Even the best-designed strategy sessions can falter without the right structure, leadership alignment, and organizational readiness—especially when scope shifts, timelines stretch, and virtual formats expose underlying fractures. This is a story of how one engagement unraveled, what we learned from it, and why honest reflection is just as valuable as a polished outcome.

We had a clear path: a focused, in-person strategy session with ten-12 key decision-makers. Then everything shifted.

What started as a tightly scoped engagement became something much broader. More voices entered the room: some essential, some emergent. The format changed, driven in part by what felt like a lack of support from leadership, even though this was a priority initiative in a growing market. The session moved from in-person to entirely virtual. And the timeline stretched from a few concentrated days to a drawn-out, months-long effort.

What initially felt efficient—early alignment and clear workstream identification—began to drain morale and resources. What happened then was momentum faded and expectations blurred.

This isn’t unusual. But it is a cautionary tale, which we’re viewing as a growth opportunity.

3 Lessons from the Pivot

1. Strategy Needs a Container—Especially When Everything Else Changes

Great strategy requires structure, not just vision. When the original frame (people, time, place) changes, the work must be restructured to maintain clarity and momentum. We learned that without a strong container, even good ideas can drift.

2. Expanding Voices Expanded Complexity

Bringing more stakeholders into the conversation surfaced valuable insights—but also introduced friction, and at times, confusion. We shifted from facilitation to orchestration, trying to maintain engagement while holding the thread of a cohesive direction.

What did that actually look like?

Breakout rooms with facilitators and note-takers. Multiple perspectives needing synthesis after each session. More logistics, more follow-up, and more risk of losing nuance in translation. The demands on time and resources grew without a guarantee of forward movement.

Still, there were bright spots. We used the shift as an opportunity to bring in guest subject matter experts who added depth and challenged assumptions. Their input revealed new angles in our target market and helped us clarify whose voices truly needed to be in the room moving forward.

More isn’t always better. But sometimes, it’s necessary to go wide before you can go deep.

3. Virtual Strategy Requires More than a Platform

Teams (or Zoom) isn’t the enemy and it’s no substitute for the trust that’s built in the room. To adapt, we shifted to sprints—or what we called “bursts”—designed with space for digestion, reflection, and realignment between sessions. Coaching helped keep decision-makers tethered to the bigger picture. In theory, the extended timeline could have strengthened long-term buy-in.

However in practice, we found there were too many side conversations outside of those bursts to check in on low engagement from key participants. We had to ask the hard questions: Is this person truly vested in this strategy? Are they even interested in growing this market? So many layers that required excavating.

Those questions eventually sparked deeper leadership conversations. They also highlighted a structural challenge: too many people involved in shaping strategy without clear roles or ownership. What could have been energizing instead became “just one more hat” to wear.

In systems where consensus is prioritized over clarity, and decision-making is diluted across too many voices, momentum stalls—and everyone feels it.

Strategy in Motion

Virtual strategy sessions can be highly effective and increasingly, they’re the norm. With the right design, facilitation, and commitment, remote work doesn’t have to mean diminished results.

Unfortunately this particular engagement was set up for struggle from the start.

The format shift wasn’t the issue—it was everything surrounding it. Leadership transitions, unclear ownership, wavering priorities, and a lack of internal alignment made it difficult to maintain momentum. The result was a drawn-out process that lost energy over time and left some participants, and even some leaders, disengaged.

Still, we don’t view it as a failure. We view it as a case study in what happens when strategy work lacks the structure—and sponsorship—it needs to thrive and succeed.

We walked away with clear takeaways:

• Strategy needs a strong container, regardless of format.
• Leadership alignment is imperative (otherwise strategy doesn’t stand a chance).
• Process design must reflect the reality of the organization’s capacity, not just its ambition.

Not every engagement sticks the landing. But each one teaches us something. And we bring those lessons into the next room—virtual or otherwise.

Your Turn

Finding your strategy process slipping off course? You’re not alone. Let’s talk about what’s still possible—and how to move forward, even when the original plan no longer fits.