In partnership with
Hello fellow Relationship Capitalists,
Here's a question for the leaders reading this: if you disappeared from work for two weeks, would things keep moving, or would everyone be waiting for you to return?
It's a question worth asking, especially after my recent conversation with Bill Flynn, CEO and Leadership Team Coach at Catalyst Growth Advisors and author of the book The Hero Trap.
Bill and I have known each other for more than 20 years, and this was a particularly interesting conversation to revisit.
The Hero Trap
This concept taps into one of our most basic instincts as humans.
The truth is, we all like feeling useful. Solving the difficult problem, saving the client relationship, jumping in when the team gets stuck. I've been there myself.
But Bill argues that being the person everyone depends on can become a problem. He breaks leadership into three approaches:
Controller: I solve the problem.
Builder: I teach people how to solve it.
Architect: I build systems so people can solve it without me.
The challenge is getting comfortable with that third one.
Why Your Team Hesitates
Something else Bill shared caught my attention. When employees don't make decisions independently, it's often because they're missing one of four things:
Authority, information, confidence, or clarity about the consequences of getting something wrong. So before asking why your team isn't taking ownership, maybe ask whether you've given them what they need.
That's where leadership and trust start to overlap.
Could AI Help Us Share Wisdom?
We also explored an opportunity for AI that feels counterintuitive in the current AI conversation.
Think about how much experience a leader shares during one coaching conversation: the questions they ask, the reasoning behind a decision, the lessons from past mistakes. Today, most of that stays with one person.
Bill believes AI could help capture that knowledge so other team members can learn from it, too.
But there's one part you can't skip. Keep the human coaching. Use AI to make the learning more accessible.
The Final Thought
Bill suggested putting one question on a sticky note:
"What did I do today to make the lives of my customers and my team better?"
I like that. Avoiding a crisis might not get you applause. But helping people become capable enough to prevent one? That's leadership worth building.
A special shout-out to Bill for a thought-provoking conversation. So much to chew on.
Listen to the full episode here:
RELATIONSHIP CAPITALISTS
The Hero Trap: Do Great Leaders Hold Companies Back? ft. Bill Flynn
This Week's Trust Builder
Give credit publicly. Take blame privately. Bill named fear of consequences as one of the four reasons teams won't decide without the boss. This is how you remove it. The next time something goes wrong on your team, own it out loud: "That one's on me." The next time something goes right, name the person who did it, in front of the people who matter to them. Do that a few times and your team stops waiting for you to make the call.
This Week's Value Deposit
Share the template you built for the thing they're about to build. Bill's Architect doesn't solve the problem. They build the system that lets other people solve it. You can do the same for someone in your network. Think of one person facing a problem you've already worked through: a hiring plan, a QBR deck, a first-90-days outline. Send them your version with one line on what you'd change next time. You saved them weeks, and they'll remember who did.
Here's to building meaningful connections,
Jason Masciarelli
To help support the podcast and newsletter, I partner with hand selected advertisers. This installment is supported by Wispr Flow 😁
Speak naturally. Send without fixing.
Wispr Flow turns your voice into clean, professional text you can send the moment you stop talking. No rough transcription you have to clean up. Actual polished text, ready for email, Slack, or any app.
Speak the way you think. Go on tangents. Change your mind mid-sentence. Flow strips the filler, fixes the grammar, and gives you text that reads like you spent five minutes writing it.