💚 How to Create an Off-site Your Employees Will Rave About

Hello and Happy Thursday!

Now that we’ve gotten through (an especially long and hard) January you might be ready to start mapping out what big company events you need to be planning for in 2025. Without question, it’s the time of year that many start thinking about hosting off-sites (or on-sites, if your team is mostly remote!).

At the same time, I’m going to assume that I’m not alone in having chosen the dates far in advance - and then scrambled to figure out what the actual programming looked like just weeks (or - er - days) before everyone gathered.

This year, we’re getting a jump on things. Because there is no larger waste of time and money than bringing your entire team together, only to completely miss when it comes to the actual experience and residual impact.

Luckily, I’ve got just the person to set us all up for success!

I’m thrilled to reintroduce you to Lindsey Caplan, who I previously interviewed for an episode of the Want To Work There podcast. Her business, The Gathering Effect, focuses on helping HR and business leaders create gatherings and other change programs to engage a distributed workforce. She knows a lot about what it takes to plan an off/on-site that actually sparks change.

We recently caught up with Lindsey to get her perspective on off-sites in 2025 and - true to her nature - she dropped some incredibly practical, actionable strategies that you can put to work immediately. So, before you start crafting your next off-site agenda, read Lindsey's best tips for capitalizing on an all-company (or all-team) gathering below.

Yours in igniting change,

Jill

Before we get into the nitty gritty about planning an off-site, let’s talk about what makes them worth the effort (and budget).

1. They create opportunities to build trust between different teams and management levels. Since employees are now less inclined to connect with people and leaders from other teams, off-sites give everyone a chance to get to know people in the company that they don’t work with regularly. It might also lead to employees moving to different teams that are a much better fit for them! Retention, FTW!

2. They provide important face-to-face interaction that can strengthen bonds. We’ve all experienced the loss of “water-cooler” talk, the chit-chat that used to be a regular part of our day that suddenly went away, and for some it hasn’t returned. We might have taken for granted just how important that was for helping us form and sustain strong working relationships with our coworkers.

3. It’s puts your company culture on display (intentionally or not!). What happens once you finally get everyone in the same room says a lot about your culture. What you focus on, who does the talking, how interactive it is, where you meet - there are a million little things that cobbled together create a lasting impression for both tenured employees and those brand new to the company.

This is why we are now so much more judicious about why and how we plan and host off-sites. Lindsey defines a gathering as “bringing a group of people together to match a message to a moment to create an effect.” It’s a chance to do a concentrated amount of work that sparks a change in people, but it’s not easy!

You might begin by thinking about how much time you’ll have together, and breaking it up into an agenda, then start filling in the blanks. We’d like to encourage you to stop, take a step back and start at the end.

1. Start with the effect

Ask yourself these questions, and some others from our worksheet: What is your objective? What change are you trying to enact? How will you know if you’ve succeeded? What will be different in a week or a month?

Once you can answer those questions, create 2-3 concise outcomes and be very clear and specific about your expectations. Make sure you give employees enough time to achieve your outcomes. The real change doesn’t happen at the off-site itself, but during the time they spend processing and reflecting.

2. Craft the narrative

Now that you’ve identified some objectives, start chunking your time around them and plan activities that support them. Try to think less about an agenda and more about the question(s) your off-site is answering. Remember to put effectiveness over efficiency and try to not to plan too much. If you stuff the agenda with an update from the CEO and an update from HR and an update from your committees, it will end up being content overload and folks will leave not remembering most of it. Make sure every activity ties back to an objective.

3. Land the Plane

This is what Lindsey calls the part of the gathering where you tie things up. Think about what happens when it’s time to land an actual plane: you put your chair upright, put away your tray table, stow your belongings, etc. Be sure to build in this time to take your people from 30,000 feet to the terminal.

Here are a couple tips:

• Every time there is a content-heavy section, give people a break or the opportunity to talk with one another and discuss the content. This will help them grasp the ideas and remember the message once everyone returns to their (home) office.

• Engage the group for 30-60 minutes at the end of the gathering for questions, takeaways, and discussion about how the team will work together differently based on this new information, and what potential obstacles will delay progress.

Here’s what Lindsey sees a lot that can prevent a gathering from being effective:

• Focusing too much on decorations (logistics) and not enough on foundation (outcomes).

• Not getting leadership buy-in. Organization and team leaders need to show that they care about making this change and set an example for others.

• Planning a “Push” gathering vs a “Pull” gathering. A Push gathering is done primarily “at” people, whereas a Pull gathering is done “with”. Consider how you can give others a role, ownership, choice, or a chance to contribute within the offsite to ensure your gathering engages others rather than simply informs.

Planning an effective off-site is hard! It’s a skill that is learned, and many of us haven’t had great experiences to draw from. It is expensive event and takes people away from their families, so we need to make sure it’s worth their time. If you feel like you could use some professional help, consider hiring a consultant, like Lindsey Caplan and her business, The Gathering Effect. She even offers free 15-minute consultations so you can make an informed decision.

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The 2025 Distributed Work Survey: If you’re an HR leader, we encourage you to share your perspective in this survey! You’ll be contributing to a rich data set that will empower employers to make informed decisions, implement evidence-based practices, and foster a thriving distributed culture, plus, you’ll get a free copy of the results report. Only one response per company will be collected so feel free to forward to the appropriate member of your team.

Black Speakers Collective: While DEI is being attacked from all angles, we still have individual agency to make inclusive decisions - like prioritizing the diversity of your speakers. This site makes it easy.

Meditations for Mortals by Oliver Berkman. His last book, Four Thousand Weeks: Time Management for Mortals, gave us a much-needed metaphorical slap in the face and the permission to stop trying to be so darn productive all the time, so we’ve got high hopes for this one.