Tips from the Experts: Tools & Strategies for Assistants to Plan Engaging Offsites

When it comes time for a company event, assistants are often tapped to take the lead on planning. Team building on zoom or department happy hours are one thing, but what about planning a company or team offsite?

Keep reading to learn about maximizing the true value of offsites as you design the agenda, the first question you need answered before planning, and how small details at your event can make all the difference.

How to plan impactful offsites that wow your colleagues and leader

In our recent Base Live panel, our panel of offsite planning experts shared their expertise and tips for how Executive Assistants can plan and execute engaging offsites:

Watch the full video below or keep reading for the highlights from the conversation!

3 factors assistants need to consider when planning an offsite

Here are three of the top takeaways from our conversation with Kirsten, Mary, and Kelsea on planning engaging offsites. Have any to add? Join our Executive Assistant Community and connect with assistants across the globe who are navigating similar experiences.

Focus on humans and connection 

What can a great offsite accomplish that day to day operations and small team building or culture initiatives can’t? Kirsten shared some pillars of focus: community, context, clarity and co-creation. You can adapt these and rank them for the offsite you’re planning, but our panel unanimously recommends you focus on community first. Creating opportunities for your team to meaningfully connect is where the true value of an offsite lies. Establishing connection first will speed up the rest of what you’re trying to accomplish.

When planning the agenda, also consider these people you’re connecting are humans with real needs that are likely heightened due to travel and being out of their routine. Mary shared being thoughtful about breakfast (don’t skimp here!), bio breaks, and time zone adjustments due to travel are crucial. Kelsea suggested varying the types of sessions on the agenda, keeping your objective for the offsite and the types of people attending in mind. Kirstin also advocated for giving people the time they need outside of planned events to take care of themselves so they don’t feel the need to leave early or arrive late.

Communicating expectations, sharing the food agenda, and even creating a Know Before You Go list are all helpful ways to make your attendees feel more at ease and able to show up to the offsite as their best selves. The panelists also suggested crowd-sourcing your team on what activities they might like to do, what swag they might like (or not want), and more to include them in the process and increase feelings of being a valued person on the team.

Answer this question first

Once you’re tasked with planning an offsite, your first question needs to be, “What is the budget?” Kelsea went on to share that once she has a budget, the dates of the event, and who is coming, everything else can fall into place like dominoes. But the budget is number one.

But what if your leader asks you to help decide the budget? Kirsten shared some helpful tools and calculators to help you think through this so you can make informed recommendations and educate around what is possible for what price per person. You can also start by getting a better idea of what categories to spend the most on based on what your leader or planning team decides is the true purpose of the event.

If you’re looking for budget-friendly options, be mindful of the venue you’re choosing. Mary shared to consider choosing a venue within walking distance of food and activities to save on transportation, or choosing one that includes shuttles to and from the airport. When it comes to activities, partnering with non-profit organizations is a great way to bond, make an impact, and cut costs.

Kelsea also shared about building your relationships with vendors over time and negotiating with them as a way to save money. Leveraging these relationships and making sure you ask how they’re able to work with you whether that’s discounts or including extras in your contract can really help.

Go for small gestures with big impacts

As keeper of all the little details, an administrative professional planning an offsite can also create a lasting impression from a few small, intentional choices. Mary highlighted flying to the offsite location early and going to Costco to grab waters and snacks to include in welcome bags. These can be available for attendees at hotel check-in, or even distributed mid-offsite when people need a pick-me-up.

Another small touch that shows consideration is giving attendees a choice when it comes to swag. This could look like offering an option for a pre-selected swag item like a hoodie, or to give a donation to an organization instead. Kirsten also mentioned an event where they had a swag station, with a smaller number of curated items attendees could choose from, instead of everyone receiving the same pens and water bottles they might not want.

The personalization aspect makes employees feel thought of, and it also decreases the chance the company is spending money on items people don’t even care about.

Lastly, Mary and Kelsea both riffed on the importance of considering those who might be attending the offsite remotely. Ensure AV is properly set up and establish norms for video calls while some people are present IRL together and some are joining remotely. Send food delivery vouchers, have an alternate social activity for remote participants, and be considerate of different time zones when planning the agenda. Making sure everyone is equally included is so important to creating an outstanding experience for everyone.

How Executive Assistants can source the best offsite planning ideas

If you’re an EA looking for more ideas on offsite planning, first, tune into the full video as our panelists shared many more tips than these highlights. Next, connect and brainstorm with other assistants in the largest group of EAs in the industry. Our community brings together assistants from businesses all over the world, so you can meet and learn from other professionals who’ve been in your event planning shoes.

You can also check out our resources for EAs, learning and development programs, and job opportunities.

Written by Natalie Turner

Natalie is a content strategist, seasoned facilitator, certified leadership coach, and formerly the Executive Assistant to the CEO and President at Base. She believes in the power of supportive relationships and rituals, both personal and professional, to change individual lives and therefore the world. She explores these concepts in Base workshops, on the Courageous Help podcast, and in her own entrepreneurial pursuits.