When is the Right Time for an Offsite?

When is the right time to start running off-sites, and what frequency makes the most sense?

Are we old enough? Big enough? Revenue-y enough to justify the cost and time of taking the leadership team offsite?

These are the questions founders ask themselves when deciding if they’re ready to run their first off-site. I’ve found that too many founders wait too long for their first off-site and then rush to overcorrect. The answer isn’t always about the size or age of a startup but rather what the leadership team needs and how much time they have together.

The 12-Person Rule

Many startups follow the 12-person rule when it comes to setting up their first off-site. The assumption is that at this point, you have enough leaders outside of the founder/CEO to justify an off-site meeting. However, following an employee or revenue benchmark is arbitrary.

It’s better to look for structural indicators that show that you’re ready for an off-site. Do you have multiple managers in charge of separate functions? Can the founder skip a meeting without the business succumbing to gridlock? Is the all-hands outgrowing the room?

If you answer “yes” to these types of questions, it’s a sign that you have enough organizational complexity for leaders to need dedicated time during an off-site to get aligned. Some companies have this at four people, while others don’t reach it until 20 people. There is no specific number that tells you it’s time for your first off-site; it’s about your structure. 

Real-World Example

In one instance, I worked with a startup that had only eight people. While the founder thought it was too early because they didn’t fit the 12-person rule, three of the eight were leading distinct functions, making independent decisions daily. That was enough structure and complexity to hold an off-site.

This turned out to be the right choice because the team was about to double in six months. We ran a one-day offsite, and six hours of structured time together saved that startup from three months of misaligned execution on their product roadmap.

Fit Into the Cadence

Once your startup has its first off-site, the goal should be to make it a regular event. For most startups in the $3-30 million revenue range, a quarterly off-site is sensible because it naturally fits into the three-month energy cycle. With the way startups at this stage are growing, there is almost always something that requires alignment, whether it be priorities, a hiring plan, or other steps that are in the works.

The cadence that startups at this level should be following will include a daily huddle, weekly standup, monthly deep dive, quarterly planning, and annual strategy. Scheduling a quarterly off-site should fit naturally into this cadence. Thus, they should be a regular occurrence rather than a stand-alone event.

The Pricing Angle Nobody Talks About

Obviously, holding an off-site is an expense, but it’s nothing compared to the cost of not having one. If the founder has to keep making the same decision or raises questions everyone thought were closed, those are signs of clear misalignment. If an off-site can correct that misalignment, you can expect a 10-20% boost in productivity, and even that’s being conservative.

If you consider one day of salary for your leadership team, plus the cost of the venue, there is a cost of holding an off-site. But if it helps you get aligned and provides a productivity boost, the ROI can be 30X or more. Just look at the table:

These numbers show the waste in payroll and lost revenue that are likely if your leadership team isn’t properly aligned. Considering the money that is thrown away when a startup isn’t aligned, the cost of an off-site is just a rounding error. This is where midstage startups either accelerate (with the right systems) or slow to a crawl (without them).

Invest in a Venue

The mistake I see founders make is trying to optimize for venue cost. They just want to meet in the office conference room instead of thinking about quality time. You can't think strategically in the same room where people Slack you about production bugs. The venue change matters not because it's fancy, but because it creates psychological separation from execution mode.

The middle path that works is a hotel conference room that’s 20-30 minutes from the office. This is far enough that people can't "just pop back for one thing," but close enough that it doesn't require flights. The total cost is around $500-1,000, but the value that it brings is that your team actually disconnects.

When You're Not Ready

If you're under 10 people and the founder is still in every meaningful conversation, you probably don't need an offsite. Instead, you need better weekly meetings. Meanwhile, if you can't articulate three strategic questions that require at least four hours of dedicated thinking time to answer, you don't need an offsite. 

Instead, you just need a longer leadership meeting. If your "leadership team" is really just the founder/CEO plus one person, take them to lunch once a month for 2-3 hours. This has the same benefit for a fraction of the cost.

The Pattern

Successful off-sites are all about getting into the right pattern. The best pattern to follow is to start off-sites when you hit 10-12 people with at least three people in leadership conversations. Run them twice a year until you're past  $10M, then move to quarterly. 

Remember to optimize for thinking quality, not venue cost. Calculate ROI based on the cost of misalignment, not the cost of the room. Finally, if you're wondering whether you're ready, you probably are. Founders who start asking if they’re ready for an off-site have probably been ready for 6-12 months. In other words, when you start asking if you’re ready, start planning one instead.

Ready to Shift Your Startup Into 3rd Gear?

If your company has found product-market fit but growth still feels chaotic, with you as the bottleneck and your team not fully owning outcomes, it might be time for systematic execution, not another quick hack. Midstage Accelerator helps post-PMF founders move beyond founder-led chaos into strategic clarity, alignment, and accountability systems that actually scale.

👉 Apply to the next Midstage Q1 Cohort and transform how your team executes, from reactive to relentless growth.

Or, book a free 30-minute 3rd Gear Diagnostic to pinpoint exactly where you’re stuck and what it takes to break through.