Think Like a CTO Alan Williamson Foreword by Ankit Mathur MANNING Think Like a CTO Think Like a CTO ALAN WILLIAMSON MAN NING SHELTER ISLAND For online information and ordering of this and other Manning books, please visit www.manning.com. The publisher offers discounts on this book when ordered in quantity. For more information, please contact Special Sales Department Manning Publications Co. 20 Baldwin Road PO Box 761 Shelter Island, NY 11964 Email: [email protected] ©2023 by Manning Publications Co. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by means electronic, mechanical, photocopying, or otherwise, without prior written permission of the publisher. Many of the designations used by manufacturers and sellers to distinguish their products are claimed as trademarks. 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Development editor: Dustin Archibald 20 Baldwin Road Review editor: Aleks Dragosavljevic PO Box 761 Production editor: Deirdre S. Hiam Shelter Island, NY 11964 Copy editor: Pamela Hunt Proofreader: Katie Tennant Typesetter: Marija Tudor Cover designer: Shawn Girsberger ISBN 9781617298851 Printed in the United States of America I want to dedicate this book to my long-time friend and mentor, Jim Milbery, fellow technologist (just don’t let him code) and founding partner at ParkerGale Capital. Jim has had a huge impact on both my professional and personal lives (and even introduced me to my wife). I would also like to dedicate this to my dear departed mother, who was with us at the start of this journey and read a few early chapters, but never made it to the end of the final product. contents foreword xiii preface xv acknowledgments xvii about this book xix about the author xxiii 1 The Chief Technology Officer (CTO) 1 1.1 What makes a Chief Technology Officer 2 1.2 Different types of CTOs 4 Prestartup, in name only 4 ■ Funded startup: The technology expert with money 5 ■ Established company: Their first CTO 6 ■ Established company with CTO 7 1.3 Determining whether we need a CTO 8 1.4 Evolution from engineer 9 The first 100 days 11 1.5 Top 10 qualities for a CTO 13 2 Managing up 15 2.1 Partnering with your CEO 16 The office of the CEO 16 ■ Types of CEOs 18 ■ Setting the tone 19 ■ Tips for a successful partnership 21 vi CONTENTS vii 2.2 Counting on your CFO 23 Getting a handle on your expenditures 23 ■ Reaching out 26 2.3 Working with peers 26 Know your company 27 ■ Speak their language 28 Find their pain 28 ■ Think strategically 29 2.4 Taking over from another CTO 30 Celebrate, not disparage 30 ■ Speak to the outgoing CTO 31 Discover the team 32 2.5 Presenting to the board 32 Know your audience 33 ■ Format of the meeting 33 Your role 34 ■ The dos and don’ts 35 2.6 Communications 36 Internal 36 ■ External 37 2.7 Internal politics 38 The major types 38 ■ Mitigating politics 39 2.8 Change management 41 Boiling the frog 41 ■ Excitement committee 42 ■ Valley of anguish 42 ■ Consequences 43 3 Visionary planning 45 3.1 The grand vision 46 The “what”/“why” part 47 ■ The “how” part 48 Define success 49 3.2 Engaging with clients 50 Know your client 50 ■ Your counterpart 51 3.3 Long-term planning 53 Timing is everything 53 ■ Keep in mind 55 3.4 Incorporating seismic shifts 56 Decision paralysis 57 ■ Identify the pillars of your vision 57 Watching the pillars 58 ■ Looking for simplicity 59 3.5 Elevator pitch 60 Creating your pitch 61 ■ Practicing and honing the pitch 62 3.6 Putting together a budget 62 What to include 63 ■ Lay out the budget 63 ■ Keeping track 65 ■ Return on investment (ROI) 65 3.7 Near-term planning and expectations 66 Communication 66 ■ Controlling the narrative 67 viii CONTENTS 4 Building a team 70 4.1 Different types of resources 71 Full-time employee (FTE) 71 ■ Contracting individuals 72 Outsourcing to vendor 73 ■ Onshore resourcing 73 Offshore resourcing 74 ■ Comparison review 75 4.2 Knowing when to hire 76 Hiring events 77 ■ Discipline matrix 80 ■ Impact of not hiring 82 4.3 Sourcing candidates 82 Referrals 83 ■ Recruitment agency 83 ■ Headhunting 84 Graduate fairs/internships 85 ■ Self-serve online 87 4.4 Creating the job description 87 Basic structure 88 ■ Title 89 ■ Description 90 ■ Minimum requirements 91 ■ Required skills 91 ■ About/legal information 92 5 Interviewing, choosing, and onboarding 94 5.1 The interview 95 Getting into the right mindset 95 ■ Your objectives 96 Phone interview (or preinterview) 97 ■ In-person interview 98 Video interview 102 5.2 Scoring candidates 104 Defining your criteria 104 ■ Marking the candidate 106 5.3 Saying no 107 Definitely not 107 ■ Definitely maybe 108 5.4 Onboarding 109 Bringing them up to speed 109 ■ Your expectations 110 Getting to work 110 6 Team management 112 6.1 Charter 113 Knowledge 114 ■ Sample charter 115 6.2 Team structure 116 Product centric 117 ■ Lifecycle centric 117 ■ Customer/vertical centric 117 ■ Hybrid approach 118 6.3 Titles 118 What is in the title? 118 ■ Ladder to improvement 119 Common mistakes with titles 120 CONTENTS ix 6.4 Team reporting 121 Define autonomy 122 ■ Reporting metrics 123 Accountability 124 6.5 One-on-one meeting 125 6.6 Education and training 126 Online libraries/resources 127 ■ Platform/software certifications 127 ■ Bootcamps 127 ■ User groups 128 Internal training 128 ■ Conferences 129 University/college courses 129 6.7 Communication 129 Email 130 ■ Meetings 131 ■ Feedback 133 7 Annual reviews 135 7.1 Skill matrix 136 Basic matrix structure 137 ■ Filling out the grid 138 Logistics 139 7.2 Handling failure 140 Initial reaction 141 ■ Investigation 141 ■ Learning 143 7.3 Termination 144 Downsizing the department 144 ■ Skills no longer required 145 ■ Poor performance 146 ■ Logistics 147 The exit interview 148 7.4 Remote working 148 Setup 149 ■ Managing expectations 150 ■ Preventing abuse 151 8 Technology decisions 153 8.1 Avoid lock-in 155 8.2 Build vs. buy 156 Buy 157 ■ Build 158 ■ Considerations 159 Checklist 159 8.3 Cloud vs. on-prem 160 Cloud 161 ■ On-prem 164 8.4 Disaster recover 167 Downtime tolerance 168 ■ Full or partial service 170 Fail forward vs. bounce back 171 ■ Managing the event 171 Cloud and DR 173