Early Praise for Become an Effective Software Engineering Manager James’s book will be at the top of my mind when I start a product company. The content is not just for software engineering managers—technical leaders, CTOs, and managers will all benefit from practical advice that helps them be successful with the people they manage and work with. ➤ Stephen Bussey Author of Real-Time Phoenix; Software Architect, SalesLoft I am really grateful that finally a book exists on how to be a good technical man- ager, with engineering-level clear instructions. This book is the only reason I have survived my first two months on the job. I followed its advice on hiring, running one-to-ones, and most importantly, managing my own time. We hired some amazing people, and the hires and my sanity are still here—so this book must be teaching me something right. ➤ Lev Konstantinovskiy Data Science Team Lead, Trading Firm This is a book I wish every engineering manager read before they stepped into the role. Bite-sized pieces of advice on engineering management that you would expect from a Pragmatic Publishers book. ➤ Patrick Kua Founder, Patkua.com There still are very few books written by hands-on engineering managers working at tech companies on how to succeed in this kind of environment. This book is exactly that. The stories are relatable, the takeaways well articulated, and the exercises will help readers become better managers. It’s the book I’ll be recom- mending to new managers transitioning into the role, managers starting at a new company, and experienced managers looking to make an organization-wide impact. ➤ Gergely Orosz Engineering Manager, Uber James comes across as a sincere author who writes from his experience in man- agement, and it shows in his writing. ➤ Chris Dudley Engineer, Brandwatch Become an Effective Software Engineering Manager How to Be the Leader Your Development Team Needs James Stanier The Pragmatic Bookshelf Raleigh, North Carolina Many of the designations used by manufacturers and sellers to distinguish their products are claimed as trademarks. Where those designations appear in this book, and The Pragmatic Programmers, LLC was aware of a trademark claim, the designations have been printed in initial capital letters or in all capitals. The Pragmatic Starter Kit, The Pragmatic Programmer, Pragmatic Programming, Pragmatic Bookshelf, PragProg and the linking g device are trade- marks of The Pragmatic Programmers, LLC. Every precaution was taken in the preparation of this book. However, the publisher assumes no responsibility for errors or omissions, or for damages that may result from the use of information (including program listings) contained herein. Our Pragmatic books, screencasts, and audio books can help you and your team create better software and have more fun. Visit us at https://pragprog.com. The team that produced this book includes: Publisher: Andy Hunt VP of Operations: Janet Furlow Executive Editor: Dave Rankin Development Editor: Adaobi Obi Tulton Copy Editor: L. Sakhi MacMillan Indexing: Potomac Indexing, LLC Layout: Gilson Graphics For sales, volume licensing, and support, please contact [email protected]. For international rights, please contact [email protected]. Copyright © 2020 The Pragmatic Programmers, LLC. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form, or by any means, electronic, mechanical, photocopying, recording, or otherwise, without the prior consent of the publisher. ISBN-13: 978-1-68050-724-9 Encoded using the finest acid-free high-entropy binary digits. Book version: P1.0—May 2020 Contents Acknowledgments . . . . . . . . . . . ix Introduction . . . . . . . . . . . . . xi Part I — Getting Oriented 1. A New Adventure . . . . . . . . . . . . 3 Beginning Your First Week 5 Creating a Snapshot 7 Making an Action List 14 And Relax… 15 2. Manage Yourself First . . . . . . . . . . 17 Let’s Get Organized! 18 How to Categorize Your Activities to Feel Productive 29 How to Measure Your Output as a Manager 33 OK, I’m Ready! 34 Part II — Working with Individuals 3. Interfacing with Humans . . . . . . . . . . 39 How to Communicate Well 42 Delegation 51 Working with Your Manager 56 Onward! 61 4. One-to-Ones . . . . . . . . . . . . . 63 Week In, Week Out 65 How to Prepare for One-to-Ones 66 Contracting: Your First One-to-Ones 67 What to Talk About and How to Do It 72 Contents • vi How to Take Notes and Assign Actions 75 Remember: You Are Not a Therapist 77 OK, What’s Next? 77 5. The Right Job for the Person . . . . . . . . 79 What Motivates People? 81 The Zone of Proximal Development 86 The Cathedral and the Bazaar 93 A Review Before Reviews 97 6. The Most Wonderful Time of the Year . . . . . . 99 Myth Busting 101 How to Prepare for Performance Reviews 103 What to Do on the Day 113 How to Talk About Money 115 Where to Next? 116 7. Join Us! . . . . . . . . . . . . . 119 Picking Who to Hire 121 Writing Great Job Descriptions 126 Setting Up an Interview Process 131 From Hiring To… 145 8. Game Over . . . . . . . . . . . . . 147 People Leaving Is Normal 149 When Staff Leave 150 Fighting the Good Fight 155 Making Staff Leave 157 Enough Goodbyes Already! 165 9. How to Win Friends and Influence People . . . . . 167 Going Beyond Your Team 169 Building Your Network 170 Giving Back 174 Time to Take It Up a Level 184 Part III — The Bigger Picture 10. Humans Are Hard . . . . . . . . . . . 187 Scrutiny and Judgment 189 Wobble 193 The Whip and the Carrot 197 Contents • vii Mount Stupid 201 It Isn’t Just Humans… 206 11. Projects Are Hard . . . . . . . . . . . 207 The Eye of Sauron 209 Victims of Your Own Success 214 Scope, Resources, and Time 217 And Relax… 222 12. The Information Stock Exchange . . . . . . . 225 Spies and Gatekeepers 227 How to Share Just Enough Information 229 Workplace Politics 236 It’s Time to Decompress 242 13. Letting Go of Control . . . . . . . . . . 243 Transcending Tasks 245 Escaping the False Productivity Trap 250 What You Do Outside of Work Matters 255 Letting Go…of This Chapter 261 14. Good Housekeeping . . . . . . . . . . 263 Communication Dictates Software Design 265 Breaking Silos with Guilds 268 Encouraging a Culture of Talks 272 Turning Problems into Learning Opportunities 277 Tools to Solve Common Problems 282 Now Let’s Organize Our Careers 285 15. Dual Ladders . . . . . . . . . . . . 287 Individual Contributor Track 289 Management Track 291 Creating a Progression Framework 293 Career Progression Troubleshooting 298 Time to Tackle the Big Issues 302 16. The Modern Workplace . . . . . . . . . . 305 Diversity and Inclusion 307 The Shift Toward Remote Working 314 Work-Life Balance 322 Notes on Culture 324 To the Land of Unicorns 325 Contents • viii 17. Startups . . . . . . . . . . . . . 327 Software Is Eating the World 328 Opportunities for Managers 329 Why Management at Startups Is Critical 337 What Does Your Future Hold? 338 18. The Crystal Ball . . . . . . . . . . . 341 Life, the Universe, and Everything in Between 342 Your Vision 344 Your Plan 349 Performing the Exercise with Your Staff 352 That’s All Folks! 354 Bibliography . . . . . . . . . . . . 357 Index . . . . . . . . . . . . . . 361