Running an offsite is one of those things that sounds straightforward until you actually try to do it. Then you realize it’s more like attempting to teach a cat how to swim.. like, it’s possible, but the trial and error is going to leave you with scars and trauma for you and the cat. The truth is, I didn’t learn how to run these from some leadership book. In fact, there aren’t many practical resources out there on this topic. Zack Urlocker (famous to me from MySQL) has a great article on the subject, and the HBR book “How to Plan a Team Offsite That Actually Works” is pretty good, and I’ve read and can partly “Retreats That Work“. But compared to other tactical or strategic business topics, there is suprisingly little stuff out there on how to plan and run what I think is one of the most important processes in a functioning executive team. So most of what I know has been pieced together by experimenting, failing, adjusting, and occasionally stumbling onto something that worked.

Over the years, I’ve realized that the best offsites aren’t just about staring at spreadsheets in a new zip code. They need to hit a few big goals if they’re going to be worth all the planning headaches.

1. First, they give us strategic focus. It’s the one time everyone can step out of the chaos of Slack notifications and email fires and actually think about the future of the company. No one is allowed to answer a support ticket from a kayak.
2. Second, they create leadership alignment. If you’ve ever tried to get a group of executives pointing in the same direction, you know it’s a bit like herding caffeinated cats (second cat reference already). Offsites are where we stop doing the daily functional stuff and agree on what we’re actually chasing this quarter or even the year.
3. And finally, they build team cohesion. This doesn’t mean trust falls or awkward icebreakers where you have to say your “spirit animal.” It means real connection. Cooking dinner together, laughing at terrible pickleball form, or having spouses bond over yoga and day drinking. That’s the glue that makes the work stick.

Strategy and alignment and synergy and other business words are important. But if you don’t also have a little fun, then honestly, what’s the point?

Who Gets Invited?

One of the first questions people ask me is who actually gets to come. The answer is simple: just the people who report directly to me. That means my VPs and my C-levels. Keeping the group small matters. Too many people and it stops being a strategy session and starts to feel like you’re at an HOA meeting with whiskey. That’s actually the only way I would attend an HOA meeting, but that’s besides the point.

The Rhythm of Our Offsites

Over time, we’ve settled into a pattern that works for us.

• We hold one-day offsites each quarter, right at the beginning of the quarter, to reset and align.
• At the beginning of Q4, we host a three-day offsite. This one is much more involved, both in planning and in structure.

That Q4 gathering has become the cornerstone of our leadership rhythm. It’s where we not only map out the next year but also strengthen the relationships that help us make better decisions together.

The Big Airbnb Weekend

The three-day offsite is a little different. Actually, a lot different. Instead of cramming into a conference room for eight hours, we rent a big Airbnb within driving distance. It has to have something that makes it feel special. Maybe it’s a weird swimming pool, a pickleball court, a river with kayaks, or a beach nearby. Basically, something that makes it feel less like a board meeting and more like an executive retreat with paddleboarding skills designed to test our key-person insurance. A lot of these places are pretty weird. Getting a place where 5 couples can comfortably stay in a single house means either super luxurious mansions, or strange homes that have winding corridors, mapping our the evolutionary path of the renovations that made it a desirable property for events like ours.

We also come prepared. That means swimsuits, a fully stocked bar, and a Nintendo Switch for late-night Mario Kart battles. For the record, those races have only ended in tears two or three times, which I consider an acceptable casualty rate.

Spouses and partners join us for the whole weekend, from Friday through Sunday. Friday night we cook a big meal together. Saturday night we all go out to dinner. In between, the partners, who jokingly call themselves “the tech wives” even though the group definitely includes men, do their own thing. They go to yoga, they day drink, they sometimes prepare lunch for us, and in return we make sure to take them out for dinners. They get a vacation, and we get the benefit of stronger connections across the group.

It might sound unusual to mix work and family life, but it has been incredibly useful. When the people at home know and trust the people at work, it changes the dynamic completely. It creates more openness, more support, and a lot more resilience when things inevitably get tough.

Timing Is Everything

When you schedule an offsite matters almost as much as where you hold it. For example, I’ve found the sweet spot for our first offsite of the year is the third week of January.

• If you schedule it the first week of January, no one is really in the office yet. Everyone is still half in vacation mode.
• If you push it to the last week of January, the new year’s energy has already started to fade.

So the third week is usually just right.

For our one-day offsites, I like Mondays. That’s already the day we hold our management meetings, which means I have two hours of my executives’ time on the calendar anyway. It’s easier to rearrange schedules if we’re already starting from that block.

The Q4 offsite follows a set pattern too. We begin Friday morning at 9 a.m. and wrap up Sunday afternoon. Since we usually rent the Airbnb through Monday, people often stick around a little longer. Sometimes kids show up and end up swimming in the pool or playing pickleball, which is honestly a pretty great way to close things out.

Wrapping Up Part 1

That’s the foundation: who comes, when we meet, and how we structure the year. These basics took a few years of trial and error to figure out, but once we found the rhythm, it became much easier to plan and run these without burning out.

In Part 2, I’ll share what actually happens inside the offsite, including how I structure agendas, the kinds of exercises we run, and why you should never try to build your offsite plan in a Word document.

There is now a Part 2!