What To Do When You've Been Asked To Plan A Company Retreat
So you’ve been asked to plan an offsite…now what? Take these immediate next steps to save you and your team as much time, money, and stress as possible.
If you’re reading The Offsite Blog, you are likely a Chief of Staff, People Ops professional, or manager (VP, SVP, “Head of”, Chief ___ Officer) with a lot of projects on your plate.
Likely, you’re working for a boss who puts in demanding hours themselves and expects you to simply “figure it out” whenever there’s a job to be done.
Your latest task? Planning a leadership team retreat, board meeting, sales kickoff, or *gulp* an All-Hands retreat for the entire company.
You’ve probably been left with limited information about the goals, budget, and expectations for the offsite, which might make the task at hand even harder to manage. Maybe you’ve never planned an offsite before, or the team has grown considerably since you last took on this job.
Below, you’ll find a framework for saving time, money, and stress when planning your next company retreat.
And of course, the Offsite team is here to help should you want it…
Click here to make a free Offsite account (no credit card required) to search our curated marketplace with over 1000 venues worldwide, where you can save up to 40% on room blocks, meeting space, and more.
We also offer end-to-end offsite planning services trusted by hundreds of companies like Reforge, 15Five, and Buffer. Click here to book a call with Jake, our Head of Sales who is a former Chief of Staff himself, or email him at jake@offsite.com. You can also click here to learn more about what we offer.
Determine The Objectives Of Your Offsite
The first step in planning a team retreat is to establish clear objectives.
Identify what you aim to achieve with the offsite—be it team-building, strategic planning, skill development, celebration of a major milestone, or a few different objectives. However, we suggest no more than two or three objectives so as to keep the offsite focused and not try to accomplish too much in a limited number of days.
These objectives will serve as your guiding light throughout the planning process and ensure that the retreat aligns with the broader goals of the organization.
It will also help you determine how much to invest in the offsite and provide a framework for determining if the offsite was successful or not.
You want to determine a high-level budget, objectives, venue search parameters, special requests, and other feedback with your CEO, boss, or other decision makers before you start planning, or you will be faced with endless delays when seeking approvals, dead ends on your hard work, and less options for venues and activities.
For example, when Offsite works with clients, we figure out things like:
what cities to explore for an offsite based on where attendees are traveling from
what the overall and per-person budget is, using a detailed budget breakdown
what agenda items should be covered, and which venues would be most conducive to offering the best environment for meaningful collaboration
what are the team’s dietary preferences, travel sensitivities, activity interests, and other “logistics” that may impact the team retreat
We explore some of these in greater depth below…
Book Your Venue (and Watch Out For Hidden Costs In Your Hotel Contracts)
Choosing the right offsite venue is crucial.
Look for a location that offers environments for both work and relaxation. Consider factors like proximity to nature, amenities, comfortable accommodations, and the ability to accommodate various team sizes in meeting spaces, breakout rooms, dining establishments, and activities on-property.
Over 50% of your offsite budget will be spent on lodging and travel to/from your chosen venue. Therefore…
Where you decide to plan your offsite is the single most important decision you’ll make.
We recommend using the free “forecast” tool at AllFly to determine which destinations will be most cost-effective for your team.
You can also create an account at offsite.com to search through over 1000 curated offsite venues worldwide where we’ve pre-negotiated up to 40% off room blocks, meeting space, resort fees, food & beverage, and other boutique options.
We’ve also pre-negotiated some of the most important contract terms, but if you are planning an offsite on your own, be on the lookout for any additional clauses, costs, and fees that seem out of place.
Negotiate everything.
Then, sign the contract and share the exciting news with your team: You’re going on an offsite!
READ NEXT: The Ultimate Guide to Understanding Team Retreat Room Block Contracts with Hotels
Send Your Team A “Pre-Offsite” Feedback Form
Just as you would manage your boss to get their feedback as early as possible in the offsite planning process, you should do the same with the rest of your team.
Send a pre-offsite feedback form to your team in order to learn about their:
Dietary preferences and/or allergies
Travel sensitivities and/or accommodations needed
Preferred activities (and/or how active or relaxed they would like activities to be)
Preferred agenda items (or what type of content they’d like to receive at the offsite)
Other logistics as needed (such as comfort level in renting a car and driving other colleagues, T-shirt sizes for swag orders, etc).
Plus, you can use pre-offsite feedback forms to ask for an employer Net Promoter Score and other employee engagement metrics to get a pulse on the company.
You could ask questions related to your business objectives for the offsite. For example, if you’re seeking to achieve greater clarity on company-wide objectives, you can ask, “On a scale of 1-10, how clear are our company-wide objectives?”
Asking for the same scores after the offsite will also give you more data to bring back to your boss (as well as your finance team!) in determining the ROI for your offsite. You can easily collect this information with a Google Form, Typeform, Airtable, or whatever other polling tool you prefer.
Plan A Detailed and Engaging Agenda
Crafting an engaging and purposeful agenda is a hallmark of a successful team retreat. Work closely with your company’s leadership and other stakeholders to determine the ideal balance of activities, workshops, and downtime.
Read the input from your pre-offsite feedback forms to understand team preferences, ensuring activities are inclusive to people of different physical abilities and interests.
Include sessions with everyone in one room, breakouts where you pre-determine who goes where (to increase cross-department collaboration and break up silos), and choose-your-own-adventure options.
If you would like some templates and additional resources on agenda-planning, we’ve covered the subject at length in The Offsite Blog. Here are some of our favorite resources to revisit:
Consider bringing in outside speakers and facilitators, especially if you’d rather focus on enjoying the experience yourself, or if you and your principal are inexperienced at running certain types of workshops like OKR planning or feedback listening sessions.
Bringing a keynote speaker could be a great way to set the tone for the offsite and also badge the event as “not your typical meeting.”
If you didn’t know, Offsite can help with Swag, Travel, Speakers, Facilitators, and more. Learn more here or email jared@offsite.com to share what kind of vendors you need for your upcoming offsite.
Create A Detailed Budget For Your Offsite And Manage Resources Effectively
A successful offsite requires upfront budgeting, as well as management of your team’s time if you’re asking leadership to prepare presentations, give talks, or lead breakout groups.
As a “People Leader” tasked with planning an offsite, you’ll need to take charge of budget allocation, expense tracking, and vendor management.
Optimize your resources by seeking cost-effective options without compromising on the quality of the retreat.
Click here to access our free budgeting template.
For example, if you are running short on budget for activities, you might consider a volunteer outing that will cost little, yet still provide a unique shared experience for attendees and photo opportunities for the “employer marketing” you do surrounding the offsite.
If you are planning the offsite with additional support from an executive assistant, someone with an operations role, or a company like Offsite, then your job is to “architect” the experience and provide budget parameters around certain decisions.
That way, when you outsource the research to others, they can provide you with great options for you to say “yes” to quickly, ensuring those options remain viable and everyone’s time is used effectively.
Triple-Check Logistics And Communicate Early/Often With Your Attendees
Keep all stakeholders well-informed about the retreat details, including the agenda, travel arrangements, accommodation, and any pre-retreat preparations.
Namely, this includes your boss, your offsite venue, and other stakeholders like finance and/or your leadership team being asked to approve budgets, prepare materials for the retreat, and otherwise ensure the objectives for the offsite are met.
When communicating with employees, they will want to know details in advance surrounding travel policies, whether or not they’re allowed to bring a “plus one”, any expectations surrounding time spent with the team during an offsite (compared to meeting up with friends or family if you’re hosting an offsite in a major city), where to share photos, where to upload notes from the offsite, and more.
With regards to vendors, triple check that they will show up on time, have all the details for your offsite, know about your team and objectives in advance, know of any last-minute agenda changes, and have emergency contact details with you or an outside facilitator.
Utilize various communication channels, such as email, Slack, and team meetings to disseminate information and address any questions or concerns promptly.
Document a “run of show” in case you get sick, flights are delayed, or some other issues arise and you are unable to continue executing the offsite logistically.
In short: over-communicate.
Facilitate The Offsite (and/or Coordinate With Internal and External Speakers and Facilitators)
If you utilize internal speakers (such as executives) or external speakers & facilitators, you will play a key role in identifying and coordinating with guest speakers and facilitators for the retreat.
You might engage key clients, subject matter experts, or industry leaders who can share insights, provide inspiration, or conduct skill-building sessions.
Provide these individuals with your “run of show” and let them know exactly where to be (and when), unless you have event production staff taking care of this for you.
If you choose to facilitate the offsite yourself, be mindful of time and keep everyone on track. Your job is to keep everyone on-agenda so you can accomplish the business objectives for your offsite while ensuring everyone makes it to activities, meals, and breaks on-time to keep everyone engaged.
If something goes wrong, stay calm and use some of your break time to catch up, outsource problem-solving to your venue or other dedicated support, and be positive. Others will follow your lead.
Reconcile Your Budget, Send A Post-Offsite Feedback Form, and Review The Takeaways From Your Company Retreat
Once the offsite concludes, it’s crucial to evaluate its success and gather feedback from the participants.
Send a post-offsite feedback form for general feedback as well as data points to get the “before and after” for any metrics you surveyed for in your pre-offsite feedback form.
Ensure action items that were committed to during various sessions are documented in Asana, Notion, or whatever project management tools and company wiki you keep. And don’t forget to send follow ups to the relevant parties.
Triple check all outstanding bills from your venue and other vendors, and then pay everyone promptly.
Reconcile your budget and let out a big exhale: You pulled off an epic offsite!!!
Determine A Cadence For Offsites In The Future
One of the best ways to leverage offsites for employee retention, engagement, and alignment (especially for remote and hybrid teams) is to develop a regular cadence for offsites.
These should not be one-off experiences.
They should be predictable so you can plan in advance, utilize feedback from previous offsites to make future experiences better for your team, and increase the ROI on each offsite you host.
With a regular offsite cadence, you and your leadership can also plan for the appropriate staff to take on this responsibility in the future, whether you continue to plan offsites but reduce scope in other areas of your job description, bring in other team members to support you, or choose to outsource offsite planning to a trusted resource like Offsite.
In conclusion, planning an offsite takes a lot of work!!!
With the resources above, we hope you are better equipped to plan retreats on your own. We hope you save yourself and your company time, money, and stress.
And of course, if we can be helpful, please reach out and let me know.
- Jared
Offsite offers a curated marketplace of over 1000 premier offsite venues globally where you can save up to 40% on room blocks, meeting space, and other expenses.
Additionally, we offer “done for you”, end-to-end retreat planning services, trusted by hundreds of top startups to help increase employee engagement, retention, and alignment.
Signing up is quick, free, and doesn't require a credit card. In a matter of minutes, you can submit requests to various curated and vetted offsite venues.
When you make an account, tell us you’re interested in end-to-end offsite planning and we’ll reach out ASAP to book a discovery call.
We can’t wait to help you plan transformational retreats for your team!