[Webinar] How To Plan High ROI Offsites in 2025 featuring Chase Warrington (Head of Operations at Doist)
This webinar will help you get approval for 2025 offsites from your finance team during annual planning efforts. Click to watch below or scan detailed notes.
Are you doing annual planning for 2025, or about to start building next year’s budget?
Will you need help getting finance to approve investments in offsites and team retreats? If “yes” to both…
Take some time today to watch the replay of our webinar on "how to" operationalize team retreats across your company, so you can execute higher ROI and more transformative retreats while staying within budget.
This all-value, no-fluff conversation featured:
Chase Warrington, Head of Operations and former Head of Remote at Doist, one of the pioneering remote-first startups
Jake White, a former Chief of Staff himself to a nuclear tech startup and employee #4 at Offsite (the "go-to" resource for planning in-person team retreats for hundreds of VC-backed companies such as Reforge, Buffer, and Remote).
And yours truly (Jared Kleinert, founder of Offsite)
I’ve added some notes below, but click the video to watch or head to YouTube.
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 if you're planning any offsites for the end of 2024 and even into 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.
Thanks as always, and subscribe to The Offsite Blog if you haven’t already.
Jared
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.
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00:00 - Effective offsite planning boosts team morale and business metrics, emphasizing the need to align retreats with company goals and secure financial support for high ROI events.
The webinar focuses on effective offsite planning strategies to optimize time, cost, and stress for team retreats, featuring insights from industry experts.
The implementation of regular retreats has significantly improved team morale and business metrics in a previously hyper asynchronous work environment.
Planning and improving retreats is a significant part of my daily responsibilities to ensure they meet company goals and provide exceptional experiences for the team.
Many clients are planning offsites for 2025, ranging from single events to numerous gatherings, highlighting the importance of aligning business objectives with team experiences.
The speaker shares their diverse background in hospitality and education, highlighting their experience in planning offsite retreats and assisting clients in achieving their business objectives.
To secure approval for high ROI offsites in 2025, it's essential to effectively pitch their value to finance, leveraging leadership support and demonstrating their impact on employee engagement and alignment.
06:15 Investing in well-structured offsite retreats, despite budget constraints, enhances team efficiency and leadership support, with costs averaging $2,500 to $3,500 per person.
Despite budget cuts during a hiring freeze, the company increased its retreat budget by 10%, strategically allocating costs based on employee location.
Establishing a clear budget and operational process for offsites can help gain leadership support and improve their effectiveness.
Avoid unrealistic budgets for offsites, as they are essential for remote companies, with average costs typically around $2,500 to $3,000 per person.
Investing $2,500 to $3,000 per person for offsite events can enhance team experience and efficiency, justifying higher costs for better time management.
Average offsite duration is three to four nights, typically starting with a kickoff on Monday and concluding by Friday, with budgeting considerations for each event.
The organization hosts three types of retreats: an annual All Hands event costing around $3,500 per person for a five-star experience, mini retreats for individual teams costing between $1,850 and $2,200, and a Leadership Retreat with similar costs to the mini retreats, each lasting four to five nights.
13:12 Strategic planning of interconnected offsites throughout the year enhances ROI by balancing business goals and team bonding while adapting to team dynamics and fostering collaboration.
To maximize ROI from offsites, it's essential to strategically plan them throughout the year as interconnected events rather than isolated occurrences.
Effective offsite planning balances business objectives and team bonding to create a meaningful experience.
Start the year with an all-hands kickoff to align everyone on the company's vision, followed by a second-quarter team meeting to address specific departmental challenges.
Offsites should adapt to current team dynamics, focusing on process adjustments, new initiatives, and cross-functional collaboration for upcoming projects.
Bringing together different teams for collaborative discussions and individual recognition during events like annual All Hands can enhance operational planning and team cohesion.
The process of running high ROI offsites involves the CEO's keynote to set a yearly theme, followed by a Leadership Retreat to plan execution, and mid-year evaluations to assess progress and adjust strategies.
19:20 Regular offsite meetings in large companies focus on building connections and psychological safety, emphasizing intentional engagement and well-being to maximize ROI.
Large companies like Airbnb and Dropbox emphasize regular offsite meetings, with employees attending two to four annually to balance remote work and in-person collaboration.
Effective offsites require careful scheduling and clear objectives to maximize ROI, tailored to each company's unique structure and team dynamics.
Offsite meetings prioritize building connections and psychological safety over productivity, following the 20-30-50 rule to balance work, planned activities, and rest.
Focusing on intentional connections rather than productivity is key to successfully planning high ROI offsite retreats.
To prevent off-site fatigue, schedule regular breaks, limit deep work sessions to 20 minutes, prioritize collaboration over information sharing, and creatively engage teams in discussions about work.
Retreats prioritize individual well-being by making activities optional and providing private rooms, allowing participants to recharge and engage at their own pace without fear of missing out.
29:09 Offsites should energize teams, celebrate achievements, align goals, and foster collaboration through intentional planning while balancing attendance and operational support.
A lean team offsite focused on energizing, celebrating achievements, aligning on goals, and allowing unstructured time for relationship-building and collaboration.
Larger companies should use offsites for strategic planning and decision-making, balancing all-hands meetings with departmental gatherings for effective team connections.
Intentional planning and structured activities are key to successful offsites that foster cross-functional relationships and effective collaboration.
Aligning all team offsites to the same week enhances productivity by minimizing disruptions and allowing for both cross-functional collaboration and focused team workshops.
Optimizing for the minority who cannot attend offsites can negatively impact the experience for the majority who are present.
Incorporate a support team during retreats to maintain operations and offer alternative experiences for those unable to attend due to unforeseen circumstances.
37:31 Effective offsite planning requires an all-or-nothing approach for hybrid teams, prioritizing in-person attendance, essential remote participation, and leveraging emerging data on trending venues.
Hybrid team experiences often lead to disappointment and inefficiency, so an all-or-nothing approach is recommended, with alternatives like compensating employees who cannot attend in person.
Include remote participants only in essential sessions and communicate any necessary service closures well in advance to manage customer expectations.
Keynote speeches are live-streamed with commentary and later recorded for global team accessibility, ensuring important points are captured despite audio challenges.
Planning hybrid offsites requires coordinating experiences for both in-person and virtual participants, accounting for time delays and engagement challenges.
By 2030, hybrid technology will improve offsite planning, but currently, remote companies favor destinations like Mexico and Bali due to visa challenges, while emerging cities in the U.S. are increasingly hosting meetings.
The speaker highlights the growing availability of data on trending offsite venues, categorized by state and city, to assist teams in planning events like sales kickoffs and executive retreats.
47:04 Outsourcing offsite planning and implementing follow-up surveys significantly enhances team connectivity, satisfaction, and productivity, demonstrating a strong ROI.
Implementing a required follow-up survey after offsite events helps measure team connectivity and demonstrates the value of the investment to leadership.
Collecting both quantitative and qualitative feedback through intentional surveys is essential for understanding team desires and improving future offsite meetings.
Companies are increasingly outsourcing offsite planning to improve efficiency and cost-effectiveness, as internal management often detracts from core responsibilities.
Outsourcing offsite logistics while maintaining internal oversight enhances planning efficiency and allows for data-driven improvements in future retreats.
Post-retreat surveys indicate a strong positive correlation between offsite retreats and increased employee satisfaction and productivity.
Investing in offsite retreats fosters strong relationships and positive ROI, even if difficult to quantify.
55:59 Investing in offsites boosts employee experience and team connections, making them a valuable asset for companies.
Investing in offsites is valuable for enhancing employee experience and operations, as demonstrated by successful companies.
Offsites are essential for fostering connections and problem-solving among team members, making them a worthwhile investment for companies.
Hiring a sales team member with a people operations or chief of staff background, while offering resources and support for planning effective team retreats.