#define CTO — Greg Brockman

Brockman's account of figuring out the CTO role at Stripe after hiring Marc Hedlund as VP Engineering. A personal story about finding leverage when your role is undefined and your skillset is spiky. Referenced in the generalist reading list as showing "the process a person with a spiky skillset can take to find their place in an organization."

The VPE hire

Brockman was doing 1:1s with all engineers every Tuesday — completely burned out by the end of day, unproductive until the following Tuesday, and repeating. He knew he faced two paths: technical route or people route. He hired Marc Hedlund as VP Engineering, starting by clarifying the one thing the role would definitely involve (lots of 1:1s) and hiring for excellence at that, then figuring out the rest together.

The discovery: most CTOs are facilitators

Surveyed ~20 CTOs. Expected "chief architect" to be universal. Found: most viewed themselves as facilitators of the technology organization — connecting senior engineers, mentoring, sometimes head of product. Only one was primarily chief architect.

Key asymmetry: good product is simple and digestible, so you can quickly distinguish bad from good part-time. Infrastructure can only be judged by building on it extensively — much harder to be part-time chief architect. This is a structural reason why "chief architect" is an unrealistic default for a delegating CTO.

The feedback loop problem

After delegating to Marc, Brockman lost his org feedback loop. All his data about what was wrong was from before Marc joined. He identified four ways to know what's happening in an org:

Doing the work — direct experience of what's good and bad
Talking to lots of people — aggregate view, sentiment
Observing the work — reading diffs; tried for a month, felt like mostly reconstructing authors' state of mind
Planning the work — not sustainable without another feedback loop

He was doing none of them. The answer was returning to doing the work.

Energy management

"It's not about time management, it's about energy management. Find activities that recharge you (independent of leverage) so you have energy to deal with the high-leverage draining stuff."

Coding recharged Brockman. Returning to it improved his organizational perspective, his ability to support people, and his ability to get them excited about what they were building.

Delegation: full or none

The only two models that work:

Delegate completely: define principles, leave execution alone
Stay involved in all details: works for one area only (e.g., Zuckerberg and product)

"Sparse micromanagement" — jumping into random issues, overturning decisions, disappearing — is the worst of both worlds. Marc and Brockman resolved this by spending more time together (two 1:1s per week), building a shared mental model until Brockman could predict Marc's reactions without checking.