24-Nov-2023 by Allison McMillan

Read Time: Approx. 8 minutes

Transforming Meh to Memorable: Secrets of Successful Offsite Planning

Think of the last offsite you attended or planned... what are the words that come up for you? In what ways did that gathering go as planned and in what ways did it fall short?

When we think of offsites (offsites/onsites/team or department get togethers... for the sake of simplicity, i'll refer to all of them as offsites here) - those pivotal events for groups that are meant to foster team building and alignment, address challenges that need to be addressed in person and bring people together, tackle complex conversation where in person time is critical, and generally recharge everyone in a different way than the usual - we often imagine them in their ideal state... as carefully curated experiences, ones where everyone walks away rejuvenated and excited about the their team, the company, and the future. Even for those who try to keep planning low-key, focusing more on hanging out, the hope is that these goals, at the very least, are accomplished. For those planning more detailed gatherings with additional goals, the ideal state is that each detail has been planned and every outcome has been achieved precisely as envisioned. This dream, buoyed by ambition and aspiration, is what sets us on the journey of offsite planning. It's a journey filled with promise, one where every session and activity we plan is expected to ignite camaraderie, stir innovation, and renew focus.

But the path to a successful offsite is seldom as straightforward as we envision. Let's delve into the nuanced reality of offsite planning, a task that is as challenging as it is rewarding.

The initial phase of planning an offsite is often marked by a surge of optimism and creativity. We start with expectations and hopes, sketching out (even just in our minds) what we envision as the perfect gathering. Engaging activities, deep-diving sessions, recognition of the most important pieces to discuss and address, and moments of genuine connection - these are often just a few of the elements we aim to weave into the tapestry of the event. We see in our mind's eye a team returning not just refreshed, but truly excited, focused on new goals and a renewed sense of purpose. This isn't just another gathering; it's a catalyst for growth and change. This vision is what you talked about and advocated for to get the budget approval to have an offsite! This vision is why people are brought together and why the cost (both monetarily and in time) is deemed as necessary.

However, as planning progresses, the unpredictable aspects of professional life begin to make their presence felt. The day-to-day demands of our jobs don't pause to accommodate our offsite planning efforts. A crisis arises that needs immediate attention, or a key project veers off course, demanding more time and resources than anticipated. Board meetings, stakeholder engagements & alignment, and unforeseen challenges continue to vie for our attention, each adding a layer of complexity to our already packed schedules. Offsite planning drops towards the bottom of the to-do list. "It's not for a while" or "this other thing is on fire and must take priority" is what we think as we re-order and adjust our "must do's".

And then, as offsite planning truly gets underway, the logistical aspect of the event takes center stage, often overshadowing the more strategic elements of the plan. The logistical labyrinth of organizing an offsite is daunting - from ensuring travel arrangements (everything from letting people know dates and times to reminding people to actually book their travel) and accommodations to managing dietary preferences and venue selection (not just for your daytime activities, but also for dinners, team fun time, and more). Each of these tasks, while seemingly mundane, is critical to the success of the event and demands a significant investment of time and effort. And, these things end up taking the "extra" time you have because, realistically, if the venue isn't reserved, or travel isn't booked, then without any participants, an offsite is a mute point anyway.

In the whirlwind of managing these logistics, the core purpose of the offsite - the content and the experiences that will make it truly impactful - frequently takes a back seat. The initial vision of meaningful and engaging sessions gives way to a race against time, with the focus shifting to ticking tasks off a checklist rather than crafting an enriching experience. This shift can leave little room for considering innovative presentation methods or exploring fresh, engaging approaches to content delivery. Because what you've done in the past has always worked "well enough", hasn't it? After all, no one has walked away hating the offsite. And so that becomes the goal... plan a "good" offsite. Plan something that people think was mostly an ok use of their time. Maybe the outcomes won't be as good, maybe you won't accomplish everything you had hoped, but surely it will be fine and some important things will get discussed, decided, and people will probably enjoy just seeing one another and hanging out together.

In response to these mounting pressures, delegation becomes a necessary strategy. Different aspects of the offsite are handed off to various team members, each contributing their piece to the puzzle. We rely on the collective effort, hoping that when these individual contributions come together, they form a cohesive and effective whole. On the journey to the venue, we often find ourselves finalizing plans and ironing out details, realizing that there hasn't been enough time to fully develop the kind of deep, engaging content we initially envisioned. We think... this will be fine and maybe next time we can make it great.

From Good to Great

In the realm of offsite planning, one of the most significant challenges is envisioning what truly exceptional looks like. Most of us have attended various offsites throughout our careers, and for the most part, they've been acceptable. They've met the basic requirements of bringing teams together, offering a break from the usual routine, and perhaps touching on some key organizational goals. A few might stand out in our memories as lackluster or even counterproductive, but generally, offsites tend to land in the realm of "good enough."

The reality of offsite planning, with its blend of high aspirations and challenging logistics, brings us to an essential question - how can we ensure that our offsites are both meaningful and feasible?

This prevalence of "good enough" sets a subtle but powerful benchmark. When our experiences are mostly of offsites that are just passable, it becomes challenging to imagine something that goes beyond this norm. How do we conceptualize an offsite that doesn't just tick the boxes but truly elevates the team's experience, engagement, and productivity? How do we even know what that looks like or feels like if our exposure to truly great offsites is limited, it's hard to set a vision that goes beyond the standard, the familiar.

And there's some good news and bad news here. The good news is, there are numerous templates and tools available to assist in the planning process. These resources can guide you through budgeting, provide checklists for logistics, and offer frameworks to get started. However, the bad news is that most of these tools focus predominantly on logistics. They often fall short in guiding you through the more critical aspect of offsite planning - the content. Templates can't capture the unique dynamics of your team or the specific goals you want to achieve. They provide a structure, but not the substance and often leave out critical budget items or checklist boxes to address this portion of the offsite.

AND, as with most ways that we address the fact that we don't know what we don't know, this is where bringing in someone with specific expertise becomes invaluable. It's about breaking the mold of the 'good enough' and venturing into the realm of the extraordinary.

The first step is to start planning early. For example, if you're thinking about a spring or early summer offsite, you should start planning now. Time is a crucial asset in this process. The earlier you begin, the more space you have to balance the logistical details with the substantive content that will make your offsite truly valuable. Second, think about working with someone. This can help crystallize your vision, aligning it with practical realities and ensuring that every aspect of the offsite, from the logistics to the sessions, is thoughtfully planned and executed.

Planning an offsite shouldn't be about settling for the average or the known. It's an opportunity to explore what greatness in team gatherings looks like, to push beyond the boundaries of the 'just okay,' and to craft an experience that resonates deeply with every participant. Imagine your next offsite as more than just another item on the calendar - but instead as an event that leaves a lasting, positive imprint on your team and organization.

Remember, no one sets out to plan a sub-par offsite. Get the support and resources you need to make your vision of an ideal offsite into a reality. You got this!

If you're eager to discover what an exceptional offsite looks like, talk about what's happening with your group right now, or have the ability to advocate for the budget to have an offsite today, Book a free consultation call with me today. With a range of pricing options and levels of involvement, I'm here to help you get to GREAT. Whether you're seeking a complete overhaul of the traditional offsite format or looking to infuse your event with fresh, impactful elements, I can help guide you through this journey.

split path and one one side cool tones that looks drab and on the other it is bright and interesting and exciting

Ready to chat?

Join my mailing list

* indicates required

Set up a free call

phone icon