Offsite Planning For EAs: How To Avoid These Common Mistakes

Executive assistants are master meeting planners. So it makes sense that they’re frequently asked to organize offsites and other in-person meetings in addition to their other responsibilities. If you’re an executive assistant tasked with planning an offsite, there is one thing you have to accept: You will make a mistake.

This has nothing to do with how skilled or experienced you are. Mistakes are common when planning offsites, or any large in-person meeting because there are a lot of moving parts that you have to juggle. From travel and hotel accommodations to arranging group meals and team building activities, the list goes on and on, and with it, the potential for mistakes grows. Some mistakes you’ll be able to solve before anyone even notices there was an issue. Others aren’t so easy to catch.

One of the best ways to avoid mistakes is to anticipate what could go wrong and plan accordingly. So … How do you plan an effective offsite meeting? Keep reading to learn about 4 common mistakes people make when planning offsites and how you can avoid them.

Business meeting

1) Poor Communication with Attendees

Believe it or not, effective communication has a ripple effect on human behavior and employee engagement. This applies to offsite attendees as well! Clear communication with your offsite attendees is essential to the success of an offsite. Your communications should clearly state the purpose, objectives, and agenda of the offsite in addition to important logistical details. 

Clear and precise communication also helps minimize confusion and misunderstandings, translating to fewer redundant questions and unexpected problems that you have to handle. There are multiple communication milestones—from sending out initial “hold the date” messages to reminding attendees to share their travel itineraries or share their agenda materials–throughout the offsite planning process, so be sure to track which communications you have and have not sent. Use an offsite meeting checklist to schedule communications in a way that aligns with the timeline leading up to the offsite.

Transparent and timely communication also promotes collaboration and teamwork among participants, building trust between team members and leadership. This trust will help to foster a collaborative environment where team members feel comfortable sharing information, exchanging ideas, and providing constructive feedback. 

Executive assistants are some of the most talented professional communicators around. By channeling your expertise, you’ll minimize confusion, improve team dynamics, and provide attendees with a great offsite experience.

business women on mobile(1)

2) Not Requesting Attendee Feedback

Failing to ask attendees for feedback is one of the most common mistakes that offsite planners make. Attendee feedback is important when planning an offsite for a myriad of reasons, from logistical details to evaluating the success of the offsite. You might be thinking, “I don’t have time to ask, and sometimes, people have too many ideas about where or when to have an offsite.” It’s ultimately up to you and the other organizers to decide whether or not to incorporate their responses. However, by inviting team members to give feedback during the planning process, you will improve attendee engagement and buy-in during the offsite. When employees feel their opinions are valued and considered, they are more likely to actively participate and contribute during the event.

Collecting attendee feedback also allows you to tailor the offsite to your team’s unique dynamic, leading to a more beneficial event. You’re likely already planning to send a survey to your attendees asking about their dietary preferences or specific accommodations. Expand that survey to include their preferences for evening activities, icebreakers, and anything else you can think of. This will make planning easier for you while also building a positive team and company culture. 

Post-meeting feedback matters too! Be sure to also send a survey to offsite attendees afterward so that you know what went well and what could be improved for the next offsite. Not only will this help you grow your skills as an event planner and professional, it can also provide valuable proof points about what attendees learned or gained from the meeting that can be shared as examples of why meeting in person matters.

business team around a boardroom table

3) A Jam Packed Agenda

Time together in person is valuable, so it makes sense to want to fill the itinerary with a lot of activities, working time, and team-building moments. However, this can negatively impact team dynamics and leave attendees exhausted and overwhelmed. Be sure to schedule breaks throughout the day and provide attendees with ample downtime. Another benefit of incorporating more breaks is how they allow attendees to take a moment to relax their minds. This positively impacts creativity and innovation, allowing space for new ideas to emerge and reserving mental energy so that participants can remain engaged and focused during this valuable time.

Another reason breaks are important is they help fight against information overload.  We’ve all experienced this before, that moment when your eyes gloss over as your brain feels like it’s too full to take in anything else. Breaks allow for attendees to digest the information presented to them, increasing the likelihood that they retain this information.

If one of the goals of your offsite is to build team morale, then breaks are particularly important. Even short coffee breaks provide an opportunity for informal networking and relationship-building among team members. These seemingly small interactions have a big impact when it comes to team cohesion, collaboration, and building trust.

Meeting room post it ideas board

4) Failing to Plan for Post-Offsite

As the person responsible for planning the offsite there will be a number of things that you need to wrap up post-event. This may include submitting expense reports, post-event communications, collecting final invoices, pulling any necessary reports, sharing the attendee feedback survey, and even publishing vendor reviews. Create a post-meeting plan that includes the various tasks and responsibilities you’ll be in charge of. You should also coordinate with any other offsite organizers to establish clear lines of responsibility regarding post-offsite tasks.

This is also a time when you should review and document the impact that your efforts had on the success of the offsite. Think about the decisions you made and how they impacted things like budget, timeline, and the outcomes of the offsite. If you had any major wins, like convincing leadership to move the location because it would save money and carbon emissions, be sure to document them. For a deeper dive into how strategic choices can lead to savings and a better attendee experience, read our detailed blog on offsite locations

Be sure to also review any attendee feedback you receive. Jot down notes about the vendors and suppliers you worked with. Were they professional? Would you work with them again? This document will help you refine your planning and execution process, ensuring future offsites are even more successful. It also provides you with evidence of how valuable you are to the organization, which is especially helpful come time for performance reviews.

Whatever your unique task list, make sure that you tie up all the loose ends before officially checking “company offsite” off your to-do list.

Business women working at her desk


Executive assistants often find themselves thrust into meeting and event planning roles, including offsites, which can be daunting, especially for newcomers. Remember, mistakes are inevitable, but learning from them is key. With careful planning and foresight, you can easily navigate common pitfalls and organize a successful offsite.

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