The Ultimate Guide to Holding an Incredible Executive Offsite – Before the Meeting

Our company was growing, we were up over 20 employees, and we’re averaging around 25% growth each year. Life was good, but as you well know, that’s only half the story in business.

The other half isn’t quite as pretty. We were struggling to hire employees fast enough to keep up. Every one of us was juggling balls while spinning plates. We might as well have been doing it with our eyes closed.

Though we were succeeding, we knew we weren’t going to continue growing at this rate if we didn’t do something to control the chaos. My two partners and I decided we needed to have an executive offsite together because that’s what all the cool kids were doing.

And yeah, I mean kids. Funny story. Being the most responsible of the group, I was tasked with reserving the condo where we would be staying. The problem was, I wasn’t old enough to sign the contract. I was 23 at the time, and you had to be 25 or older to sign (and rent a car, which I found out that same trip).

Anyway, as we were getting ready for our fancy offsite on the Florida coast, I realized I had a pretty big problem on my hands. I had never been to an executive offsite, and now I had to lead one. I had no idea what to do.

I did my best to piece together what I could after a quick Google search or two. Back then, I thought the event was a decent success. Looking back on it now, I’d give myself a solid C+.

We had an idea of where we were going over the next few years and a rough plan to get there. But we wasted so much time getting caught in the weeds. 

We debated the color and placement of a button on our website for over two hours.

We tried to take notes, but because we covered so much minutia (and because we were terrible notetakers), we didn’t understand them once we got back to the office.

We focused too much on what and how at the expense of getting aligned on our why.

We focus too much on what and how at the expense of getting aligned on our why. Share on X

Over the next 10-years, I led dozens of executive team meetings, some went really well, and some went not so well.

In this series, I’m going to boil all that research and personal experience for you. By the end, you’ll be ready to run a killer offsite that is not only a lot of fun but also moves you and your team downfield further and faster.

In this article, I will show you how to prepare for an offsite and provide some simple but profound advice from what I’ve learned along the way.

In the next article, I will give you a complete agenda and teach you everything you need to know to crush day one of your next offsite. You and your team will end the inspired, informed, and ready for day two.

In the following article, I’ll give you a complete agenda to build on everything you accomplished during day one and carry all that momentum into day two, where you’ll define the next steps and transform your discussion into action!

And in the final article, I’ll show you some of the mistakes I made after the offsite and how you can avoid those same common mistakes with your team.

Nuts and bolts

Before we dig into the strategies and agenda, I want to address a few logistics that can make or break your meeting.

1. Keep it small. Keep the number of attendees as low as possible. It will be easier to plan the event, have rich conversations and debates, and make decisions. Don’t let inclusiveness limit your effectiveness.
2. Manage your energy. Keep sessions at or below 90 minutes. Have water, coffee, and tea in the room and some snacks and fresh fruit. Take frequent breaks, but keep them short. And keep the event at three days or less. Less is more. Remember Parkinson’s law? “Work expands to fill the time allotted.” You’ll probably start to see a drop in energy on day three.
3. Get away from your office. You cannot meet in your office. It won’t work. There are too many distractions. Your attention will get pulled away from the important issues you need to discuss.
4. It doesn’t need to be far or expensive. When money was scarce and time was tight (lots of young families with kids to care for), we rented an office at a local co-working space. It cost us a couple of hundred bucks but was enough of a change of scenery to give us the space we needed to focus.
5. Don’t feel pressure to entertain. Sometimes it’s a lot of fun to kick back together (at the meeting place, a restaurant or bar, or a sports event) or have an adventure together (zip-lining, horseback riding, wave running, or hiking). Other times, you need to get down to business. Try it both ways and see what works for you.
6. Schedule the event well in advance. I was so bad at this, and it was a constant source of frustration for my team and me until I set repeating dates for the same weeks of each year. Then, the administrative effort was virtually nothing, and the team had a schedule they could plan around. 
7. Take great notes. I’m a terrible notetaker. Many leaders are. But you will cover so much information that you can’t afford to forget to take notes. Designate someone as the notetaker (admin assistant, etc.). We would bring a stack of giant sticky notes and place them all over the walls in the room. Then we’d take turns taking notes. Because everyone could see it, it was easier to remember to take notes, and it was easier to highlight areas of confusion during the meeting. Then one person would take the stickies back to the office, consolidate them into a nice, neat report, and distribute it to the team.
8. Have a clear agenda. Don’t try to wing it. The point of an offsite is to create clarity for your team. Winging it will either create confusion or point you clearly in the wrong direction or both. Distribute the agenda and the relevant data two weeks BEFORE the meeting. I know this can be hard in a small organization, but it is extremely important. If you follow this advice, your decisions’ quality and ability to execute those decisions will increase dramatically. I’ll explain this one in more detail.

If you’ve never had an offsite before, or if you’ve always just used the ol’ make-it-up-as-we-go approach, or if your meetings feel boring and unproductive, then check out next week’s article. I’ll show you how to make Day 1 of your offsite a day that will be so productive and energizing that you and your team will never forget it!