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Amazing CTO

The missing manual for managing

This book is 100% completeLast updated on 2026-06-21
Stephan Schmidt

Your hard skills landed you the management position, but it’s your soft and management skills that will drive your success. Numerous books cover architecture and processes, "Amazing CTO" stands out as the essential guide for managing effectively, authored by influential CTO Coach Stephan Schmidt.

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About

About

About the Book

Your hard skills landed you the management position, but it’s your soft and management skills that will drive your success. Numerous books cover architecture and processes, "Amazing CTO" stands out as the essential guide for managing effectively, authored by influential CTO Coach Stephan Schmidt.

The one book for CTOs and techmanagers. The CTO role is the most difficult role from the perspective of diverse skills and change. With AMAZING CTO the job gets much easier with proven advice and many ideas to succeed.

Example Rule

#14 Sets up people for success not failure

In my coaching one of the common mistakes is to hire someone or delegate something but then set up the person for failure. Happy for the help, and because the reason was to safe time, they do not invest enough time to make the employee successful. When I hear a coachee say, "That developer failed, he was a mis-hire" I say "Most probably you did set up the developer for failure." Set up for failure is not investing into a new hire. The Amazing CTO sets people up for success. She thinks, "What are all the things I can do to make the person successful?" Does the person need to know something? Do I need to communicate his role? Do I need to introduce him to someone? Does he need tools? Does he need a budget? Do I need to give authority? Setting up people for success leads to a happier work environment that gets results instead of a string of failures.

Excerpt Table of Contents

The book has nine parts of rules, here the example of one part:

“Hunting High And Low” . . . . . . . . . . . 66
Takes leaving not personally . . . . . . . . 67
Actively promotes . . . . . . . . . . . . . .68
Knows technology is a fashion industry . . . 69
Knows processes are swimming wings . . . . . 70
Knows processes are solved conflicts . . . . 71
Handles underperformers . . . . . . . . . . .72
Fires people herself . . . . . . . . . . . . 73
Is a professional . . . . . . . . . . . . . .74
Manages her boss . . . . . . . . . . . . . . 75
Leads the team . . . . . . . . . . . . . . . 76
Knows what she loves . . . . . . . . . . . . 77
Budgets expenses . . . . . . . . . . . . . . 78
Does dailies when hiring . . . . . . . . . . 79
Is kind . . . . . . . . . . . . . . . . . . .80
Gives honest feedback . . . . . . . . . . . .81
Is creative . . . . . . . . . . . . . . . . .82
Encourages people to think . . . . . . . . . 83

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Author

About the Author

Stephan Schmidt

Stephan launched his tech career as a self-taught coder, mastering the art of programming as a kid in a department store back in 1981 with ambitions of creating video games. His passion for technology led him to university, where he delved into computer science, specializing in distributed systems and artificial intelligence, while also exploring the realms of philosophy. With the dawn of the internet era, Stephan became a pioneering coder and engineering manager for several startups.

His journey in the tech world expanded as he founded a venture capital-funded startup and tackled architecture, processes, and growth challenges in various fast-growing VC-backed companies. His roles have included engineering manager at ImmoScout24 and CTO of an eBay Inc. subsidiary. Following the successful sale of his wife’s startup, the couple relocated to the seaside, where Stephan embraced his role as a CTO coach, guiding technology leaders through the intricacies of their evolving roles.

The Leanpub Podcast

Episode 294

An Interview with Stephan Schmidt

Testimonials

Reader Testimonials

Contents

Table of Contents

Part 1 - Introduction

  1. Foreword to the Expanded Edition
  2. 140 opinionated rules for engineering managers
  3. Prolog
  4. My Story
  5. Be An Amazing CTO

Part 2 - Rules

  1. “Relax”
  2. Starts with a yes
  3. Asks for help
  4. Does ruthlessly 1:1s
  5. Knows it is all about people
  6. Holds people accountable
  7. Is explaining the world
  8. Gives purpose
  9. Does not take shortcuts
  10. Loves technology
  11. Is curious
  12. Is not defensive
  13. Talks about expectations
  14. Has passion
  15. Sets up people for success not failure
  16. “Land of Confusion”
  17. Gets the cow off the ice first
  18. Is not her tools
  19. Knows the business side
  20. Self validates
  21. Is not letting people wait
  22. Does not waste other peoples time
  23. Lives up to her commitments
  24. Delegates everything
  25. Recruits herself
  26. Cares about bugs
  27. Is listening
  28. Works on things with impact
  29. Is focused
  30. Knows the Why
  31. Is inclusive
  32. “Running Up That Hill”
  33. Is prepared for a meeting
  34. Is a storyteller
  35. Develops her reports
  36. Cares about privacy
  37. Doesn’t do illegal things
  38. Is agile
  39. Is a tortoise not a hare
  40. Is not a CIO
  41. Guides people
  42. Has a meeting agenda
  43. Talks last
  44. Changes her mind
  45. Admits when being wrong
  46. Gives negative feedback in private
  47. Compliments others
  48. Delivers
  49. Admits not knowing everything
  50. “Hunting High And Low”
  51. Takes leaving not personally
  52. Actively promotes
  53. Knows technology is a fashion industry
  54. Knows processes are swimming wings
  55. Knows processes are solved conflicts
  56. Handles underperformers
  57. Fires people herself
  58. Is a professional
  59. Manages her boss
  60. Leads the team
  61. Knows what she loves
  62. Budgets expenses
  63. Does dailies when hiring
  64. Is kind
  65. Gives honest feedback
  66. Is creative
  67. Encourages people to think
  68. “Self Control”
  69. Is a coder at heart
  70. Knows missing Disaster Recovery can kill him
  71. Takes quality to her heart
  72. Translates tech for business
  73. Translates business to tech
  74. Builds the right product
  75. Does not ignore problems
  76. Is transparent and open
  77. Aligns employees and teams
  78. Moderates meetings
  79. Does not work in a feature factory
  80. Encourages responsibility
  81. Fixes retention before she hires
  82. Has a mentor
  83. Works with peers
  84. Has an opinion
  85. “Maniac”
  86. Is a role model
  87. Manages security
  88. Cares about his health
  89. Knows herself
  90. Actively manages her time
  91. Is in control of the tech zoo
  92. Capitalizes development costs
  93. Knows how to deal with pressure
  94. Does not invent excuses
  95. Does not take failures personally
  96. Trusts people
  97. Earns her trust
  98. Knows assumptions are bad
  99. Fixes performance first
  100. Automates everything
  101. “Call me”
  102. Says no
  103. Has sit-downs to solve conflicts
  104. Knows her role
  105. Lives radical simplicity
  106. Invests in her growth
  107. Has weekly team meetings
  108. Encourages leadership
  109. Gives responsibility
  110. Invests in relationships
  111. Gets the best out of people
  112. Does not go to all meetings
  113. Invests in recruiting
  114. Forces decisions
  115. Manages technical debt
  116. “Brothers in Arms”
  117. Does skip level meetings
  118. Manages culture
  119. Knows her talents
  120. She innovates
  121. Picks her battles
  122. Can scale a team 10x
  123. Can scale systems 10x
  124. Invests in employer branding
  125. Doesn’t make tech decisions
  126. Stops the buck
  127. Works on deep features
  128. Helps others with their careers
  129. Knows they are not bound by rules
  130. Is a team player
  131. Pays the right salary
  132. “Xanadu”
  133. Supports the CEO
  134. Wants to be amazing
  135. Is on top of things
  136. Knows fear
  137. Takes the blame
  138. Acts and doesn’t ask
  139. Invests half her time in the team
  140. Understands the nature of a crisis
  141. Knows what to build and what to buy
  142. Trains a successor
  143. Gives talks
  144. Thinks about the future of software development
  145. Has a vision
  146. Knows that strategy is for people
  147. Connects with the tech community
  148. Deals with politics
  149. Has a personal brand
  150. Knows her team can’t tell her she’s wrong
  151. “Computer Liebe”
  152. Has a vision for AI
  153. Owns the AI strategy
  154. Matches the company’s risk appetite
  155. Knows it’s not about code
  156. Knows AI doesn’t fix bad management
  157. Understands LLMs and their limits
  158. Knows the tools
  159. Experiments relentlessly
  160. Focuses on data
  161. Guards the company’s deep knowledge
  162. Treats AI as infrastructure
  163. Builds an AI-friendly codebase
  164. Implements guardrails for AI
  165. Wants correctness, not determinism
  166. Invests in prompt infrastructure
  167. Shields the company from model drift
  168. Rolls out AI in phases
  169. Treats AI adoption as a delegation problem
  170. Acts
  171. Uses AI to reshape, not rewrite
  172. Doesn’t lay off developers
  173. Changes roles not just tools
  174. Redefines what senior means
  175. Coders and Creators
  176. Doesn’t let AI split the team
  177. Protects how juniors learn
  178. Doesn’t let AI erode culture
  179. Takes fear seriously
  180. Knows its about control
  181. Control is your bottleneck
  182. Doesn’t outsource thinking to AI
  183. Doesn’t blame the AI
  184. Is not paralyzed by hype
  185. Shows leadership
  186. Makes sense of the AI world
  187. Educates the CEO and board on AI
  188. Doubles down on branding
  189. Teaches everyone to talk to machines
  190. Thinks bigger

Appendix

  1. Lists and Checklists
  2. 1:1 Questions
  3. The CTO Blues
  4. AI Guardrails and Governance
  5. ChatGPT Proof Interviewing
  6. Checklist for Job Ads
  7. Delegation Checklist
  8. Hiring Notes
  9. Roles during an incident
  10. Interview Questions
  11. Laying someone off
  12. Onboarding
  13. Performance Feedback
  14. Performance Factors
  15. Very Basic Security Checklist
  16. Someone Resigns
  17. Models
  18. Pyramid Of Change
  19. Motivation Model
  20. Pyramid Of Relationships
  21. Delegation Vicious Circle
  22. The Management Triad
  23. Employee Life Cycle
  24. 9 Box Talent Model
  25. Four States of a Development Team
  26. Culture Model
  27. ZigZag Model of Strategy and Vision
  28. Three Gaps of Management
  29. Startup Phases
  30. Icebergs of Development
  31. The Coding Cycle
  32. Examples Of Developer Roles
  33. The Staircase of Control

Reflections on the future of CTOs

Epilog

About Stephan

About the cover

OST Amazing CTO Book

The Curious Incident Of The Vending Machine in the Night-Time

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