How CTA approaches intentional, in-person retreats!
Retreats. Offsites. In-person all-hands time. These things mean all sorts of different things to different organizations depending on their size, scope, and remoteness.
At CTA, we think our Team Retreats are pretty special, so we thought we’d not-so-humbly brag about how we approach them, and maybe share some good ideas with others in our position. With an all-remote team (or even with an in-person one), it’s so easy to get caught up in the day-to-day, to let certain things slide, and to lose sight of the mission, connection, and larger picture of why you’re a team.
“I can’t say enough how much I appreciate CTA’s commitment to doing these. I think it truly adds and retains so much to our team culture and to why I and others like to work here. I know how much work, time, energy, and expense go into these, so thank you!”
At CTA, we’re scattered across 15 states, and we maintain many rituals and processes to stay connected across time zones and screens. However, it’s imperative that we deliberately make time and invest in face-to-face human interaction as often as possible. For us, that has meant planning 1-2 team retreats each year (the goal being two meet-ups, the reality sometimes managing just one). Our retreat priorities are as follows:
Spend time together as humans, reconnecting, and making sure we step away from the day-to-day to get to know each other on a personal level.
Review and revise our raison d’etre, both to link and align our everyday work with the bigger picture, but also to make sure we account for changes and ensure new team members are fully read in.
Focus on HOW we are together, rather than WHAT WE DO together. This includes aligning on working agreements, reviewing team communication processes, and our community DEIA work.
Occasionally, we have tried to also jam project working sessions into these objectives, and I will say those are sometimes productive, but they are not a key priority of our time together.
“Doing this in-person …helped more and different people participate than what might have happened virtually.”
How we structure our time together shapes what we get out of it. We traditionally have a one week retreat schedule - no, we’re not in meetings that whole time:
Monday: Leadership travels in
Tuesday: Leadership retreat day - We align on yearly priorities, big shifts, and the All team retreat time. On this day the rest of the team travels.
Wednesday: All team retreat Day 1: We spend 10am-5ish together - then have an optional evening dinner and fun activity
Thursday: All team retreat Day 2: Again we spend 10-5ish together - with optional evening dinner and fun activity
Friday: Everyone travels home
Some tenets that helped us build this schedule:
The team cannot balance other work and actually be present. We tell our clients and partners that we’ll be offline for retreat days, and we stick to it (aside from urgent BenDesk tickets). The team cannot be dipping in and out for calls or other work and still be present and intentional humans with their teammates. The same goes for leadership.
Travel time is work. We can’t expect well-rested brains to squeeze in travel around normal business hours. And we can’t not compensate the team for the time we ask them to spend traveling.
Two days of 6-8 hours together is a LOT. People’s brains and bodies get tired. We ask our leadership team to do three full days - and by the end we are generally exhausted (but very fulfilled!).
Mandatory fun isn’t fun. Giving people the option to spend more time together is critical - but forced fun outside business hours is inhumane. We find that lowering the requirements to hang out actually results in our team choosing to spend even more time together.
Drinking isn’t an activity. While we do offer optional “happy hour” time, and everyone is welcome to imbibe during after-hours gatherings, we always make sure our post-work meetups have an activity outside just drinking. Whether it’s skeeball, boardgames, a sporting event, or an art installation - we get creative to ensure we’re centering shared experience over anything else.
“I enjoyed spending time with folks and getting to know the new staff - I appreciate how many social spaces we include in retreats!”
Major content keys to retreat success
Leadership should lead - don’t outsource this. We believe the team wants and needs to hear from the leadership of our organization, and while they should not be the only ones the team hears from, they cannot abdicate the responsibility for setting an intentional agenda and truly LEADING the retreat. Of course, other voices should heavily contribute to the presenting or activity-led time, but too often we’ve experienced leaders sitting in the back of the room, disengaged, and not driving the content and outputs of these types of meetings. To be clear, a talented, hired facilitator is a fantastic resource. But they don’t know your team, organization, or goals in the same way.
Kick-off and post-lunch team building activities. The words “team building” or “icebreaker” might be cringe, but there’s no better way to galvanize some laughter and ‘get-to-know-you-time.” Carve out 30 minutes at each juncture to get the team’s personalities shining, wiggles out, actually break the ice, and allow time for experiential learning about each other. We generally scour the internet for good game ideas, but some favorites have included:
Build the tallest sticky-note tower - also can be done as the spaghetti/marshmallow challenge
Rotating portrait drawing - In advance, create profiles of the team, with fun anecdotes, like ‘favorite weekend activity.’ Have the team rotate through drawing a portrait of their colleague for 30 seconds, learning from their profile. Present portraits to their owner.
Build a ramp/tower challenge - Requires a few sets of Jenga blocks and a few ping pong balls. Challenge multiple teams to build the ramp that makes the ball run the longest. Challenge: construct silently, or with some members blindfolded.
Short and sweet narrative section on the company's status, mission, vision, and transparency into the financial future. Our leadership team likes to start with a section we call “State of the Prog” – a rundown of CTA’s mission and how we’re accomplishing it. We also include a transparent financial update, so the team knows where our small company stands regarding stability and growth. We strive to keep this under 1 hour, but if we have enough new team members, we might stretch this a bit to ensure everyone clearly understands our goals and accomplishments.
Listen to feedback and track follow-ups. The team knows what works and what doesn’t, and actually tracking and integrating feedback from previous retreats is the key to success. We balance our approach to feedback – not ranking sessions necessarily, but looking for and listening to the team’s reactions to the flow of the day, the breakouts, etc. We are also incredibly diligent about follow-ups. What were the outcomes of the sessions, and what are the resulting actions? Letting these fall by the wayside is a sure-fire way to let the team know that what was discussed in person didn’t really matter.
We don’t share content in advance (with exceptions for accessibility). This might be difficult for some, but we feel strongly that the point is to create present and creative conversations. The team doesn't need to prep for any content (aside from actual presentations) in advance. We want them to bring their full selves to each session, and there’s no homework involved in that.
“I really liked how Day 2 moved us from the Strategic and Conceptual and “Here’s where we are/how we want to head” of Day 1 and brought things through through our active projects—-both current and future. It also seemed to very smoothly flow from mostly Leads on Day 1 to many additional people on Day 2. It is exciting to be in a place where so many additional people are taking such roles!”
Retreats aren’t rocket science, but they can feel unproductive and disengaging for teams, and like a waste of time for leadership. At CTA, we’re proud of the process we’ve built to ensure we leave our retreats feeling more connected, more productive, and energized to tackle the challenges of our mission. In the end, we’re a team of humans, not Slackbots, and we need time to laugh and align in-person to be the best team we can be.
CTA Retreat - August, 2025
