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5 Common Mistakes When Planning Executive Retreats (And How to Avoid Them)

Executive retreats—where corporate leaders come together to get off site and discuss company problems, progress and goals—are often high stakes. This is usually the one time executives can collaborate to push a company forward in the same space without distractions.

With this pressure comes planner responsibility to organize a retreat that is both reenergizing and highly productive. This meeting is nuanced, according to Dianne Davis, vice president of Tulsa, Oklahoma-based TulNet Meetings and Events, who has planned many executive retreats throughout her career.

“Sometimes you need to forget everything you know about meeting and event planning; if you haven’t done one of these before, it might not necessarily apply to executive retreats,” she said.

To help you avoid any stumbles out of the gate when planning important executive retreats, we tapped Davis’ expertise, along with the help of a few more few seasoned executive meeting professionals, to identify the most common mistakes planners make, and how to best avoid them.

Mistake #1: Working in a General Corporate Meetings Mindset

Perhaps the biggest mistake you can make when beginning work on an executive retreat plan is approaching it like any other corporate meeting or event. Executives are different than your typical attendee: they are setting budgets, making big company decisions and influencing the top-down work culture.

“Some people try to retrofit an executive retreat into the mindset of your basic conference,” Davis said. “There’s so many competing personalities, you have executives’ staff you need to deal with and coordinate with. Be on your toes and take your time to really understand the goals and outcomes of these retreats.”

Failing to work with the team well ahead of the retreat to identify the goals and desired outcomes can later derail the meeting and leave executives frustrated.

Shake yourself out of the typical meeting planner mindset by identifying these items early and building the entire retreat plan around them.

Mistake #2: Meeting in Office and Conference Spaces

“We want to get people out of their normal grind—if you think you can do this in the office or conference room just stay home, don’t do it,” Davis said, stressing the importance of removing executives from familiar spaces.

Executives spend most of their time in an office, conference room or hotel. If you really want to foster creative thinking and productivity to help them achieve their retreat goals, uproot them from their typical environments.

Ideal characteristics of an offsite venue for executive retreats include:

  • Easy access to an airport.
  • Relatively remote. Provide access to the outdoors, but still within reasonable distances of restaurants or breweries.
  • Secluded boardrooms and meeting spaces for productive work sessions.
  • Excellent cellular and Wi-Fi service: Executives need to be reachable in case of company crises.
  • Centrally located destination: If your executives are coming from around the county or around the globe, pick a location that is easy for everyone to access.

Davis cited one of the most successful destinations she’s used for executive retreats include Colorado mountain cities, like Breckenridge, which is less than two hours from Denver.

Mistake #3: Not Hiring an Outside Facilitator

A third-party presence may be the differentiator between an executive retreat flop and a home run success. Davis recommends working with an outside facilitator to bring neutrality and reason to the group.

Dianne Davis“We work with outside facilitators to come in and talk to each one of the executives to determine what the needs are of the company,” she said. “I can’t recommend them enough. They get those hard conversations [with the executives] out of the way up front and help determine what the needs are of the retreat. Then they come to the retreat and I work with that person to create an overall agenda.”

Photo: Dianne Davis, vice president of Tulsa, Oklahoma-based TulNet Meetings and Events.

Though she mentioned they aren’t an inexpensive, they can make a huge difference in the retreat results and are often worth the investment. Book them early—in Davis’ experience, hiring a facilitator two months out of the retreat or earlier is ideal.

As a general rule, plan the entire retreat very far in advance. In addition to securing an outside facilitator, matching that person’s availability up with the schedules of the executives can be difficult.

“Everyone is a VIP, everyone is always used to everyone else’s schedule revolving around their schedule. That’s 10 very incredibly difficult schedules to coordinate,” Davis said.

[Related: Venues With All the Necessities for Stellar Executive Retreats]

When evaluating your budget for the executive retreat, make an outside facilitator a top priority spend after the venue and travel to ensure success.

Mistake #4: The Keynote is Too General

Keynote speeches are staples in corporate meeting agendas. Larger conventions tend to cover a wide range of topics, but generally, executives want to take a deep dive into the topics most important to their organization.

If the keynote message is too general, you may not be facilitating the learning, problem solving and progress expected from executives at these retreats. Selecting the correct speaker and scheduling their involvement in the retreat will help you avoid this misstep.

“I’d recommend picking two or three issues that are top-of-mind for the leadership team. Rather than having a speaker come in for a 60-minute keynote, have an expert who can present information and also facilitate group discussion of how the issue impacts the business,” advised Bill Conerly, an economist who speaks frequently to business groups. “And have the expert stay around for the reception and dinner to provide more one-on-one discussion.”

Mike Taubleb, owner at Promenade Speakers Bureau—who has worked with hundreds of planners and speakers—echoes this advice in his checklist for hiring executive retreat speakers. He recommends speakers with “working knowledge of your industry gleaned from ownership, executive, advisory and speaking experience; strategic, futurist outlooks; deep experiences with complex business issues” and more.

Mistake #5: Not Sending Pre- and Post- Executive Retreat Surveys

As stated earlier, identifying goals and desired outcomes of executive retreats is crucial to the planning process. An easy way to identify these items is to conduct a pre-event survey with the participants. From there, the facilitator and meeting planner can work together to build the meeting around them.

Additionally, a pre-event survey may help participants anonymously identify any company issues that need to be worked through prior to meeting. Davis cited a retreat where problems were missed before the retreat, and it derailed the meeting focus.

“During one of our retreats [the group] felt cheated in the end because they didn’t get done what they wanted to,” Davis explained. “There hidden issues that were uncovered [during the retreat] and there was no way to move forward unless we worked through the issues. So, we had to refine and work through this. Next time, we are adding two full workdays to the retreat.”

Sending a post-event survey can also help influence the structure of the retreat for following years. Attendees can give their honest opinions on locations, retreat length, schedule of events and more, and help planners pivot for future retreats.

“If you’re good enough to make the plans you’re good enough to change the plans,” Davis concluded.

Read next: Dianne Davis helps ex-inmates make the break from prison

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About the author
Danielle LeBreck | Senior Content Director

Danielle started at Meetings Today in March 2019 after seven years of editorial experience in the travel and food industries. She oversees all of the destination content for Meetings Today and collaborates with the team on digital content strategy and content marketing initiatives.