4 Reasons You Should Have a Facilitator
Here's a scene I've witnessed too many times: A team spends weeks planning a retreat, books a great venue, creates a detailed agenda, and then designates the Executive Director or Director of Operations to "lead" the retreat.
What happens next? The leader spends the day glancing anxiously at the clock, struggling to participate in discussions while simultaneously trying to manage the room, and stifling conversation because people are intimidated to speak openly.
Sound familiar?
I get it. Bringing in an outside facilitator might feel unnecessary — you have a smart and capable team! It's another expense on top of an already-expensive retreat! But after over a decade of facilitating retreats and strategic meetings, I can tell you the cost of not having professional facilitation is often much higher.
Here are my four reasons why having a facilitator can transform your next retreat from "just another meeting" to a genuine turning point for your organization.
1. Leaders Get to Actually Participate
A dedicated facilitator ensures everyone on your team, especially those in leadership, can participate. When you try to participate and facilitate, you can't do either well. A facilitator allows leaders to focus on the meeting content and relationship-building, while the facilitator handles the rest.
This reduction in cognitive load means leaders can:
Listen more deeply to their team members
Contribute their best thinking to discussions
Notice patterns and connections they might otherwise miss
Model full participation and engagement
Leave the retreat feeling energized rather than drained
2. The Power of a Neutral Third Party
I once facilitated a retreat for a company undergoing a major team restructuring. During a session on team communication, multiple staff members raised issues they had never mentioned in internal meetings. Later, when I asked why they felt comfortable sharing those issues, one person said, "You don't have a stake in which department gets more resources or whose idea wins."
An external facilitator brings neutrality to sensitive conversations, creating a space for honest dialogue.
An outside facilitator doesn't have the same baggage or preconceived solutions. Nor does a facilitator have a stake in the outcome. That fresh perspective alone can help break through long-standing barriers. This becomes especially valuable when:
Discussing team roles and expectations that might be changing
Creating space for giving and receiving feedback
Navigating tensions between different departments or perspectives
Addressing power dynamics that might silence certain voices in internally-led meetings
3. Get to Real Outcomes
The retreat's cost isn't just the venue and facilitator's fee. It's also the opportunity cost of having your entire team away from their work. That's a steep investment. A facilitator helps ensure your time together is designed to deliver results.
Every retreat has moments where conversation stalls or gets stuck. These moments can feel awkward, but they're actually opportunities for breakthrough.
I facilitated a strategic planning session for an advocacy org that hit an impasse when discussing their theory of change. After 20 minutes of the same few points being repeated, I decided to shift the format completely. We broke into small groups with a specific prompt for a visual ladder of engagement mapping exercise. When the team came back together, they had a new framework for thinking about their approach.
The TLDR is that facilitators bring a toolkit of techniques to help move past stuck points constructively, meaning you can get to the outcomes you're seeking. This could be:
Alternative formats for approaching the same question
Frameworks for making implicit disagreements explicit
Methods for separating creative thinking from critical thinking
Tools for making decisions when consensus isn't emerging naturally
Ways to acknowledge tensions without requiring immediate resolution
4. Letting Experts Do Their Work
Most teams are experts in their field — they're not experts in retreat design or facilitation. A facilitator, on the other hand, is an expert. A facilitator knows which activities work best for different goals, when to push for deeper discussion versus when to move on, and how to sequence conversations so they build over time.
I once received a call from a marketing agency that had planned their own retreat. Their draft agenda looked something like:
9:00-10:30: Brainstorm new campaign ideas
10:45-12:00: Discuss team dynamics
1:00-2:30: Strategic planning for next year
On the surface, sure, that works. But when I asked about how those sessions would be structured and what outcomes they wanted from each session, or how the activities built on each other, there was silence on the call. Imagine the silence that might lead to during your retreat!
A facilitator can expertly build an agenda, manage a room, adjust on the fly, and make sure you get to the outcomes you need.
Is Professional Facilitation Always Necessary?
No! Not every meeting needs an external facilitator. Your weekly staff check-in or standard project review is fine with internal facilitation. But consider bringing in a professional facilitator when:
The stakes are high (strategic planning, organizational restructuring)
Sensitive topics will be discussed (team dynamics, performance issues)
You're at an inflection point as an organization
Past attempts at similar conversations have stalled or gone sideways
Team leaders need to be full participants in the content
You're making significant decisions that require buy-in from the whole team
The Bottom Line
A facilitator doesn't just make your retreat run smoothly — they can transform what's possible. They create the conditions for your team's best thinking to emerge and ensure that thinking translates to meaningful action.
Think of it this way: You wouldn't represent yourself in a complex legal matter or perform your own dental work, even if you could technically read up on how to do it. Some things are worth bringing in a professional for – and the rare, valuable time when your entire team gathers to chart your collective future is definitely one of them.
Planning an upcoming retreat or strategic meeting? Let's talk about how facilitation can help you maximize the impact of your team's time together. Get in touch to discuss your needs and how I can support your next gathering.