Planning Executive RetreatsSeptember 15, 2023

Tips For Planning Effective Retreats By
September 15, 2023

Planning Executive Retreats

Tips For Planning Effective Retreats
Executive Retreats are also great for networking. Pictured: (L) Jamie Hess, co-founder of NYCfitfam and (R) Nikki Sharp, transformational coach, best-selling author & wellness expert, who was a guest speaker at the event. Photo by DT Creative

Executive Retreats are also great for networking. Pictured: (L) Jamie Hess, co-founder of NYCfitfam and (R) Nikki Sharp, transformational coach, best-selling author & wellness expert, who was a guest speaker at the event. Photo by DT Creative

Corporate executives face a tremendous amount of pressure and stress in their roles as the company’s top decision makers. That’s why many corporations utilize executive retreats to allow executives to relax, recharge and refocus. While executive retreats can be extremely effective for helping executives renew themselves, creating retreats that are effective and not seen as a waste of an executive’s time, is paramount.

How have executive retreats evolved over the years and what are today’s executives asking for in retreats? Beth Surmont, CMP, vice president of event strategy and design at 360 Live Media in Washington, D.C., said that the biggest change she has seen is that executives are valuing their time much more, which can affect the form and duration of the retreat.

“They have higher expectations for what a retreat can and should accomplish,” Surmont said. “Also, how long a retreat should take, is of importance, even if it should be done in-person. I have more corporate clients who are opting for remote meetings now, where they would have done an in-person meeting without a thought before.”

If people do go in-person to retreats, they want the experience to be worthwhile. Some of the important aspects of executive retreats include a venue that is easy to get to, good food and a program that feels like it is moving things forward, not just a lot of talk. It must also have meaningful team building, not something generic or mundane, but something that allows people to really get to know each other better.

As Surmont explained, the entire point of an executive retreat is dedicated time for discussion and strategy, so there should be time and space set aside for this. The expectations for accomplishment need to be laid out at the start, and the group should continually check-in on them to ensure they are on track.

“Another key element is the opportunity for people to get to know each other on a different level,” Surmont said. “This can take many forms from icebreakers, to table topics at lunch, to the opportunity for casual conversation during an activity, golf, or a tour.”

During her corporate event planning career, Surmont has planned many executive retreats. She has found that success in executive retreats comes from the balance of deep work, reflection and bonding time. It all begins with the advance planning for what the group wants to accomplish.

“The retreat leader, oftentimes the CEO or sometimes a professional facilitator, needs to clearly lay out what the expectations are before attendees even arrive at the retreat,” Surmont said. “Having some prompts for people to think about prior to arrival can help to prime the conversation. Ground rules are important. Attendees should agree on how they want to be together, laptops open or closed, and the opportunity to speak freely.”

Surmont has been a part of sessions where a token has been used such as a talking stick or toy animal to help people feel as if they have permission to speak freely.

The schedule also should include downtime so that attendees can check in on things back at the office. This allows them to be fully present during the working sessions.

“There should be quiet time at the end of the day, before evening activities, so that attendees can recharge and reset,” Surmont said. “And there should be group dining, to allow for the casual conversation and bonding, but it should not go too late into the evening.”

Venues For Executive Retreats

The location for an executive retreat depends on a company’s budget, attendees’ tastes, the duration of the retreat, number of attendees and where they may be traveling from. During the planning phase, check in with the executives to see their preference for the location of the event. Does a resort with golfing opportunities fit the bill? Or are they looking for a secluded spa resort that will allow them to truly relax and unwind?

When it comes to finding the ideal venue for an executive retreat, there are some key things you need to consider. From a logistics perspective, a retreat space should have a room where everyone can see and hear each other, ideally around one table. In addition, flipcharts or whiteboards are a must, to capture the real-time ideas.

“It is nice when a retreat is set in a space where attendees can take time to think and reflect, so avoid the downtown or airport hotels and look for something that has aspects of nature around,” Surmont said. “Don’t underestimate the importance of some good dinners; this is often where the magic happens with the team bonding. Local restaurants nearby, ideally with private dining spaces, are important.”

Jack Feichtner, director at BlueStar, a solutions-based distribution for auto ID, point-of-sale, mobility and RFID products in Hebron, KY, has planned several board meetings and executive summits at Casa Marina, Key West, Curio Collection by Hilton in Key West, FL.

“I have been doing this for over 50 years,” he said. “I suggest choosing an eclectic venue that will give all executive retreat attendees something to remember. Key West is known for the best place to visit any time of year, making it a fantastic location for an executive retreat. The weather is almost always perfect and there are many things to do on-site and off-site. The ambience and fluidity of a majestic historic venue to impress the most discerning attendee is not easily found. Casa Marina is just the place. The food is very creative and tasteful and the meeting spaces are very functional, which both help lead to a successful event.”

Executive retreats held in locations with a wealth of outdoor beauty like this allows attendees to participate in year-round activities.

Other corporate meeting planners turn their attention to such idyllic places as Colorado and the natural beauty of the Rocky Mountains.

Tracy Orpin, senior meetings and events planner at The National Association of Insurance Commissioners in Kansas City, MO, has organized high-end executive gatherings at the Broadmoor in Colorado Springs, CO. Hosting executive retreats at a high-end resort, with beautiful surroundings, incredible food and beverage is one of the biggest attractions for many busy executives.

“At the Cheyenne Lodge on the Broadmoor’s property, which is a five-minute shuttle ride from the main hotel, it makes you feel like you are far up in the mountains. The views are spectacular and it is a quick, easy ride. No one wanted to leave the dinner,” Orpin said. “We had a wonderful guitarist that played, the food was spectacular and the location and surroundings were gorgeous. It was like living in a fairy tale.”

At another event during the week, a wine pairing dinner was a huge success as hired sommeliers spoke to the executives about the wines and why they paired so well, she mentioned.

“The budget I had to work with was decent so I had that luxury, which makes planning this type of event easier,” Orpin said. “And when it comes to planning executive retreats in general, I advise other planners to consider doing something different. Select a different menu, make it a spouse event, do something that is completely different and gives that ‘wow’ effect. And make sure you select an interactive, engaging location with great food.”

Mistakes To Avoid

Executive retreats are a unique niche within the meeting planner arena. As such, corporate meeting planners are bound to make some mistakes due to the unique aspects.

The first mistake to avoid is not understanding what the retreat is meant to accomplish. A planner should ask what success means for the retreat, so that it can be incorporated into the logistics.

“If success is a more bonded team, then the meeting planner would look for more activity-based venues,” Orpin said. “If success is a focused plan, then the planner should look for quiet meeting space that is isolated from other groups.”

The meeting planner should also focus on developing an agenda that combines the purpose of the executive retreat, like focusing on business goals while also allowing the leadership team to come together outside of their comfort zone. A pre-retreat survey can help pinpoint what each member of the leadership team is looking for from the executive retreat, which will help the meeting planner create a solid balance of business activities and retreat experiences.

“Another mistake is having to go to many different places to accomplish things,” Surmont said. “If your retreat is activity-heavy, you don’t want to waste too much time on transportation. Ideally, you should be able to find a single location that offers everything you need.”

A final mistake is not ensuring the logistics are tight. Just like any meeting, you want to ensure that everything runs seamlessly. You don’t want your executives wasting time and getting frustrated because a projector isn’t working, or the markers have run dry. Pay extra attention to the small details to ensure a productive experience.

For many years, Jamie Hess, event planner and co-founder of NYCfitfam in New York City, planned small and large-scale experiential retreats and events for executives. Recently, she planned an executive retreat for her own company, with an exclusive group of 30 executives, influencers and practitioners at Lake Nona Wave Hotel in Orlando, FL.

Called the “Reset Retreat,” the thoughtfully curated program featured diverse activities like invigorating workouts, soul-nurturing meditations, inspiring keynotes, hyper-personalized clinical work, life coaching, brain-mapping and fine dining at the hotel’s two destination restaurants.

“The hotel’s serene environment and modern amenities served as the perfect backdrop for major moments that fostered an atmosphere of relaxation and rejuvenation,” Hess said. “The seamless integration of the hotel’s offerings ensured the utmost comfort and convenience, creating an unforgettable and transformative retreat experience.”

As Hess explained, all executive retreats should leave the participants feeling like their lives have been changed forever. The retreat should be jam-packed with memorable, transformative experiences.

“To achieve this, it’s essential to put together engaging and diverse programs that cater to personal and professional growth,” Hess said. “Think inspiring keynote speeches, interactive workshops, physical workouts, mindfulness moments, team-building activities and moments for networking and reflection. Choosing venues with a relaxing and conducive atmosphere, top-notch amenities and excellent service is key.”

Also, keeping things well-coordinated, paying attention to the little details and fostering a sense of community among attendees all contribute to a successful and unforgettable executive retreat.

“The little details, things that are unexpected and surprise-and-delight moments are what attendees will remember forever,” Hess said. “Go into the experience with a servant’s heart. This means an attitude of gratitude instead of a tornado of anxiety, which, believe me, I know can be challenging! The key to being able to do this is being completely buttoned-up before the event kicks off, which means being a detail junky, and also delegating when needed.”

Continuous Evolution

Today’s executive retreats are mere shadows of their former selves. In the past, when executives would head out of town, they would end up in hotel boardrooms, getting down to the same level and intensity of business that they left back at the corporate headquarters. These days, wellness, nature and plenty of rejuvenation experiences are mandatory.

As executive retreats continue to evolve, Surmont believes that there will always be a need for leaders to come together with dedicated time to plan for the future of their organizations. Going forward, she thinks that these retreats will be shorter, 1.5 to two days, instead of three.

“I think that people will be cost-conscious and consider the perception of the location,” Surmont said. “I also think that organizations will do more work between retreats, with regular executive deep dives that work to move things forward, instead of saving everything for a once a year meeting.” C&IT

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