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Should the CTO be coding?

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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. 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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Should the CTO be coding?

  1. 1. Should The CTO Be Coding? Joshua Hoffman (Independent) Amsterdam | April 2-3, 2019
  2. 2. Who am I?
  3. 3. Experience Highlights • Red Hat • Tumblr • SoundCloud • LeaseWeb
  4. 4. Who is this talk for?
  5. 5. 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
  6. 6. Should the CTO be coding?
  7. 7. What is a CTO?
  8. 8. “Executive-level position focusing on scientific and technological issues.”
  9. 9. “The CTO develops policies and procedures and uses technology to enhance products and services.”
  10. 10. “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.”
  11. 11. What is a Startup CTO?
  12. 12. “Nobody really knows.”
  13. 13. “It’s a fuzzy sort of role that doesn’t really fit in a box.”
  14. 14. “It totally depends on the startup.”
  15. 15. Some Types of Startup CTO • A Technical Founder • Solo Engineer • Lead Engineer of a small team • Head of Product Team • Head of Engineering Team
  16. 16. It totally depends on the startup.
  17. 17. The CTO Spectrum Startup———————ScaleUp—————————BigCorp
  18. 18. The CTO Spectrum Startup———————ScaleUp—————————BigCorp 1-4 15-30 50-100 500+
  19. 19. The CTO Spectrum Startup———————ScaleUp—————————BigCorp 1-4 15-30 50-100 500+
  20. 20. How did I get here?
  21. 21. Why be a Technology Leader?
  22. 22. “Taking the lobotomy” Photo by https://commons.wikimedia.org/wiki/User:Bz3rk Creative Commons Attribution-Share Alike 3.0 Unported
  23. 23. Management Chooses You
  24. 24. My First Management Experience Photo by https://commons.wikimedia.org/wiki/User:Bidgee Creative Commons Attribution-Share Alike 2.5 Australia
  25. 25. Management vs Leadership
  26. 26. What does a Startup CTO do?
  27. 27. 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?
  28. 28. My Top Startup CTO Priorities • Deliver top quality products and/or services • Be a great place to be an engineer
  29. 29. Recruiting
  30. 30. –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.”
  31. 31. –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…”
  32. 32. Positive Candidate Experience
  33. 33. Integrity
  34. 34. 5 Open Interview Questions
  35. 35. “What advice would you give someone who is considering a career change to software engineering?”
  36. 36. “What is one book every software engineer should read and why?”
  37. 37. “What advice would you have for a junior engineer on their first day of work?”
  38. 38. “In your opinion, what is the difference between a Junior and Senior software engineer?”
  39. 39. “What would you like to learn from us and what can you teach us?”
  40. 40. Coaching and Mentoring
  41. 41. Coaching Advice or assistance that is immediately actionable.
  42. 42. Coaching • Immediate feedback • No relationship required • Practical • Incremental focus
  43. 43. Mentoring A trusting relationship, built over time, typically in which a more experienced person advises a less experienced person.
  44. 44. Mentoring • Thoughtful advice • A long term relationship • More questions than answers • Long term focus
  45. 45. Career Growth
  46. 46. Engineering Career Levels
  47. 47. Engineer Level 1 • Influence: self • Communicates clearly and effectively • Actively involved in learning new skills • Asks for help when stuck
  48. 48. 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
  49. 49. 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
  50. 50. Performance Management
  51. 51. Leadership Example How to change the behavior of 100+ engineers
  52. 52. Uptime 96% Photo by https://www.flickr.com/photos/dirrksv Creative Commons Attribution-ShareAlike 2.0 Generic
  53. 53. Outages occur primarily during working hours
  54. 54. Outages mostly effect new/active projects
  55. 55. MTTR >180 minutes
  56. 56. –John Alspaw “All outages are the result of someone doing their job.”
  57. 57. 7 Requirements To Complete Any Task
  58. 58. Awareness
  59. 59. Tools
  60. 60. Skills / Knowledge
  61. 61. Capacity
  62. 62. Standard
  63. 63. Definition of Done
  64. 64. Measurement
  65. 65. Motivation
  66. 66. 7 Requirements To Complete Any Task 1. Awareness 2. Tools 3. Skills / Knowledge 4. Capacity 5. Standard / Definition of Done 6. Measurement 7. Motivation
  67. 67. Solution: Uptime Academy
  68. 68. Prepare a service for production
  69. 69. Respond to an incident
  70. 70. Conduct a post mortem investigation
  71. 71. Uptime 99.9% Photo by https://www.flickr.com/photos/dirrksv Creative Commons Attribution-ShareAlike 2.0 Generic
  72. 72. Uptime Academy 1. Prepare a service for production 2. Respond to an incident 3. Conduct a post mortem investigation
  73. 73. Team Structure
  74. 74. Team interdependency is a direct result of architectural choices
  75. 75. Tech Debt
  76. 76. Engineering Culture
  77. 77. Way of Working
  78. 78. Vision of The Future
  79. 79. Should the CTO be coding?
  80. 80. The CTO should SOMETIMES be coding.
  81. 81. –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.”
  82. 82. 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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