CTO Katas

May 8, 2017 · New York, United States of America

Note: We will start at 6:30 exactly.  

One of the biggest goals for CTO School is to encourage expertise sharing and connecting with each other. 

In October, we had a very well-received session called CTO Katas.  CTO Katas are modeled after Architecture Katas, which is a fun exercise for architects to practice architecting.  

We'll go through CTO Katas, which will be more focused on technology strategy, people and process issues.  


CTO Katas are intended as a small-group (max 6 people) exercise, with two-to-three groups doing the same kata.  

Rules:  • Co-Workers are not allowed to be in the same group. 

• Each group will discuss the scenario for about 20-25 minutes. 

• You may ask the moderator questions about the scenario. 

• After the time is up, each group will present what they decided to do.  

• Afterwards, we'll briefly open it up to the larger audience for feedback. 

• We will try to do two or three kata rounds during the meeting 

If you have ideas for scenarios (especially real world) that you'd like to suggest, 

please share (email me privately) them so we can try to include them!

Example Kata: 

1. Suppose you are brought into an early stage startup that just raised a $5M round. Their product looks good and is getting traction, but it was built by a team of offshore contractors for cost reasons.   They believe that it's not scalable, both on the team and code perspective.  They want you to put together a first 30 days plan for getting the company out of this situation, with at least two or three alternatives and advantages / disadvantages. 

2. Suppose you join a company that is growing rapidly.  Even though you are not a security expert, you notice that the security practices are practically nonexistent.  You view this as a risk and would like to convince your boss and senior executives that more investment is needed.  How would you go about doing this, and what concrete ideas would you suggest to get the ball rolling. 

3.  Your largest customer just called your CEO because you had three downtimes in the last two weeks.  Availability and performance is a problem.  Most of engineers have been focused on product development, and you accumulated technical debt.   Also, you operate in a very waterfall-like manner.  However, the new products are considered strategically important.  CEO wants a number of suggestions for how to save this account and improve the non-functional aspects while still being able deliver on product commitments.      

4. You join a new company as VP Eng.  The company has had some attrition, and the overall level of team is quite junior.  The team is demotivated and one of the complaints is that people are not learning a lot of new things.   What are some of the things would you suggest to improve the situation?


As always, a group of us will hang out afterwards at a bar nearby.  

We like to hang out at Rye, which is at 11 W 17th St, New York, NY 10011, between Avenue of Americas and 5th.   They have both drinks and food.   http://ryehousenyc.com/

Event organizers
  • CTO School

    A group of NYC Startup CTOs, VP of Engineering, Tech Leads, and technologists who would like to become better leaders. Membership is by approval, and ONLY technical people are encouraged to join.   The membership is open to senior and mid-level technical leaders, or people on the cusp of getting there (e.g. lead developers). The goal is to have an ongoing forum for technical leaders (esp. in startups) to discuss their issues, whether the issues are related to people management and leadership, process or te

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