Out of Office: The Power of a Well-Planned Retreat


GateWay_Canyons2Today’s frenzied, do-more-with-less work week has presented senior business leaders with a challenging paradox—namely, how do you discuss strategic planning, brainstorm on new business opportunities, and spend quality time as a group to improve overall team chemistry when you’re already inundated with tedious conference calls and tactical staff meetings?

A well-planned executive retreat solves this contradiction by providing CEOs and their top leaders with a dedicated opportunity to come together and focus on top-of-mind issues and initiatives that are critical to business. While there are some who might argue that off-site retreats aren’t necessary, or that on-site meetings are a viable alternative, most well-run businesses recognize the value of dedicated time away from the office for senior leaders to work together on important issues. Without it, they will be continually distracted by staff updates and the regular demands of their daily grind, turning a well-intentioned on-site meeting into an apologetic conga line heading for the hallway.

“Retreats are about getting away so that people can focus and the human side of work can come out,” says Katrina Kent, CMP, CMM, and director of corporate events for financial services firm TD Ameritrade. “If you are making an investment to bring people together in a nontraditional setting, you’re trying to get people to connect to an emotion and helping them to see each other differently. That’s what benefits the business. By taking them away from the office, you are creating the right environment for these executives to take their business relationships to a new level. You’re helping them create more trust, enhance their relationship parameters, and helping them build deeper loyalty to each other.”


Determine the Goals
The first and most important step you can take to deliver this type of experience for an executive team is to work with the retreat’s sponsor to define the meeting’s goals and objectives. “It’s really important to have consensus on the purpose of the meeting, and its agenda, especially if you have more than one host,” Kent says. “That sets you up for success. If the stakeholders aren’t on same page, it’s confusing for attendees, and the program becomes fractured.

“Then you have to be specific with the invitees about what they’re doing, and why. If you clearly define it up front, you’re going to make the right decisions, and you’ll feel confident about the investment.”

Obviously, planning a corporate retreat isn’t akin to dropping kids off for a day of arcade games and ice cream at the local mall. You need to place your executive team in an environment that is conducive to the goal of their meeting. The minimum basic requirement is a comfortable, appropriately equipped facility that delivers the services, amenities, and ambience to help ensure a productive, inspiring retreat. Additionally, you have to meticulously plan the details well in advance so that the attendees never have to think about logistics, from the moment they leave for the destination until the moment they return from it. Their objective is, after all, to come together to develop strategy, solve problems, overcome challenges, and open new lines of communication—not to find an available conference room with a functional projector in it.

“We go through all of the organization’s goals and objectives, from the details of the agenda to knowing about each attendee and helping determine whether there should be a guest speaker,” says Renee Black, cofounder, principal, and senior event producer of Planit Omaha, a high-level meeting and event producer for corporate clients. “We do everything from helping to find the right venue to making sure each guest’s room is stocked with bottled water to picking out the attendees’ favorite foods, desserts, or drinks. We take a look at every aspect and dive in to make it fun and match the CEO’s goals.”

Determine the Destination
A main key to planning a successful retreat revolves around finding a well-matched venue to hold it. “One of the most crucial questions you have to ask yourself is, ‘How critical is it that the destination is easy to get to?’” Kent says. “Are attendees flying in and out from everywhere, or are they from a specific area?”

03Ease of travel is a key consideration because some of best places to hold a retreat aren’t necessarily a hop, skip, and a jump away, especially when the host is looking to organize extreme or unique activities that are off the beaten path. “It has to be worthwhile to take that flight, change planes, fly again, and then drive an hour,” Kent says. “The payoff has to be worth it for people to take extra steps.”

Location isn’t the only criteria, though. The only way to narrow down the prospects and identify a handful of viable matches is to know the meeting sponsor’s expectations. “Do they want a fun networking event, something they’ve never done before, or a five-star experience for well-seasoned business travelers?” Black asks. “A lot of time it’s about convenience, and hotels and venues are designed to handle that. However, fantastic remote venues can be extremely successful as well.”

This means you’re going to need fundamental details up front, such as when the event will occur, who will be invited to attend, and what types of activities to plan so you can confirm that the prospective destinations are available at that time and have the ability to meet all of your expectations.

“It’s always great to have one to two years’ advance notice for planning,” Black says, “but sometimes you only have a few months. When you’re pulling together something in a short time frame, the stakes are raised. Short-term bookings can work, though, because a venue you’re considering may be looking to fill in business, and sometimes both parties can be more flexible about dates and rates. If there’s need on both sides of the table, it behooves everyone to figure out a way to make it work.”

Along with those typical issues come more tedious constraints, such as assessing how important cell phone coverage may or may not be for attendees, or how much travel time is required to get to the nearest commercial airport. “You have to get into the weeds with folks to find out what’s important. If someone is bringing in 100 top executives, it’s probably more important for them to be able to fly in and out quickly,” Black says. “But you have to make them aware of the other considerations so that they can understand the options.”

Giving your sponsor at least two potential destinations that meet all—or at least most—of their criteria is your starting point, Kent says. “Present one that is very safe, as far as easy to get to, not a stretch for anyone, and will work based on what they’ve specified. Then talk about a unique alternative that might be harder to access, and explain the return. We present a few recommendations or scenarios, talk through what it would be like to be an attendee in any type of scenario, and then we go from there.

“I think part of the value you can add is being able to come in with a point of view and clear reasoning,” Kent adds. “You’re a stakeholder in the event, as well, so when you invest time and energy to have an informed perspective, and you start the conversation with your other stakeholders, you really impact the final decision. It’s not just, ‘Here’s your menu, let me take your order.’ People are looking for your expertise. Good leaders know they can’t be experts at everything.”

Dot the I’s & Cross the T’s
Once you’ve done the hard research and jumped through fiery hoops to get the destination locked down, it’s time to start buttoning up the agenda details and revving up the excitement to make the upcoming retreat resonate with the participants in a significant way.

Obviously, e-mail and social media are convenient channels for this purpose, but leveraging regular mail to send a tangible hint or teaser—such as coffee beans in advance of a retreat in Jamaica, for example—can be an effective tool. “If you have a keynote speaker who has a brand new book, you can engage attendees by sending them a copy in advance,” Kent says. “If you can send something ahead of time that provides an advance look at what the experience will be like, that’s what will get them to connect in a human way.”

Once the destination, transportation, facilities, activities, and meals have been booked and the multitude of related details have been double-checked, it’s important to take a deep breath and review each day’s agenda of meetings and activities one last time to ensure that each day is structured to be productive and that attendees have enough downtime factored in. “They’re going to need time to digest everything that’s being discussed, and they’re also going to need to check e-mail, check in at the office, and at home,” Black says.

04Kent agrees, saying that keeping the agenda streamlined and free from too many competing objectives is key. “Overload is a killer for people. If you don’t know what the three key things are you want to accomplish, and you don’t have everyone signed up to support that, you’ll have an unfocused meeting,” she says.

With the top-line expectations for the retreat addressed and the agenda well defined, your focus invariably turns to helping the executive team stay focused so that what they expected before departing for the retreat is what plays out the minute they are on-site, Black says. “That means making sure everything is perfect regarding audiovisual equipment, including minutiae like checking that microphones have fresh batteries, so that there aren’t any disruptions. Little things like that can irritate executives.”

Your post-retreat goals are simple, she says. “When the meeting wraps up and the invited guests all depart for the airport, they should leave knowing that everything they experienced was good, even if the topics discussed weren’t all positive. They should know that everything that happened was supposed to happen.

“It’s your job, then, to capture and measure that level of satisfaction and get feedback about each attendees’ most important take-away from the meeting.”

Black recommends following up with each attendee by e-mailing a survey or posting photos from the meeting online. “If people are engaging with your photos and videos, that provides you with the best possible metrics—if they’re still interested, you know it was a success. You’re able to document that they’re accessing it, which is a good way to prove success.” In other words, that’s a tangible, trackable return on investment that any executive will be happy to see.”

VIP VENUES …………………………………………………………………….

The Ahwahnee  Yosemite, CA
Four-diamond hospitality, legendary cuisine, and the splendor of Yosemite National Park.

Alisal Guest Ranch and Resort  Solvang, CA
Trail riding, tennis, golf—and business—in the wine country just north of Santa Barbara. www.alisal.com

Bellasera Hotel  Naples, FL
Warm hospitality and classic Italian design in the heart of Old Naples. www.bellaseranaples.com

The Brazilian Court Hotel & Beach Club
Palm Beach, FL  Catering to the elite since 1926, steps from world-class shopping and the beach.

Canary Hotel  Santa Barbara, CA
An urban hideaway at the heart of the Santa Barbara scene. www.canarysantabarbara.com

Canyon Ranch  Tucson, AZ
A health-minded escape designed to energize groups, on 70 acres in the Tucson foothills.

Cavallo Point–the Lodge at the Golden Gate
Sausalito, CA  History and sustainability facing the iconic bridge, bay, and hills of San Francisco.

Gateway Canyons Resort & Spa
Gateway, CO  A high-desert getaway created by the man behind the Discovery Channel.

The Inn at Palmetto Bluff, an Auberge Resort
Bluffton, SC  Authentic Lowcountry elegance with a focus on nature. www.palmettobluffresort.com

Meadowood Napa Valley  St. Helena, CA
A classic pairing of business and pleasure on 250 acres in Napa Valley. www.meadowood.com

Ocean House  Watch Hill, RI
A Gilded Age original by the sea for the golden age of corporate getaways. www.oceanhouseri.com

Rough Creek Lodge  Glen Rose, TX
All-inclusive luxury and convenience, hunting, fishing, and more in the Texas Hill Country. www.roughcreek.com

The Ranch at Emerald Valley
Colorado Springs, CO  A ten-cabin wilderness hideout within minutes of The Broadmoor’s golf, spa, and dining. www.broadmoor.com/ranch

Rancho de los Caballeros  Wickenburg, AZ
Everything from spa treatments to golf to cowboy cookouts in the high Sonoran Desert.

Sanctuary on Camelback Mountain
Paradise Valley, AZ  One of the greater Phoenix area’s most coveted havens—complete with custom
corporate programs. www.sanctuaryaz.com 

WaterColor Inn & Resort  Santa Rosa Beach, FL
A friendly beach-house vibe well away from it all on the Gulf of Mexico. www.watercolorinn.com

Willows Lodge  Woodinville, WA
Focused on peace, quiet, and Pacific Northwest cuisine on five lush acres—near 97 local wineries.

Mexico and the Caribbean
Capella Pedregal Cabo San Lucas, Mexico
Off by itself in a hidden cove—yet just minutes from city attractions. www.capellapedregal.com

Peter Island Resort & Spa  Tortola, BVI
Accessed by helicopter, yacht, or ferry, a private-island escape for groups with VIP tastes. www.peterisland.com

Villa La Estancia Riviera Nayarit
Nuevo Vallarta, Mexico  A secret hideaway, luxury resort, and seaside hacienda all in one.

Casa Angelina  Praiano, Italy
Maximum luxury in minimalist lodgings on the Amalfi Coast near Capri, Positano, and Naples.

Cliveden  Berkshire, England
The former country estate of three dukes, an earl, a prince of Wales, and Lord and Lady Astor.

Conservatorium Hotel  Amsterdam, Netherlands
Once a music conservatory, today a stylish hotel that blends Old World style with cutting-edge design.

Culloden House  Inverness, Scotland
Highlands hospitality in a historic manor hidden by 40 acres of Scottish countryside. www.cullodenhouse.co.uk

Dylan Hotel  Dublin, Ireland
High style and five-star hospitality in an intimate retreat at the heart of Dublin. www.dylan.ie

Hotel Marques de Riscal  Elciego, Spain
Designed by architect Frank Gehry for the vine-covered hills of Elciego, Spain’s City of Wine.

Inverlochy Castle Torlundy–Fort William, Scotland
Seventeen stately guest rooms and Michelin-starred cuisine in the Outdoor Capital of the UK.

La Residencia  Deià, Majorca, Spain
In good hands with Orient-Express, a luxury hideout on the isle of Majorca. www.hotel-laresidencia.com

Park Hyatt Paris–Vendôme  Paris, France
Quiet, discreet five-star hospitality in the heart of the French capital. www.paris.vendome.hyatt.com

Villa Rothschild Kempinski  Frankfurt, Germany
A historic refuge of 22 lodgings cushioned by 25 acres of wooded parkland.

Photo credits: Alisal Guest Ranch and Resort, The Ranch at Emerald Valley, Shutterstock, Cavallo Point—The Lodge at the Golden Gate, The Ranch at Emerald Valley.

Guest Writer

Guest Writer

Leave a Comment