Engineering Leadership: The Hard Parts

Chapter 5. Setting Direction

You rarely walk into a team with too little to do. More often, you inherit the opposite: a wall of priorities, each louder than the last, all of them deemed “critical.”

When Juan led Stripe’s LATAM engineering team, the outside story was all momentum. Headlines talked expansion: new markets, new products, new partnerships. Inside, the truth was rougher: a growing team facing 30 competing priorities, and no clear agreement on what mattered most.

Some priorities were tactical: supporting existing customers, fixing bugs, maintaining deployments. Others were strategic monsters: exploring expansion into three new countries, navigating deep regulatory compliance in Mexico and Brazil, launching new local payment methods like OXXO and Boleto, and supporting internal infrastructure and security efforts across the company. Each request came with urgency attached and each one appeared to be high priority. So, the team said yes to everything.

On paper, it looked like progress—closed tickets, shipped code, and calendars stuffed with meetings. But underneath, the wheels were spinning. Engineers were stretched thin across regulatory compliance, customer support, expansion research, and new feature development. There was wasted energy leaking in every direction and doubts arose about whether the work even mattered.

From the outside, chaos looks like momentum. From the inside, it feels like drift. Drift doesn’t just waste effort; it erodes ambition. And that erosion ...