Understand Why Board Retreats Often Fail

Dull content, boring facilitators, and no fun are common reasons why board retreats often miss the mark. Retreats are time- and labor-intensive, and expensive. Make sure you’re putting the right effort into board retreats to make them fun, worthwhile, and productive for all involved.

A Good Facilitator Makes All the Difference

The facilitator you choose for your board retreat can make the difference between an event attendees will remember, and one where they’re constantly checking their watches. Make sure your facilitator has real-world board experience, is an exceptional public speaker, and keeps things fun. 

Keep Logistics in Mind When Planning

Hosting a productive, successful board retreat doesn’t end with the facilitator. The venue, pre-event preparation, preparing for potential interpersonal conflicts, and facilitating personal connections can all make the difference between a good retreat and a bad one.

Webinar Recap: Tom Iselin, CEO at First Things First, shares practical tips for planning and executing a board retreat that’s high-value, impactful, and fun.

Design Lines

Board retreats involve a significant investment of money, time, and resources. But often, directors and staff leave retreats and planning sessions feeling like they’ve wasted their time. 

It’s imperative to plan the best, most effective board retreat possible. But what exactly does that entail? 

At a recent ATLAS Leadership Session, Tom Iselin, CEO at First Things First, led a discussion on why board retreats matter and how organizations can plan and execute effective, engaging events. “I want you to have the board retreat you wish you had,” said Iselin. 

During the session, Iselin covered topics including: 

  • What to seek when hiring a retreat facilitator
  • The key attributes of a great board retreat
  • What criteria to consider as you plan your retreat

Here, we share key takeaways from the session.

Board Retreats Are Important

Board retreats are common. But are they even necessary? 

According to Iselin, board retreats are very important. “It’s really important because in the end, you want to build a high-performance board and a badass organization that makes things happen,” he explained. “You want to have a great day.” 

A board retreat, when it’s done well, can achieve myriad goals, including:

  • Unifying the board
  • Propelling a vision or mission
  • Increasing sales or revenue
  • Reaching or impacting more people

All Too Often, Board Retreats Miss the Mark

Well-planned board retreats can leave directors feeling energized and engaged. But often, that’s not the case.

“One of the biggest beefs I hear from people is that they’re tired of having crappy retreats,” said Iselin. “They’re horrible.” 

In fact, many directors and staff dread board retreats. It often boils down to factors including:

  • Dull, irrelevant content
  • Boring facilitators
  • No fun

“One of the reasons you’re having your board retreat is because you want to take your board to the next level. You’re looking to the future,” said Iselin. “But if there are no solid outcomes, what good is that?”

The Right Facilitator is a Game-Changer

A facilitator sets the tone for the entire board retreat. “You might think this is obvious, but it’s not,” said Iselin.

A dynamic, engaging facilitator can captivate and motivate audiences. But a dull facilitator can leave attendees checking their watches on repeat.

Iselin shared provided tips for what boards should seek in a potential retreat facilitator.

In-the-trenches experience

Great facilitators provide valuable insights they draw from their own success and challenges. “They know what it’s like to be in your shoes because they’ve walked in your shoes,” Iselin said.

He advised attendees to look for facilitators with diverse and high-level work experience who have built and run multiple organizations. He also warned attendees to be wary of charlatans.


Great retreat facilitators are credible. “You might think that’s obvious,” said Iselin. “But it’s not as obvious as you might think.”

Credibility goes beyond a client list and references. “Great facilitators are trusted authorities,” he explained. 

Iselin advised directors to look for evidence that a potential retreat facilitator is a trusted thought leader. This evidence might come in the form of:

  • A client list and reference
  • Written and video testimonials
  • Published books and articles
  • Blog, video channel, and/or podcast
  • Guest on national media
  • Clean, organized website

Exceptional speaker

“How many times have you been on a board retreat and the person is boring?” asked Iselin. Probably more times than you’d care to admit.

Boards must aim to find a facilitator that is an exceptional speaker. They should be a master storyteller, with energy and enthusiasm that’s contagious.

“People are motivated to make change when inspired by great speakers and great content,” said Iselin. “You don’t need Tony Robbins or Simon Sinek, but find someone close. You can probably find someone who’s pretty darn good.” 

Confident facilitator

Great facilitators aren’t just going through sides. Instead, “great facilitators confidently take you on a journey of education, exploration, discussion, and action.” 

Iselin shared examples of questions to ask about potential facilitators:

  • How do they handle steamrollers and hijackers?
  • How do they manage disputes and ensure everyone has a voice?
  • How do they create buy-in and build consensus?


Of course, business is the focus of a board retreat. However, board retreats can also be fun.

“People like to do business with people they like and trust,” said Iselin. “Strong relationships build teams.

Iselin encouraged attendees to learn what makes a potential facilitator’s retreats fun and lively. In addition, he advised directors to find out what icebreakers, team building exercises, and group work the facilitator uses. These are all opportunities for boards to get to know each other and have fun.

An Outstanding Board Retreat Isn’t a Pipe Dream

A great facilitator is key to a successful board retreat. However, there are other actions that organizations can take to ensure the event exceeds expectations. 

Find an inspiring venue

“A good venue can set the tone for the day,” said Iselin. Think beyond the windowless hotel conference room. A boutique hotel, yacht club, or country club may be good options. The venue should have plenty of space for group work and team building. Windows are a bonus.

Prepare the board

During board retreats, directors are often bogged down with work. “Too much day-of work can tire people and squelch creativity and enthusiasm,” said Iselin. 

Instead, Iselin suggested boards have their members do prep work before the retreat. “Then, they can focus on strategy, rather than all the stuff that can be done ahead of time.”

Address the elephants

At board retreats, directors often avoid sensitive topics. But that’s not the right approach.

Iselin encouraged boards to address these topics head-on. “You want to make sure you’re encouraging people to do what’s right, not what’s convenient or easy.”

Iselin also advised boards to be prepared to manage emotional flare-ups sensitively. “They’re going to happen,” he said. “Ask your facilitator how they’ll handle these things.” 

Make time for personal connections

Iselin reiterated that “people like to do business with people they like, trust, and know.” As such, he recommended making time for building personal connections. 

Small group work can be a great opportunity to get to know fellow directors. Downtime and fun team-building exercises can also help. 

Provide engagement opportunities 

Engaged boards are effective boards. At the board retreat, be sure to provide engagement opportunities for directors. These opportunities might be something a director can learn, do, or contribute to. Be sure to create an ownership process so directors do what they’ve said they’ll do. 

Are you looking to streamline your board succession planning? Join us for “Board Succession Planning for Continuity,” featuring Stuart R. Levine, CEO of Stuart Levine and Associates and an independent director; Sheila Hooda, CEO of Alpha Advisory Partners and an independent director; and Jim Grogan, a board director for Drees Homes and U-Haul Holding Company. 

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