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Will Larson - An Elegant Puzzle: Systems of Engineering Management

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Will Larson An Elegant Puzzle: Systems of Engineering Management
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Theres a saying that people dont leave companies, they leave managers. Management is a key part of any organization, yet the discipline is often self-taught and unstructured. Getting to the good solutions of complex management challenges can make the difference between fulfillment and frustration for teams, and, ultimately, the success or failure of companies. Will Larsons An Elegant Puzzle orients around the particular challenges of engineering management--from sizing teams to technical debt to succession planning--and provides a path to the good solutions. Drawing from his experience at Digg, Uber, and Stripe, Will Larson has developed a thoughtful approach to engineering management that leaders of all levels at companies of all sizes can apply. An Elegant Puzzle balances structured principles and human-centric thinking to help any leader create more effective and rewarding organizations for engineers to thrive in.

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Summary Theres a saying that people dont leave companies they leave managers - photo 1
Summary Theres a saying that people dont leave companies they leave managers - photo 2
Summary

Theres a saying that people dont leave companies, they leave managers. Management is a key part of any organization, yet the discipline is often self-taught and unstructured. Getting to good solutions for complex management challenges can make the difference between fulfillment and frustration for teams, and, ultimately, between the success or failure of companies.

Will Larsons An Elegant Puzzle orients around the particular challenges of engineering managementfrom sizing teams to managing technical debt to succession planningand provides a path to the good solutions. Drawing from his experience at Digg, Uber, and Stripe, Will Larson has developed a thoughtful approach to engineering management that leaders of all levels at companies of all sizes can apply. An Elegant Puzzle balances structured principles and human-centric thinking to help any leader create more effective and rewarding organizations for engineers to thrive in.

Bio

Will Larson has been an engineering leader and software engineer at technology companies of many shapes and sizes, including Yahoo!, Digg, SocialCode, Uber, and, since 2016, Stripe.

He grew up in North Carolina, studied Computer Science at Centre College in Kentucky, spent a year in Japan for the JET Program teaching English, and has been living in San Francisco since 2009.

An Elegant Puzzle draws from the writing in his blog, Irrational Exuberance!, that he has been updating since graduating from college. It is currently, and will always be, a work in progress.

An Elegant Puzzle Systems of Engineering Management - image 3@lethain
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An Elegant Puzzle: Systems of Engineering Management

2019 Will Larson

All rights reserved. No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording, or any other information storage and retrieval system, without prior permission in writing from the publisher.

First published in 2019 in hardcover

in the United States of America

by Stripe Press/Stripe Matter Inc.

Stripe Press

Ideas for progress

San Francisco, California

press.stripe.com

Printed in Canada

ISBN: 978-1-7322651-8-9

Ebook by Bright Wing Books (brightwing.ca)

First Edition

Contents
Landmarks
Preface The first blog post that I ever wrote was on April 7 2007 and was - photo 5
Preface

The first blog post that I ever wrote was on April 7, 2007, and was titled Finding Our Programming Flow. It was not very good. That year I wrote 69 posts, the last being Miyajima and Hiroshima, a collection of pictures from a trip I took while teaching English in Japan. The next year, 2008, I wrote 192 posts. The writing still left much to be desired.

It took 200 more posts and another decade to cobble together a written voice and to make enough mistakes that my experience might become worth reading. Im fortunate that that moment coincided with my time at Stripe, an environment where folks routinely do things that might in other contexts seem out of reach: things like starting a technology magazine or publishing a book.

This book is the lucky alignment of that happy moment at Stripe, a decade of writing and a decade of learning about both leadership and management, and the good fortune to work with colleagues who suggested collecting my writing into this book.

I hope that everyone who picks up this book gets something useful out of it. Your comments and thoughts are appreciated at:

.

Acknowledgments

A few particular thanks are in order. This book came together in the months preceding my wedding, and Im grateful to Laurel for her thoughts and partnership. Thank you to Brianna Wolfson and Tyler Thompson, without whom this book would not exist. Finally, thanks to my sister, Hope, who has long been the talented sibling, showing that the path to authorship is attainable.

1 Chapter 1 Introduction 11 Introduction Some people go into management out - photo 6
1
Chapter 1
Introduction
1.1 Introduction

Some people go into management out of a desire to be of service. Others become managers in a cynical pact, exchanging excitement in their current role for the prospect of continued salary bumps and promotions. There are even folks who initially go into management because theyre entirely fed up with their own manager and are convinced that they could do better.

I wont say which of those, if any, describes me.

Regardless of what motivation first brings you into management, it can feel as if youve entered a troubled profession. Skilled practitioners are scarce, and only the exceptional company is willing to invest in growing its managers.

If training programs are peculiarly uncommon, concerns that todays managers are ill-prepared are not. I was lucky early in my management career to have a coworker describe me as the best leader they had worked with. It took several additional years of practice for another to declare me their worst.

While Davids cloak is increasingly suspicious draped from the shoulders of Silicon Valleys Goliaths, the vast majority of technology companies are well-meaning chrysalises that hope to one day birth a successful business, and they are guided by managers who are learning to lead, one unexpected lesson at a time. For many such people, the entry into engineering management begins with a crisis, and their training is a series of hard knocks.

This was certainly my experience: my path into management began at Digg, paved by a pair of layoffs in 2010. The three one-on-ones Id had at my previous job had not, surprisingly, culminated in a rigorous framework for management, and I had absolutely no idea what I was doing.

In the years since, Ive worked to educate myself on the topic, reading anything that seemed even distantly relevant. There are some wonderful resources out there (many of which Ive listed in the Books Ive found very useful appendix), but the rare answers I uncovered continued to be drowned out by my ever-increasing sea of questions.

It was only when I got the opportunity to work at Uber, which was growing its engineering team from 200 to 2,000 over two years, and then at Stripe, which was experiencing similar rapid growth, that I had to opportunity to truly refine my approach to management through exposure to an endless variety of challenges. There are few things peaceful about managing in rapidly growing companies, but Ive never found anywhere better to learn and to grow.

As Ive become more experienced, my appreciation for management, and engineering management in particular, has grown, and Ive come to view the field as a series of elegant, rewarding, and important puzzles. This book is a collection of those puzzles, which Ive had the good fortune to struggle with and learn from. It starts with the most important tool in my kit, Organizations. Organizational design gets the right people in the right places, empowers them to make decisions, and then holds them accountable for their results. Maintained consistently and changed sparingly, nothing else will help you scale more. Next, well review a handful of fundamental Tools of management that Ive found useful across a wide variety of scenarios. These range from systems thinking to vision documents, from metrics to migrations, from reorgs to career narratives. Perhaps the easiest way to use this chapter is to skim over the ideas quickly, and then reread them when it seems as if they might be useful.

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