The One Question That Helps Define Your Boldest Vision
Most leaders feel like they should have a crystal-clear vision for their company. After all, isn’t that what great leaders do—chart the course, see the future, and guide their teams with unwavering clarity?
But let’s be real. Most leaders don’t have it all figured out. And if they’re honest, vision-setting feels intimidating as hell.
It’s not because they lack ambition or intelligence. It’s because crafting a compelling vision often feels like staring into a blank void—too many possibilities, too much pressure to “get it right,” and the nagging fear that they should already know the answer.
So, instead of aiming for perfection, what if we aimed for momentum? Instead of obsessing over the right words, what if we just started talking?
There’s one simple question that unlocks the boldest, most authentic visions: "Wouldn’t it be great if…?"
The Simplicity That Unlocks Big Thinking
The best vision-setting sessions aren’t complicated. In fact, the simpler they are, the better the outcome.
When you ask a team to define their vision in a polished, buttoned-up way, they freeze. It feels too official, too weighty—like they should know better, be smarter, have something profound to say. But when you give them an open-ended, playful prompt like “Wouldn’t it be great if…”, it unlocks something powerful:
It removes the pressure to have all the answers.
It shifts the focus from what is to what could be.
It allows for unconstrained thinking, where no idea is too wild, too big, or too ridiculous.
And sometimes, the most unexpected ideas are the ones that spark something real.
How One Bold Statement Changed Everything
I recently led a vision workshop for a global manufacturer in the document management solutions space. Not the sexiest category in the world—at least, not on the surface.
I kicked off the session with the prompt: “Wouldn’t it be great if…” and let the silence settle.
This moment—right after the prompt, right before the first response—is always the most telling. Who’s going to speak first? Who’s looking around the room, waiting for permission? And more importantly, how will leadership show up?
After a long pause, the CEO leaned forward and said, “I’ll go first. Wouldn’t it be great if people thought printers were sexy?”
The room erupted in laughter. It was so out of character, so unexpected—but also, refreshingly honest.
And just like that, the energy shifted.
Because here’s what happened:
The ice broke. People relaxed. They realized this wasn’t about saying the “right” thing—it was about speaking freely.
A shared joke emerged. Throughout the session, people kept referring back to it, which created a sense of team alignment and connection.
It signaled that boldness was welcome. If the CEO could throw something crazy out there, so could everyone else.
And from that one offhand comment? A real conversation emerged about how they could push the perception of their brand, differentiate themselves, and rethink their category.
Why This Approach Works (And How to Use It)
A vision isn’t something you pull out of thin air. It’s crafted from the inside out, built on the voices, perspectives, and experiences of the team. The best leaders don’t dictate the vision—they shape it collaboratively.
So, how do you bring this to your own team?
Ask the question: Start with “Wouldn’t it be great if…” and let the silence sit. Don’t rush to fill it. Observe. Who jumps in first? Who hesitates?
Let the responses build: Encourage people to build off each other’s answers. No idea is too big or too small.
Find the themes: Patterns will emerge. The most surprising insights often hold the most truth.
Shape the vision collaboratively: Your job isn’t to have all the answers. It’s to pull the best ideas forward, refine them, and align the team around something they genuinely believe in.
Your Turn: What’s Your "Wouldn’t It Be Great If…" Moment?
If defining a vision feels overwhelming, simplify the process. Start with “Wouldn’t it be great if…” and let the conversation unfold. The best ideas often emerge when there’s space for bold, unfiltered thinking. Listen for themes, build on each other’s perspectives, and shape something that feels true to your team. The most powerful visions aren’t dictated—they’re discovered.
