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Brainstorming. Ugh. You’re either a brainstormer or you’re not.
Either way, it may feel like a corporate assignment where you know your ideas will likely get trampled, and nothing will come from all the ideas tossed out and captured on the whiteboard. Yet another fruitless exercise.
I read The Road Less Stupid by Keith J. Cunningham, and he insists that all business owners need to put Thinking Time into their schedules. This is time set aside to not do anything but sit and ponder questions you have for your business. Write out the questions and allow yourself time and space to contemplate and take notes. He says the questions “will spark different possible ideas, insights, and answers” and that he’s optimizing his Thinking Time “for possibilities, not completion.”
I think of conversations of possibility in a similar way. It’s time where you engage in a dialogue about what could be. You don’t need to limit where the conversation goes or how realistic the resulting ideas must be. You don’t need to have money to fund the ideas or people to accomplish them. The ideas may skip beyond what you’re currently capable of, but maybe they’re something you can work toward in the next iteration of the business. Or maybe it’s a whole new venture you’re envisioning.
Anything is on the table in a conversation of possibility because it could become possible with the right circumstances. We’re not here to judge the possibilities today. We’re here to get caught up in the fantasy of what could be.
How it’s shaped me
I started my career in a tech start-up, and it was powered by possibility. Our company was creating one of the first products to allow personal computers to connect to the Internet easily. Our team was invigorated by the possibilities of what the World Wide Web could be and how we could get people there (which feels a bit like the Stone Age at this point!).
When I came into the office in the morning, the windows were often covered with notes from late-night sessions where ideas had to escape, and a marker on a window made the perfect whiteboard.
I’ve surrounded myself with big thinkers and have always been prone to thinking well into the future. Early on, Kevin would ask me to pull my thoughts back into the present, but I don’t operate well within those confines. I need to know what the next two, three, or four steps ahead will look like. They may change along the way, and my visions can change with them.
I need a destination to go toward. And conversations of possibility create that vision.
When I started my first business (a creative meeting facility), my partner and I had two meeting rooms, and we called them "Think Big" and "Focus." If you follow that order, that’s exactly how the ideas come to life. Start with the big ideas and eventually narrow them down to something realistic you can execute.
Lighting the fire
I was talking with Kalli Ortega and described the conversation we were having as a conversation of possibility. It struck her immediately—she got the importance of the idea and went on to post about it on LinkedIn, stimulating some great conversation. Kalli beautifully articulated how the concept resonated with her, sparking ideas around personal empowerment and meaningful dialogue. She explained that the idea of conversations focusing on potential rather than constraint was refreshing and aligned with her vision for ethical collaboration.
The beauty of possibility-driven conversations isn’t only in the ideas—they’re about the people. These conversations thrive in environments where individuals are seen and valued for who they are, not just what they do. In the LinkedIn post, we talked about the importance of the human element, sharing how meaningful conversations arise when we take the time to see and care for each other. In workplaces where individuals are genuinely cared for, the conversations open up and more feels possible.
This isn’t just a feel-good sentiment—it’s practical. When people feel supported and seen, their contributions flourish. The freedom to explore possibilities comes from a foundation of trust, respect, and genuine connection.
When paired with execution, possibility-oriented conversations fuel innovation, driving teams to develop new solutions and forge stronger collaborations. They don’t reject practical outcomes—they embrace the potential to make things happen in new ways.
Start your own conversation
Being perfectly honest, most of my conversations of possibility don’t start from a scheduled session. They typically happen over a meal or from a spontaneous conversation. They require an open mindset when you’ve let your guard down and released your stress.
When entering a conversation, leave behind the need to control the outcome or keep things within the bounds of what's currently known. Instead, lead with curiosity, openness, and a willingness to explore and expand, both personally and professionally, and invite others to do the same.
Conversations of possibility are more than a way to talk; they’re a way to think and lead. They inspire us to see beyond the immediate and to imagine new futures. By embracing these conversations, we can create more human workplaces, foster innovation, and move from dreaming to doing.
Take a moment this week to have a conversation of possibility. You might be surprised at what you discover.
Content originally published on Q4intelligence
Photo by dotshock
