Common offsite and retreat planning challenges

This post is an excerpt from our free offsite planning resource. Download the full guide here.

Planning an offsite is complex. Expect to face roadblocks in the process—but don’t get discouraged. Even if you don’t have much planning experience, determination and finding the right resources can get you a long way.

Let’s look at a handful of the challenges organizers commonly encounter.

Research dead ends

One of the most time consuming parts of planning an offsite or retreat is finding hotels, coworking spaces, restaurants, activities, and anything else that needs to be booked in advance. This is largely because of just how many factors you’ll be keeping in mind while searching.

Is it in the right part of town? Is it within budget? Is it available on the dates you need? Can they accommodate your group size? Does it align with your attendees’ preferences? All of these questions and more will play a role in every single search you type and list of recommendations you read. In many cases, an option that seems perfect might not end up working out for one reason or another. These research dead ends are disheartening at times, especially when they begin to stack higher and higher, or as time to find something viable runs out.

Planning and timeline overwhelm

If you are an event organizer whose full time job is wholly unrelated to events, it’s very likely that you might at some point become overwhelmed by the process and the amount of time, thought, and communication it can require.

This sense of overwhelm is generally at its worst when planning has to be rushed within a tight timeline, when budgets are highly restrictive, or when event support within an organization is very limited.

Communication

Just as offsites are complex for an organizer, they can also be somewhat hard to keep track of for attendees. These events often take place over multiple days and are composed of multiple components that can easily get mixed up. That means an organizer’s inbox in the weeks leading up to an event (and during) can be filled with constant, repetitious messages about the details of your plan.

Want help navigating each crucial stage of planning an offsite? Download our new resource for event organizers.

Featured resources

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8 Steps for Planning Your Company Retreat

A resource for new organizers on creating fun, productive, and successful corporate events.

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