New CTO Starter Pack

Overview

Starting as a CTO can be overwhelming. This collection provides a structured path through your first 90 days, combining tactical frameworks with strategic insights.

Target Audience: New CTOs, first-time CTOs, VP Engineering → CTO transition

Time Investment: ~2 hours of reading, lifetime of value

Outcome: Clear framework for your first 90 days with actionable checklists

Phase 1: First 30 Days - Listen & Learn

Week 1-2: Assessment

1. First 30 Days as a New CTO

Time: 15 min | Priority: Critical

Your roadmap for month one. Covers:

Who to meet (in order of priority)
What questions to ask
How to assess without alarming the team
Quick wins to establish credibility

Key Takeaway: Listen 80%, talk 20% in first month

2. Engineering Team Assessment Framework

Time: 20 min | Priority: Critical

Systematic framework to evaluate:

Team composition and skills matrix
Process maturity (planning, code review, deployment)
Technical capabilities
Cultural health

Tool Included: Assessment scorecard (download)

Action: Schedule 1-on-1s with each engineer using this framework

3. Technical Debt Prioritization Matrix

Time: 15 min | Priority: High

How to assess and prioritize technical debt:

Risk assessment framework
Business impact scoring
Effort estimation
Prioritization matrix

Output: Your first tech debt backlog, ready to discuss with exec team

Week 3-4: Understanding

4. Understanding Your Architecture

Time: 10 min | Priority: High

Checklist for evaluating current architecture:

Scalability assessment
Single points of failure
Integration complexity
Technical risk areas

Action: Create architecture diagram if one doesn't exist

5. Stakeholder Mapping for CTOs

Time: 12 min | Priority: Medium

Identify and prioritize stakeholders:

CEO, Board, Exec team
Product, Sales, Customer Success
Engineering team
External (vendors, partners)

Tool: Stakeholder influence/interest matrix

Phase 2: Days 31-60 - Plan & Communicate

Week 5-6: Strategy

6. 90-Day Engineering Strategy

Time: 25 min | Priority: Critical

Build your 90-day plan:

Top 3 priorities (not 5, not 10)
Resource allocation
Success metrics
Communication plan

Deliverable: One-page strategy to share with CEO

7. Board Communication for CTOs

Time: 15 min | Priority: High

How to communicate with the board:

What metrics matter
How to present risks
Making asks effectively
Quarterly update template

Bonus: PowerPoint template included

Week 7-8: Quick Wins

8. High-Impact Low-Effort Wins

Time: 10 min | Priority: High

Catalog of quick wins to build credibility:

Process improvements (code review, deployment)
Tool upgrades (monitoring, CI/CD)
Team morale boosters
Cost optimizations

Goal: Ship 2-3 quick wins by day 60

Phase 3: Days 61-90 - Execute & Establish

Week 9-12: Execution

9. Engineering OKRs Framework

Time: 18 min | Priority: High

Set clear objectives and key results:

How to set engineering OKRs
Alignment with company OKRs
Avoiding vanity metrics
Quarterly cadence

Example: 3 complete OKR sets for different scenarios

10. Hiring Your First Leadership Team

Time: 20 min | Priority: Critical

Build your bench:

When to hire managers vs ICs
Engineering manager vs technical lead
Interview framework for leadership
Onboarding plan

Bonus: Interview question bank

11. Establishing Engineering Processes

Time: 15 min | Priority: Medium

Core processes to implement:

Sprint planning (if Agile)
Code review guidelines
Incident response
Architecture review board

Template: Process documentation starter kit

12. Building Psychological Safety

Time: 12 min | Priority: High

Create environment where team can thrive:

What is psychological safety?
How to measure it
How to build it
Warning signs it's missing

Assessment: Team health survey template

Bonus Resources

Templates & Checklists

1-on-1 Meeting Template
Engineering Onboarding Checklist
Incident Postmortem Template
Architecture Decision Record (ADR) Template
Engineering Standards Doc

Success Metrics

Track your progress through the first 90 days:

Day 30 Checklist

Completed 1-on-1s with all engineers
Identified top 3 technical risks
Created initial team assessment
Established relationship with CEO
Delivered 1-2 quick wins

Day 60 Checklist

Presented 90-day strategy to exec team
Made first board presentation
Implemented 1-2 process improvements
Started first strategic hire
Identified and started addressing critical tech debt

Day 90 Checklist

Delivered on 90-day commitments
Established quarterly OKR rhythm
Built trust with team and exec team
Created roadmap for next quarter
Have clear understanding of organization's needs

What Success Looks Like

After completing this collection, you should have:

✅ Clarity on your team, technology, and organizational dynamics ✅ Credibility through delivered quick wins and clear communication ✅ Strategy for your first year with measurable objectives ✅ Processes that scale beyond your direct involvement ✅ Relationships with key stakeholders across the organization

Next Collections

Ready for more?

Scaling to 50+ Engineers - Growing your team
Technical Excellence Program - Raising the bar
CTO Crisis Management - Handling emergencies

Community Support

Join other new CTOs:

CTO Peer Network - Private forum
Office Hours - Monthly Q&A with experienced CTOs
CTO Mentorship Program - 1-on-1 guidance

Total Read Time: ~2 hours Best Consumed: Over 2-3 weeks, alongside doing the work Update Frequency: Quarterly

Questions? Contact us or join our community