Engineering leadership and strategy mindset

Stop coddling engineers—give them real responsibility and accountability.

Sheltering engineers from hard problems prevents growth; instead, place them in senior leadership roles and hold them accountable.

Why: Accountability unlocks career growth and allows engineers to tackle meaningful challenges.

"I think that we often treat engineers a little bit like children, instead of giving them the responsibilities and ability to actually thrive as adults."

Model reality with stocks and flows, then debug where the model conflicts with reality.

Represent any process as accumulating stocks (e.g., candidates, fish) and flows between them; the gap between model and reality is where learning happens.

Why: Reality is always right—your model is wrong; the conflict reveals where to improve.

"Reality is never wrong. Reality is always right. Your model is always wrong if it's in conflict with reality."

Write the strategy down—even if it’s boring—so you can debug and improve it.

Every org already has a strategy; documenting it exposes misalignment and enables iteration.

Why: Unwritten strategies can’t be debugged or improved.

"The first rule of strategy is that if you write it down, then you can like improve it"

Use deliberate constraints to focus limited resources on what truly matters.

Examples: Stripe’s Ruby monolith, Uber’s no-cloud policy; constraints force innovation inside boundaries.

Why: Constraints prevent fragmentation and align engineering effort with business priorities.

"the goal of good strategy is to dictate how we invest the limited capabilities we have into the problems we care about"

A good value must be honest, applicable, and reversible.

Values must reflect real behavior, guide daily decisions, and be something a company could plausibly reject.

Why: Identity-level values (e.g., “we build good software”) are useless because no one would ever disagree.

"good values have to be honest"

Measure something imperfect and educate stakeholders on its limits.

Start with DORA metrics or any visible metric; use it as a conversation starter to teach nuance.

Why: Refusing to measure anything leaves non-experts in the dark; imperfect metrics still guide improvement.

"you just have to get comfortable measuring something that's not perfect, but you can actually measure and reporting on it"

Give EM-PM pairs the same performance rating to align incentives.

When both roles share one rating, they must jointly solve for all constraints instead of optimizing locally.

Why: Shared ratings force collaboration and surface hidden constraints early.

"our Chief Product Officer, Bruce Shally and I spend a fair amount of time calibrating together"

Understand the other side’s true needs before arguing about solutions.

EMs worry about team morale with boring work; PMs worry about shipping impact—surface these underlying needs first.

Why: Most conflicts dissolve once real constraints are visible and joint compromises emerge.

"make sure you actually understand what they care about"