True Love Is Letting the Agents Go
The hardest thing in my career has been when I need to let go of the details. It’s hard to build frameworks, hire, people, and trust it to work.
A lot of times, I thought I was delegating. But I was distributing tiny details. I thought I was empowering. But I was just double-checking everything after the fact. The control was still there, just hidden under layers of “helpfulness.”
Sometimes I got it right. At times, I didn’t.
But now that shift is happening again — for everyone. Not with people this time. With agents.
Nobody is talking about this.
We’re asking people to trust AI agents they didn’t hire, didn’t train, and didn’t grow alongside. Agents that show up inside your workflow and start making decisions — and you’re supposed to just go with it.
That’s not a UX problem. That’s a leadership problem.
Because trusting agents is a different kind of leap. There’s no relationship history. No gut sense. No shared mission. (So far…) It’s just: here’s what the agent says, now go.
Some people will adapt fast. Others will quietly stall things, slow-roll adoption, micromanage the logic, or try to override it “just in case.”
Not because they’re wrong. Because trust without history is hard. And most people haven’t had to do that before.
The irony is, we’ve built up decades of leadership coaching, management frameworks, and trust-building rituals — all centered around people. Does any of that apply here?
You can’t coach an agent into being more self-aware. You can’t pull it aside after a rough quarter and talk about values. It either works, or it doesn’t. You either trust it, or you don’t.
And that binary is uncomfortable for people who have spent their careers mastering nuance.
This transition won’t be neat. It won’t track with seniority or EQ or how good someone is at leading teams. Some junior ICs will fly. Some seasoned operators will flinch.
And the ones who make it through? They’ll be the ones who figure out how to trust systems they didn’t build. Not blindly. But fast enough to move forward.
I’m mostly writing this for myself.
Because I know what it feels like to grip too tightly. To confuse quality with control. To stall momentum in the name of standards.
The game is changing. The teams are changing. And the skill that matters most now?
It’s still trust. Just aimed in a new direction.
This idea is also why I want to build agents that encode the knowledge within a business - it’s effectively your team and way of doing things having trained the agent, making it easier to trust. Follow along at EndeavorCX.
Trust Is the New Skill.