
Summary
Board retreats and strategic planning sessions are too important to waste. With the right preparation, structure, and facilitation, they can strengthen board culture, sharpen strategy, and move your organization forward.
Listen to the podcast “Get the Most from Your Next Strategic Planning Session and Board Retreat” and use Tom’s 17-point checklist to create a high-impact day your board will be talking about for months.
Additional Resources:
Related Articles
Tom's Books, Podcasts, and YouTube Channel
About the Author
Tom Iselin is recognized as one of America’s leading authorities on high-performance nonprofits. He has built nine sector-leading nonprofits and two software companies, written six books, sits on multiple boards, and has been rated one of America’s Best Board Retreat and Strategic Planning Facilitators. His work on nonprofit strategy, board leadership, and culture has been featured on CNN, Nightline, and in Newsweek.
Tom is the president of First Things First, a firm specializing in board retreats, strategic planning services, fundraising strategy, and executive coaching for nonprofit CEOs.
Board Retreats & Strategic Planning
If you’re looking for a board retreat facilitator or strategic planning facilitator who has been in the trenches and understands real-world nonprofit challenges, Tom can help your board gain clarity, build alignment, and create an actionable plan that improves performance and impact. His sessions propel organizations to the next level of performance and impact . . . and they're fun!
Board Retreats and Strategic Planning Services:
858.888.2278
