
“We’ve been business partners for over 20 years, but I had no idea he felt that way.”
That’s what one of two co-owners said after a recent session I facilitated.
They had built a successful venture side-by-side. One of them is data-driven, always analyzing the facts and the numbers. The other leads with instinct, generally moving more quickly. The first intentionally considers all options; the second relies on gut checks.
While their business has been largely successful, they hadn’t communicated clearly or consistently for a long time. They had each grown increasingly frustrated with their processes and decision-making. They had avoided important conversations. And now, as they were thinking about their next steps, they felt misaligned and stuck.
So, they hired me to facilitate a series of conversations.
After some individual sessions to explore their concerns and needs, we met together so that they could communicate directly and figure out a path forward. In these discussions, they spoke openly about their frustrations, fears, and hopes. They talked through specifics of what they wanted for their business and for their teams. It was the most honest conversation they’d had in years. And while it wasn’t easy, it served as a springboard to resume moving forward productively.
Here’s the takeaway: consistent alignment doesn’t happen by accident.
Just because you’ve worked together for decades doesn’t mean that you’ve communicated openly or effectively—or that you’re on the same page. It’s so easy to let time go by, avoid the hard conversations, ignore the elephants in the room, and make assumptions about the other person.
Real alignment happens when we create space to pause, to check in honestly, to name the hard stuff, to ask the right questions, and to really listen to others.
Whether you’re a co-founder, a leader, or part of a team, don’t wait for critical moments. Have the real conversations, early and often.
And if you aren’t sure how to approach these discussions, feel free to reach out; I’m happy to help!

