How to create your first offsite

“Tiring, taxing, not a great use of our time as a team”. When feedback poured in from her team's most recent offsite, Jamie knew she needed help.

Thirty team members flew to Chicago expecting an engaging and unique opportunity to learn and connect with their team. What they received instead was a day-long rotation of back-to-back department updates.

Designing and leading team offsites is new to Jamie and many leaders like her. And when we find ourselves in unfamiliar situations, many repeat or fall back on what feels familiar. At our offsites, this often looks like full days of department presentations instead of a more dedicated and deliberate approach. 

Yet our employees now know there is a much higher bar for their time and their effort -- especially when it means leaving their families at home. Here are 4 ways Jamie can improve her next scheduled offsite, and you can too. 

Start with the effect 

Before: start with the information

After: start with the effect

We tend to start with information first. What content should we share? Who should present? What topics are folks interested in? 

But, beginning with the information we want to share is akin to a carpenter who attempts to increase business by starting with the tools they’ll use (nails, hammer, saw) instead of what he or she is creating and the effect they and the customer wants (a table that doesn’t break, a new closet, a bookshelf for your child’s room). 

Get crystal clear on what this tool (an offsite) is meant to accomplish. Ask yourself and a small group of stakeholders:

  1.  What does success look like? Can you tell a story about the before and after?

  2. What specific outcomes do you want to see?

  3. What do you want participants to think, do, say, and feel at the end of the offsite?


Narrow down to 2-3 objectives maximum. Or, ask yourself what is the one problem we most want to solve in this offsite, or the central question you want to answer. 

These questions remind us that underneath the request for a gathering is a change request, for something to be new or different.  Even if we lead with the content, it’s the effect we’re ultimately after. And if we’re not clear on what this need is and why it matters, those we’ve gathered won’t be clear either.

Pull together, push apart 

Before: Do everything synchronously

After: Maximize asynchronous and synchronous communication 

It may seem counter-intuitive, but a key step in planning a great offsite or event is to determine if you should, or need to have one in the first place. This is one way you can avoid the “this offsite could have been an email or recording” lament. 

Follow the motto: Pull together, push apart.

“Can you just send me the slides?”. If people are only present to be pushed information (like Jamie’s team was), the value of being together synchronously declines.

You’ll find much more bang for your gathering buck if you reserve synchronous gatherings for those that need that engagement (buy-in, behavior change, or ownership from others). Here we’re doing more than transmitting information - we’re pulling people together to spark a change in thinking or behavior. But, beware: not every gathering requires engagement.

Use this flow chart to also help you determine what’s worth your time.

Add in breaks

Before: Pack everything in

After: Pack Effectively 

Although we may be tempted to, we never actually buy every single item in the grocery store when we go shopping. We may want to consume all of the food - but we can’t. There are limitations to consider from our budget to freshness, storage space, usability, etc. We also know the store will still be there next week, and we can go back for more.

These same limitations exist for our employees, from cognitive capacity, to transfer ability, and relevancy - whether it’s a class, offsite, new hire orientation, or all-hands.

Though we may be intrigued by the amount of information we’ll receive, we can’t necessarily consume or recall it all, at least not meaningfully. This means days of department updates aren’t just time poorly spent, it’s time wasted.

Here are 4 tips to create a more brain-friendly and consumable gathering:

  1. Create a grocery list: Have clear objectives that help you easily discern what you need to include and what you don’t. It’s self-control for slide decks.

  2. Speed limits do apply: When it comes to remembering or retaining information, the speed of information flow matters. Build explicit nudges and breaks (at least 15 minutes every 2 hours) into the gathering so people can process what they just consumed, alone or with each other. 

  3. Ask a few pointed questions - “how will you apply what you learned?”. You want to know, just like a game of telephone, how much is that learning being passed on? Without this time or energy, we are less likely to take up the information and find our own relevance to it. 

  4. Do a “review and preview” to remind people what they heard yesterday (or last time) and preview today’s content.

Land the plane 

Before: hurried wrap-up

After: Time to reflect and apply learnings 

Many gatherings don’t land the plane, aka they don’t bring the gathering home.

Our job when we gather isn't just to share content. It's to close the gap between the info we share and someone's ability (and motivation) to do something with it. Landing the plane ensures ROI. For offsites, this means to: 

  1. Spend as much time learning "it" as you do discussing "us", and how you'll work together because of what did.

  2. Discuss what could get in the way of the content sticking

  3. Have employees teach back or teach each other what they learned

  4. Clarify decisions, next steps, calls to action, and summarize key points 

Lindsey Caplan is a screenwriter turned organizational psychologist who helps HR & business leaders create experiences that boost motivation, engagement, and performance

Say hello@gatheringeffect.com

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