Offsites vs. Retreats: How Leaders Can Make the Most of Team Time

Q4 is here, and many leaders start planning offsites and retreats to set the tone for the year ahead.

But let’s be clear: they are not the same thing.

• Offsites are about business planning, strategy, and execution.

• Retreats add space for connection, reflection, and relationships.

Both matter.

The real question is: how do you make the most of that time?

1. Co-design the agenda
Unless it’s a brand-new team, you don’t need to plan everything. Invite your team to design parts of the experience.
When people help shape the agenda, they show up as partners, not just participants.

2. Create white space
The value is in the connections, not in back-to-back sessions.
Add a walk-and-talk breakfast. A lunch hike. Cooking dinner together, family-style.
Build natural spaces for 1:1 or small-group conversations. That’s where trust grows.

3. Build reflection into the rhythm
Give your team structured time to exchange feedback, surface real challenges, and reflect together.

4. Model asking for feedback
Close with one simple question: What worked, and what could work even better next time?

The bottom line - Team time is not about perfection—it’s about practicing how to move through challenges together as a team.

Don’t avoid challenging moments. Strong teams know how to face challenges together and call on each other when things don’t work or they move in circles. If you are not sure how to partner with your teams in those moments, and as Brene Brown calls it, “rumble,” then partner with someone who feels comfortable navigating the team through that.

That’s what makes you stronger for whatever next year brings on your way.

Want to design an offsite or retreat that actually works for your team? Let’s talk.