Want Your Retreat to Succeed? Here’s a Winning Retreat Planning Strategy
- Dorien Morin-van Dam
- Jul 11
- 3 min read
What makes a retreat not only memorable, but so impactful that attendees are asking about your next one before they even leave?
On a recent episode of Strategy Talks, I had the pleasure of speaking with Sara Munro, event planner and retreat strategist, about what it really takes to host a successful in-person retreat. Sara, who has decades of experience planning retreats, conferences, and professional development programs, shared practical advice to help business owners and entrepreneurs create retreats that deliver real value and lasting connections.
Whether you’re thinking about your first retreat or want to improve an existing event, this conversation is packed with insights on building a retreat planning strategy that works.
Why Small Retreats Are Gaining Popularity
I opened our discussion by asking Sara why so many entrepreneurs are shifting from large conferences to small retreats. Sara shared:
“People want a deeper experience. Smaller, intimate spaces let you dive deeper, build connections, and offer clear, actionable takeaways. Big conferences can’t always do that.”
The shift is also driven by how we connect today. Many of us spend hours on Zoom or attending virtual events. In-person retreats offer what virtual meetings can’t—shared meals, side conversations, and that human connection we’ve all missed.
Build Your Retreat Planning Strategy From the Ground Up
Sara and I agreed that successful retreats don’t happen by accident. A smart retreat planning strategy starts with these essentials:
Visualize the attendee experience — From the moment someone registers to the time they leave, map out their journey. Consider parking, welcome materials, and how they will feel entering the space.
Think about user experience, not just logistics — How will you make attendees feel comfortable physically and emotionally? Sara emphasized thinking about everything from seating arrangements to how emails are answered before the event.
Leave space to breathe — Sara recommends trimming at least 20 percent from your planned agenda. Adults need breaks, time to process, and moments for side conversations.
Set expectations and agreements — Early on, define group agreements around sharing time, confidentiality, and participation. This helps create psychological safety and ensures all voices are heard.
How to Prepare Attendees for the Right Mindset
A strong retreat planning strategy includes getting people ready before they arrive. This means:
Providing pre-event materials or sessions to set the stage.
Offering clear instructions on what to bring, what to wear, and how to prepare mentally.
Encouraging attendees to think about their goals and what they want from the experience.
As I noted during our conversation, these steps help participants arrive with a sense of ownership and peace of mind, ready to engage fully.
Fostering Connection and Avoiding Pitfalls
Sara shared several tips for keeping your retreat inclusive and engaging:
Use team-building tools — Start with group agreements to help everyone feel safe and included.
Design activities that encourage sharing — Icebreakers, small group discussions, and even walks or creative activities help build bonds.
Watch out for cliques or dominant voices — Be ready to guide conversations, invite quieter voices to share, and gently redirect when needed.
Sara pointed out that small touches, like personalized door signs or thoughtful snack choices, can create magic and make everyone feel valued.
Following Up: Making Your Retreat a Long-Term Success
Sara and I both stressed that a retreat shouldn’t end when the last session wraps. A complete retreat planning strategy includes follow-up:
Build a community where attendees can stay connected, whether through a text group, Slack, or private online forum.
Offer post-retreat workshops or check-ins to reinforce learning.
Help participants commit to next steps so they can act on what they’ve gained.
As Sara put it:
“What is your goal after the retreat? Is it one and done, or do you want an ongoing relationship? Plan for that from the start.”
Watch the live video replay here.
Smart ChatGPT Prompts for Further Exploration
“How do I create a retreat planning strategy for small business owners?”
“What are the key steps to planning a successful in-person retreat?”
“How can I design a retreat that builds community and trust?”
“What are best practices for setting group agreements at a retreat?”
“How do I handle dominant voices during a small event?”
“What are creative icebreakers for business retreats?”
“How do I structure pre-event communications for a retreat?”
“What post-retreat follow-up strategies keep attendees engaged?”
“How can I choose the perfect venue for a small retreat?”
“What tools help manage retreat logistics efficiently?”
