Planning an Impactful Offsite

Planning an Impactful Offsite

Who plans company events? In my experience, while HR, People Managers, and small business owners certainly plan their fair share of events, the assistant is often the first employee contact. About 10% of my sales calls begin with executive or regular assistants.

When it comes to organizing company events, assistants often find themselves at the forefront of planning, and many times they have no experience in this field of work. While virtual team building and company happy hours have become commonplace, orchestrating a successful company or team offsite is a different ballgame.

In this week's Leading On Purpose newsletter, discover the key elements to maximize the value of offsites.

Field Day Survivor inspired activity with Cornerstone Home Lending in Palmetto Bluff, photo by Mike Ritterbeck

Factors Every Assistant Should Consider

Pinpointing the Objective

Is there something an offsite can deliver on that can't be met in day to day operations? You wouldn't want the deliverable for an entire company offsite to be something that could be met with an after work bowling night or in-office team building game.

Before delving into the logistical details of your next team offsite, it's crucial to lay the groundwork for success. Defining the purpose and objectives of your real-life meeting will serve as the cornerstone for your event's planning. Consider your goals: Do you envision a focused, two-day strategic planning session for your leadership team? In that case, an isolated and serene setting, equipped with the tools for brainstorming , collaborative work, and creativity, is essential. Perhaps you're bringing together your entire sales team to enhance their skills, boost morale for the upcoming quarter, and foster camaraderie. In this scenario, a spacious venue with ample time for team-building activities and even a celebratory event at the end is necessary.

The initial step in planning your team offsite is goal-setting. Clearly defining your objectives not only guides logistical decisions but also engages attendees and team members from the outset. By communicating these goals in advance, you enhance engagement and preparation, ultimately elevating the overall quality and value of your event.

Remember you are planning an event for human beings with human needs. Be thoughtful about meals, breaks, time adjustments due to travel, etc. Give people plenty of downtime outside of planned events to rest, sight see, read a book, chat with co-workers, and call family.

Provide employees the agenda before the event so they can know what to expect. Leaving room for surprises is ok. Your team probably has some great suggestions that can make the event even better and ensure they feel valued for allowing them to take part in the planning.

Creating the Budget

Maybe the organization provides the budget off the bat. But what if the organization asks the assistant in charge of planning the offsite what the budget needs to be? Talk about adding even more responsibility and stress to one person!

Having a budget, event dates, and list of attendees streamlines the planning process. If asked to determine the budget, leverage tools and calculators to make informed recommendations aligned with the event's purpose. Understanding the goal of the event in advance also helps you know what categories to allocate more of the budget to based on needs.

For budget-friendly options, consider venues within walking distance of food and activities. Partnering with non-profits for activities not only fosters bonding but also cuts costs. Build vendor relationships over time and negotiate for discounts or added extras to save money.

This is also a great opportunity to call an expert. Leveraging a team building organization like On Purpose Adventures to help plan your offsite gives you access to our years of experience in budgeting, planning, and facilitating a successful event.

Dealing with Logistics

Though it's important to deal with big picture stuff like goals and budgets first, at some point you will have to begin planning logistics, and I recommend planning these details early. Especially if you are managing hybrid or remote teams, gathering people together for an in-person offsite can be costly and time-consuming. Getting a jump on these details is also a savvy financial move, often resulting in cost savings through early bookings.

Here is a break down of some essential logistical steps whether you're orchestrating an event for a large or small group:

  1. Location: Are you selecting a location based on convenience for the majority (regionally) or one with the most flights into? If you are selecting a destination because of the climate or sights, are you including outdoor activities or day-light free time?
  2. Accommodations: Are you booking hotel rooms or a shared space like a house on Airbnb?
  3. Sleeping Arrangements: Shared rooms or individual sleeping arrangements?
  4. Transportation: Origin points of attendees and logistics for getting them to the offsite location?
  5. Venue: Where will the primary event activities take place? Inside or outside? If outside, what is the backup plan if weather forces activities indoors?
  6. Facilities: What facilities are necessary for your planned activities? Will certain technologies be required?
  7. Agenda: Using the T.E.A.M Method, identify how much of the overall time spent will be Informing, Building, Bonding, or Entertaining.
  8. Layout: Depending on size of the group, will all sessions be in one room with a stage? Will there be breakout rooms? What is the flow? The layout of a room is almost as important as the conversation being had.
  9. Team Building Activities: How will you encourage employees to work as a team through fun and engaging activities? There are a litany of options to choose from. Be sure to consider the weather and location. If you have selected a beautiful location with no daylight time planned outside, consider why? What about a custom Scavenger Hunt where employees can explore the location, break the ice, and work as a team?
  10. Food: Is the venue catered, or do meal arrangements need to be managed independently? Do employees have any dietary restrictions? Will there be alcohol served?

Taking a proactive approach to these logistics ensures a seamless and well-prepared team offsite.

Lowcountry Offsite with On Purpose Adventures team building activities

Getting the Small Gestures Right

As the keeper of details, administrative professionals can leave a lasting impression through intentional choices. Preparing a welcome bag and giving attendees choices for swag to increase personalization are small details that pack a punch.

Plan a fun ice breaker session for the event kickoff to boost engagement and make everyone feel welcome and a sense of enjoyment right from the start.

Consider the employees attending the event remotely - ensure the technology is properly setup to create as few problems as possible, establish video call protocol, and provide these virtual employees as many of the same fun things as in-person attendees i.e. through food and swag delivery. Be considerate of different time zones when planning the agenda. Ensuring all employees feel included is essential when planning an impactful offsite. Make the audio/visual component for remote attendees a priority, not an afterthought.

How can On Purpose Adventures help?

The first way we can help is with experience. When an assistant is asked to plan an offsite for potentially hundreds of people, the task can feel overwhelming to say the least. That's where we can help.

We have learned to stay in our own lane. We provide what we provide and that is content. This content includes experiential team building and bonding programs either in Charleston or elsewhere.

On Purpose Adventures' Yellow Camo Crew

When you get into the planning phase, if you cannot plan internally and if you have the budget, it's a great idea to hire a 3rd party destination management or corporate event planning company. Here are our recommendations:

These are all great partners that we have worked with in the past. Some have limited geographic reach and some are global. We work seamlessly with these organizations where they help plan the event and we help facilitate the activities.

We have facilitated hundreds of events for thousands of people. We know how to manage different employee personalities, mitigate problems that are sure to arise no matter the amount of planning, and create fun experiences that bring people together.

We can also create custom on-site experiences and suggest nearby offsite locations that can lessen travel and create more wiggle room in the budget. We know all the best Charleston area locations to host large teams while also being experts in creating custom offsites in new cities all over the world.

So, whether you are planning an offsite on your own or would like to give us or one of our partners a call for help, I hope you have learned more about planning and facilitating an impactful offsite through this newsletter. While the initial idea of creating an event for hundreds of your co-workers can feel daunting, it's a fun and educational experience, and one your co-workers would love to share their input on if you'll allow them.

To help with the planning process, we have created an Offsite Planning Checklist that takes you step-by-step through the planning process. Click here to download!

If you have planned a successful offsite before, please leave your #1 tip in the comments.


In this week's Cohesion Corner? with Dr. Troy, I recount challenging childhood moments when I asserted, "I can do it myself. I don't need your help." A familiar narrative for many of us, right?

But buried beneath those assertions was a crucial realization—it wasn't about rejecting help; it was about desiring autonomy. The parallel to leadership is striking. The newsletter delves into the importance of teachability as the foundational attribute of a successful leader. Leadership isn't about having all the answers but about having the humility to seek guidance and learn continuously.

Click here for to learn if you are teachable.


All the best,

Ben-Jamin Toy

Ben-Jamin Toy ?works with elite clients spanning the globe, from well-known Fortune 500 companies to special ops forces representing five countries. He is the founder of?On Purpose Adventures , a driving force in purposeful, unconventional, and effective team building for over a decade, and co-founder of Cohesion Culture? . A sought-after facilitator, consultant, and speaker, Toy continues to focus his heart, soul and substantial knowledge of culture wellness into each learning experience, promising a fun and engaging encounter with tangible results.

Ben-Jamin Toy

Experiential Team Building: Keeping your remote, in-person, and hybrid workforces productive & engaged.

1 年

Would love to get any additional insights for executive assistants from the event pros we work with often. (companies tagged in the newsletter) Tracy Mitchell, CMP, Kate MacCoy, Kate Jeffords, DMCP, Todd Hunter, Tiffany Lucca, Lee Blakely, CMP, DMCP, Taylor McKenzie, CMP, DMCP, David Rome CMP, DMCP

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