How to Host the Best Board Retreat Ever! Here’s Your Winning Checklist – 17 Keys to Success

Updated: Oct 25

Below is an outline of a blog I wrote for the amazing software company Qgive. They offer mobile giving, donations, peer-to-peer and much more. Plus, they are super affordable. Check them out at:

The complete blog can be found at:

Have you ever sat through a board retreat and thought, “What a waste of time!” You’re squished in a windowless room, squirming in a chair that feels like granite, and longing for the next break. Worse yet, the facilitator is boring, the content is useless, board members are texting, and the food is stale!

If you’re in the process of planning a retreat, don’t settle! It’s possible to put together an amazing day that’s engaging, meaningful, memorable, and fun. All it takes is a little planning and ingenuity. Use the following checklist to make sure you have all the essential elements in place to ensure the retreat is a resounding success.

1. Hire an Outstanding Facilitator

If you want to host a retreat that has everyone raving, “This is the best board retreat ever!” you need to hire an outstanding retreat facilitator. Bringing in someone from the outside can crack the humdrum atmosphere often found at board meetings, where the same people tend to lead and dominate conversation and the same baggage and drama deaden the mood.

The best retreat facilitators are objective, providing a fresh vibe for the day with new insights and perspectives. When scouting a facilitator, look for exceptional experience and credibility by asking yourself:

  • Have they been in the trenches? Any yahoo can get a “facilitation” certificate from an online course. You want to find a facilitator who’s walked in your shoes; someone who has a long history of building nonprofits and managing boards. These facilitators can draw on their successes and failures to provide firsthand understanding and perspective on the issues you’re facing.

  • Do they stand out? There are hundreds of facilitators out there, but to find a gem, you’ll need to rummage through a lot of gravel. Look for someone who is as passionate about improving the quality of your board as you are and has the skills and track record to make it happen. They should be inspiring and motivational and use a variety of speaking and facilitation tactics to make the day high-impact, remarkable, and fun.

  • Do they have a long list of clients and references? If yes, call some. If not, move on. You’re paying good money. The best board retreat facilitators will have dozens of clients who love them and gladly sing their praises. Do your homework, make calls, and find a facilitator who exceeds expectations.

  • Have they written books? Do they write a blog, produce tutorial videos, or host a podcast? The best facilitators are passionate about creating and sharing content to help others. A quiver of good content is a simple way to validate your facilitator’s knowledge of important topics and situations nonprofits face.

  • Do they have a professional website? If a facilitator’s website looks like a messy dorm room—run! Their site should look clean and include all the information you’re looking for: background, experience, clients, content, offerings, testimonials (written and video), process, outcomes, and fee structure.

For the complete blog, click here!

2. Find an Inspiring Venue

3. Prepare the Board

4. Unify Your Nonprofit Board

5. Include Key Staff

6. Address the Elephants

7. Discuss Fundraising

8. Learn Institutional Knowledge

9. Practice Telling Stories

10. Provide Engagement Opportunities

11. Work in Small Groups

12. Make Time for Personal Connections

13. Assign a Notetaker and Change Champion

14. Create a Theme

15. Have Fun!

16. Serve Light Food

17. Keep the Spirit Alive


In the end, the best board retreats will unite and inspire a board and key staff. They are strategic, yet practical. They are fun, yet bold. But most importantly, a meaningful and memorable retreat will leave everyone feeling motivated, passionate, and committed to making the changes necessary to take your board to the next level of performance, engagement, and impact so your mission can soar!

Looking for more resources to help you support your board? Check out the following resources:

Additional Resources:

Finding the Best Board Retreat Facilitator – 7 Things to Look For

Finding the Best Strategic Planning Facilitator – 7 Things to Look For

Tom Iselin

“Rated one of America’s 10 Best Retreat Facilitators”

First Things First

Tom Iselin has built four sector-leading nonprofits and four foundations. He’s written six books, sits on six boards, and hosts a video blog and podcast. Each year, Tom speaks to more than 5,000 nonprofit leaders at conferences across the country. He is considered a leading authority on high-performance nonprofits, and his impact on the industry has been featured on CNN, Nightline, and in Newsweek. Tom is the president of First Things First, a business specializing in board retreats, strategic planning, fundraising, and executive coaching. To relax, he loves mountain biking, hiking, skiing, tennis, and baking.

If you’re in the hunt for one of the best board retreat/board development facilitators, or one of the best strategic planning facilitators, it would be a privilege to learn more about your organization and the aspirations you hope to achieve as you work to propel your noble mission. Jot me an email to set up a meet-and-greet call.

To learn more, visit:

Author: Tom Iselin

Best Board Retreats - H3 Retreat

First Things First Homepage


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