Is it Time to Plan a Team Offsite? How to Make it Count
Are you responsible for organizing team offsites—whether for your own team or for leaders across your organization? Are you thinking about planning one this summer?
If so, you’re in the right place.
After designing and facilitating several executive team offsites this spring, I wanted to share some high-level tips to help you craft an offsite that’s not just another meeting in disguise—but one that truly energizes your team, fosters deeper collaboration, and aligns people around what matters most.
In today’s fast-paced, hybrid-first world, uninterrupted time together is rare—and incredibly valuable. Done right, a well-planned offsite can offer the kind of breakthrough thinking, shared connection, and strategic clarity that teams often struggle to find in the day-to-day grind.
Here’s a simple but powerful 5W framework—Why, How, What, Where, and When—to help you design an impactful team offsite:
WHY: Start with a Clear Purpose
As Priya Parker reminds us in The Art of Gathering, purpose should be the anchor of any event. A team offsite needs a clearly articulated why—and ideally, a focused one.
Your purpose might be:
Strategic: e.g., “Generate three bold ideas for new revenue streams.”
Cultural: e.g., “Deepen trust and collaboration to manage conflict within this team.”
Restorative: e.g., “Help the team recharge and reconnect with the mission.”
The key is to define your purpose early—and keep coming back to it throughout planning. Avoid the temptation to cram in too many goals. A packed agenda may feel productive, but it often dilutes the impact. When it comes to offsites, less is more.
HOW: Create a Safe, Thoughtful Environment
Once you have your purpose, turn to the how—the structure and tone of the experience.
Here are a few things that can set you up for success:
Psychological Safety First: Set ground rules upfront. I use the 5 Ps: Presence, Participation, Play, Privacy, and Pithiness. These simple norms invite engagement while keeping things grounded and focused.
Optimize for Creative Thinking: Start with individual reflection, then move to pairs or small groups before opening up to full-team discussions. This layered approach allows a greater diversity of ideas, allows introverts processing time and encourages more thoughtful contributions.
Engage the Senses: Don’t underestimate the power of hands-on activities. Whether its asking group members to create visual maps or drawings, role play curated case studies and/or compete in thought-provoking games or puzzles, offsites are opportunities to break with routines and play with ideas and one another to foster greater shared identity as a team. Include movement—rotate rooms, change group configurations, and/or use physical movement or walk arounds to spark energy and creativity.
Curate Breakout Groups with Intention: Thoughtful pairings matter. While AI can randomize groupings efficiently, human curation allows you to consider interpersonal dynamics, trust levels, areas of expertise and team history—factors that can make or break the experience and/or the quality of the outputs.
WHAT: Focus on What Matters Most
Use your offsite to tackle the kinds of critical, big picture conversations that cannot happen over Zoom or in back-to-back meetings. Assessments and data collected in advance should support the critical business and team conversations but not require so much time to make sense of that they over-intellectualize the conversations and experience.
Some examples of critical conversations:
How do we break down silos and enhance true collaboration/efficiencies between regions and/or departments?
What risks and opportunities emerging from today’s geopolitical landscape?
Where do we need to reinvent—strategically or operationally?
What can we stop, start, continue in this uncertain moment?
What kind of team culture and norms do we want to model for the organization and ourselves?
These conversations can feel messy, but just need time and space to explore. Clarity often comes on the other side of the dialogue. And the shared sense of grappling supports the development of real team cohesion.
WHERE: Choose a Space That Signals a Shift
You don’t need a luxury resort (although that’s nice when feasible). What matters most is that your location feels like a true break—psychologically and physically—from the daily grind.
Look for spaces that are:
Private and comfortable, with natural light
Equipped with key tools (whiteboards, flip charts, fresh pens and sticky notes, round and board room tables, open areas )
Spacious enough for both small and large group discussions
Even shifting to a creative offsite venue nearby can send a signal: This is different. This is worth your focus.
WHEN: Timing Is Everything
Schedule your offsite outside the organization’s busiest periods. Offsites are most impactful at moments of transition: new leadership, reorgs, strategic pivots, or team changes.
In the agenda itself:
Tackle meaty topics in the morning when brains are freshest.
Save energizing or social activities for after lunch.
Build in three or more breaks—food, fresh air, and downtime are not luxuries; they’re essentials for sustained focus and connection.
Especially in today’s remote and hybrid world, in-person time away from computers and phones is precious—and vital for reducing future conflict, friction, and disconnects.
Make It Worth the Investment
In conclusion, the best offsites are not “check the box” exercises, but rather tailor made to the culture of the group and result in team members feeling renewed, connected, and aligned. That work can’t be done through AI generated agendas alone—it takes care, creativity, and facilitation with heart.
Here’s what one recent client shared with me after a retreat this spring:
“The team feedback on the retreat was outstanding. Thank you for working with us—you and your approach were perfect for our group. We all came away energized and ready to do it again! (But first we have homework to do).”
Another said:
“We give you this book with gratitude and admiration for your wonderful service to our team and with best wishes for many more contributions ahead!”
Here’s to making your next offsite not just productive—but also inspiring and energizing and most importantly, humanizing of the people around the table.
