90 Day Plan for a CTO in a New Job

Starting as a CTO in a new organization is like conducting an orchestra you’ve never heard before. You need to understand the musicians, learn the repertoire, and quickly establish your rhythm—all while the performance continues. This framework will help you navigate those critical first 90 days with intention and impact.

I’ve refined this approach through my experiences at Knight Ridder, Condé Nast, and The New York Times, and I continue to evolve it. Think of this not as a rigid prescription but as a scientific method for organizational transformation. Test, learn, adapt, and make it your own. If you discover improvements, I’d love to hear them—leadership is a shared journey.

The key is to approach these seven areas iteratively, making incremental improvements while building momentum for larger changes.

1. Understand Your Job. Learn the Organization and Industry You Are In.

Your first priority isn’t to change things—it’s to deeply understand what already exists. Too many CTOs arrive with predetermined solutions to problems they haven’t yet identified. Instead, approach your first weeks like an anthropologist studying a new culture.

Map Your Responsibilities

Begin by creating a comprehensive inventory of your domains. In most CTO roles, these cluster into three major areas:

Technology Foundation: This encompasses Software Engineering, Infrastructure Engineering, DevOps, Cyber Security, Systems Operations, and Application Support. Understand not just what each team does, but how they interconnect. Are your engineers siloed by function or integrated into product teams? How mature are your DevOps practices? With the rise of containerization and Docker adoption, many organizations are in transition—understand where you stand.

Product Excellence: Product Management, Project Management, User Experience, and User Interface Design form the bridge between technology capability and customer value. Assess whether these functions operate as partners or in sequence. In today’s mobile-first world, how well does your UX team understand responsive design? Are product managers truly owning outcomes or just managing features?

Data Capabilities: Data Science, Data Engineering, and Data Visualization are increasingly critical differentiators. Evaluate whether data is treated as a product or just a byproduct. With the explosion of real-time analytics and machine learning applications, understanding your data maturity is essential.

Build Your Knowledge Network

Knowledge lives in people, not documents. Schedule one-on-ones with every direct report, key stakeholder, and influential individual contributor. But don’t just ask about challenges—ask about victories. What are they most proud of? What innovations excite them? Understanding aspirations reveals more than cataloging complaints.

Extend this network beyond your walls. Connect with:

Customers who can share unfiltered product feedback
Peer CTOs who’ve navigated similar challenges
Industry analysts who understand competitive dynamics
Former employees who can provide historical context

I strongly recommend establishing a relationship with an executive coach early. The CTO role can be isolating, and having an objective thought partner accelerates your growth while providing crucial perspective.

Synthesize Patterns

As you gather information, resist the urge to immediately categorize issues as “problems to solve.” Instead, look for patterns:

What themes appear across multiple conversations?
Where do stated goals conflict with actual behaviors?
Which metrics drive decisions versus which should?
What technical debt is acknowledged versus hidden?

Create a living document—I prefer mind maps—that captures the interconnections between culture, technology, and operations . This becomes your strategic compass.

2. Define and Revise Measurements for Success

Metrics are the language of organizational alignment. But most companies measure what’s easy rather than what matters. Your job is to establish measurements that drive the right behaviors.

Start with Shareholder Value

Every metric should ultimately connect to company success. List the key performance indicators that matter to your board and investors. These typically include:

Revenue growth and customer acquisition costs
Operational efficiency and margins
Market share and competitive position
Innovation pipeline and speed to market

Cascade to Team Metrics

Now translate these into technology and product metrics that your teams can actually influence:

Deployment frequency and lead time (DevOps maturity)
System reliability and incident response times
Feature adoption and user engagement rates
Technical debt ratio and code quality scores
Team velocity and predictability

The art lies in balancing leading indicators (which predict future success) with lagging indicators (which confirm past performance). For example, code review turnaround time is a leading indicator of deployment frequency, which leads to faster feature delivery, which drives customer satisfaction.

Prune Outdated Metrics

Equally important is identifying which metrics to stop tracking. Legacy measurements often drive outdated behaviors. I once inherited a team optimizing for lines of code written—a metric that actively discouraged elegant solutions. Be ruthless about eliminating metrics that no longer serve your strategy.

Introduce Future-Focused Metrics

In 2016’s rapidly evolving technology landscape, consider adding metrics that position you for tomorrow:

API adoption rates (for platform thinking)
Mobile performance scores (for user experience)
Security vulnerability resolution time (for increasing threats)
Cross-team collaboration indices (for breaking silos)

3. Articulate Your Vision and Strategy

Vision without execution is hallucination, but execution without vision is merely activity. Your role is to paint a compelling picture of the future while providing a clear path to reach it.

Craft Your North Star

Your vision should be ambitious enough to inspire but concrete enough to guide decisions. Avoid generic statements like “be the technology leader.” Instead, articulate what leadership means in your context:

“Build the most trusted financial platform by making security and reliability our fundamental architecture principles”
“Become the fastest-moving media technology team by embracing continuous deployment and data-driven decisions”
“Create products our customers can’t imagine living without by obsessing over user experience and iterating rapidly”

Communicate Relentlessly

A vision unshared is merely a personal dream. You need multiple channels and consistent repetition:

Regular Rhythms: Establish predictable communication cadences. Weekly one-on-ones with direct reports aren’t just status updates—they’re coaching opportunities. For organizations under 100 people, monthly all-hands meetings build community. Larger groups benefit from quarterly gatherings with departmental meetings filling the gaps.

Multiple Mediums: People absorb information differently. Combine:

Written updates for detail-oriented processors
Visual presentations for big-picture thinkers
Interactive sessions for kinesthetic learners
Recorded videos for distributed teams

Bidirectional Dialogue: Communication isn’t broadcasting—it’s conversation. Create forums for questions, challenges, and ideas to flow upward. Some of my best strategic insights have come from junior engineers brave enough to challenge assumptions.

Build Stakeholder Alliances

Your vision needs champions beyond technology. Invest time with:

Sales leaders who can validate customer needs
Marketing partners who can amplify your message
Finance colleagues who can support investment cases
Operations teams who depend on your platforms

Remember: human relationships trump organizational charts. A coffee conversation often accomplishes more than a formal presentation.

4. Organize People for Success

Structure isn’t just about reporting lines—it’s about creating conditions for teams to thrive. The best organization design balances efficiency with growth, stability with flexibility.

Design for Evolution

Traditional hierarchical structures struggle with modern technology’s pace. Consider organizational patterns that promote agility:

Product-Aligned Teams: Instead of functional silos, create cross-functional squads that own entire user experiences. This reduces handoffs and accelerates learning cycles.

Platform Capabilities: Centralize foundational services (authentication, payments, data pipelines) that multiple products consume. This prevents duplication while maintaining team autonomy.

Guild Structures: Overlay communities of practice across formal teams. A mobile guild might include iOS and Android developers from different products who share knowledge and standards.

Review my detailed thoughts on three-dimensional team organization for balancing product delivery, stakeholder needs, and career development.

Revitalize Talent

Organizational change creates opportunity for individual growth:

Career Pathing: Implement dual-track career progression that equally values technical mastery and people leadership. Not every brilliant engineer wants to manage, and forcing them into management roles wastes their gifts.

Title Standardization: While maintaining some flexibility for creativity , establish clear title progressions that enable external benchmarking and internal fairness.

Non-Linear Growth: Recognize that careers zigzag . The engineer who becomes a product manager who returns to engineering brings valuable perspective.

Recruit Strategically

Your early hires set cultural tone. Beyond technical skills, assess for:

Growth mindset and learning agility
Collaboration and communication abilities
Alignment with your nascent culture
Complementary skills to current team

When possible, implement working interviews where candidates solve real problems alongside potential teammates. This reveals more than any algorithm question.

5. Build Culture

Culture isn’t perks or policies—it’s the sum of daily behaviors. As CTO, you don’t just inherit culture; you actively shape it through your actions and decisions.

Establish Cultural Cornerstones

Psychological Safety: Teams need to feel safe to experiment, fail, and learn. Model this by openly discussing your own mistakes and what you learned. When someone surfaces a problem, thank them publicly.

Shared Purpose: Align teams around common goals that transcend individual objectives. Make it clear that internal competition is toxic —we win together or not at all.

Continuous Learning: Technology evolves rapidly. Encourage conference attendance, lunch-and-learns, and experimentation time. What seems cutting-edge today (like React’s recent dominance) will be table stakes tomorrow.

Reinforce Through Rituals

Recognition Rhythms: Implement regular appreciation practices. This could be shout-outs in all-hands meetings, peer bonus programs, or simple thank-you notes for excellent work.

Celebration Ceremonies: Mark both professional and personal milestones. Product launches deserve parties, but so do team members’ marathons, new babies, or educational achievements.

Feedback Frameworks: Design performance review systems that emphasize growth over grades. Focus on future potential rather than past mistakes.

Live Your Values

Your calendar reflects your true priorities. If you value work-life balance, model it by taking vacation and respecting boundaries. If you champion innovation, allocate time and resources for experiments. Consider progressive policies like flexible vacation that trust people to manage their time.

I’ve found that experimenting with workplace practices —like opening your office to anyone—can reinforce cultural values while keeping the environment dynamic.

6. Revise Processes for Success & Delivery

Process should enable excellence, not enforce conformity. Your goal is creating just enough structure to ensure quality while preserving agility.

Systematize Wisdom

Transform tribal knowledge into shared resources:

Operational Checklists: Document critical procedures like incident response or vendor evaluations . These become training tools and quality guarantees.

Best Practice Libraries: Encourage teams to document and share what works—from productivity tips to architectural patterns. Make contributing to shared knowledge part of performance expectations.

Decision Frameworks: Create scorecards for project prioritization that balance strategic value, effort required, and risk factors.

Embrace Productive Meetings

Meetings have terrible reputations because most are terrible. Transform yours through:

Clear agendas distributed in advance
Defined decision rights and outcomes
Time-boxed discussions with parking lots
Action items with owners and deadlines
Follow-up mechanisms ensuring execution

Portfolio Discipline

Not all projects deserve to live forever. Implement regular portfolio reviews using the Trinity Method to evaluate what to start, stop, and continue. This prevents zombie projects from consuming resources better allocated to innovation.

7. Upgrade Technologies

Technical transformation requires balancing immediate needs with long-term vision. You’re simultaneously maintaining current systems while building tomorrow’s platforms.

Address Technical Debt Strategically

Technical debt isn’t uniformly bad—sometimes speed to market justifies shortcuts. But unmanaged debt compounds into crisis. Categorize your debt:

Critical Infrastructure: Reliability, security, and performance issues that threaten business continuity demand immediate attention. If you’re still running unencrypted HTTP in 2016, SSL certificates are non-negotiable.

Developer Productivity: Tools and processes that slow teams compound over time. Investing in continuous integration, automated testing, and deployment pipelines pays dividends.

Scalability Constraints: Architecture that worked at startup scale breaks with growth. Moving to microservices and containerization with Docker positions you for elastic scaling.

Build for Autonomy

Modern architecture should enable team independence:

Service-Oriented Architecture: Whether full microservices or well-designed monoliths with clear boundaries, ensure teams can deploy independently.

Cloud-Native Thinking: Leveraging AWS or similar platforms isn’t just about infrastructure—it’s about embracing elasticity, automation, and managed services.

API-First Design: Every service should expose clean interfaces, enabling future flexibility and potential platform business models.

The Continuous Journey

This framework isn’t a one-time exercise—it’s an iterative cycle. Each quarter, revisit these areas with fresh perspective:

What’s changed in your understanding?
Which initiatives show results?
Where do new challenges emerge?
How can you raise the bar higher?

Leadership is about constant growth, both for yourself and your organization. Stay curious, remain humble, and remember that victory comes from winning people over to a shared vision, not just defeating obstacles through force.

Thank you for reading this guide. I hope it accelerates your journey to CTO excellence. Please share your experiences and improvements—together we can elevate technology leadership across our industry.

This article is mirrored on LinkedIn . It is a part of the ctobook series of articles related to #culture, #technology, and #operations: three critical parts of a Chief Technology & Product Officer’s job.