What Are We Even Doing Here? Tactical Tips For Better Offsites

Picture this.  The team has an offsite coming up.  It’s somewhere fun.  

As you’re on the plane heading to the venue, you wonder if you should have done something specific to prepare.  

What’s this offsite about, anyways?  Whatever, you think - you’ll figure it out as you go.  

Fast forward a few days.  You’re on your way home.  The offsite was awesome: You got to know your team a bit better, you had some great meals, and you spent some time working together.

Fast forward a few days.  You’re at your desk.  What was the offsite about again?  What did you and the team agree to?  You’re not quite sure, but no matter, there are a few open tasks to get to, and off you go.

Cue the end credits as the offsite fades into a distant memory.

If any of this sounds familiar, worry not - it doesn’t have to be this way.

Here are a few tactics to focus your offsites to propel your teams forward with clear, documented direction.

What are we doing here, anyway?

The first thing is the most important thing (after picking your venue) - figure out with your team what success for your offsite looks like - AKA - what’s the goal of your offsite?  Maybe you’re figuring out your next set of features, or determining the scope of your next product launch, or figuring out a direction for a next marketing campaign.  Whatever it turns out to be, this is the North Star, and having this figured out in advance is the key to a successful offsite.

“Figure out with your team what success for your offsite looks like. Whatever it turns out to be, this is the North Star, and having this figured out in advance is the key to a successful offsite.”

Determining your goal up front will help guide your agenda (and yes, you need an agenda).  Once you know what the point of the offsite will be, you can break that down into individual sessions with their own goals and even, if it makes sense, assign a theme and set of sessions to each day that you’ll be working and meeting together.

Critically, throughout your offsite, you’ll want to come back to the goal of your time together.  Ask your team at the start and conclusion of each session: are you making progress on the offsite goal?  Are you making progress on the session goal?  If not, consider changes you can make to make the most of your time together.

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Pre-work is the way for offsite success

Research has made it pretty clear that brainstorming in a group is not a great way to come up with the best ideas.  Teams do their best work when they have the opportunity to think about a problem on their own and come up with creative solutions, and then bring those together to discuss.

The way to make this happen for your offsite is through thoughtful pre-work.  At this point in your  preparation you’ve figured out an overall goal and laid out daily sessions.  Those sessions need owners and the owners should think about whether the session should include pre-work.  More often than not, pre-work is a helpful addition.

Teams do their best work when they have the opportunity to think about a problem on their own and come up with creative solutions, and then bring those together to discuss.The way to make this happen for your offsite is through thoughtful pre-work.

Consider what questions you want the team to think about ahead of time and provide links to whatever context they should consume ahead of the exercise, articles, internal strategy pages, whatever is appropriate.  Don’t forget to timebox your pre-work (don’t spend more than 30 minutes or an hour per chunk of pre-work) and be sure to circulate your list of pre-work with enough lead time before the offsite so things don’t become a scramble.

If a tree falls and nobody’s there to document it in Notion, did it really fall?

OK.  You’re at the offsite.  You’ve got your sessions.  Everyone’s done their homework.  It’s go time.  Now what?

Every session must have a scribe!  Ideally this is not the session leader. The scribe is responsible for capturing an artifact for the session.  This might be a page of notes with a summary up top.  Or if it’s a creative session, there might be some other kind of artifact, like an arrangement of sticky notes or drawings.  In those cases, notes might include photos or even video from the session, whatever makes sense.  But the key is, there has to be some documented expression of the session that you can refer back to later.

Reducing all the artifacts to an offsite summary right after the offsite is key to maintaining all that momentum you picked up from your time together.  Document, circulate, and don’t delay - do it right away.

But what do I do with all these artifacts?  At the end of the offsite, the offsite leader is going to take all of the artifacts together and put together an overall summary that answers one question: did we meet the goal of the offsite, including a summary of what was learned, figured out, decided, or whatever.  And if the offsite’s goal wasn’t reached, why, and what the team is going to do about it.

It’s critical that the team doesn’t delay at this stage.  Reducing all the artifacts to an offsite summary right after the offsite is key to maintaining all that momentum you picked up from your time together.  Document, circulate, and don’t delay - do it right away.

Remember: Free time is an investment in focus time

Offsite time is precious, and you may have to resist the urge to over-program every minute with sessions and work.  Attention, unfortunately, is limited.  

If you spend every minute of your offsite working, you’ll end up losing focus and your offsite might derail.  Be mindful and build in breaks in between sessions.  Be careful about travel time and time zones - these can sap productivity and if you have enough time in your schedule, you might consider building in travel days to get to and from your venue.  

Think of your sessions as mini sporting events - you want your athletes in peak condition for each session to end up getting maximum performance for your team.  Plus it’s no fun if you just grind the whole time.  🙂

Damn that sounds like a lot of work!

This is a lot of stuff.  To recap, ahead of time…

• Figure out why you’re meeting and reduce that into an Offsite Goal.
• Break your offsite into sessions, and assign session leaders.
• Leaders have to create pre-work, and get that to your team well in advance so they have time to do it.
• Capture your sessions into artifacts.
• Use those artifacts to summarize the whole thing right after it ends.

While that’s a lot to do, the alternative is dire.  Offsites are super costly, and not just in terms of dollars.  You’re asking your teams to leave their personal lives and any care giving obligations they may have, to stop work on any ongoing projects, and to focus entirely on the goal of the offsite (with breaks and snacks, of course).

By being intentional and thinking through the why of getting together ahead of time, and making sure you document what you learn as you go, and summarize it all in the end, you’ll capture the magic in a bottle.

That’s a tall order, and you have to make it count.  By being intentional and thinking through the why of getting together ahead of time, and making sure you document what you learn as you go, and summarize it all in the end, you’ll capture the magic in a bottle.

It will be clear whether the offsite was a success, and the chances that it will go well will be greatly improved by thinking it through in advance (both in terms of setting up the offsite and collectively working through the pre-work).

Teams will leave the venue with a clear sense of what was accomplished, and be able to maintain their momentum in the ensuing weeks.  There won’t be ambiguity about any of this because you wrote it all down.

Everyone wins!