5 Common Mistakes When Planning an Executive Retreat

By Brett
(And how to avoid them)

Contact Sara Zeleznikar when you’re ready to start planning your next retreat!

Executive retreats are essential for companies looking to develop strong work relationships, create effective strategies, and successfully address stakeholders’ concerns to plan for the company’s future. They provide the perfect setting for collaboration, brainstorming and problem solving while allowing time away from daily operations, organizational structures, distractions, and familiar work settings which can be an obstacle to creativity and productivity.

Planning a successful executive or board retreat requires careful consideration to ensure that all goals are met with success. We’ll discuss the five most common mistakes made when planning a corporate retreat and how to avoid them for your company’s next retreat to ensure that it is successful for your company and its stakeholders.

In addition, we’ve invited Jen Bertsch, a transformative speaker, teacher, and coach who’ll provide her take based on her experiences leading teams and retreats.

#1 Failing to Set Clear Objectives

One of the most common mistakes when planning an executive or board retreat is not setting clear objectives for the executive retreat. Defining the goals and objects of the retreat at the onset and communicating them to all the participants is essential to success. A clear set of objectives will cause the executive or board retreat to be much more effective.

Objectives should include the expected outcomes for the event, along with the topics that need to be addressed and discussed, as well as planned activities. The goals should be detailed and measurable, so that progress can be monitored during the retreat and evaluated afterwards.

Additionally, every team member should know his or her role, and what is expected of them in terms of participation and contribution. Establishing a timeline for the retreat can also help participants stay focused on their tasks while ensuring all topics are covered in the allotted time frame.

By having a well-defined set of objectives beforehand, the executive teams will have better direction throughout their retreat and find it easier to come to meaningful decisions at the end of the executive retreat.

Let’s put an emphasis on the “afterwards.”

What do you want to be different in your organization or team? How will you measure the difference? Once that change happens, what is the possible ripple effect for your organization?

Jen Bertsch

LeadWell Academy
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#2 Ignoring the Needs and Expectations of Participants

Another common mistake is not considering the needs and expectations of the participants joining the executive retreat. Organizing an executive or board retreat requires attention to detail, including being aware and knowledgeable about the participants involved in the company’s retreat. The retreat planner should be attuned to the participants themselves so each will have the ability to succeed and contribute to the processes.

When considering and understanding participants’ preferences and learning styles during the planning process, the members participating in the retreat will be able to contribute at their highest level. Adding a variety of activities to the agenda that accommodate different learning styles is essential in ensuring everyone feels included and engaged. For example, workshops and roundtable discussions may be better suited for those who learn more effectively through auditory means, while hands-on activities may work better for individuals who collaborate best through physical methods borne out of brainstorming sessions.

Be careful with your assumptions about what your team knows. One mistake I see is the team leader assuming the team knows the reasons why the team is coming together. For example, one CEO told me, “I told them the strategic vision ‘that one time’ at the annual meeting.”

You will need to share the vision. A lot. More than you think. Connect the dots for your team.

Jen Bertsch

LeadWell Academy
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#3 Not Investing in Facilitation

Failing to invest in a facilitator or choosing an inexperienced facilitator can lead to a less productive retreat. A facilitator can be invaluable in guiding discussions, keeping the retreat on track, and ensuring that all participants have a chance to contribute and have their voices heard.

A skilled facilitator will be knowledgeable about effective techniques such as active listening, open-ended questions, and brainstorming strategies which foster collaboration and productive discussions. They will also have the capacity to move between topics quickly while ensuring that each topic receives enough time for discussion without derailing the session. Lastly, a facilitator will be able to foster an environment of trust where every individual feels encouraged and safe enough to contribute their ideas freely without fear of judgment or criticism. These skills are important to keep participants engaged throughout the retreat and not check out during these critical activities for corporate strategy.

Engagement is the difference maker with retreats. Find a facilitator who is excellent at drawing your people out. This is the top benefit of pro facilitation and it’s easier for the facilitator to help your team (and you) tiptoe into the uncomfortable zone - which we know is where the growth happens.

To invest in a retreat and not have engagement will make you feel like retreats aren’t a good use of time or budget when what you really need is better facilitation.

Jen Bertsch

LeadWell Academy
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#4 Overloading the Schedule

Another mistake made when organizing a board or corporate retreat is not allotting sufficient time for informal activities, such as team building and group bonding exercises. Overloading the schedule with too many activities can leave participants feeling overwhelmed and stressed.

It’s important to strike a balance between having a structured schedule with enough team building activities and allowing for unstructured or leisurely time to allow for personal reflection. Not only do these activities help foster collaboration and creativity, but they also give participants the opportunity to take a break from the structured agenda and connect with their colleagues on a deeper level to form better connections. Additionally, having some unstructured time built into the schedule can allow for spontaneous conversations which may provide valuable insights that could otherwise be overlooked.

To achieve maximum productivity and meaningful outcomes, it's important to find the right balance; a successful retreat isn't necessarily measured in terms of quantity but rather quality of output.

The best advice I ever got about retreat agendas can be summed up in two words: Cut. Stuff.

Less really is more. If you want to get to ALL the ideas you have, use the retreat as a kickoff to a main topic and use the extra content to do “micro-training” (a 3-to-7-minute concise training) as a tieback to the main topic each month at a team meeting.

Or, if you follow suggestion number three, have your facilitator do a virtual or live follow up session approximately one-month post-retreat and add a micro-training with the new sub-topic to that follow up session.

Jen Bertsch

LeadWell Academy
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#5 Failing to Evaluate the Retreat

Evaluating the retreat's success once it has ended is crucial to identify areas of growth and ensure that future retreats are even more effective. Setting goals beforehand allows you to determine how successful various strategies were when put into practice after the retreat. By keeping track of KPIs over time, companies will be able to recognize their full short-term and long-term successes following a corporate retreat.

On the other hand, post-retreat surveys can give an immediate indication of progress after the retreat. The survey questions should focus on the retreat experience, the participants' perspectives of company goals and objectives, as well as their role in achieving those targets. With insightful responses from these inquiries, not only can planning for subsequent retreats be done more quickly and easily but also ensure that every participant is engaged, contented, and motivated to perform at a high level.

As a part of retreat planning, schedule post-evaluation meetings. I suggest 90 days, 6 months and 1 year out. 

If you’ve answered the questions I shared above in point number one, you’ll have a baseline to assess against, and you will be able to do an evaluation post-retreat. 

Planning team development (retreats) proactively vs. reactively is a lot more fun and will give you a better return. However, if you need to do “culture clean up” and reset some expectations, get to it. It’ll only get worse if you put it off. Get intentional with your planning.

Jen Bertsch

LeadWell Academy
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For more retreat tips & ideas 
or leadership training visit Jen at
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