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.”