How to plan ahead and budget for your company’s team retreats

This is a guest blog written by Jared Kleinert, Founder and CEO of Offsite.

Team retreats, or offsites, are a powerful tool for increasing employee engagement, retention, and alignment at remote-first companies. But, planning an offsite is a complex process. Many remote-first and hybrid companies are still uncertain about when and how often they should plan team retreats, which makes budgeting and annual planning difficult. 

Just as your business needs operational excellence to survive in the unpredictable world of startups or a reliable global HR platform like Remote to power your hiring needs, you also need an effective business and offsite cadence to keep your teams aligned and motivated. 

As the founder and CEO of Offsite, which provides end-to-end offsite planning services for hundreds of remote-first teams, I’ve discussed team retreat planning with people leaders from around the world and across a wide range of industries. Drawing on my expertise, we’ll discuss, in this article, some key insights on how to plan and budget for your company’s team retreats, and how to create an offsite cadence that works for your business. 

How to budget for offsites

To invest in offsites, you must decide on a reasonable budget that considers all expenses you may incur during a team retreat. Once you decide how much you are willing to spend, you can focus on planning a successful offsite and increasing the return on investment by bringing your teams together in-person regularly. 

Forward-thinking companies can reinvest savings from reduced office expenses into growing a predictable offsite cadence. Planning ahead allows you to use the standardized budget across all offsites, enabling you to plan more and better retreats within the same budget.

Some expenses to consider when planning an offsite, include, but are not limited to, accommodation, travel, meals, meeting space, activities and entertainment, event supplies, swag, keynote speakers and/or facilitators, event coordination, photography and videography, swag, and insurance.

Offsite, a marketplace for booking offsite venues, speakers and facilitators, and travel providers, has created a free time-saving budgeting template. Once you decide how many offsites you plan to host in the following year, simply plug in details of your estimated expenses to generate a budget breakdown per offsite throughout the year. 

To save time, money, and stress, you’ll want to plan as early as you can. Doing so can save you 10-20% of your budget by increasing the likelihood of savings on hotel room blocks, meeting spaces, travel, and other notable categories of spend. 

Key things to consider when planning your offsites

In addition to budget considerations, certain other factors come into play when determining your company's offsite cadence.

Employee distribution 

Depending on your budget and business needs, consider where your team members are located before you budget and plan offsites for the year. It's easier for teams distributed regionally to meet more often compared to teams spread nationally or internationally. 

Business objectives

Every company will have a different number of offsites planned each year, in line with the company’s business objectives. For example, business models like Traction and Scaling Up, as well as business literature such as Patrick Lencioni's “Five Dysfunctions of a Team,” recommend quarterly offsites for leadership teams. Major company changes or pivots may also necessitate offsite gatherings. Sales leaders may plan annual Sales Kickoff and President’s Club events to incentivize performance.

Each offsite should have a clear purpose, an actionable agenda, and a post-event review process to promote continuous improvement. This will increase the likelihood of receiving CFO approval for your offsite plans and will make annual planning easier in the future.

Headcount

Smaller companies may be able to get all their employees to meet with fewer offsites. In contrast, larger companies may need to plan more offsites, typically by teams or departments, with smaller attendee counts compared to larger gatherings such as All-Hands meetings or Sales Kickoffs.

Frequency

According to Harvard Business Review, the frequency of offsites should be flexible. Smaller teams can benefit from quarterly offsites, while larger organizations may opt for biannual or annual events. More mature organizations will have a mix of team-specific offsites and larger gatherings such as All-Hands meetings, requiring each employee to attend an average of one offsite per quarter.

What is the ideal offsite cadence for your business? 

The frequency of offsite meetings significantly impacts your organization's ability to align, innovate, and build strong teams.  Although there's no one-size-fits-all answer, there are some general guidelines based on company size:

<25 employees

Smaller companies, typically startups, can benefit from quarterly offsites. These frequent gatherings help maintain a strong sense of cohesion and keep all team members well-informed.

25 – 50 employees 

Companies at this stage may transition to a mix of quarterly and biannual offsites. This allows for more in-depth planning every six months while still maintaining regular quarterly alignment.

51–100 employees 

At this size, hosting quarterly offsites alongside semi-annual strategic offsites could be effective. The latter can focus on more extensive goal-setting and provide more time for team bonding.

101 – 500 employees

Larger companies may adopt a cadence involving quarterly offsites, semi-annual strategy sessions, and an annual “grand offsite” or All-Hands encompassing larger strategic planning initiatives, workshops, and comprehensive team-building activities.

With even larger teams, it's a good idea to continue the previous cadence while introducing specialized offsites for different departments or teams. It is not uncommon for Offsite clients to have 10, 20, or more offsites scheduled throughout the year across different teams, once headcount is measured in hundreds of people. 

500+ employees

At this scale, companies should consider hosting department-specific offsites, monthly or quarterly cross-functional offsites, semi-annual leadership summits, and an annual global offsite. This tiered approach ensures alignment at all levels.

Examples from other remote-first companies

In recent years, offsites are not just limited to discussions about quarterly results or long-term objective planning. They have become platforms for problem-solving, team-building, and employee rejuvenation. Striking the right balance between the frequency and timing of these offsites is key to their success.

Let's explore what some companies are pioneering in this space:

Dropbox: The 90/10 rule for remote work

According to Dropbox founder and CEO Drew Houston, Dropbox has adhered to the “90/10” rule for remote work since 2021. Under this rule, 90% of working days are spent in a “remote-first” setting, and 10% of working days are reserved for company offsites. 

This roughly translates to 25 days per year spent at offsites for Dropbox team members, possibly in the form of quarterly offsites lasting three to five days each, along with additional “offsite” time at conferences and client meetings. 

While some public companies are calling for a “return to office,” Houston champions a remote-first approach for Dropbox, with offsites playing a central role in promoting business cadence.

Airbnb: A new design for remote work

In April 2022, Airbnb founder and CEO Brian Chesky announced that Airbnb employees would have the freedom to work from anywhere. One of the core expectations was regular offsite meetings. 

Airbnb's offsite policy primarily focuses on quarterly offsites at the team or department level, along with larger retreats scheduled less frequently. These larger gatherings may involve senior leadership and teams that benefit from additional in-person collaboration. Chesky's vision emphasizes flexibility and recognizing that meaningful connections happen in person. 

GitLab: Self-organized meetups 

GitLab, the original remote-first, publicly traded company, and one of the pioneering remote-first companies ever since, has experimented with various approaches to facilitate in-person connections. Some notable practices include an annual All-Hands meeting, a subsidized travel allowance for employees to visit team members, and open-sourcing many of their company operations. 

Through their internal company wiki, which is also public much like Remote’s company handbook, employees can themselves organize offsites. They are given budget guidelines, predetermined approval to processes, and access to tools like Offsite’s curated marketplace to save time and money on venue selection. Such practices have proven to be invaluable in building strong teams and keeping team members aligned.

How to start planning your next offsite

With the rise of globally distributed teams and hybrid workplaces, it’s become more important than ever to plan and budget for team retreats or offsites. Apart from sharing business goals and company updates, or discussing organizational performance and improvement, organizing an in-person meet-up can keep your team motivated, and promote a positive work culture.

Planning corporate events of any scale can be challenging and stressful. Planning offsites involves spending a significant amount of time and resources on coordinating travel, booking event venues and speakers, and arranging entertainment and accommodation, among other things.

Some key considerations you have to keep in mind before planning your next offsite include your business objectives, budget, number of employees, employee distribution, number and how regularly you should conduct offsites. 

Alternatively, you can use an end-to-end planning service like Offsite to make it easy for you to organize your next offsite. For more information about global expansion for startups, from hiring employees to managing global payroll, check out Remote’s blog.