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The Great Retreat

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Of all the responsibilities you might typically associate with being a CEO, planning an executive retreat isn’t one they teach you about in business school. However, a recent survey of CEOs conducted as part of Chief Executive’s February CEO Confidence Index research clearly shows that many of today’s CEOs consider their role in arranging retreats an important task—something they consider well worth their time and energy.

More than 81 percent of 285 CEO respondents said they are involved in selecting locations for board, management, customer and other off-site meetings and retreats. Furthermore, survey results suggest that most CEOs put a lot more effort into the retreat-planning process than simply worrying about the hotel’s proximity to golf courses.

Massachusetts’ Charles Hotel

Executive retreats are critical events on the corporate calendar. “I sit on numerous local and national boards,” says Terry MacRae, CEO of Hornblower Cruises & Events, an international marine company. “Despite how some people will squeeze budgets and try to make retreats go away, when you look back to watershed moments in a company’s history, you can often trace them back to a retreat.”

What’s in a Retreat

Far more than back-to-back meetings in a windowless conference room, a retreat is about you and your team getting away from distractions of the office and rolling up your sleeves to solve specific issues, overcome challenges, set new goals and think creatively about your future—and hopefully to have real fun together. “People get so caught up in the inertia of business and watching the bottom line that CEOs and senior executives rarely have time to slow down,” says Christine Corelli, president of Christine Corelli & Associates, a Chicago-based Fortune 500 consulting firm. “The goal of an executive retreat is to slow down so that you can speed up business.”

Alaska’s Boardwalk Lodge

“You and your team need to stop and think, ‘What are we doing right, where do we need improvements, how are we doing in our efforts to meet goals?’” she says. “Sometimes it’s about who is performing and who isn’t, or what is working and what isn’t. Retreats are about getting away from the office to go through the important aspects of your business: marketing, customer service, sales, everything related to the business, what complaints are we hearing. You go away with your team to where the thinking can be clear and uninterrupted by day-to-day operational objectives, and, hopefully, you do it in a creative setting where you have time to take off your jacket, sit down and have an open conversation about where we were, where we are, where we’re going, and how we’re doing.”

Colorado’s The Broadmoor

Retreats are an opportunity to create a long-view mindset for your team and each individual on it, asserts John Crosby, principal of Tucson, Arizona-based Architecture for the Soul, a consulting firm that specializes in business coaching and executive- team, change-management strategy. “Think of a mouse running in grass and looking for cheese. Then, think of stepping up and out of that perspective, and becoming a hawk,” he says. “People who spend all week long in meetings and their weekends immersed in the rote detail of going through 1,400 emails, lose sight of the larger picture. When you’re running as fast as you can and don’t feel you can do it faster, the only option is to do it faster. The retreat allows your team to think with insight, inspiration and awareness; and when everyone’s making choices and decisions from that place, you’re realizing your overall vision.”

Planning is Everything

Enhancing creative thinking, helping to build relationships, boosting morale and improving cross-functional collaboration and corporate culture are among the many benefits of retreats cited by survey respondents. However, achieving these outcomes is far from assured. You’ll need careful planning, both of the actual event itself (including choosing the destination, the accommodations, the activities, etc.) and of the goals and agenda you set.

New York’s Glenmere Mansion

Once you’ve made the decision to hold a retreat, the next step is to choose a venue—which is more complicated than it may sound. Your location needs to be determined well in advance of the actual retreat and it should be comfortable, convenient and conducive to fruitful discussions. Ideally, it should also be an inspiring locale that provides the right backdrop for creative thinking, socializing and rejuvenation. (See p.52 for a list of great retreat venues.)

Given the importance of having all those factors in place, it’s critical to think hard about the type of venue you want. “Begin by visualizing your event,” suggests Lisa Ross Faust, managing partner at the Contemporary Events Group, an Atlanta-based corporate meetings, special events and convention-management firm. “Do you want a hot climate or or a cold one? Are you willing to travel a full day to get there? How is the food, and what things can you do there? You have to qualify what you want and what you have time for before you can begin planning the actual trip.” Other key criteria include assessing what facilities, services and amenities you’ll need (e.g., a single boardroom, or multiple meeting rooms of varying sizes), what team-building and downtime activities are readily available onsite or nearby, and whether the location has an event team capable of managing all of your catering and planning needs.

Florida’s Creek Ranch

Sometimes budgetary concerns or concern about the perception of lavish spending influence venue planning, adds Ross- Faust, who cautions against waiting too long to book your retreat. “In this current economy, we’re seeing many companies hold onto their dollars, even though they know they have a meeting tentatively planned,” she says. “If you wait until the last minute to put it together, it can end up costing more.”

Once you’ve identified potential venues, compare and contrast them by submitting requests for proposals then reviewing what each contender has to offer. Consider rates and specifications for accommodations, meeting facilities and services, food and activities during the dates you are looking to book. For companies tackling the booking process on their own, travel experts stress the importance of emailing or calling the venue’s sales manager to discuss the particulars before booking—rather than relying on potentially outdated website information.

The Details

Unless your company is small enough to bring your entire senior team, you need to weigh who needs to be there and whether their attendance is mandatory. Then, communicate that information clearly. Be sure to factor transportation into your planning. Your team will need to get to the retreat, move around while there and make the return trip back. Depending on the destination, these logistics can prove to be significant obstacles.

Florida’s Doral Golf Resort

Whether you opt for a conveniently located hotel or a resort with a history of serving the wants and needs of corporations or something more remote and specialized (e.g., a pheasant-hunting lodge out in the wilderness or a health and wellness spa ensconced deep in some forgotten hills) to set a different tone, your next step will be establishing your meeting goals and building an agenda that will interest, challenge and engage your participants. The mechanics of the event—what you’ll do while there—are important, but nothing should trump defining your goals and planning your agenda, says Katharine Halpin, founding principal of Phoenix-based The Halpin Companies, a leadership strategies and executive-coaching firm. After all, that’s what inspired you to have the retreat in the first place.

Arizona’s Miraval

“You want to create an environment where people can speak with more honesty than normal and feel comfortable enough to share their deepest concerns and form better connections,” says Halpin, who notes that getting everyone’s contributions to the agenda is crucial. “The true measure of success in the workplace is not whether your team members are measurement-centric, have high IQs or have mastered the skill sets required for their jobs. Those things are all very important, but your team can only be effective if the individuals master their emotional intelligence. Retreats help nurture and groom people to become more intelligent; and when conflict arises down the road, they’ll have developed the tools and strengthened those connections to work through challenges.”

Most meeting facilitators and leadership coaches advise investing the time to develop a prioritized list of discussion topics in advance by holding one-on-one meetings with participants prior to the retreat. “You should speak with all the attendees individually about your planned agenda,” says John Baldoni, president of Ann Arbor, Michigan-based Baldoni Consulting, an executive coaching and leadership-development firm. “Let them know where you think you’re headed and get their feedback on issues that can be raised.” Avoid scheduling wall-to-wall meetings, he adds. “Your meetings should be set up with the bulk of the heavy-lifting slated for mornings, after which you should allow attendees some personal time to enjoy socializing or participating in formal or informal activities that are unique to the location. Your focus isn’t on presentations and meetings; it should be on thinking out loud, debating, deliberating and socializing.”

Virginia’s Jefferson Hotel

Once you’ve set the agenda, says Baldoni, share it, then develop and circulate materials that will be referenced during your meetings so that participants can arrive prepared with comments, questions and concerns. By preparing participants in advance, you’re encouraging them to be involved and equipping them to hit the ground running. Encouraging everyone to participate on an equal basis may make for some heated conversations, he says, but they’ll likely be productive conversations; and when the retreat is over, your team members will have a better understanding of each other due to those frank discussions and positive opportunities to bond.

Finally, avoid the pitfalls of overreaching. Don’t overwhelm and overtax participants by setting unreasonable goals and an exhausting itinerary. “You have to be realistic about what you can accomplish in your agenda,” explains Halpin. “Be strategic, set outcomes, be authentic and follow through. Whether your goals are strategic planning, a project kickoff, customer service issues, improving morale or launching a new product, you have to set clear goals—and not too many of them.” After all, ultimately, you want your employees to return engaged and enthusiastic—excited about what’s possible and their role in making it happen.

Nebraska’s Lied Lodge


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