Why Chiefs of Staff Face a Hidden Cost When Facilitating Strategy Sessions
Here's a counterintuitive insight from my time as a Chief of Staff: the more you facilitate, the less you contribute.
During my startup days, I ran every strategy session - from annual planning retreats and quarterly OKR sessions to bi-weekly strategy check-ins. Made sense, right? Running meetings smoothly was literally in my job description. I was great at managing time, ensuring everyone got heard, and keeping discussions on track.
But something felt off.
The Cost of Being "The Facilitator"
In every session, I found myself split between two roles: facilitator and strategist. While my mind formed connections between departments and spotted emerging patterns, my attention stayed locked on managing the room, tracking time, and ensuring everyone got heard.
The problem wasn't my facilitation skills. It was that facilitation itself prevented me from contributing my most valuable strategic insights.
Jonathan Courtney of AJ&Smart perfectly described facilitation like being a Brita filter for group dynamics. You're constantly filtering the "dirty water" of tension, politics, and misalignment into "clean water" of productive discussion.
But here's the thing - when you're busy being the filter, you can't also be part of the fresh, clean stream of ideas.
The Unique Strategic Position of Chiefs of Staff
While Chiefs of Staff occupy a unique position…
working across every department
seeing how decisions ripple through the organization
understanding both the CEO's vision and operational realities
spotting patterns others miss
making connections between seemingly unrelated challenges
…we can't fully share these insights when we're busy running the room.
The Power of Stepping Back
I get it. I resisted bringing in outside facilitators too. My mental blocks looked like:
"It'll show I can't handle everything"
"No one else could run these sessions as well as I do"
"It's literally my job to make meetings run well"
All of these turned out to be wrong.
What Actually Happens When You Step Back
When you bring in an external facilitator, two major shifts occur:
First, your cognitive load drops dramatically. Instead of splitting attention between process and content, you can focus entirely on the strategic discussion. You notice patterns you would have missed. You make connections that surprise people. You contribute insights that change the direction of the conversation.
When someone else performs this filtering role as Jonathan would put it, your mind is freed to spot patterns and make connections that would otherwise get lost in the noise of managing group dynamics.
The Role of External Facilitators
A skilled external facilitator doesn't just run meetings - they shoulder the entire burden of collaboration, focused on:
Absorbing and redirect group tensions
Visualizing discussions so everyone can build on ideas
Handling the mechanics of participation and time management
Transforming frustration into forward momentum
But something even more interesting happens: your role in the organization shifts. When executives see you thinking deeply about strategy instead of just managing process, they start treating you differently. You become known for your insights, not just your execution skills.
Breaking Through the Chief of Staff Ceiling
Most Chiefs of Staff eventually hit a ceiling. We get pigeonholed as excellent operators who can execute anyone's strategy. Breaking through requires proving we can think strategically. But we can't prove that while we're busy facilitating.
Some worry that stepping back from facilitation means giving up control. But good facilitators don't control - they create spaces where teams think better together. They bring structure without constraining the conversation.
Making the Transition
When you stop facilitating and start fully participating, you:
Contribute insights that wouldn't otherwise surface
Build deeper relationships with your executive team
Shape strategy instead of just implementing it
Conserve energy for the complex work of execution
Starting Small
If this resonates but feels uncomfortable, start small:
Bring in an external facilitator for your next significant strategy session
Notice what you can contribute when you're not running the show
Watch how your team responds to your insights
To borrow Jonathan’s observation - you see people's eyes light up when they're freed from the burden of managing collaboration and can focus purely on problem-solving and decision-making. As a Chief of Staff, that's exactly what you (and I!) want - your team (including you!) operating at their highest strategic level while someone else handles the mechanics of productive group work.
The Path Forward
Remember: Your unique value isn't in running perfect meetings. It's in the patterns you see, the connections you make, and the strategic insights you bring. Don't let facilitation get in the way of that contribution.
Sometimes doing less means you can contribute more.
