Retreat or Deep Dive? How to Choose the Right Format for Your Team
Tools to improve your team gatherings
Do You Really Need a Retreat?
Sometimes you just need time to focus on one thing at a time.
We've all been there: The team feels scattered, progress on important initiatives has stalled, maybe the organization is facing a significant organizational transition. Someone announces, "Let’s host a retreat!"
Before you start booking that offsite venue and planning two days away from the office, let’s ask this vital question: Does the team really need a retreat? Would a focused, extended meeting serve us better?
The answer depends on what we’re trying to accomplish.
When You Actually Need a Retreat
First, let’s define ‘retreat.’
Retreats usually happen off-site (or at least outside your normal meeting space), and they generally last 4-6 hours (minimum), sometimes over the course of 2-3 days. This ensures that retreats offer what they promise: time and space for both structured work and (formal or informal) relationship building.
Additionally, retreats generally focus on multiple, interconnected, big-picture topics. Yes, they can be powerful tools – but they're designed for very specific purposes.
A retreat makes sense when your group needs to:
Think bigger about fundamental questions. This includes exploring or revisiting your mission, vision, strategic goals, core values, or theory of change. These conversations require expansive thinking and the mental space that comes from stepping away from day-to-day operations.
Honor significant transitions. Whether you're welcoming new leadership, marking an organizational milestone, or navigating major changes, retreats can provide the ceremonial and reflective space these moments deserve.
Invest in team and relationship building. The extended time together, combined with a different environment, creates opportunities for deeper connections that regular meetings simply can't provide.
Here's a few examples of retreats I've facilitated with these purposes in mind: I gathered a collection of organizations together to build cross-city relationships and connections; I met with foundation staff to revisit and recommit to the organization's core values; and I helped a member-based organization clarify and reactivate members’ commitment to the mission.
When You Need an Extended Meeting
Sometimes what we call a "retreat need" is actually a need for focus. Maybe we don't need to think bigger – we just need to think deeper about a specific topic or work on one single project, without the regular interruption of daily operations.
Extended meetings (or, "deep dives") are perfect when you want to:
Explore one topic thoroughly. Whether it's developing a new program, solving a persistent operational challenge, or working through a complex decision, some issues require sustained, uninterrupted attention.
Focus on a single deliverable. When you have a specific outcome in mind (like finalizing a strategic plan, making an agreed-upon budget, or developing a new process of operations), an extended meeting can provide the concentrated work time needed to actually finish one thing.
Co-work intensively on one project. Sometimes teams need dedicated time to collaborate, iterate, and make real progress without the fragmentation of regular work schedules.
These extended meetings can happen within your regular work space (but that’s not a requirement). They generally last 2-3 hours (maximum) and focus on one single topic with clear boundaries. Other daily task and routine updates are explicitly excluded from the meeting agenda.
Here's a few examples of extended meetings I've facilitated or been part of: As part of a nonprofit organization, we met for a few dedicated hours to finalize our branding guide; I helped a nonprofit board host a long meeting to draft a policy around conflicts of interest; for a public initiative, we met to create and confirm the schedule of events for our year-long youth program; and within a non-hierarchical non-profit, I facilitated a meeting to clarify roles and responsibilities among the co-leaders. .
‘Go Deep, Not Wide’
Extended meetings often accomplish more than retreats, precisely because they require us to focus. When we have more time within a retreat setting, we can attempt to tackle everything all at once (clarifying the mission, the vision, strategic planning, team building, plus operational challenges) - and we end up doing none of these things! We're left with surface-level conversations and little (or no) progress on anything.
That’s why I often say: A series of focused extended meetings might be more effective than one 2-day retreat (because of limited time). This approach gives people time to marinate on ideas between sessions instead of trying to jump from big-picture thinking in the morning to detailed action steps by the afternoon. Some thoughts need time to percolate (and there’s more than one way to make this happen).
Think frequency, not intensity. While retreats might happen annually (if that), we can more realistically hold 4-6 deep dive meetings throughout the year. This regular rhythm of focused attention often serves organizations better than trying to solve everything at once in a single intensive offsite retreat.
This approach also takes enormous pressure off an annual retreat. Instead of expecting one or two days to address every organizational challenge, the retreat can focus on what it does best: Big-picture thinking and relationship building (or maybe even… rest). Meanwhile, regular focused and extended meetings can handle the operational and project-specific work that needs sustained attention.
Real-World Examples
Case Study 1: The Board That Needed Bylaws Clarity. I was recently facilitating an extended meeting with a board that really needed to focus on getting aligned on a couple parts of their bylaws – specifically, board member expectations and their conflict of interest policy. They needed outside perspective, time to laser-in, and some support with document preparation – but they didn't need to necessarily make a whole day out of it.
We scheduled a focused 2.5-hour session solely dedicated to working through these governance issues. No other agenda items, no updates, no "while we're all here" additions. Just sustained attention to get these foundational pieces right.
The single-topic focus allowed board members to ask detailed questions, work through scenarios, and reach genuine consensus. By the end, they had new documents for both board member expectations and the conflict of interest policy, plus an updated board meeting calendar that reflected their clarified processes. A full retreat would have been overkill for this specific need – they just needed dedicated time to get it right.
Case Study 2: The Library Leadership Team That Needed to Reconnect. Last year I worked with a library leadership team that was actually moving along fine day-to-day. There were no glaring operational issues. However, they were weighed down with fatigue and just hadn't checked-in with each other in a while. People were feeling like they couldn't (or shouldn't) ask for help, which was creating a benign but unconscious lack of collaboration.
It was also a time of significant transition – they were ending a major capital project with a new building opening, and key leaders were moving on to new roles. It had been over a year since they had met outside of their library buildings.
They needed a retreat. The one-day offsite retreat gave them space to acknowledge the weight they'd been carrying, celebrate the completion of their major project, and have honest conversations about support and collaboration. The change of environment was crucial – being away from their desks and daily responsibilities allowed them to see each other as whole people again, not just colleagues managing tasks.
The retreat didn't solve specific operational problems, because there weren't major ones to solve. Instead, it restored their sense of connection and shared purpose, which improved their day-to-day collaboration for months afterward.
Making the Right Choice: A Quick Decision Tree
The Bottom Line
Not every organizational challenge requires a retreat to address it. Sometimes the solution isn't thinking bigger – it's focused thinking.
So before you book that offsite venue, consider whether what you really need is just the discipline to focus on one thing at a time, with the distractions of daily operations temporarily set aside.
Your team (and your budget) might thank you.