Resources / Leadership

When a winning mode becomes a cage

Growth can stall from too much delegation or too little. In Jon’s work, the deeper pattern is often the same: rigidity.

In A Tale of Two Startup CEOs, Jon describes two founders who would not recognize themselves in each other. One built a full executive team and led from the org chart — “that’s what I hired them for” — while growth stalled and the team went defensive. Another was inside every product decision, customer call, and follow-up email — “if I want to win, I have to do it myself” — until the company became a one-person machine wearing a startup costume.

Neither logic is wholly wrong. Both become costly when they are the only available mode.

Two archetypes in the stall

Snowballers shine when motion is tangible. They can hit a wall when systems cannot carry momentum without them — then double down because motion is the only state that feels safe.

Breakers light up in genesis moments. After the org is designed, they can mentally move on, searching for the next breakthrough while the existing machine quietly deteriorates — mistaking organizational design for organizational health.

Behavioral flexibility is range, not inconsistency

Jon uses the phrase deliberately. It is not “doing whatever the moment asks” at random. It is the capacity to consciously expand responses beyond your default — in service of a specific outcome. For founders: know which mode the situation requires, and access it even when it is not your natural inclination.

“Are you defending your mode as a principle or as a preference?”

That diagnostic question separates earned trust from rationalization. Principles hold when they cost you something. Rationalizations collapse under honest scrutiny.

What contextual adaptability looks like

• Read the signal, not the preference: what does this situation require right now?
• Hold dual awareness: be in the work and observe yourself choosing to be there.
• Earn the right to elevate: you cannot delegate to an undeveloped system.
• Know your X-factor levers: Snowballers may need designed early wins; Breakers may need ritual re-engagement with the weeds.

Adapted from A Tale of Two Startup CEOs. Composite CEO vignettes are from that public essay; they are not named client identities.