Making the Most of Your Next Leaders’ Retreat: 5 Strategies to Leave Stronger, More Aligned, and Ready for the Work Ahead

It’s that time again — as the weather warms up, many remote or hybrid organizations are flying their leaders in over the next few months to step back and gear up for the work ahead.

As these orgs well know, a well-planned leaders’ retreat can repair some pinches, build a shared picture of success, and make space for the tough questions it’s hard to tackle thoroughly between meetings, check-ins, and the whirlwind of day-to-day work.

Here’s what we also know: lots of leaders’ retreats don’t meet that bar. While they’re often good for building camaraderie, they don’t always improve team cohesion or move the work forward. Sometimes, when sessions are poorly scoped or planned, they can even break trust in meaningful ways. And with all the stress our sector is facing right now, the last thing we need is unforced errors.

As an expert retreat facilitator and trainer, here are the five considerations I hold front of mind to make the most of these containers, especially in a nonprofit context:

• Have a Very Clear Picture of Success for the Time. Even in high-performing organizations, it’s common to walk into a leaders’ retreat with generic or canned goals — and it shows in both the agenda and the outcomes.

• Less but Better: Instead of over-scheduling a bunch of tightly-timed, check-the-box sessions, focus on fewer topics with well-thought out questions or activities and enough time to explore them fully and come to meaningful conclusions.

• The Just-Right Amount of Time: It's my experience that right now folks in our sector are particularly sensitive about time on the road — especially if they have caregiving responsibilities (parents, pets, kids, even plants) or chronic health conditions. A 3-day retreat, while meaningful, just isn’t workable for everyone; in my experience, 1 or 2 days (or a dinner, then a full day) can usually do the job!

• Pre-Work that Matters (or None at All): Pre-work can be helpful — when it genuinely advances the work or lets you use retreat time more effectively. But if it’s just busywork, it’s better to leave it off people’s plates. Consider pre-work that allows for processing time on rigorous questions, or beginning thoughts on untangling thorny problems and avoid heady articles or other things you can unpack virtually at any time.

• A Planned Cadence of Accountability and Follow-Up: A retreat without follow-up, clear owners, and a plan for accountability is just an expensive trip. The insights you gain are only as useful as the actions you take after. Each session should end with clearly defined owners and next steps. If your org struggles with this, build in 15 minutes into each session to ensure next actions and owners are identified, and you have a plan to keep the momentum from the session and develop a shared notetaking doc where session leads share those next actions.

What’s hard about planning these retreats is that the prep usually happens on top of the day-to-day demands crossing a leader’s desk and competing for their attention. With that said, I can't think of a high-performing leader I work with that doesn't prioritize time away with their team. I’ve seen firsthand in my own work and with the executive leaders I coach how the time and intentionality you invest in these retreats can shape the tone for your entire quarter, sometimes even your year. This is especially true when you’re onboarding new leaders or resetting team culture. Even if you're busy, even if there are a lot of urgent fires to put out, I invite you to protect time in the next quarter to think about the next time you will pull leaders aside to level up, align, and prepare for the next season. As the context around our sector gets more volatile, uncertain, complex, and ambiguous, (VUCA) these retreats matter even more.

If you're a leader who’s stuck or just needs a thought partner for your next retreat, my team is here for you — schedule a quick complimentary sounding board session by emailing scheduling@breaker28.com.