The Cadence: How To Plan Offsites Throughout The Year

When and how often should you plan team retreats? We discuss in detail and walk through examples from "pioneering" remote companies like Dropbox, Airbnb, GitLab, and 15Five

Oct 19, 2023

Right now, most companies (including yours, perhaps) have no “strategy” a round planning offsites or team retreats.

Many People Leaders responsible for planning offsites get stuck in a vicious cycle of convincing their CEOs/Founders to plan team retreats, then waste valuable time going back-and-forth on everything from budget to destinations to agenda, only to be left with limited time to plan an offsite.

Still, the ROI from these offsites ends up being quite high, leading to a commitment for future offsites, only to repeat this cycle by department with each quarter and each year.

Just like you need a rhythm of business, or operational excellence to manage the chaos of startups, you need a predictable offsite cadence.

With 2024 approaching, you might be evaluating your offsite plans for next year. What is the optimal offsite cadence to keep your team(s) aligned, motivated, and adaptable to the ever-changing business climate?

At Offsite, we’ve planned hundreds of team retreats for VC-backed startups, publicly-traded companies, Inc 5000s, communities like YPO and YEC, nonprofits, etc.

Before then, I (Jared Kleinert, Founder/CEO of Offsite) was one of the first ten employees at 15Five, an early remote-first company who leveraged its offsites to build award-winning culture as an enterprise SaaS company that assists thousands of other organizations with increasing employee engagement, retention, and alignment.

With my personal experience, our company’s collective offsite-planning experience, and examples from other companies like Dropbox, GitLab, and Airbnb, I wanted to start the conversation with you about what offsite cadence is best for your company based on the size of your team, the nature of your business, and your unique goals heading into 2024.

What Others Are Doing:

In recent years, offsites have become more than just an opportunity to discuss quarterly results and long-term objectives. They are now platforms for problem-solving, team-building, and rejuvenation. To make the most of these events, you need to find the right balance between offsite frequency and timing.

For case studies on how to plan the right offside cadence, we look to Dropbox, Airbnb, and GitLab who have all publicly shared ideas on their remote work policies.

1. Dropbox: The 90/10 Rule for Remote Work

According to a recent interview with Dropbox founder/CEO Drew Houston, Dropbox has followed the “90/10” rule for remote work since 2021.

90% of working days at Dropbox are spent in a “remote-first” setting, and 10% of working days are spent at a company offsite.

Out of ~250 working days per calendar year, this means roughly 25 days are spent at offsites for Dropbox team members, which likely translates to quarterly offsites for all employees lasting 3-5 days each, plus additional “offsite” time at conferences, co-working while traveling to meet clients, etc.

While some public companies like JPMorgan and Goldman Sachs are attempting “return to office” campaigns, Houston has insisted on a remote-first approach for Dropbox. Offsites are a core component to making this possible.

2. Airbnb: A New Design For Remote Work

In April 2022, Airbnb founder/CEO Brian Chesky announced that Airbnb employees will be able to live and work from anywhere, along with five tenants to explain how this would work.

One of core expectations was that employees would meet regularly for offsites.

Quarterly offsites at the team/department level became the main offsite policy, with other larger retreats scheduled less frequently that may require certain employees more frequently (perhaps senior leadership and/or teams who’d benefit from additional in-person collaboration, such as product and engineering teams).

“Why did we come up with this design? The world has become more flexible. Our business wouldn’t have recovered as quickly from the pandemic if it hadn’t been for millions of people working from Airbnbs. We also had the most productive two-year period in our company’s history—all while working remotely.
Two decades ago, Silicon Valley startups popularized open floor plans and on-site perks. Today’s startups have embraced flexibility and remote work. I think this will become the predominant way companies work 10 years from now. Companies will be at a significant disadvantage if they limit their talent pool to a commuting radius around their offices. The best people live everywhere.
But there’s a tension. The most meaningful connections happen in person. Zoom is great for maintaining relationships, but it's not the best way to deepen them. And some creative work is best done in the same room. The right solution should combine the efficiency of Zoom with the meaningful human connection that happens when people come together.
Our design attempts to combine the best of both worlds.” - Brian Chesky

For the full list of policies from Airbnb and reasons for meeting regularly, you can read Chesky’s full tweet thread here.

3. GitLab: Experiments with Co-working Retreats and Self-Organized Meetups

As one of THE pioneering remote-first companies (and the first publicly-traded company to be remote-first, to my knowledge), GitLab has experimented with a wide range of ways to facilitate in-person connections as a remote-first company.

Luckily for us, they also open-source much of the company operations, so we can read on their public handbook about various ways in which they facilitate offsites.

Some of the highlights include:

an annual All-Hands meeting - while they admit this is less of a “differentiator” today, it is a foundational practice for running a remote or hybrid company. I’d argue you MUST bring your entire team together at least once per year because otherwise you run the risk of disengaged team members who don’t trust each other and/or aren’t aligned on company strategy. At 15Five, the annual All-Hands meeting was one of the highlights of every year, contributing to being named #3 on Glassdoor’s “Best Places To Work” list in 2020.
Subsidized travel to visit team members - GitLab developed a program to subsidize certain employee travel when visiting other team members because in-person work can lead to greater empathy, cultural understanding, and innovation,.

There are countless other examples at offsite.com where we have case studies with clients on their offsite cadences, why those type of retreats work for them, and how you can save time, money, and stress in planning your company’s team retreats.

Factors To Consider In Determining Your Offsite Cadence

Some of the main factors to consider in planning your company’s offsite cadence are:

Employee distribution - it is easier for regionally-distributed teams to meet more often, compared to teams dispersed nationally or internationally.
Business objectives - certain business needs will dictate more frequent offsites. For example, many business operating models (from Traction to Scaling Up) and business literature (such as Patrick Lencioni’s Five Dysfunctions of a Team) suggest leadership teams plan quarterly offsites. If you experience a RIF, or a major pivot within the company, you may also wish to “rally the troops” with an offsite. Additionally, a sales leader may wish to plan a Sales Kickoff at the beginning of each fiscal year as well as a President’s Club event to incentivize performance.
Headcount - smaller companies can include most or all employees with less offsites, whereas larger companies may have to plan more offsites (by team or department, most likely, consisting of smaller attendee counts compared to All-Hands meeting, Sales Kickoffs, and other larger gatherings).
Budget - remote and hybrid companies who plan ahead can reinvest savings from reduction or removal of office expenses like rent, snacks, meals, and more into a predictable offsite cadence. If you plan ahead, you can standardize budgets across all your offsites throughout the year, so each team spends roughly the same on their retreats, and you can ultimately plan more (and better) offsites for the same amount of money.

Harvard Business Review suggests that offsite frequency should be flexible. Smaller teams can benefit from quarterly offsites, while larger organizations may opt for biannual events.

15Five encourages every offsite has a clear purpose, actionable agenda, and a post-mortem for continuous improvement is critical for any organization.

The key is to adjust your approach according to your team's unique needs and your overall business goals.

How Often (And When) Should You Plan Offsites?

The frequency of offsite meetings can significantly impact your organization's ability to align, innovate, and build strong teams. While there is no one-size-fits-all answer to how often a company should plan offsites, there are some general guidelines to consider based on company size.

25 Employees: For smaller companies, typically startups, quarterly offsites are a great choice. These frequent gatherings help maintain a strong sense of cohesion and keep all team members well-informed.
50 Employees: At this stage, transitioning to a mix of quarterly and biannual offsites could be effective. This allows for more in-depth planning and reflection every six months, while still maintaining regular quarterly alignment.
100 Employees: Companies of this size may benefit from hosting quarterly offsites in addition to semi-annual strategic offsites. The latter can focus on more extensive goal-setting and provide more time for team bonding.
250 Employees: A well-balanced cadence for mid-sized companies could involve quarterly offsites, semi-annual strategy sessions, and an annual "grand offsite" or All-Hands encompassing larger strategic planning initiatives (like multi-year planning or preparations for an IPO), workshops, and comprehensive team-building activities.
500 Employees: Larger organizations may find it beneficial to continue with the aforementioned cadence, while also introducing specialized offsites for different departments or teams. For instance, hosting division-specific offsites alongside company-wide events can enhance the alignment of smaller groups within a larger entity.
1000+ Employees: At this scale, companies should consider hosting monthly or every-other-month department-specific offsites, quarterly cross-functional offsites, semi-annual leadership summits, and an annual global offsite. This tiered approach ensures that everyone from individual teams to company leaders remains aligned and focused.

To optimize your offsite cadence for 2024, it's crucial to plan the timing of these meetings strategically.

Here's a suggested yearly roadmap based on company size:

25 Employees: Start with a kickoff offsite in Q1 to set the tone for the year. Follow up with offsites in Q3 and Q4. Hosting an offsite during the second quarter can be helpful for mid-year evaluations.
50 Employees: Similar to the 25-employee companies, kick off the year with an offsite in Q1. Schedule additional offsites in Q2, Q3, and Q4 to keep alignment and momentum.
100 Employees: Begin the year with a grand offsite in Q1 for comprehensive planning and strategy. Follow up with cross-functional offsites in Q2 and Q4. Conduct semi-annual strategic offsites in Q2 and Q4.
250 Employees: A yearly plan for larger companies could involve a kickoff offsite in Q1. Continue with department-specific offsites in Q2 and Q4, and have a grand offsite in Q3. Run leadership summits in Q2 and Q4 for comprehensive planning.
500 Employees: With more extensive teams, consider hosting department-specific offsites monthly, company-wide offsites in Q1, Q3, and Q4, and semi-annual leadership summits in Q2 and Q4.
1000+ Employees: Develop a cadence that aligns with specific departmental needs, such as monthly departmental offsites, quarterly cross-functional offsites, an annual global offsite in Q3, and semi-annual leadership summits in Q2 and Q4.

Continuing The Conversation

Incorporating these strategies and adjusting your offsite cadence according to your organization's growth and objectives will contribute to a successful 2024 and beyond.

Every company is different, and so the team at Offsite is committed to being a resource for you as you work to ensure your team(s) remain agile and ready to tackle whatever problems and opportunities come your way.

Email me anytime at jared@offsite.com, or visit offsite.com for client case studies to see how other companies are planning their offsite cadence.

If you haven’t already, subscribe to The Offsite Blog below for agenda templates, budgeting spreadsheets, and more thought leadership like this post around offsite planning, remote work, increasing employee engagement, and more.

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Plus, we offer end-to-end offsite planning services if you want a “done for you” experience. See why companies like Buffer, Webflow, 15Five, Linear, Metabase, Hampton, and others trust Offsite for their team retreats.

Thanks for reading!

-Jared

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