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
Pros:
Nothing to change
Things stay their course
Cons:
No improvements
No changes
CTO Improves
How?
“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
Goal:
Build alignment
Build empathy
Pros:
CTO stays on board
Requires:
Regular check in
Regular enforcement
Introduce Complementary Role (CPO, VP of E)
Some organizations have engineering report to the Chief Product Officer.
Pros:
CTO stays on board
CTO gets to do what they enjoy
Cons:
Have to find a person suitable for the role
Concerns:
Replacement needs to complement CTO
Need to define responsibilities of each individual
CTO gets assigned/responsibilities reduced
How:
Reduce responsibilities
Define responsibilities
Pros:
CTO stays on board
See Jeff Bezos and Amazon’s first CTO Kaphan
Responsibilities slowly reduced
CTO Leaves
Pros:
Hopefully more transfer of knowledge
Hopefully done in good faith
Cons:
Requires replacement
Firing of CTO
Pros:
Clean slate
Cons:
Loss of technical knowledge
Requires replacement
Difficulties:
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
Architecture
Infrastructure
Technical
Domain Knowledge
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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