The Problematic CTO

CTOs that do more harm than good

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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