# The Startup CTO's Handbook
Table of contents of the book The Startup CTO's Handbook: Essential skills and best practices for high performing engineering teams. The book is also available as a single markdown file.
The Author
Using this Book
3.1 Management Fundamentals
The Professional Skill Tree
Kaizen: Continuous Improvement
Coaching
Find a Management Mentor
1:1 MEETINGS
SKIP-LEVEL MEETINGS
COACHING MANAGERS
1:1 Meetings with Engineers
1:1 Content and Agenda
1:1 Playbooks
Radical Candor
Benefits of Overcommunication
EMAIL
SYNCHRONOUS CHAT
ASYNCHRONOUS COMMUNICATION
ASYNCHRONOUS CULTURE
DOCUMENTATION
On Acronyms at Work
Meetings and Time Management
TIME MANAGEMENT
MEETING TIMING
ENGINEER'S TIME RECOMMENDATION
The HIPPO
TO-DO LISTS
CALENDAR RETROSPECTIVES AND TIME BALANCE
Mini Management Frameworks
THREE STAGES OF MANAGEMENT PROBLEM-SOLVING
TEAM-BASED DECISIONING MODELS
Two Types of Decisions
BREAKING TIES
Task Triage The Urgent/Important Matrix
PEOPLE-PUZZLE SOLVER
Joining a Team
Actionable Management Tips
BEING HIRED TO LEAD
Giving Technical Advice to Friends/Strangers
Traffic: Funnels and Umbrellas
Your First Team
Working With The CEO
ALIGNING SPECIFIC OBJECTIVES
ALIGNING BUSINESS DIRECTION
ALIGNING CULTURE AND VALUES
Delivering Bad News
Speaking the Language of Your Audience
Technical Communication Best Practices
3.2 Hiring and Interviewing
Hire like a Startup
Speed is Your Friend!
WHEN TO HIRE: HEADCOUNT PLANNING
ROLE NEED/TEAM GAP
ROLE PRIORITIZATION AND TIMING
BUDGETING FOR NEW HIRES
Hiring Goals and Objectives
EFFICIENCY
SUCCESS RATE
CANDIDATE EXPERIENCE
EQUITABLE OPPORTUNITIES
SCALABILITY
The Job Description
Surveying the Market
Creating Clarity on a Role
Job Descriptions as an Advertisement
Sourcing Candidates
INBOUND RECRUITING
OUTBOUND RECRUITING
REFERRALS
A Note on the Mathematics of Incentivizing Referrals
Interviewing Best Practices
REJECTED CANDIDATES OPINIONS MATTER
BE TIMELY AND MAKE SCHEDULING EASY
ASK ONLY NEW QUESTIONS
AVOID BIASES
USAGE OF AN APPLICANT TRACKING SYSTEM (ATS)
SELLING CANDIDATES
Phone Screen
Culture Interview
Coding Challenge
Predictive Ability
Candidate Experience and Drop-Off
Technical Interviews
METHODOLOGY
Technical Focus Interview Guide
Hiring Juniors vs. Seniors
The Interview Itself
Executive interviews
Reference Checks
TIMING
CONTENT
Making an Offer
PRESENTING THE OFFER
3.3 Onboarding
Boy Scout Rule: Onboarding
Onboarding to the Team vs. the Company
Onboarding Documentation
THE ENGINEERING GUIDEBOOK
WELCOME TO [YOUR COMPANY NAME] ENGINEERING, DAY 1 GUIDE
Onboarding Milestones aka The Ninety-Day Scorecard
THE SCORECARD
HANDLING A SCORECARD FAILURE
LETTING A NEW EMPLOYEE GO
Onboarding Timeline
Competency Matrix and Leveling
OVERVIEW
Creating the Competency Matrix
Compensation and Leveling
Competitive Rates & Market Rate Data
Job Titles
Engineering Individual Contributor Titles
Manager Titles
Review Cadence
Reviewer Selection
Review Questions
Result Calculation
Result Discussion
Compensation Adjustment Rollout
Changing Seats
Brilliant Jerks
Firing
3.5 Team Makeup
Seniority Makeup
Technical Specialization
Project Maintenance: The Two Crews Philosophy
Team Organization
Managing Remote Teams
Documentation
Asynchronous Work
In-Person Meetups
Time Zone Overlap
Create Social Opportunities
Camera On
Recording Meetings
3.6 Leadership Responsibilities
Product and Design Teams
Design Systems
PRDs and Specs
EPD
Product vs. Project Management
Managing Managers and Manager Training
Finances and Budgeting
The Budget
Working with your CFO
Measuring Engineering Velocity/Health
Cycle Time
Work Time Allocation
Fundraising and Due Diligence
Vendor Management
Sales Qualification
Negotiation
Signing
Post-Sales
3.7 Which Type of Startup CTO Are You?
The Tech-Focused CTO AKA The Chief Architect
The People-Focused CTO AKA the VP of Engineering (VPE)
The Externally Focused CTO AKA The Head of Technical Sales/Marketing
Transitioning Between Types
4.1 Tech Culture and General Philosophy
Ten Pillars of Tech Culture
4.2 Tech Debt
Tech Debt And The Product Lifecycle
Defining Tech Debt
Tech Debt Bankruptcy
Measuring Debt The Debt Inventory
Strategies For Paying Down Debt
Just-In-Time Payment
Periodic Paydown
Continuous Paydown
Communication of Tech Debt
4.3 Technology Roadmap
Timeframes
Short-Term/Horizon One
Medium-Term/Horizon Two
Long-Term/Horizon Three
Timeline Communication
4.4 Tech Process
Workflow
Waterfall
Agile/Scrum
Shape Up
Engineering Estimates
Burndown Charts
Choosing A Workflow
Cooldown/Innovation Sprints
Technical Planning And Specifications
Tech Spec Leads
Time For Planning
Prototyping as Part of Spec Writing!
Tech Spec Content
Tech Spec Approval
Review Goals
Review Process
Leaders In Specification Review Meetings
Technical Specifications As Documentation
4.5 Developer Experience (DX)
Prioritizing Developer Experience
Easy Developer Experience Wins
5.1 Architecture
Domain-Driven Design
High-Level Patterns
Monolithic Architecture
Service-Oriented Architecture (Soa)/Microservices
Choosing Between A Service-Oriented Architecture And A Monolith
Source Control for Service-Oriented Architectures: monorepo and manyrepo
The Distributed Monolith
Writing Readable, Good Code
Choice Of Language And Ecosystem
Static Code Analysis
Greenfield vs. Brownfield
Coding Patterns
Object-Oriented Programming (OOP)
Purity
Functional Programming
Extreme Programming And Test-Driven Development (TDD)
Dependency Injection
Domain-Driven Design
API Contracts
API Design Governance
API Architecture
HTTP-Based APIs
Non-HTTP APIs
Documentation
Idempotency
Idempotency Keys
5.2 Data And Analytics
Transactional Data
Analytical Business Intelligence Data
Behavioral Data
General Tips And Best Practices For Architecture Design
Put Business Logic In The Backend
Make Services Externalizable
Use As Few Languages As Possible
Implementing Internal Technology Radar
Boring Technology
Budget
Tracking
5.4 DevOps
Four Key Metrics (DORA)
Reproducibility
Containerization
Container Management Best Practices
Design Containers to Build Once/Run Anywhere
Build Images in CI
Use a Hosted Registry
Keep Image Sizes as Small as Possible
Dockerfile Best Practices
Container Orchestration
Hosted Container Management
Self-Managed/Kubernetes
ClickOps vs. IaC
Continuous Integration
Continuous Deployment
Feature Branch Environments
Managing DNS
Decoupling Shipping Code from Shipping Features (Feature Toggles)
System Monitoring: APMs and RUMs
5.5 Testing
Testing/Quality Assurance Teams
Test Quality
What To Test
Testing Type Comparison
Unit Tests
Integration Tests
End-To-End Tests
Visual Regression Testing
Manual Testing
Specialized Manual Testing
Unspecialized Manual Testing
Semi-Automated Testing
5.6 Source Control
Peer Review
Ship, Show, Ask
Branching Models
Long-Lived Vs. Short-Lived Branches
5.7 Production Escalations
Implementing Escalators
ROOT CAUSE ANALYSIS (RCA) EXERCISES
RCA Documents
RCA Meetings And Timeline
Choosing the RCA Lead Author
5.8 IT
5.9 Security and Compliance
Auth Security Terminology
Security At Startups
Compliance
7.1 Digital References