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Craig Kerstiens

Guidance for conducting offsites

Offsites an invaluable tool in getting a team aligned. I’ve been a part of organizations where offsites never happened, and then when they happened at a regular interval. Just because offsites happened it didn’t mean they had the same significant impact to alignment and ability to execute moving forward. What follows is a few key principles around conducting an impactful offsite.

Get out of the office

An offsite isn’t reserving a conference room for a full day and just sitting there meeting on special topics. A change of scenery is important, and nice scenery will impact your abiltiy to collaborate. One long time friend and colleague communicated to me about 10 years into his working career, that the thing he most values in a workplace is natural light. He remarked younger him wanted free food and drinks, now he finds him much happier and more productive with natural light above all other amenities. A similar environment for an offsite is very helpful.

The best option isn’t a hotel with a rented conference room, but rather an AirBnB with each person their own room, a large kitchen, and large living room. More on the why for each of those later.

From working with some teams that are often local and a portion of them remote, hosting the offsite within a 2 hr drive of your primary office can be good. You don’t waste the full day traveling, for remote team members they can also budget 1-2 days in the office to see other team members in addition to the time spent at the offsite.

Collaboration is key

Get rid of powerpoint presentations and someone presenting on a screen. That isn’t collaboration, that is a presentation. If you have a team of 8 and each person presents for an hour you haven’t collaborated for 8 hrs, you’ve been presented to for 7 and presented for 1. I personally don’t like team building exercises, but I’ll admit they can be useful here.

A presentation by the leadership at the offsite for a few minutes to frame things can be helpful. It’s key to not have a projector and folks staring at a screen. Instead having a few prepared notes and ability interactively discuss is great. Collaborating on a large notepad, or using sticky notes for ideas and brainstorming is great. One of my favorite things to do at an offsite is a gridding exercise.

2-3 days is ideal

You don’t need a full week offsite, but a 1 day offsite doesn’t really provide ideas to evolve and change over time. The ideal to me is 3 days where you can make some statements about ideas on day 1, and then drill deeper into those on day 2 or 3. Having the ability to do research on data and evaluate any plans you make is helpful. You also then can have good collaborative time, but also set aside time for contentious topics. If you cover a contentious topic and then jump right into collaboration without time to change your mindset you’re going to get a very different outcome. Breaking things up across days makes this way easier.

2-3 days also allows time for non work activities. Coming together as a team will let you work better in the future. Boardgames are a common favorite, video games are an occasional activity. Sometimes sitting by a fireplace and enjoying a nice glass of wine and just catching up.

Those moments can live on for a very long time. Many colleagues from years ago will recall how when playing “We didn’t play test this at all”, we brought back online an archived server intentionally to cause a page so an engineer would pick up his phone, only for one of us to play a card causing him to lose the game due to holding his phone. Those stories create a foundation and shared experience to build on in the future for how you work together

This takes me onto the next point…


Too often offsites are a day of meetings in a conference room, followed by dinner out at a nice restaurant. The exact opposite works better. We’ve already talked about location. But food should be collaborative as well. Over 2-3 days you may do one dinner out, but even that isn’t the norm. Instead make a meal list ahead of time, and people spend time in the kitchen together. You’ll typically find you have 1-2 more cooks in the team than others, but then you have a lot of helpers.

It actually reminds me a bit of my wedding reception back home. I smoked about 80 lbs of meat for the reception. As we were taking the meat off, I walked back in to 4 generations of in-laws, the older ones teaching the younger ones how to pull pork.

Cooking together is another form of collaborating. You can easily learn about cultures and backgrounds. I didn’t realize melon with proscuitto was always supposed to be server with port if you’re in France, but now I can eat it no other way. Splitting up the duties so that 2-3 help cook a meal means you don’t spend all your time cooking, but you get people working together.

Don’t steal a weekend

I mentioned 2-3 days is ideal. Please don’t use one of those days as a weekend. As the leader or coordinator of such you may not have weekend obligations and happy to give up a day of it. But many on your team may have other commitements and such, an offsite is valuable, but asking people to give up their weekend to essentially do more work isn’t a great look.

Offsites for everyone

Offsites aren’t just for management. The folks in boots on the ground doing the work has as much need and value as the leadership team sitting there determining the next 5 year strategy. Allowing engineers that are building things, supporting customers, answering pages to brainstorm and collaborate on how to more effectively design the systems and move more quickly will pay huge dividends. You’ll find experiments, and then new tools and systems that allow you to ship things faster with higher quality. Collaborating with the product team is key as well, an engineering offsite in isolation leaves out the voice of the customer. A product offsite without engineering leaves you daydreaming of solutions without being grounded in the reality of what is possible.