Scaling Your Engineering Organization Checklist

A guide to help engineering leaders navigate the changes to their teams, processes, and leadership skills as their company grows.

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Who is the checklist for?
Who is is behind this checklist?
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Engineering Team Growth 👇

5 -> 20 engineers
20 -> 100 engineers
100 -> 250 engineers
250+ engineers
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You

Your Team

Your Processes

Have regular personal retros to redefine your role

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5 -> 20 engineers
Have regular personal retros to redefine your role

Document everything

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5 -> 20 engineers
Document everything

Dive into engineering leadership books

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5 -> 20 engineers
Dive into engineering leadership books

Run great retrospectives

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5 -> 20 engineers
Run great retrospectives

Create a code of conduct

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5 -> 20 engineers
Create a code of conduct

Implement a career progression plan

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5 -> 20 engineers
Implement a career progression plan

Make sure you’re building a diverse team

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5 -> 20 engineers
Make sure you’re building a diverse team

Learn from experienced leaders with podcasts

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5 -> 20 engineers
Learn from experienced leaders with podcasts

Give and receive feedback (often)

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5 -> 20 engineers
Give and receive feedback (often)

Build a consistent recruiting process

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5 -> 20 engineers
Build a consistent recruiting process

Join communities of like minded leaders

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5 -> 20 engineers
Join communities of like minded leaders

Create a proper incident response process

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5 -> 20 engineers
Create a proper incident response process

Align on code quality/standards

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5 -> 20 engineers
Align on code quality/standards

Adopt a growth mindset

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5 -> 20 engineers
Adopt a growth mindset

Have a system to track work & progress

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5 -> 20 engineers
Have a system to track work & progress

Subscribe to the best engineering leadership newsletters

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5 -> 20 engineers
Subscribe to the best engineering leadership newsletters

Become an expert interviewer

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5 -> 20 engineers
Become an expert interviewer

Develop excellent communication & presentation skills

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5 -> 20 engineers
Develop excellent communication & presentation skills

Adopt a “confidence vs. competence” attitude

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20 -> 100 engineers
Adopt a “confidence vs. competence” attitude

Start building an engineering intelligence team

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20 -> 100 engineers
Start building an engineering intelligence team

Stay away from the consensus trap

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20 -> 100 engineers
Stay away from the consensus trap

Master the art of decision-making

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20 -> 100 engineers
Master the art of decision-making

Create a proper on-call process

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20 -> 100 engineers
Create a proper on-call process

Go to conferences for engineering leaders

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20 -> 100 engineers
Go to conferences for engineering leaders

Define an onboarding process for new hires

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20 -> 100 engineers
Define an onboarding process for new hires

Align tech & engineering strategy with business goals

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20 -> 100 engineers
Align tech & engineering strategy with business goals

Focus on continuous delivery

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20 -> 100 engineers
Focus on continuous delivery

Create a great candidate experience

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20 -> 100 engineers
Create a great candidate experience

Start building an Engineering Intelligence team

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20 -> 100 engineers
Start building an Engineering Intelligence team

Hire a VP of Engineering

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20 -> 100 engineers
Hire a VP of Engineering

Deal with underperformance

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20 -> 100 engineers
Deal with underperformance

Don’t forget about security

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20 -> 100 engineers
Don’t forget about security

Map your PRs to Tickets

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20 -> 100 engineers
Map your PRs to Tickets

Invest in and pamper your CI

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20 -> 100 engineers
Invest in and pamper your CI

Get a mentor

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20 -> 100 engineers
Get a mentor

Write more

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20 -> 100 engineers
Write more

Automate operational processes

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20 -> 100 engineers
Automate operational processes

Ensure your teams are autonomous

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20 -> 100 engineers
Ensure your teams are autonomous

Build a great engineering culture

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20 -> 100 engineers
Build a great engineering culture

Hire a VP of Engineering

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20 -> 100 engineers
Hire a VP of Engineering

Start tracking Velocity, Quality, and Outcome metrics

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20 -> 100 engineers
Start tracking Velocity, Quality, and Outcome metrics

Have clear decision-making processes

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20 -> 100 engineers
Have clear decision-making processes

Learn how to delegate

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20 -> 100 engineers
Learn how to delegate

Buy tools to solve problems (vs. hiring more engineers)

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20 -> 100 engineers
Buy tools to solve problems (vs. hiring more engineers)

Formalize your org. & responsibilities

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20 -> 100 engineers
Formalize your org. & responsibilities

Keep an eye on tech debt

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20 -> 100 engineers
Keep an eye on tech debt

Define an onboarding process for new hires

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20 -> 100 engineers
Define an onboarding process for new hires

Cultivate cascading information sharing through the org.

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100 -> 250 engineers
Cultivate cascading information sharing through the org.

Adopt an “executive 1st, functional leader 2nd” mentality

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100 -> 250 engineers
Adopt an “executive 1st, functional leader 2nd” mentality

Build your engineering teams around the product

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100 -> 250 engineers
Build your engineering teams around the product

Strengthen team alignment + team dependency mngmt

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100 -> 250 engineers
Strengthen team alignment + team dependency mngmt

Implement metrics for continuous improvement

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100 -> 250 engineers
Implement metrics for continuous improvement

Start tracking app ownership

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100 -> 250 engineers
Start tracking app ownership

Continuously provide purpose to your engineers

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100 -> 250 engineers
Continuously provide purpose to your engineers

Use constraints to boost your creativity

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100 -> 250 engineers
Use constraints to boost your creativity

Learn from other industries

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100 -> 250 engineers
Learn from other industries

Train your managers & team leads to delegate

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100 -> 250 engineers
Train your managers & team leads to delegate

Create a clear hiring scorecard

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100 -> 250 engineers
Create a clear hiring scorecard

Make sure your team leaders contribute to the strategy

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250+ engineers
Make sure your team leaders contribute to the strategy

Uphold a culture of authenticity & radical candor

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250+ engineers
Uphold a culture of authenticity & radical candor

Build a culture of innovation to find your next growth levers

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250+ engineers
Build a culture of innovation to find your next growth levers

Become a mentor

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250+ engineers
Become a mentor

Focus on removing the biggest blockers to your business goals

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250+ engineers
Focus on removing the biggest blockers to your business goals
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Frequently asked questions

Who is the checklist for?
Engineering Leaders who are on a journey to scale their engineering team (CTO, VP of Engineering, Head of Engineering etc.).
Engineering Managers and Team Leads who want to help their teams and scale with the company.
Future Engineering Leaders (Developers) who want to start improving their skills.
Who is behind this checklist?
This checklist wouldn’t be possible without precious feedback from:
- Jason Warner, who helped scale Github from 50 to 2000 engineers
- Jose Caldeira, who helped scale Outsystems from 20 to 700 engineers
- John Laban, who helped scale PagerDuty from 1 to 150 engineers
- Renaud Visage, who helped scale EventBrite from 1 to 250 engineers

And the numerous guests from the Developing Leadership Podcast including: Charity Majors, Meri Williams, Erik Bernhardson, César Lugo, and more.
Can I contribute?
We support and welcome contributions, questions, comments, additions to this checklist. We reserve the right to accept additions at our discretion. Get in touch!

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