[Webinar] How Executive Assistants Can Plan High ROI Offsites
Featuring Kelly Munoz, Executive Assistant to the CEO of Cumulus Coffee, and Creator of EAs To The Rescue. Sponsored by Vimcal.
As an Executive Assistant, you're often asked to plan important team retreats for leadership, for a department or team, or possibly even for the entire company.
How can you plan a high ROI team retreat while also balancing your "day to day" roles and responsibilities as an Executive Assistant?
We discuss this and go into a lengthly Q&A with 50 executive assistants who joined us live for a webinar on Tuesday, December 11, 2025 featuring Kelly Munoz and Offsite’s very own Jake White (former Chief of Staff, turned Head of Sales).
We discussed topics such as:
how to increase attendance at Offsites
how to better manage your CEO or executives to unlock more realistic budgets, lead times to plan offsites, and insights into what a high ROI offsite looks like
how to negotiate discounts on offsite vendors such as hotel room blocks, meeting space, AV providers, etc
different session ideas to keep attendees engaged during a multi-day offsite
practical uses of AI during the offsite planning process, and more….
I’ve added some notes below, but click the video to watch or head to YouTube.
In case you missed our last webinars, I'll link them below (there's full video replays as well as comprehensive, admittedly AI-generated notes for you).
[Webinar] How To Create Better Remote + Hybrid Company Culture
[Webinar] How To Increase Employee Engagement, Retention, and Alignment Via Offsites
We'd love to host more webinars and write more content that actually helps you and your team, so if you have any requests...reply and let me know!
I read each response personally, and I lead all our marketing efforts here at Offsite :).
Thanks,
- Jared
As always, some friendly reminders:
1. Our curated marketplace can save you up to 40% on room blocks, meeting space, F&B, and more at over 1000 premier offsite venues globally. Click here to make a free account and begin submitting booking requests ASAP for any offsites you are planning in Q1 2025.
2. We can also help you source other offsite vendors like swag, speakers, facilitators, day-of coordination / event production, travel, visas, on the ground shuttles and transportation, and more. Click here to submit your booking requests and we'll follow up with our recommendations.
3. We also offer end-to-end offsite planning services, and have helped hundreds of companies plan team retreats, customer conferences, and more.
This is perfect for those who want guidance on how to run the highest ROI offsites, while saving as much time as possible in planning because you're outsourcing everything to us.
We pay for ourselves in discounts with vendors, plus save you countless planning hours while thinking through how to help you give your team the most transformational experience possible. Book time with us to learn more here.
Special thanks again to Vimcal for sponsoring this webinar.
Main takeaways from this webinar:
Note - I used some experimental AI to generate these takeaways, so there may be some small issues here and there. Click into the timestamps at the beginning of each bolded section to watch that part of the interview to hear directly from us.
—
00:00 Executive assistants can maximize ROI on team retreats by clarifying goals, leveraging resources, and networking, despite budget constraints.
Executive assistants can effectively plan high ROI team retreats by leveraging resources and networking opportunities.
Applications for the quarter are closed and will reopen in March, so follow on LinkedIn for updates.
Executive Assistants often juggle multiple responsibilities while being tasked with planning high-ROI offsites on short notice and limited budgets.
Clarify the desired vision and vibe for an offsite to effectively negotiate a realistic budget and options.
04:49 Identify business objectives and engage stakeholders early to plan effective, budget-conscious offsites
Identify the business objectives and desired outcomes before planning an offsite to ensure a focused and effective experience for the team.
When planning a team retreat, set realistic budget expectations with executives to facilitate productive discussions about business objectives and vision.
Engaging stakeholders can provide valuable insights and guidance for executive assistants to effectively execute projects, as CEOs often lack awareness of the intricate details involved.
In planning offsites, ensure all relevant stakeholders are involved and clarify budget constraints to effectively manage logistics and expectations.
Understanding stakeholder needs and involving them early is crucial for planning effective offsites, especially when access to key individuals is limited.
10:06 Plan high ROI offsites by prioritizing clear objectives, engaging experiences, and inspiring venues while accounting for potential emergencies.
Account for a 10-20% buffer for emergencies when planning offsites, then prioritize objectives and estimate costs for execution.
Focus on the unique in-person benefits of collaboration and strategic discussions when planning high ROI offsites, rather than relying on traditional presentations.
Determine the in-person goals and objectives for team gatherings to maximize their value and effectiveness.
Ensure stakeholder availability is prioritized when planning offsite events to avoid scheduling conflicts and surprises.
To achieve high ROI from offsites, focus on creating engaging experiences that clarify team goals and foster motivation, rather than subjecting attendees to uninspiring environments and unclear objectives.
Selecting an inspiring venue and designing meaningful activities that foster genuine connections are crucial for planning high ROI offsites.
18:44 Plan offsites by considering attendees' schedules, enhancing engagement through thoughtful logistics, and using feedback to optimize participation and focus.
To increase ROI for offsites, consider attendees' schedules, especially working parents' academic calendars, during the planning process.
Creating engaging and comfortable offsite experiences requires attention to venue aesthetics, mental breaks, transportation logistics, and tailored seating arrangements to enhance participant interaction and enjoyment.
Offsites should prioritize team engagement and focus, with participants fully present and not distracted by emails or devices, to achieve the intended objectives.
To efficiently determine attendee availability for offsites, use pre-offsite feedback forms to gather essential information and focus on key decision-makers to streamline the process.
Narrow down event date options to three or five and inquire about attendees' needs to facilitate higher attendance and better planning.
Creating a personalized staff landing page with essential resources and personal details streamlines the onboarding process and facilitates efficient planning.
27:42 Create a personal operating system for new employees, incorporate breaks and structured sessions in offsite planning, and communicate effectively to enhance productivity and team efficiency.
Creating a personal operating system for new employees that includes their values, social media handles, hobbies, and communication preferences can enhance community building and assist in planning offsites.
Incorporate frequent breaks and flexible work periods into offsite agendas to allow for both productivity and social interaction.
To enhance offsite productivity, incorporate breaks between sessions and rotate team members for essential tasks to avoid back-to-back scheduling.
Effective offsite planning should incorporate structured sessions based on human attention spans, including breaks and pre-work preparation.
Proper pre-planning and communication about unavailability during offsite meetings can enhance team efficiency and client expectations.
Using bold text, highlights, and GIFs effectively communicates important office closure information.
33:45 Negotiate aggressively for savings, secure written terms, build venue relationships, create a common enemy, engage participants early, and prioritize interactive decision-making for high ROI offsites.
Negotiate aggressively by comparing multiple options, focusing on negotiable fees, and leveraging competing offers to achieve savings of 20-40%.
Always get pricing and details in writing before signing contracts to avoid unexpected costs and leverage negotiation opportunities.
Building strong relationships through vulnerable negotiation with venues can lead to better collaboration and support.
Create a common enemy to drive negotiations, ensure contract terms are negotiable, and focus on engaging content to maximize ROI during offsite events.
Providing an agenda and engaging team members in advance fosters participation and helps identify those who may not be engaged during offsite meetings.
To ensure effective and engaging offsites, incorporate frequent breaks, interactive discussions, and prioritize decision-making over information sharing while considering participants' travel fatigue and needs.
44:42 Investing in tailored external speakers and leveraging AI tools can significantly enhance engagement and decision-making in offsite planning by aligning presentations with team needs and company objectives.
Investing in external speakers and facilitators for offsites can enhance decision-making and engagement, but their value varies by industry and team needs.
Effective offsite planning requires understanding team-specific needs and outcomes, often necessitating tailored speakers and facilitators.
Leaders should align their presentations with the audience's interests to maintain engagement and trust, ensuring that offsite sessions inspire and motivate participants towards the company's mission.
Encourage leaders to align their passionate topics with audience goals and broader business objectives to enhance engagement and strategic outcomes during offsites.
Using AI tools like ChatGPT can enhance offsite planning through engaging communications and reminders, but it's important to personalize the content to avoid a robotic tone.
For effective offsite planning, send concise reminders and calendar invites, highlight key information, and provide additional details through links instead of lengthy emails.
53:39 Executive Assistants can boost high ROI offsite planning by leveraging AI for creativity, ensuring thorough pre-work, and utilizing resources like EA to the Rescue and Offsite.com for budgeting and agenda development.
AI is ineffective for selecting venues but can enhance offsite planning through brainstorming and creative tasks like generating custom materials.
AI can be a useful tool for planning, but it may provide outdated or inaccurate information, so thorough pre-work is essential.
Executive Assistants can enhance offsite planning by utilizing resources like EA to the Rescue and Offsite.com for effective budgeting and networking.