In a recent interview on workplace culture, flexible work guru Brian Elliott shared that when it comes to hybrid work, offsites are not just a nice-to have, but a must:

"Nowadays, teams are often spread across different cities, or even countries. Bringing them together 3-4 times a year, with a balanced approach (typically a 50/50 split between deep work on business goals and time for social connection) can accelerate alignment and strengthen relationships." - Brian Elliott. 

The data confirms his thesis.

Atlassian, one of our favorite remote-first companies, has internal data showing that employees who meet with their teams in person experience a 27% boost in connection, which lasts for four to five months. This increase is even greater for new hires and recent graduates, and it provides more value than random in-office encounters.

So, how can HR and workplace leaders plan those offsites for maximum impact, especially for hybrid and remote teams?

Purpose, duration, and timing: 4 key data points for planning your next offsite.

A recent report by Worktripp, the Offsite Trends Report, provides the answers.

Key findings include:

1. Connection and belonging are primary purposes for offsites, while learning and skill development rank among the lowest drivers for companies to hold these events. 
2. 3.5 is the average number of nights for all surveyed teams. This should give you a quick sense of the ideal timeframe for your own offsite agenda.
3. September is the most popular month to organize offsites. This aligns with companies' efforts for post-summer resets, strategic realignments, and preparation for the final quarter of the year (Q4).
4. Planning timelines vary by role, with HR-related roles planning the furthest in advance, while founders tend to plan on the opposite end of the spectrum.
5. Spending ranges from $520-$2,600 per person. The team size and stage of the company, as well as the industry, plays a role in determining your budget.

Let’s dive in to explore further!

1. Connection & Belonging Tops Reasons To Plan Offsites

34% of teams cite "Improving Connection & Belonging" as the top reason for offsites, emphasizing the need for distributed teams to build stronger bonds through in-person meetings. As Worktripp CEO Sophie Bailey commented exclusively for FlexOS:

"Connection and belonging is always the number one driver for all offsites. This is because we need to continually top up trust and psychological safety, before any higher-level strategic work is realized and especially important when we might work remotely, and in a world of AI." - Sophie Bailey, co-founder of WorkTripp.

"Improving Communication & Productivity" is the focus for 22% of teams, showing that many companies use offsites to realign, foster better communication, and boost future productivity. For very large teams, this goal is especially critical for maintaining alignment and reducing silos.

Another 22% prioritize "Planning & Looking Ahead," using offsites as a strategic platform for setting a future vision—particularly essential in fast-growing environments. Larger teams, in particular, allocate more offsite resources to planning while balancing team dynamics.

However, Sophie notes that this doesn’t mean connection and belonging aren’t also high priorities for large companies:

“When extra-large teams meet, communication and productivity also move up the ladder in terms of goals. Why? Because as teams scale, efficient and effective communication becomes more challenging. Power dynamics, fear of judgment, and diffusion of responsibility all come into play.” - Sophie Bailey

This is why Sophie advises HR leaders should break down offsites into smaller groups. “We find that breaking down into smaller groups is more effective to build that trust, connection and ultimately the strategic work you're looking to get done,” she said.

2. The Most Popular Length of Stay is 3.5 Nights

Wondering how long your offsite should be?

The average length of time teams spend together is 3.5 nights.

But how long a company actually spends together in an offsite often depends on the size and stage, which determines the type of offsite companies embark on:

• Off-sites: Strategic meetings aimed at bigger picture planning and critical business strategies that are particularly effective in building trust and enhancing communication.
• Retreats: Focus on team bonding and innovation. Retreats are crucial for strengthening interpersonal relationships among team members.
• Coworking and Cross-functional Anchor Weeks: These gatherings are for outcome-based goals and urgent deliverables, facilitating quick decision-making. Coworking sessions advance project progress and decision-making.

According to the report, offsites and retreats typically last 1-2 nights, while co-working weeks can last up to 7 nights.

3. September is the Most Popular Month for Offsites

September sees the highest volume of offsite requests, aligning with companies’ goals for post-summer resets, strategic realignments, and preparing for the final quarter. It’s a pivotal time for leadership to reconnect with teams after summer breaks and set a focused tone for Q4 performance and goals.

June is another peak month, due to mid-year reviews and team-building efforts before summer holidays. Many companies use this time to evaluate progress, refine strategies, and ensure teams are aligned before the break.

This suggests that quarterly offsites are becoming essential for many businesses, which is aligned with what Brian Elliott shared with me:

“Quarterly team gatherings can have a huge impact (to build connection and culture). Quarterly team gatherings work, and are essential for distributed teams” - Brian Elliott

Pro tip? Quieter months like February and April are an opportunity for companies to schedule offsites when competition for venues is lower, offering better rates and availability.

4. Founders and HR Leaders Approach Planning Differently in Terms of Timing

How long before an offsite should you start planning? It depends.

According to the Worktripp data, people-related roles plan the furthest in advance, with an average lead time of 136 days. Marketing roles average 117 days, while Executive Assistants (EAs) and Operations roles have similar planning windows of around 110 to 106 days. Chiefs of Staff generally allow about 86 days on average. 

Those with the title of COO (Chief Operating Officer) tend to give themselves around 76 days to plan offsites, which is just over two and a half months. Founders plan with the shortest lead time, averaging 63 days.

The reason for such a big gap between founders and other leaders comes down to team size as well as a level of spontaneity, says Sophie:

"People managers may work at slightly larger, better-resourced organizations. These companies are more likely to hold annual offsites rather than team-level ones, leading to a longer planning cycle. Founders and COOs, however, often feel an urgent need to bring everyone together, typically within a 3- to 6-week timeframe. They’re also managing more with fewer resources, explaining the tighter planning timelines." - Sophie Bailey

5. Budget Allocations Vary Significantly by Industry

The data reveals interesting patterns in how different sectors approach offsite budgets. The average per-person budget across all companies is $688, while the median sits at $389, indicating a wide range of spending approaches.

Tech companies tend to lead in budget allocation, with per-person spending ranging from $520 to $2,600. This higher investment often reflects their focus on innovation and team building, particularly crucial for companies working at the cutting edge of technology.

As Sophie Bailey explains:

"Technology companies often view offsites as crucial investments in innovation and team cohesion. The higher budgets we see in this sector reflect a strategic approach to building strong team cultures, especially important in fast-moving tech environments." - Sophie Bailey

The data shows distinct patterns across different sectors:

• Technology and Software Companies invest the most, allocating up to $2,600 per person
• Financial Services and FinTech maintain robust mid-to-high range budgets
• Consulting and Professional Services tend toward mid-range budgets
• Venture Capital and Startups, despite smaller team sizes, often maintain higher per-person budgets

This spending variation reflects different industry priorities and approaches to team building. While tech companies might emphasize innovation workshops and extended collaboration sessions, consulting firms often focus on shorter, more focused gatherings.

Offsites: The Bottom Line

It’s clear that offsite planning is no longer just an ad-hoc “nice-to-have.” For most companies, offsites and retreats are a strategic investment in their people, with connection and belonging as a dominant focus for most companies.‍

Eager to get started? Check out the FlexOS guides to planning remote company retreats. Have an opinion to share? Feel free to email me.