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Joshua Hoffman - Should the CTO be Coding? - Codemotion Amsterdam 2019

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What is the job of a CTO and how does it change as a startup grows in size and scale? As a CTO, where should you spend your focus? As an engineer aspiring to be a CTO, what skills should you pursue? In this inspiring and personal talk, I describe my journey from early Red Hat engineer to CTO at Bloomon. I will share my view on what it means to be a CTO, and ultimately answer the question: Should the CTO be coding?

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Joshua Hoffman - Should the CTO be Coding? - Codemotion Amsterdam 2019

  1. 1. Should The CTO Be Coding? Joshua Hoffman (Independent) Amsterdam | April 2-3, 2019
  2. 2. Set the radio to channel 1!
  3. 3. Who am I?
  4. 4. Experience Highlights • Red Hat • Tumblr • SoundCloud • LeaseWeb
  5. 5. Who is this talk for?
  6. 6. This Talk Is For • Engineers thinking about a career change to management • New Startup CTOs (especially with rapidly growing teams) • Anyone who wonders what a startup CTO does
  7. 7. Should the CTO be coding?
  8. 8. What is a CTO?
  9. 9. “Executive-level position focusing on scientific and technological issues.”
  10. 10. “The CTO develops policies and procedures and uses technology to enhance products and services.”
  11. 11. “The CTO examines the short and long term needs of an organization, and utilizes capital to make investments designed to help the organization reach its objectives.”
  12. 12. What is a Startup CTO?
  13. 13. “Nobody really knows.”
  14. 14. “It’s a fuzzy sort of role that doesn’t really fit in a box.”
  15. 15. “It totally depends on the startup.”
  16. 16. Some Types of Startup CTO • A Technical Founder • Solo Engineer • Lead Engineer of a small team • Head of Product Team • Head of Engineering Team
  17. 17. It totally depends on the startup.
  18. 18. The CTO Spectrum Startup———————ScaleUp—————————BigCorp
  19. 19. The CTO Spectrum Startup———————ScaleUp—————————BigCorp 1-4 15-30 50-100 500+
  20. 20. The CTO Spectrum Startup———————ScaleUp—————————BigCorp 1-4 15-30 50-100 500+
  21. 21. How did I get here?
  22. 22. Why be a Technology Leader?
  23. 23. “Taking the lobotomy” Photo by https://commons.wikimedia.org/wiki/User:Bz3rk Creative Commons Attribution-Share Alike 3.0 Unported
  24. 24. Management Chooses You
  25. 25. My First Management Experience Photo by https://commons.wikimedia.org/wiki/User:Bidgee Creative Commons Attribution-Share Alike 2.5 Australia
  26. 26. Management vs Leadership
  27. 27. What does a Startup CTO do?
  28. 28. Stuff a Startup CTO Typically Does • Recruiting • Coaching and Mentoring • Help define Career Paths • Help define Team Structure • Influence Engineering Culture • Maintain a Vision of The Future • Coding?
  29. 29. My Top Startup CTO Priorities • Deliver top quality products and/or services • Be a great place to be an engineer
  30. 30. Recruiting
  31. 31. –Amsterdam Economic Board Report: Fighting The Odds “Developer and data scientist vacancies are constantly open and it usually takes… more than 12 weeks to fill these vacancies.”
  32. 32. –Amsterdam Economic Board Report: Fighting The Odds “The demand for Junior IT talents has doubled in the past year, reaching 1 candidate per 26 vacancies, with developers still being the most sought-after candidates…”
  33. 33. Positive Candidate Experience
  34. 34. Integrity
  35. 35. 5 Open Interview Questions
  36. 36. “What advice would you give someone who is considering a career change to software engineering?”
  37. 37. “What is one book every software engineer should read and why?”
  38. 38. “What advice would you have for a junior engineer on their first day of work?”
  39. 39. “In your opinion, what is the difference between a Junior and Senior software engineer?”
  40. 40. “What would you like to learn from us and what can you teach us?”
  41. 41. Coaching and Mentoring
  42. 42. Coaching Advice or assistance that is immediately actionable.
  43. 43. Coaching • Immediate feedback • No relationship required • Practical • Incremental focus
  44. 44. Mentoring A trusting relationship, built over time, typically in which a more experienced person advises a less experienced person.
  45. 45. Mentoring • Thoughtful advice • A long term relationship • More questions than answers • Long term focus
  46. 46. Career Growth
  47. 47. Engineering Career Levels
  48. 48. Engineer Level 1 • Influence: self • Communicates clearly and effectively • Actively involved in learning new skills • Asks for help when stuck
  49. 49. Engineer Level 2 • Influence: team • Regularly facilitates team communication • Actively involved in learning and sharing new skills • Helps others when asked • Can solve small problems independently
  50. 50. Engineer Level 6 • Influence: industry • Regularly writes research papers and/or conference talks • Actively involved in coaching and/or mentoring other team members • Contributes to engineer onboarding program • Can lead a large project involving multiple teams
  51. 51. Performance Management
  52. 52. Leadership Example How to change the behavior of 100+ engineers
  53. 53. Uptime 96% Photo by https://www.flickr.com/photos/dirrksv Creative Commons Attribution-ShareAlike 2.0 Generic
  54. 54. Outages occur primarily during working hours
  55. 55. Outages mostly effect new/active projects
  56. 56. MTTR >180 minutes
  57. 57. –John Alspaw “All outages are the result of someone doing their job.”
  58. 58. 7 Requirements To Complete Any Task
  59. 59. Awareness
  60. 60. Tools
  61. 61. Skills / Knowledge
  62. 62. Capacity
  63. 63. Standard
  64. 64. Definition of Done
  65. 65. Measurement
  66. 66. Motivation
  67. 67. 7 Requirements To Complete Any Task 1. Awareness 2. Tools 3. Skills / Knowledge 4. Capacity 5. Standard / Definition of Done 6. Measurement 7. Motivation
  68. 68. Solution: Uptime Academy
  69. 69. Prepare a service for production
  70. 70. Respond to an incident
  71. 71. Conduct a post mortem investigation
  72. 72. Uptime 99.9% Photo by https://www.flickr.com/photos/dirrksv Creative Commons Attribution-ShareAlike 2.0 Generic
  73. 73. Uptime Academy 1. Prepare a service for production 2. Respond to an incident 3. Conduct a post mortem investigation
  74. 74. Team Structure
  75. 75. Team interdependency is a direct result of architectural choices
  76. 76. Tech Debt
  77. 77. Engineering Culture
  78. 78. Way of Working
  79. 79. Vision of The Future
  80. 80. Should the CTO be coding?
  81. 81. The CTO should SOMETIMES be coding.
  82. 82. –Lisa Cash Hanson “Leadership is the ability to guide others without force into a direction or decision that leaves them still feeling empowered and accomplished.”
  83. 83. Seven Secrets Of The Successful Startup CTO
  84. 84. Never Stop Learning
  85. 85. Never Stop Teaching
  86. 86. Tech Over Taste
  87. 87. Elevate Others
  88. 88. Make Decisions
  89. 89. Plan For Tech Debt
  90. 90. Build and Maintain Your Network
  91. 91. Seven Secrets of The Successful Startup CTO 1. Never Stop Learning 2. Never Stop Teaching 3. Tech Over Taste 4. Elevate Others 5. Make Decisions 6. Plan For Tech Debt 7. Build and Maintain Your Network

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