Almost every business I’ve been part of — as an employee, a founder, or on the board — has hit the same moment: this is what we’ve built, but the future is over there. Are you willing to risk what you have for what’s next?
Most companies don’t navigate that well. It’s genuinely hard. And the hardest part usually isn’t the strategy. It’s the people.
Why change shakes people
The people who are with you early are often the most loyal people you’ll ever work with. They’ll see you through anything. But as you grow, new voices come in, and suddenly things aren’t done the way they’ve always been done. People feel like they’ve lost the control or influence they used to have. Their world gets shaken.
You can’t skip that. You can lead through it.
My approach: brainstorm, refine, repeat
When I see a shift coming, I start talking about it long before I decide anything. I’ll sit down with my key leaders like it’s a brainstorm:
What if we did this one day? I think the market is heading this direction — what do you think?
Then I listen. Every objection is information. I take the feedback, figure out how to address it, and refine the idea. Then I do it again. Ten, twenty, thirty times — as many as it takes.
What happens is that by the time I say, “This is the plan, this is what we’re going to do,” the idea isn’t new to anybody. It’s that thing we’ve all been kicking around for months. It’s ours, not mine.
Then put it on paper
Talking isn’t enough. When you’re small, you talk through a hundred ideas and carry out maybe two percent of them. Writing the plan down is the moment it becomes real — when people know what their focus is.
Brainstorm it until it’s shared. Refine it until it’s sharp. Write it down until it’s real.
That’s how you turn a pivot into a plan people actually follow.