CTO Checklist for all technology leaders

A comprehensive CTO checklist that technology leaders keep circling around, and the three main categories such as:

1. People
2. Processes
3. Technology

CTO Checklist

People

Your team

• Develop your leaders
  - The very best leaders develop their team to the extent that their leadership position can be successfully handed on to one of the team (Level 5 leadership)
• Delegate to your leaders (more on this later)
• Stay in touch with your whole org
  - Meet with individual teams, listen to what they have to say
  - Do skip-level 1–1s with a broad range of your org
• Lead with trust and transparency to get the best out of your team

Personal development

• Have a documented career ladder
• Have good definitions for each level of the ladder, including examples of meeting and exceeding expectations
• Technical training matrix with expectations for each role
• Management training program
• Ensure that every single person in your org has a career path and a development plan to help them get there
• Have a robust, transparent performance review process
• Set expectations that feedback will be given throughout the year — promptly and constructively. There should be no surprises at annual review time.

Exec team

• Invest in your relationship with key execs
• Understand key opportunities and challenges your company faces
• Contribute to company strategy
• Ensure tech strategy exists and supports company strategy

Delegation

• Be clear on what responsibilities you own and what you delegate
• Set clear expectations when delegating
• Use delegation as growth opportunities for your team

Culture

• Develop psychological safety in your team — lead by example
• Enable innovation by setting guard rails and pushing down decision making
• Move at the right speed — not too fast, not too slow

Networking

• You won’t have a peer who is a CTO at the company — find some who are at other companies then speak to them regularly
• Present at public events: paying it forward / back and raising the profile of your company
• Consider writing articles from time to time, e.g. on your company tech blog

Processes

Hiring

• Have a quick hiring process — you can’t hire the best candidates if you don’t move on them quickly
• Build a team whose priority is hiring
• Ensure your hiring team runs consistent interviews (different questions but with clear goals) and have consistent expectations for each role
• Plan ahead for open roles
• Market your company

Scaling

• Know the roles you need to fill to support company growth
• Know the team structure that can support growth
• Know how many member changes a team can tolerate in a year
• Be prepared for your company to switch from a small company culture where everyone knows each other and rules are in people’s heads, to a large company culture where teams work independently and rules are documented

Getting shit done

• Identify the people who can help you get shit done and build a relationship with them, e.g. Product
• Have a clear vision and a strategy to guide how you realise it
• Build momentum — make sure there is a constant stream of delivery
• Ensure the small frequent deliveries contribute to your larger goals

Budget

• Know your budget and share it with your teams
• Know where your budget is being spent
• Give teams a budget where possible — push decision making down

Change

• Have a robust company-wide change process, e.g. DACI Framework

Technology

Architecture

• Document high level principles: what and why
• Document guard rails (the goal is autonomy and alignment)
• Document golden paths for common needs, e.g. distributed tracing
• Document coding standards

Data

• Document guidelines for source data, data lake, data warehouse
• Process for moving data between source, lake, WH
• Top level schema for warehouse data

Security

• Application, OWASP top 10
• Network, Principle of Least Privelege
• Ongoing testing
  - Pen testing
  - White hat hackers, e.g. bugcrowd
  - Vulnerability scanning
  - Static code analysis
• Compliance

Software delivery

• Developer tooling — IDEs
• Source control
• Build processes
• Release pipeline
• Observability
• Pre-prod development & testing environments

Infrastructure

• Infrastructure-As-Code
• Dev, Sandbox, Prod environments

Software delivery monitoring

• DORA metrics
• Dev productivity tool e.g. jellyfish

Testing and quality

• Document clear expectations on quality
  - Static analysis
  - Merge Request expectations
• Quality assurance processes
• Testing expectations
• - Coverage levels
  - Test execution time
  - Test plan expectations, in dev and prod
  - Defect density

Developer productivity

• Use DORA metrics to help understand productivity
• Understand feedback loops
• Dev productivity dedicated team / individuals

SRE

• Operations or SRE team
• Monitoring and alerting
• SLAs, SLOs, SLIs
• Incident response procedure

Documentation

• Best practices
• Guardrails
• Projects
• APIs & UI based applications

Industry trends

• Have a process for staying up to date with industry trends

Refer: https://medium.com/@tom-neal/cto-checklist-1a2ef3d6502