In one of my past ventures, my business lost millions, because I allowed a “Hero” to occupy the C-Suite. This is a hard truth to admit because I pride myself on my boundaries. But, I used his clear lack of boundaries as a buffer to avoid enforcing my own and to keep my peace – a peace that eluded me.

My co-founder was the quintessential “Servant Leader”—genial, calm, tireless, and always the first to jump into the trenches. He believed he was building a high-trust, flat culture. I watched as he eroded his own sovereignty, allowing the normalized audacity of his team to treat him as a safety net rather than operationalizing our vision at scale.

And I let it happen because it was convenient for me.

This didn’t make me a passive bystander; it made me an accomplice. My clean hands were actually a form of negligence. I was so focused on protecting my own comfort that I kept quiet on the fact that my trusted partner – a man I genuinely liked – was setting the building on fire with his heroism.

At some point, I knew my options. As majority shareholder, I could:

Fire him.
Demote him.
Hire more under him.

I wanted to avoid the conflict of the first two, so we kept hiring.

In failing to make the decision I knew I should have made, I did a massive disservice to the company. I should have fired him and replaced him with someone who could rebuild the team. But in my role driving revenue, I was “crushing it”—having fun, making friends, being interviewed—and I didn’t want to pivot into such a crucial, painful conversation.

The Costs of Avoiding Confrontation

Because I chose personal comfort over conflict, the rot in the organization didn’t just stay static; it metastasized. My decision to hire more under him was the exact moment the business model broke. I threw capital at a structural problem, increasing the velocity of our dysfunction. The results were devastating.

A Culture of Learned Helplessness

By hiring expensive talent under a “Hero,” we added to his work. Because my co-founder couldn’t set a boundary, he couldn’t delegate. The new hires quickly realized that they didn’t actually have to deliver excellence—they just had to cry for help and have it escalated to him. We were paying top salaries for people to watch my co-founder burn himself out.

This sent a silent but lethal message: “I don’t actually trust you to handle this.” The result wasn’t a supported or empowered team; it was a culture of learned helplessness.

The Skill Gap: Engineers stopped learning how to solve complex problems because they knew the boss would swoop in and do it for them. They got stuck in their skillsets and delayed their own promotions and career advancements. That later brewed resentment that showed up with sudden departures, sabotaged work, or simply checked-out employees.

The Ownership Void: Work was no longer seen through to the end; it was merely “started” and then “escalated” for the boss to finish. The team wasn’t owning their work; they were merely funneling the hard labor off to the equity holder.

The Hostility Pivot: As the stakes grew, the “high-trust” culture soured. Because no one was truly responsible for their own results, “dropping the ball” became the norm. They had the normalized audacity to say “Well, he wasn’t around to help us, he is always too busy.”

Writing this I just remembered how we had a long list of items under a ridiculous status “Waiting for Executive”.

Revenue Subsidized Risk

This is where my culpability cuts the deepest. Because I was crushing it on revenue, I masked the operational bleeding and increasing risk.

Every big deal I closed bought us more time to ignore the broken machine. My success created a false sense of security. I looked at the P&L and saw growth; I downplayed the spiraling risk of catastrophe of having reduced competency down to one person.

My poor boundaries around conflict avoidance blinded me. I told myself this chaos “was just part of being a successful startup.” Even though by any metric, we should have been operating like a mature organization. Revenue growth served as justification for my silence.

The Cost of Lost Clients

Eventually, the bill came due. Client deliveries began to miss their marks—massive, high-six-figure misses. Then catastrophe struck. Major outage – 100% caused by the environment we had allowed to take shape.

Millions lost overnight.

The genial atmosphere evaporated, replaced by defensive finger-pointing. Since the co-founder had touched every project, he took the blame for every failure. It was the antithesis of what I had envisioned. We lost years of sales efforts in a week, all because our COO was unable to focus on his role, and because I had allowed it to continue.

All this was a painful lesson more than a decade ago, but one I’ll never forget:

Leaders with poor boundaries are bottlenecks who prevent their people from growing up.

The Invisible Perimeter: How Boundaries Define Leadership

I experienced this in my company, but I see it everywhere. Lacking boundaries manifests in many ways across the C-Suite:

The Vague Visionary: Has poor boundaries around their own curiosity. They change the company strategy often, creating “Strategic Whiplash” for the team.

The Filterless Communicator: Has poor emotional boundaries. The leader “over-shares” their anxieties or half-baked ideas with the entire staff, causing unnecessary panic because they haven’t learned to use their board or a coach as a perimeter.

The Approval Seeker: Has poor boundaries around time. Because they haven’t set a boundary around their deep-work time, they become a high-paid administrator reacting to every department’s priorities.

And so on, and so forth with countless examples.

The Impact of Poor Boundaries

A boundary is the psychological and operational perimeter that protects a founder’s most valuable asset: Clarity of Judgment.

You are not measured by tasks completed, but by the quality of your decisions regarding Vision, Capital, and People.

Impact on Vision: The Competence Trap

Vision requires a CEO to look at the horizon. When you lack strong boundaries, you succumb to the gravitational pull of “doing what you’re good at.” Rewriting copy or debugging code feels safe—it provides a dopamine hit of “value.”

But when you do this, you are a symphony conductor who has sat down in the string section. You might hit the right notes, but the orchestra has lost its cohesion. You have traded the podium for a chair, and the music suffers.

Impact on Capital: The Dilution of Velocity

Without clear boundaries, your capital becomes a humidifier—misting the air in ten directions instead of a laser cutting through your target market. A leader who says “yes” to marginal ideas wastes the velocity of capital. The result may be a product that is feature-rich but profit-poor, sold in markets you have no business being in.

Impact on People: The Culture of The Shadow

When you have poor boundaries around role—answering Slacks at 2 AM or jumping into channels you don’t belong in—you cast a destructive shadow. You create a “theatre of productivity” where people stay online just to be seen. High performers leave for autonomy; those who tolerate micromanagement stay for the paycheck.

The Identity Trap: You Can’t Just “Read” This Into Practice

If you are nodding your head right now, be careful. That’s probably just a dopamine hit, not transformation.

Boundaries are tied to identity beliefs held for decades. “My value is my utility,” or “I am a good person because I help.” The list goes on.

Deep work is required.

Without the deep work, the brain will revert to its old identity the moment pressure spikes. You will justify stepping back into the trenches as “necessary” when in reality, it is a retreat to a comfortable, destructive identity.

True change doesn’t happen by learning a new “hack”; it happens in transformative work where you rewrite your identity and safely get to strengthen and practice it.

The Boundary Audit: A Process of Inquiry

If you want to move from “nodding” to “being,” you must audit your life through the lens of open, curious, self-inquiry. Often! I did the work for many years myself, and still do, and didn’t know it would lead me to eventually helping other founders and executives.

A great coach ask questions to your blind spot and holds space for you to show up and do the work. Coaching questions show up uniquely to every person, but some examples to uncover old beliefs might look like:

“How am I complicit in creating the conditions I say I hate?”
“What is the ‘payoff’ I get from jumping in?”
“Does solving this fire make me feel more valuable than the long-term work of strategy?”
“If I died tomorrow, which of these processes would stop immediately?“
“Why have I built a system where I am so needed all the time?”
“Am I actually helping my team, or am I stealing their opportunity to become competent so I can stay relevant?”

Examples of Boundaried Responses

Once your identify changes, your language changes. Leaders who go through the deep work learn to attune to their intuition and consequently develop language that helps them show up healthy under pressure. Again, from my own experience, I can share some examples:

The Shift

There is no hack. True change doesn’t happen in the reading. It happens in the deep work of transformation. You become who you need to be, or you revert to who you were.

Boundaries make the difference between a founder who “hustles” and a CEO who “leads by vision.” By defining where you end and the company begins, you don’t just save your sanity—you give your people the space they need to grow. And if you build a culture where your people grow, by extension and consequence and good fortitude, your company will grow and thrive.