How to Plan an Effective Executive Retreat

Think that executive retreats are something less than serious, akin to a leisure escape or at worst, wasteful folly? That was the glaring view in the meltdown-inspired “bad optics” era, but then as now, these annual (or quarterly, or even monthly) summits could not be more serious—when properly planned and executed.

In fact, for companies that do them well the retreat is where fundamental decisions impacting the company’s direction and future are often made. More critically, it is the CEO’s meeting to own. And, while the agenda may be complex, following a set of common-sense, logical, unambiguous steps can help pave the way for success.

“First, determine an objective, and commit to an outcome,” advises Bob Frisch, who, as managing partner of Boston-based Strategic Offsites Group, has been helping senior executive teams and boards master critical strategic and organizational challenges for more than 30 years. “The CEO should let the team know precisely why they are there and what to expect, which issues are most critical to the business and which—while potentially important—are out of scope for this particular meeting.”

“Time away from the office, even locally, is a major cost that only multiplies when taking the retreat to a destination property,” he says. “Optimizing the investment means maximizing the time together,
which starts with diligent pre-retreat planning.”

Update memos, PowerPoint presentations, business cases and voluminous research binders are fine for regular meetings—but not the retreat. “These waste time and should happen beforehand,” Frisch says. “The off-site is for getting straight to discussing, debating, discovering and making decisions, not for sharing information that should have been absorbed before the meeting starts.”

Another operative word is “closure,” though not through a forced decision. “Certain strategic decisions will need additional fact-gathering, evaluation and such, and so post-meeting planning is also crucial,” Frisch says. He recommends reconvening the same team between 30 to 60 days out. “With momentum and sense of purpose from the retreat, that’s when you close,” he says. “Don’t expect everything—
especially challenging issues—to be resolved at the end of a couple of days.”

The team should be as streamlined as the agenda. “Invitees beyond the CEO and the top management team can impact the character of the conversation,” he says. “Adding people can be like a Christmas tree overhung with ornaments.” That said, “no law says you must have the same people in the room for every session,” Frisch continues. “For example, the first day can be just the CEO’s direct reports, with vice presidents joining on day two or three.”

He also sees variable models around destination and venue selection. “While travel constraints and stigma related to 9/11 and the financial crisis have eased, most companies still stay close to home for
off-sites,” says Frisch. “Jetting off to a destination or resort is usually a function of how well the company is performing. Some CEOs will even base retreats near their vacation homes, with the team housed in a nearby inn or B&B. That can sometimes be more ego-driven than practical; travel time definitely needs to be considered.”

Frisch also advises separating work from play. “Play golf and relax before or after the retreat, but not amid the discussions,” he says. “Talking strategy, making decisions and producing outcomes are the
priorities.” He also cautions against using subject experts as facilitators. “Experts can join in to help clarify issues, but when they act as facilitators they can push the group to their point of view. Or they feel like they need to be the center of attention to justify their fees for being there. This is the CEO’s meeting—he or she is responsible for coming home with the team and objectives fully aligned.”

Regular Resets
With extensive hands-on experience in planning and leading strategy off-sites for large-scale enterprises, Eric Korman is a Frisch client well “aligned” with best retreat practices. As senior vice president, mergers and acquisitions for global media and e-commerce giant IAC (InterActiveCorp.), Korman helped organize annual retreats attended by top executives from IAC’s holding company (Barry Diller among them), portfolio companies and strategy group.

In subsequent roles as president of Ticketmaster Entertainment and then as president of digital and global e-commerce for Ralph Lauren, Korman took full charge of strategic off-sites. “Like IAC, these summits typically involved between 150 and 200 senior leaders flying in from around the globe,” relates Korman, who “owned the meetings from top to bottom.”

Today, his team retreats are significantly scaled down. Passionate about consumer brands and interacting with consumers online, Korman left Ralph Lauren in 2014 to found Austin, Texas-based Phlur, his innovative “reimagining” of how to market and distribute fine fragrances.

“Presently at 12 people, we see each other every day, are in the same information cycle and innately get what we are doing,” he says. “Nevertheless, retreats, following the same fundamental principles around alignment, decision-making and closure, are critical for developing the business strategically and culturally.”

In fact, Korman organizes a local off-site each quarter, using conference space affordably provided by a business partner. “Offering a moment in time to physically separate from daily routine and pressures, retreats help us reset as an organization every 12 weeks,” he says. “Agenda-wise, the primary focus is on clarifying the strategies that will carry us forward and defining why they are priorities, so that people have the contextual framework to make decisions and execute their part of the business plan without repeatedly checking in with me.”

In terms of “owning” the off-site as CEO, Korman believes in balancing “non-negotiables” with “the collective voice.” In his view, “while corporations are not democracies, and generally will not function on a purely consensus-driven basis, the off-site optimizes shared discussion and discovery around what is working, and what may require pivot and change.” Plus, he adds, “there’s the intrinsic value of a communal, ritualized event—people look forward to coming and contributing.”

Reaching Deeper Levels
Headquartered in The Woodlands, Texas, just north of Houston, Benchmark is a leading global hospitality company founded in 1980 by Cuban émigré Burt Cabañas. Taking over as CEO in 2013, his son Alex has continued to expand Benchmark’s worldwide portfolio of managed hotels, resorts and conference centers through a series of mergers and acquisitions, while adding asset management, an owner’s
advisory group and other services under the company’s umbrella.

Presently also global president of IACC (formerly, the International Association of Conference Centers), which counts 385 member venues in 22 countries in the Americas, Europe and Australia, Alex Cabañas is front and center in all Benchmark strategy and other meetings—including his annual executive retreat. When interviewed for this story, in fact, he was in the midst of planning the 2017 edition, at luxurious Benchmark-managed Turtle Bay Resort in Hawaii.

“All CEOs should lean into executive retreats as a top priority,” says Cabañas. “This is my opportunity to take my already highly functional team of 12 away and make us even better, in terms of the dynamics around how we discuss and make decisions around internal change, business strategy and other issues. Everybody is responsible for arriving prepared and bringing their ‘A’ game, toward discovering
deeper levels of trust, transparency, understanding and, for each individual, deeper self-actualization.”

Another theme is leadership development. “We have a diverse and distributed global workforce of some 10,000 people,” continues Cabañas. “How do you align them with strategy and objectives? It starts with fostering and encouraging individual leaders at the top, who then influence the management layers below them.”

While prioritizing business-driven outcomes, however, he is all for balance. “The retreat is also a celebration of our company, culture and people,” Cabañas says, “so dinners, outdoor activities and exceptional experiences are very much part of the agenda. Leisure pursuits and unstructured time may qualify as ‘inefficient’ when measured against the hard costs associated with taking the team away from the office. Their intangible value more than rewards the investment, however—including translating back to how we create experiences for our corporate customers.”

Case in point: last year’s retreat, which Cabañas organized at a local residential-style enclave complete with gourmet kitchen, library and outdoor fire pit. “There was much complaining about overloaded schedules beforehand,” he recalls. “Afterwards, the team called the experience ‘epic and life-changing.’ The bonding we developed over deep dive conversations and social time became a lasting source
of stories—and another example of invaluable intangibles.”

Planning Partners
Paul Van Deventer, CEO of Dallas-based Meeting Professionals International (MPI), the world’s largest association for the meetings and events industry, affirms the value of the well-organized retreat. “I have participated in numerous executive and board retreats over the course of my career and found them to be valuable opportunities for leveraging the collective intellect of the leadership team in
strategic planning,” says Van Deventer, who also presently co-chairs the D.C.-based Meetings Mean Business Coalition, a global cross-industry communications and advocacy initiative promoting the power of business meetings. “Face-to-face meetings in general deliver significant ROI for businesses, allowing for instant collaboration, real-time productivity and net income growth,” he says.

Matthew Marcial, MPI’s vice president, education and events, agrees. “When well executed, executive retreats are a great opportunity for the leadership team to spend focused time away from their business conducting strategic planning and prioritize organizational initiatives,” he says.

For the hands-on CEO seeking to maximize ROI from the retreat, “the role of a meeting professional has truly evolved to become a key strategic resource for an organization,” adds Marcial. “While CEOs have a vested interest in the experience and the overall success of the retreat, they should trust their planning teams to take their vision and objectives back and create a successful event from start to finish, freeing their time to focus on the business.”

Foremost in planning is a clear understanding of objectives. “This influences everything from destination and venue selection to the program format,” Marcial continues. “Clear goals should be established to gauge the success of these events. Deliverables need to be defined and measured.”

CEOs should provide the vision—with the retreat planner as a key partner. “In addition to trusting and empowering their meeting planning team, I would advise CEOs to be clear and transparent on their objectives, engaged in the meeting design process, open to new and fresh ideas and to also provide timely feedback when their input is requested,” says Van Deventer.

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