Engineerication

Leaders clear their calendars to code alongside teams for deep operational context

David Singleton
Building a culture of excellence | David Singleton (CTO of Stripe)

Engineerication

"I'll clear several days in a row, three or four days, actually join a team, pick up a small task, hopefully a small feature that we can get all the way from start to finish in production and do that going through the exact experience the team has." - David Singleton

What It Is

Engineerication (a portmanteau of "engineer" and "vacation") is a practice where engineering leaders clear their calendars for 3-4 consecutive days to join a team, pick up a real task, and ship code to production. The goal is to experience exactly what the team experiences - the developer tools, build infrastructure, code review process, documentation quality, and deployment pipeline.

The name comes from treating it like a vacation: when you're on vacation, the world goes on without you and everything is fine. By treating these days as a vacation from normal responsibilities, leaders can fully immerse in the maker's schedule and gain deep context they couldn't get otherwise.

This practice is particularly valuable for engineering managers in their first quarter to six months at a company, and then annually thereafter.

How It Works

  1. Clear your calendar completely: Decline every meeting for 3-4 consecutive days. Treat it like you're on vacation.

  2. Join a team and identify a buddy: Pick a team and have someone on that team be your guide. They'll help you with unfamiliar technologies and processes.

  3. Pick up a real task: Choose a small feature that can realistically go from start to finish into production within the time window.

  4. Experience the full loop: Go through everything - writing code, getting it reviewed, testing, deployment, and seeing it live.

  5. Keep a friction log: Document your experience throughout. Note what's working well and what's difficult.

  6. Share your learnings: Write up the experience as a report. This aids your own memory and demonstrates to the team that you understand their reality.

How to Apply It

Actionable steps for implementing engineerication:

  1. Schedule it intentionally - Block 3-4 consecutive days on your calendar and decline all meetings for that period
  2. Identify your buddy upfront - Find someone on the team who can pair with you and help when you're stuck
  3. Be vulnerable - Accept that you may not know the technology (David Singleton learned Ruby during his first engineerication) and embrace being a beginner
  4. Treat code review normally - Ask reviewers to give you the same feedback they'd give anyone else
  5. Document as you go - Keep a running friction log of your experience
  6. Share the write-up - Distribute your findings to the team and use them to inform prioritization

When to Use It

  • During your first quarter to six months at a new company
  • Annually to stay connected to the developer experience
  • When you suspect developer productivity has degraded
  • When you're making decisions about tooling or process investments
  • When teams are expressing frustration you don't fully understand

Source

  • Guest: David Singleton
  • Episode: "Building a culture of excellence | David Singleton (CTO of Stripe)"
  • Key Discussion: (00:46:47) - Detailed explanation of the engineerication practice
  • YouTube: Watch on YouTube

Related Frameworks

  • Leaders in the Details - Brian Chesky's concept of leaders staying close to the work
  • Friction Logging - Documenting user/developer experience issues
  • Managerial Leverage - Andy Grove's concept of high-leverage leadership activities
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