The skill that changes everything when you scale

Dear SUCCESS family,

I’m navigating something right now that I believe a lot of leaders are—and the playbooks are just now being written.

Scaling a business has always meant scaling trust. You have to trust people with ownership, with decisions, with outcomes you can’t fully control. That’s hard enough on its own.

But now there’s a second trust layer, and it’s changing leadership entirely.

Recently at SUCCESS, we’ve shifted to a Single Threaded Leader model where each team member owns their domain end to end. We’ve been working toward this model for years, however now with the advent of AI it’s become a reality. We’re not waiting for permission. We’re building—real platforms, real products, real systems—and most of the team is using AI as their primary tool in their arsenal.

Trust isn’t just trust in people—it’s also trusting the robots more and more. It means identifying individuals with their own level of discernment and wisdom, and trusting them to make the right calls within their domain. When they’re off track, I try not to take over—I try to ask better questions. We’re also working to create a culture of sharing and solving between team members.

Our team does the exact same thing with AI. They coach it. They nudge it. They use their judgment to steer it toward better output than either of them could produce alone—and in a fraction of the time.

I’m learning how to trust people with more autonomy. My team is learning how to trust AI with more of the process while keeping their hands on the wheel. In both cases, the magic isn’t in the control. It’s in the quality of the coaching.

The thing that keeps hitting me is this: the ability to guide without micromanaging, to trust without abdicating, to know when to nudge and when to let it run—that’s the same skill whether you’re leading people or working with AI.

Wisdom and judgment aren’t being replaced. They’re being pushed throughout the organization. The person who knows what to build and why it matters will always outperform the person who’s just fast at building. AI handles the speed. Humans supply the discernment.

I’m still learning this myself. Every day I fight the urge to jump in and do it for someone. But I’m watching a team of owners emerge—people getting better at leading and better at leveraging AI at the same time—and I honestly don’t know where the ceiling is on that.

Scaling trust isn’t a one-time decision. It’s a daily practice. And right now, I think it’s the most important skill any leader can develop.

—Glenn