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CTOs that do more harm than good

The Problematic CTO

Attributes of the problematic CTO

  • Toxic
  • Holds the business and product hostage
  • Bottleneck at the company
  • People want to leave the company because of the CTO
  • Not accountable to anyone
  • Doesn’t respect non technical people
  • “Know it alls”
    • Think they are the best
    • “One trick pony”
      • May not implement the best relevant tech
    • Challenges everyone
  • Unpredictable
    • Delivery deadlines
    • Availability
  • Poor understanding of product

Personal Notes

What do I dislike about technical people:

  • Over inflated egos
  • They think they are the best
  • They think they know it all
  • They don’t consider weaknesses and problems in their designs
  • They don’t see their faults
  • They don’t see the faults of their thinking
  • They have one tool, and only use it
  • “When all you are given is a hammer, you see everything as a nail”
  • Don’t consider hiring difficulties
  • Tendency to use new tech, or architectures, makes it harder to hire
  • Don’t mention migration strategies
  • No consideration of MVP; or “lean startup”
  • Tendency:
    • To glorify things
    • Rebuild the wheel
  • Magpies; attracted to shiny new tech
  • Don’t know how to build for long term, or longevity
  • They are not product oriented

Hopeful Goals

  • CTO stays on
    • Maintain organizational and technical knowledge
  • CTO learns growth mindset
  • CTO becomes accountable
  • Transfer of knowledge
  • If CTO leaves, a transition plan is prepared

Overall risks/concerns:

  • CTO leaves
  • Bad blood
  • Nothing changes
  • Things get worse
  • Impact to company/business

Biggest risk

  • CTO destroys IP
    • Take down servers and data
    • Holds them ransom

Mitigated by:

  • Getting keys and backups

Options of handling CTO

No Changes


  • Nothing to change
  • Things stay their course


  • No improvements
  • No changes

CTO Improves


  • “Founder therapy”
    • Talk about problems
    • Find alignment
    • Unbiased third person
    • Regularly; once a week
  • Mentorship
    • More hands on
    • Regularly; once a week
  • Conduct a performance improvement plan (PIP)
    • Define what you want to see improved
    • Define expectations of what you plan to see
    • Make them accountable to someone


  • Build alignment
  • Build empathy


  • CTO stays on board


  • Regular check in
  • Regular enforcement

Introduce Complementary Role (CPO, VP of E)

Some organizations have engineering report to the Chief Product Officer.

See CTO Roles and Responsibilities


  • CTO stays on board
  • CTO gets to do what they enjoy


  • Have to find a person suitable for the role


  • Replacement needs to complement CTO
  • Need to define responsibilities of each individual

CTO gets assigned/responsibilities reduced


  • Reduce responsibilities
  • Define responsibilities


  • CTO stays on board

See Jeff Bezos and Amazon’s first CTO Kaphan

  • Responsibilities slowly reduced

CTO Leaves


  • Hopefully more transfer of knowledge
  • Hopefully done in good faith


  • Requires replacement

Firing of CTO


  • Clean slate


  • Loss of technical knowledge
  • Requires replacement


  • Difficult to fire an employee in Malaysia
    • May require documented notices
    • May require a “performance improvement plan”
  • CTO may take company hostage
    • Holding on the database access and keys

Transition Plan

  • Knowledge to be transferred
  • Goal
    • Improve transfer of knowledge
      • Identify information that only the CTO knows
    • Derisk bottleneck of CTO
      • Information, knowledge, operations, processes
    • Reduce impact to the business
    • Identify gaps that were missing
    • Restore investor confidence
    • Define CTO responsibilities

Pre Kick Off

  • Understand goals and expectations
  • Speed at which they want the execution
  • Form a rough plan

Kick Off

  • Involve stakeholders
  • Have a rough plan

Follow Up

  • Do an assessment, and create documentation
  • Identify tools, fires, glossary, org chart

Questions to help me think about the transition process:

  • How can we make this transition a success?
  • What would cause this transition to fail?
  • What is everyones expectations?
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