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17 Best-of-the-Best tips on How to 17 Best-of-the-Best tips on How to Host the Best Board Retreat or Strategic Planning Session Ever!

Updated: Apr 25

board members attending Top Iselin's best board retreat facilitation event

17 Best-of-the-Best tips on How to Host the Best Board Retreat or Strategic Planning Session Ever!

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 ya-hoo 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 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 nonprofit’s 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.

2. Find an Inspiring Venue

If you operate a hunger relief organization, hosting a retreat there could provide inspiring reminders of why everyone is passionate about the mission. But offsite venues can be powerful too. They can provide beautiful and neutral settings: A retreat center with lake views, a boutique hotel with city views, or a country club. Look for a venue that’s roomy with windows and has additional space for small group work. If the venue has outdoor access for team-building exercises, group work, and breaks, that’s even better. Budget is always a factor, so tap into your board; they might have a connection to secure the perfect spot.

3. Prepare the Board

The last thing you want to do at a retreat is spend half the time reading and reviewing material. Boring! The best board retreats prepare board members before the retreat. Depending on the nature of the retreat, board members may be required to take a survey, review material, complete worksheets, read books, and take part in interview calls. They should know in advance the theme and purpose of the retreat, including the agenda, and should be told—in detail—how to prepare for the retreat so everyone is clear about the purpose of the retreat and the outcomes it hopes to achieve.

4. Unify the Board

Division and discord are surefire ways to squelch the productivity of a board. A healthy board should be diverse (people, experience, background, thought), but it also should be unified so it can work collectively to effectively fulfill its obligations and propel the organization’s mission. The root of a unified board is its culture so the best board retreats address the fundamental culture questions, “What should it mean to be part of this board?” and “How should our culture be manifested in board behavior and contributions?” Culture is one of the most important issues to address at a retreat because board culture establishes the ethos of how and why a board operates. Everything stems from this.

5. Include Key Staff

It’s a “board” retreat, so why include staff? Key staff, those with supervisory roles, are essential cornerstones that help keep an organization running smoothly. They often have relationships with board members and many make frequent presentations at board meetings. Include key staff at your retreat because they can provide invaluable insights about important operational issues that most board members can only guess at—programming, human resources, volunteers, operations, facilities, etc. But most importantly, staff participation can help unite the board and staff, and increase the organization’s overall impact.

6. Address the Elephants

The best board retreats have the courage to address uncomfortable issues facing the board. Topics such as engagement, fundraising, responsibilities, and performance are often brushed aside at retreats because they ignite emotional flare-ups. But a retreat isn’t about beating down a board with its troubles; it’s about inspir­ing and motivating a board to be more effective. The best facilitators will address these issues in a sensitive, thoughtful, and helpful manner so the board can snip the ropes that tie these touchy anchors. They will also send out a pre-retreat survey to solicit thoughts and feelings about uncomfortable issues.

7. Discuss Fundraising

Let’s face it, the majority of board members loathe fundraising. And for good reason, most stink at it. And if a board member stinks at asking people for money, then you risk getting no money, less money, or upsetting donors. Not good. However, fundraising is a primary responsibility for most board members so how do you iron out the tension in this dichotomy?

The best board retreats find ways to uncover their board member’s personal strengths and interests to engage them in the fundraising efforts of the organization. Some members may be great speakers and can make presentations at corporations and civic functions. Some may be great hosts and could throw fundraising parties. Some may have influential connections to potential supports. And yes, some may be “closers” and enjoy asking people for money (rare, but loved!). Come up with exercises and forms that allow board members to choose ways that will excite and motive them to support your fundraising efforts.

8. Learn Institutional Knowledge

All board members should be enthusiastic ambassadors of their organizations. This requires board members to be armed with a quiver of key facts, accomplishments, and information, yet most board members know far too little about such things. The best board retreats design short, fun games that help board members learn important information about their organization. Have members pick a partner and practice reciting the mission. Play speed games to learn things like: The number of beneficiaries you serve, the size of your operating budget, and the percentage of funds that go to administration. Practice giving a brief overview of the programs you offer or a summary of your history. At the end of the exercise, pass out a sheet with all answers so members can take it home to study.

9. Practice Telling Stories

Another skill of being a good mission ambassador (and fundraiser) is the ability to tell stories. Sharing information about an organization will satisfy people’s rational questions, but what emotionally moves people to give money, inspire commitment, and incite action, are compelling stories. Set aside time at the retreat for board members to break into pairs or small groups to share their “personal connection” stories: how they got involved, why they got involved, and what is their favorite way of being involved. Then have them share an “impact story.” This type of story is about the work and impact they’ve seen at the organization. It may be a firsthand experience they had while volunteering, or it maybe it’s an emotional story of a beneficiary who went through one of your programs.

10. Provide Engagement Opportunities

Many boards have “seat warmer” board members. These people pat themselves on the back and tell all their friends they sit on the board, but when it comes to helping, they’re nowhere to be found. When called out, they’re quick to say, “We’re volunteers” or “We’re a governing board” so we shouldn’t have to “work.” Phooey. Today, the best boards, no matter how big the organization, do work. At the end of the retreat, pass out an “engagement form,” listing dozens of ways members can get involved and contribute to the work of the board and the organization. Break the lists into categories (fundraising, advocacy, volunteering, committees, other work, and skills you’re looking for). Collect the responses and assign a committee to oversee members’ commitments, and see to it that they fulfill their commitments.

11. Work in Small Groups

The best board retreats spend lots of time having people work in pairs and small groups (occasionally switching pairs and groups). This structure deepens personal relationships and allows quieter people the opportunity to share opinions that might otherwise get muted in a large group setting. Most small group talk is dominated by one or two people. Therefore, encourage everyone at the retreat to ask at least one person in their small group the four-word conversation starter question, “What do you think?” This is a simple and effective technique to involve all people in the important discussions of the day.

12. Make Time for Personal Connections

Studies show that the deeper and more authentic the relationships between board members, and between board members and key staff, the more cohesive and effective the entire group will be. There will also be less drama and more fun. This is why it’s imperative to carve out time at your retreat for people to make personal connections. Besides small group work, have board members pair up with a different person every 30 minutes or so to share an answer to a fun question that can be answered in less than 30 seconds. For example, “What are your favorite interests or hobbies?” or “What food do you detest and why?” For laughs, have a few people share the unusual responses they heard from their partner.

13. Assign a Notetaker and Change Champion

Board retreats can be a lot of fun, but the best board retreats achieve specific outcomes and impact. This is why it’s important to assign a notetaker who can track the retreat’s key takeaways and To-Dos. Most retreat facilitators complement this process by providing step-by-step instructions on ways to implement the out­comes from the day. This often includes a combination of tools such as a dashboard, an accountability process, and a variety of management templates. Yet, outcomes are meaningless unless they get imple­mented. Therefore, you’ll want to assign a person, team, or committee that is responsible for managing the outcomes of the day and see to it that the assigned work and tasks get completed.

14. Create a Theme

You create themes for fundraising events because they establish mood and atmosphere. When hosting a board retreat, you don’t need to festoon the room with streamers and party favors (but some people do), but a good theme title and some exciting swag can set the tone and inspire a vision for the day. Think of a theme title that is aspirational. For example: “Impact Leadership: Ownership, Action, Results!”

15. Have Fun!

The best board retreats are powerful and meaningful, but they’re also FUN! Besides asking goofy “get-to-know-you” questions, plan two or three teambuilding exercises. There are hundreds on the web. Choose exercises that take 10 minutes or less and get people laughing and out of their comfort zone. Yes, get a little wild and crazy. If you do this, the day will fly by, no one will get tired, and everyone will be walking around with smiles saying, “What a great retreat!”

16. Serve Light Food

A surefire way to put people asleep at a retreat and dull everyone’s enthusiasm is to serve heavy food. Forget the eggs, bacon, and cinnamon rolls at breakfast, and the spaghetti and meatballs at lunch. Instead, serve yogurt, fruit, and small muffins for breakfast. For lunch, think tasty salads, soups, and small, finger sandwiches. Use small plates. Serve water and diet drinks, and keep fatty snacks to a minimum. Offering light and nutritious food and beverages will ensure sharp minds and high energy throughout the day.

17. Keep the Spirit Alive

If you’ve hosted an outstanding retreat, those who attended will be fired up and ready to act. They will also feel a deep sense of connection with one another. To keep the momentum of your team spirit alive, it’s important to make time to celebrate your culture and achievements on a regular basis. At the retreat, create a game to brainstorm outings the board and key staff (or entire staff) can do to have fun and connect with each other. For example, you could host a barbeque, go bowling, attend a sporting event, or do a wine tasting. You may even want to include spouses/partners. It’s all about spending time together to smell the roses, nurture relationships, share experiences, and have fun.


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 your 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!

17 Best-of-the-Best tips on How to Host the Best Board Retreat or Strategic Planning Session Ever!

Additional Resources:

Tom Iselin

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

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.

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