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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.

True business transformation starts when teams stop just planning and start confronting the real barriers. It’s in those honest conversations and bold visions that real change takes root.

“If we don’t feel uncomfortable, we probably haven’t done our job.”

One of the participants said this during an Operational Health and Safety strategy workshop, and it’s been stuck in my head ever since.

This wasn’t your typical planning session with flip charts and sticky notes. We were there to shake things up—to challenge the way this team had always done business and help them see what was actually possible.

The Reality Check: Great Work, But…

Here’s the thing about this team: they were really good at what they did. The technical work was solid, clients were happy, and projects kept coming in. But scratch beneath the surface, and you’d see the cracks.

Everyone was working in their own little bubble. The West Coast team rarely talked to the East Coast team. The technical folks stayed in their lane, and the business development people stayed in theirs. Sure, they were busy, but they were stuck in a cycle of small, one-off projects instead of building the kind of deep client relationships that really move the needle.

When they talked about doubling their market in five years, it felt less like a vision and more like wishful thinking. Something had to change—not just in how they worked, but in how they thought about their work.

The Workshop: Getting Uncomfortable (On Purpose)

We knew we couldn’t just throw another strategic planning template at this team. They needed something different: part provocation, part collaboration.

Before we even got in the room, we had them do some homework: SWOT analyses, stakeholder surveys, vision-setting by region. Then, during the actual workshop, we mixed things up with real client stories, live testimonials, and hands-on exercises that forced them to look at their business through fresh eyes.

Some of my favorite moments:

• Client stories that opened eyes: Nothing beats hearing directly from clients about what they actually value (spoiler alert: it wasn’t always what the team thought)
• Visual mapping: We used MURAL to help them literally see the growth opportunities they’d been missing
• “Start/Stop/Keep” sessions: Making strategy concrete by asking, “What do we actually need to change?”
• Giving the younger folks a voice: The young professionals became our secret weapon—they asked questions the senior team had stopped asking years ago

We pushed them to dream bigger while also getting practical about what it would really take to get there.

What We Discovered (And What Surprised Us)

As the conversations got deeper, some really interesting patterns emerged:

The growth mindset shift was real. Once people started talking openly about being stuck in a “same old, same old” mentality, they couldn’t unsee it. Suddenly, everyone was asking why they’d been playing it so safe.

Collaboration wasn’t just nice-to-have—it was essential. The “aha” moment came when they realized their biggest opportunities required expertise from multiple regions and functions. No more going it alone.

Quality over quantity. Instead of chasing every RFP that crossed their desk, they started talking about choosing clients more strategically and building real partnerships instead of just completing projects.

The next generation was ready to step up. Some of the best ideas came from the younger team members, and the senior leaders started to see them as future business builders, not just technical contributors.

Leadership had to show up differently. The days of “set it and forget it” planning were over. Real growth meant getting hands-on, removing obstacles, and actually following through.

Naming the elephants in the room. From talent shortages to “that’s not how we do things here” thinking, they finally started talking about the real barriers holding them back.

What Changed (Beyond the Buzzwords)

By the time we wrapped up, this team had:

• A growth vision that actually excited people
• A clear picture of where they needed stronger leadership
• A prioritized list of clients worth investing in
• Concrete plans for working across regions
• New ways to stay connected and track progress

But here’s what mattered most: they were talking to each other differently. There was an energy in the room that hadn’t been there before—a sense of “we can actually do this” instead of “maybe someday.”

The Real Lesson

We know one workshop isn’t going to solve everything, but it can be the spark that gets things moving.

When you give people permission to be honest about what’s not working, challenge them to think beyond their current reality, and support them in figuring out how to get there, something shifts. The conversation changes and the possibilities expand.

Real strategy really is about changing how people see what’s possible and getting them excited about building it together.

Sometimes transformation doesn’t require a complete overhaul. Sometimes it just requires getting in a room, asking better questions, and being willing to get a little uncomfortable in the process.

What’s keeping your team playing it safe? We’d love to hear about the workshops or conversations that actually moved the needle for you.

Strategy that grounds you. Growth that moves you.™