If you’re reading this, then you’re a kind soul who is willing to offer some advice on this proposal! I’m considering writing an engineering leadership book, and would love your suggestions on what I’ve written here. Please send thoughts to lethain@gmail.com.

Particularly helpful would be answers to:

1. Is this a terrible idea?
2. Is this a book that you would buy? Why or why not?
3. What content is most interesting?
4. What interesting content is missing?
5. What would you change?

Thank you, and let me know how I can return the favor!

Overview

Software engineering management, especially in Silicon Valley, is exceptional for how inexperienced the typical manager is, how little training we provide for this critical role, and how much we expect from managers. As we gain mastery, we should indeed be developing our own styles that mesh with our personal strengths, but there is so much more we can do a lot more to support new managers in the transition from novice to journeyman, and from journeyman to master.

“Systems for…” explains my approach to a wide variety of engineering leadership topics, especially around organizational growth, to help new managers navigate change effectively. Building from the concrete explanations, it also breaks down the reasoning behind the approaches, with the aim of helping leaders adapt dynamically to new circumstances beyond those in the book.

Motivations

I hope this book can raise the floor for engineering management and leadership practices in the software industry, particularly for folks who are early in their management career. I’d further like to extend my writing platform to a wider audience, where a broader reach increases my rate of learning, speaking opportunities and changes to meet interesting people.

Audience

Engineering leaders and those who aspire to engineering leadership. As much as possible, the goal would be to be relevant beyond just managers. The sort of people who loved The Manager’s Path and are still referencing Peopleware.

Contents

The proposed table of contents is:

1. Introduction

Organizational design

1. Sizing teams
2. Staying on the path to high performing teams
3. A case against top-down global optimization
4. Productivity in the age of hypergrowth
5. Where to stash your organizational risk?
6. Succession planning

Tools

1. Introduction to system thinking
2. Product management: exploration, selection validation
3. Visions & Strategies
4. Metrics and baselines
5. Guiding broad organizational change with metrics
6. Migrations: the sole scalable fix to tech debt
7. Running an engineering reorg
8. Identify your controls
9. The briefest of media trainings
10. Model, document and share
11. Scaling consistency: designing centralized decision making groups
12. Presenting to senior leadership
13. Time management
14. Communities of learning

Management

1. Your philosophy of management
2. Managing in the growth plates
3. Ways engineering managers get stuck
4. Partnering with your manager
5. Finding managerial scope
6. Setting organizational direction
7. Close out, solve or delegate

Culture

1. Opportunity & Membership
2. Select project leads
3. Make your peers your first team
4. Consider the team you have for senior positions
5. Company culture and managing freedoms
6. Kill your heroes, stop doing it harder

Interviewing, hiring and performance

1. Roles over rocket ships, and why hypergrowth is a weak predictor of personal growth
2. Running a humane interview process
3. Acing your architecture interview
4. Cold sourcing: hire someone you don’t know
5. Hiring funnel
6. Performance management systems
7. Career levels, designation momentum, levels splits, etc
8. Creating specialized roles like SRE or TPMs
9. Designing an interview loop

Appendix

1. Tools for operating a growing organization
2. Book I’ve found very useful
3. Papers I’ve found very useful

That’s it.

Inspiring and related books

The related books I am inspired by are:

• The Manager’s Path by Camille Fournier in 2017. People love this book and I still see frequent references to it on Twitter. I think it does an amazing job of being accessible to both engineers and engineering managers, where it could be easy to be too focused on the later. It has a lot of nice features, like “Ask the CTO” sections which are random, interesting tidbits, that keep it from being dry, despite being a tome of best practices. “Think of this book as a reference manual for engineering managers, a book focused on practical tips that I hope will be useful to you throughout your management career.”
• The Lean Startup by Eric Ries in 2011. It’s 290 small pages, but managed to significantly change folks perspectives.
• Mythical Man-Month by Fred Brooks in 1975. Essay driven exploration of software development that is memorable without being exhaustive. Many terms it introduced are now canonical.
• Peopleware: Productive Projects and Teams by Lister and DeMarco in 1987. About 200 pages. Essay driven, but memorable. Frequently cited by folks looking for examples of clear-eyed management advice. Somewhat uniquely data driven.
• Principles by Ray Dalio in 2017. I’ve read about half of Principles, and what’s interesting is that it should be quite dull, but is in practice very interesting! Does a phenomenal job of explaining reasoning behind ideas.

Other comparable books are:

• Managing Humans by Michael Lopp in 2007. Largely a collection of his blog, Rands in Repose. Sections are “The Management Quiver”, “The Process is the Product”, “Versions of You”. About 314 pages.
• Accelerate: DevOps… by Nicole Forsgren and Jez Humble in 2018. A bit dry in my opinion, taking a very structured and framework driven approach to explaining how organizations can improve. Very much not essay driven. However, it is very data driven.
• The Phoenix Project by Gene Kim, Kevin Behr, George Spafford in 2013. A fable based approach, essentially a retelling of The Goal. Not sure I would want to write a fable-styled book, but I do think it was memorable and easy to read as a result. Especially relative to Accelerate, which is more-or-less the same content in a different format (and with lots of data).
• Building Great Software Engineering Teams by Josh Tyler in 2015. I haven’t read this, rather discovered it while googling. It’s about 120 pages. It seems like it got a muted response, and I would hope to get a bit more traction that it appears to have gotten.
• The Effective Engineer by Edmond Lau. A well known book, although I haven’t read it (I did read these notes from a random gist though). I think most remarkable for Edmond building an entire conversion funnel and content program around it.
• Modern CTO by Joel Beasley in 2018. About 130 pages. Skimmed through since it’s on Kindle Unlimited. Voice is “authoritative and fun.” More list driven than I’d like to be, feels a bit light on content.