How to Run a Company Retreat That Won't Crash and Burn

Are attendees checking their phones and rolling their eyes? Oops. You should have planned more carefully.

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By Daniel Patrick Forrester


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It's 3 p.m. in the afternoon. You're only halfway through your agenda when you notice 90 percent of your attendees checking their phones, and one rogue executive derailing the conversation by focusing on an extremely technical and completely irrelevant topic.

Related: 5 Reasons Why a Retreat Is Good for Your Business

Welcome to the annual company retreat -- which you had hoped would refresh your company's strategy and renew the team's esprit de corps. But this is nothing of the sort; in fact, it's devolved into yet another monotonous corporate meeting. Sound familiar?

Unfortunately, this is a common scenario, with dire consequences. Companies that fail to run a successful retreat squander resources and waste executives' time. And while the total price covers fancy meeting space, travel, meals and "late night cocktails," the largest and least appreciated cost is a missed opportunity to create a meaningful experience.

And that's a cost which dwarfs every penny spent.

Retreats can achieve huge benefits for your business. They allow leaders to imagine pathways to future growth. They address difficult questions. They facilitate open feedback among employees and managers. And they provide opportunities to plan, debate, forge new relationships, reach a consensus, align around a vision and -- gasp -- allow people to have a bit of fun.

Our company has facilitated and participated in countless retreats for some of the most influential organizations in the United States. We've seen it all firsthand and heard it from dozens of leaders: the good, the bad and the ugly about corporate retreats.

So, we're on solid ground offering what we see as the five most common pitfalls to running a retreat and how you can avoid them.

1. The agenda and goals are not clearly defined.

Let's face it. Boards of directors and executives will always have slightly different objectives for a retreat. But the time to address these differences is months in advance, not in the middle of a workshop. Waiting until the last minute causes attendees to disengage and even to question your leadership. That's the exact opposite of what you're trying to accomplish.

For a recent three-day retreat that we facilitated for a leading global health organization, we spent approximately 15 to 20 hours planning -- for each hour of retreat time. If that ratio seems high, it's because a retreat is not a fleeting moment. Its value is derived before, during and after the event.

Retreat: 5 Extreme Retreats When You Want to Unplug

In the case I cite, we drafted goals and an agenda and went through several rounds of iterations with lead clients (especially the CEO) to review and refine until we had reached consensus and created a sense of ownership among the leadership team. The benefits of the retreat were enormous -- but they wouldn't have been possible without intelligent and extensive preparation.

The right people are not in the room (and some of the wrong ones are).

page1image22296Determining whom to invite to a retreat is a bit like planning a wedding. It might get a little awkward, but ultimately, it's the CEO's day to imagine and make the call on. Make sure that the people you need on hand to create, implement and promote your vision are in the room. And don't be afraid to use invitations strategically.

For example, you can reward high-potential employees who are being groomed for senior management positions. At the same time, you shouldn't hesitate to exclude individuals who might "make a scene" and derail your agenda, as they are unskilled at the art of what author Bill Isaacs calls, "thinking together."

Similar to "the big day," a retreat isn't solely the result of meticulous planning. It's the byproduct of the energy, spontaneity and magic of the people in the room. Invite wisely!

3. It's boring.

We've all had to sit through a two-hour presentation in which the presenter read word for word from PowerPoint slides that resembled the Rosetta Stone. Don't do it! Instead, limit one-way communication by sending out pre-reading materials or other media (such as videos) in advance. You can only engage people during the retreat if they are well-prepared before the retreat.

And remember that the retreat itself is an opportunity for interaction. As you plan -- a process that we call "storyboarding" -- create situations in which attendees share their opinions, affect the outcome and connect with one another.

These types of situations facilitate conversations and generate ideas that may not have otherwise happened. They also break from the traditional format and help build excitement for a a new idea.

One activity that we often employ is a "gallery walk," which enables attendees to get out of their seats and engage with the visual representation of an idea. We typically use the gallery-walk concept as an end-of-day activity that allows attendees to see and reflect on work they have completed earlier in the session.

It's a powerful way to drive home the accomplishments of the group, as well as give them a sense of pride in their work. It also makes the retreat fun and gives attendees a stake in the outcome.

4. The difficult questions go unanswered.

It's easy to avoid conflict, to "agree to disagree" and to postpone decision-making. But strategy is a contact sport, and retreats are the perfect opportunity for hard-hitting communication -- a time to get into the game, hash out ideas and move forward as a team.

There are several ways that you can make sure to tackle the tough questions. First, solicit an outside perspective to help identify what those questions are. Then, provide pre-reading materials for attendees so they can prepare in advance. (This is especially important for individuals who are less comfortable sharing their thoughts spontaneously in a group atmosphere.)

Lastly, engage a skilled facilitator able to drive the conversation forward, navigate disagreements and help the group reach consensus. Often, this individual will have to come from outside the organization so he or she can rise above group politics.

page2image25448In our work with leading organizations, we employ a number of tactics that make the sessions run more smoothly. For example, we employ ground rules for the session, which establish a social contract between speakers and attendees.

One ground rule that is always a part of our retreats is to "resist the urge to say why something new cannot be done, and focus instead on "upgrades and suggestions.'" This small reminder to support the other attendees in the group when they have the courage to voice an opinion or idea can lead to breakthrough conversations

There's no follow-up.

The best agenda, the perfect group of attendees and the greatest strategy are useless without follow-up and execution. Before the retreat, appoint a scribe (perhaps a more junior employee) to document the event, with notes, photographs and video. Then, use this data to summarize conversations, record key decisions and create an execution plan, with metrics and milestones.

Finally, commit to a structured communication plan that will hold everyone accountable and put your organization in a better position to achieve its strategic objectives. Within days of the retreat, the CEO should follow up with a call to accountability and a recap, as "back to business as usual" will simply deflate the inspiration engendered at the retreat itself

Make your retreat great, and the results will show.

We believe that your organization can accomplish more during a three-day retreat than in six months of weekly meetings. But in order to do so, you must avoid the common pitfalls and create a meaningful experience that capitalizes on the opportunity to take a step back and reflect in person -- without the overwhelming barrage of day-to-day tasks.

If you do, you'll walk away with more than a refreshed strategy. You'll build relationships, foster an improved culture and create advocates who will promote your ideas throughout your organization. There is a deep longing for human connection that retreats fill -- in this age of digital proxies.

Related: 4 Unexpected Benefits of a Company Retreat

Retreats can move people's minds and souls -- but the pitfalls along the road to human vision and inspiration can be many. Take care to avoid them.

Daniel Patrick Forrester

Author, Strategist, THRUUE Founder & CEO

Daniel Patrick Forrester is an author and strategist of organizational and cultural change who challenges leaders and boards to be guided by big ideas and act purposefully to realize intended impact. The ideas behind THRUUE, for which he serves as founder and CEO, come from his book Consider: Harnessing the Power of Reflective Thinking in Your Organization.

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