The Art of Letting Go (of the Agenda)
Planning is important. All the tools we use to organize around the work—agendas, roadmaps, stakeholder decks, decision frameworks—are critical for keeping teams aligned and moving in a shared direction. But, despite all that structure, your weeks still might be filled with:
A roadmap review that turns into a debate about ownership and trust
A strategy session where everyone outwardly agrees, except you can feel that they don’t
A delivery conversation that’s really about resourcing, priorities, or leadership expectations
Structure is your friend, but it’s not the whole picture.
As I’ve moved into mid-career and mid-life, I’ve facilitated more workshops that simply refused to be contained by even the best-laid plans. And I’ve learned that rigid adherence to the plan can actually slow progress instead of enabling it.
So, how do we learn to see tension as an invitation to be curious, and to recognize when deviation from the plan is actually in the team’s best interests?
Here, I’ll share examples that indicate your team needs a pivot, along with tips for building muscle memory around departing from the plan.
The Tension Between Structure and Curiosity
Last spring, I facilitated a session for a leadership team tasked with aligning on a 10-year vision for the business.
On paper, the agenda was solid. Big-picture thinking. Long-term bets. Clear outputs.
But midway through the morning, it became obvious that a fundamental misalignment—about priorities, power, and risk—was sitting just beneath the surface.
Sticking to the plan would have produced a polished vision that no one truly owned.
So we stopped.
I named the tension. Reworked the agenda in real time. And we focused on resolving the underlying disconnect before returning to the future-facing work.
The result wasn’t just a better vision. It was a leadership team that could execute together with far more confidence.
Letting go of the agenda doesn’t mean abandoning structure. It means developing the judgment to know when the plan is no longer serving the outcome.
How to Pivot in Real Time
So how do you know when you need to pivot?
Early in my career, I treated these moments as distractions. Things to “park” so we could get back to the plan. (And honestly, sometimes this is the case!)
But now, rather than defaulting to the parking-lot approach, I see it differently.
These moments are not just noise. They’re signals.
Signals that something important is unresolved. That alignment is assumed but not real.
To be effective at leading teams, it’s critical to know how to:
Sense when misalignment is emerging
Create space to address it before it derails delivery
Trust that slowing down briefly can unlock speed later
In practice, this often looks like:
Pivoting mid-meeting when a conversation reveals a deeper strategic misalignment
Pausing execution talk to clarify decision rights, principles, or constraints
Choosing depth over coverage, even if it means fewer slides or unfinished topics
This can feel uncomfortable at first.
Misalignment and tension don’t fit neatly into an agenda. But pretending they aren’t issues comes at a cost.
Letting Go to Move Forward
If you’re constantly navigating stakeholder pressure, team friction, and the gap between strategy and execution, remember:
Structure creates momentum, but openness creates alignment.
Having a defined plan is important—essential, even—but it must be balanced with curiosity and adaptability. This value has been front and center in my work over the past few years (for more reading on this topic, I recommend Emergent Strategy by adrienne maree brown and Power and Love by Adam Kahane; they introduced me to new ways of holding space for change and complexity).
Since adapting this mindset, I’ve seen time and time again that teams move faster after these pivots because they’re no longer carrying hidden friction into execution.
Sometimes the most strategic move you can make is letting go of the agenda long enough to deal with what’s actually in the room.