The Deprogramming
A Journey from Authoritarian to Participative Leadership
For a decade, I carried around a leadership operating system that was fundamentally corrupt. I contracted it in investment banking (Goldman, Bank of America, Deutsche Bank) where the model was brutally simple: decisions flow down, compliance flows up, fear is the primary management tool. This wasn’t some rogue manager’s pathology. It was institutional design.
Then I left, ran my own company for four years, and somehow managed to bring all those broken patterns with me. When I joined Etsy in 2016, I thought I’d shed the banking mindset. Turns out I’d just taken off the suit.
The Infection: Banking’s Management Pathology
Goldman, 2002. Post dot-com bust, investment banking was still the destination for a specific kind of ambition, the kind that accepted brutal hours and authoritarian culture as the price of admission. In Likert’s framework, this was textbook “System 1: Exploitative Authoritative.”1 Its tenets were control, fear, and top-down decision-making.
Public humiliation was standard operating procedure. Engineers got dressed down by their managers in the open (outside offices, in hallways) for mistakes both major and trivial. The performance was the point. Everyone absorbed the lesson. Fear works. It enforces compliance. Employee well-being was an HR checkbox, not operational reality. Professional development meant mandatory compliance training on SOX and KYC regulations. The concept of a one-on-one as a coaching space didn’t exist. You met with your manager twice a year: annual review, comp discussion. That was the relationship.
By Deutsche Bank, I’d encountered managers who tried to soften this, people who were genuinely more humane. When I moved into management myself, I tried not to be an asshole. But I was still running the same OS. Management, as I understood it: make decisions, communicate them, hold people accountable. The idea that management might be a craft, a practice with learnable skills that required deliberate development, wasn’t part of my model. I thought I was being a good manager because I wasn’t actively cruel. The bar, little did I know, was underground.
Four Years in the Wild
mohchi, 2011-2015. Running a startup should have been the reset. Small team, no corporate bureaucracy, the freedom to build whatever culture I wanted. And in some ways it was. I learned to ship fast, iterate, fail forward. But here’s the problem with mental models: they’re invisible until something forces you to see them.
A founder-CEO with six people operates with enormous authority. You make unilateral decisions because the company will die if you don’t move fast. You skip process because there’s no time. This feels different from banking. Jeans instead of suits, collaboration instead of hierarchy. But the underlying pattern is identical: concentrated authority, top-down decision-making, benevolent dictatorship. The startup gave me founder chops and product sense. It didn’t deprogram the prior decade.
The Inoculation: A Hard Collision with a Healthier Culture
It is more difficult to move from an authoritarian style to a democratic style than vice versa.
Etsy was different. Radically different. One-on-ones weren’t performative check-ins, they were the connective tissue of the organization. Decisions weren’t announced, they were made participatively. Caring about employee development wasn’t mission-statement theater, it was baseline operational expectation. I had no reference for this. It was like watching people have a conversation in a language I didn’t know existed.
A few weeks in, I did what felt natural. Designed a new team process, sent it out via email. Top-down, efficient, done.
Five minutes later: “Can we talk?”
My manager took me to one of Etsy’s many dedicated 1-1 rooms, a thing that had never existed in my professional universe, and asked a simple question: “Did you run this by the team before you sent it?”
He knew I hadn’t. He understood where I’d come from. Though I suspect he thought the problem was banking, not realizing I’d spent four years as a founder and still hadn’t learned this. The feedback was humane and surgical: that approach doesn’t work here.
First reaction: defensive. A flicker of “are you serious?” Then: embarrassment.
I’d recently read Carol Dweck’s Mindset,2 and I’d been trying to internalize growth mindset thinking, the idea that you’re not captive to your history, that patterns can be unlearned. If I hadn’t been actively working on that, I don’t think I could have set my ego aside. But I did. And what I heard was that involving people in decisions that affect them isn’t a nice-to-have, it’s foundational. The skill didn’t exist in my toolkit. The category of thought wasn’t there.
Four years running a startup with total freedom to do things differently, and I’d replicated the exact same authoritarian patterns I’d learned in banking. Just without the org chart to formalize them.
In hindsight, this conversation was one of the most pivotal moments in my career.
What Actually Changed: The Compounding Returns of Trust
The more I practiced participative leadership (at Etsy, Shutterstock (105 people), Candid (scaling through hypergrowth), RepeatMD) the more unambiguous the results became. A model built on trust and genuine collaboration isn’t just more humane. It’s dramatically more effective. When you meaningfully involve people in decisions, when you actually care about their development as more than a retention strategy, you unlock engagement and ownership that command-and-control can never achieve.
This sounds obvious. It’s not. Or it wasn’t to me. Deeply embedded assumptions don’t announce themselves, they just run in the background, shaping every interaction. Seven years in banking, four years as a founder replicating those patterns, and it took one difficult conversation to begin seeing the operating system I’d been running.
The deprogramming was slow. Old habits surfaced constantly, defaulting to unilateral decisions under pressure, forgetting to loop people in, treating collaboration as a time sink rather than an investment. But the shift from “managing through people” to “leading with people” compounds. The teams I’ve led since have been stronger, more resilient, more capable of solving complex problems. Not because I got smarter, but because I stopped treating leadership as the exercise of authority and started treating it as the cultivation of conditions for others to thrive.
Banking taught me rigor. Running my own company taught me to ship. But Etsy taught me something neither of those experiences could: that the best outcomes are achieved with people, not through them. You can’t learn that from a book. You need someone to point out that the way you’re doing it is broken, and you need to be humble enough to listen when they do.
Wikipedia, “Likert’s management systems,” June 2, 2025, wikipedia.com.
Dweck, Carol. Mindset: The New Psychology of Success. New York: Ballantine Books, 2016.