You just accepted the CIO role. Congratulations—you're now responsible for a budget you didn't create, projects you didn't approve, a team you didn't hire, and a technology stack you didn't build. The board expects you to "transform IT" while the organization expects you to keep everything running perfectly. You have about 90 days to figure out what's actually happening and establish a credible direction forward.
The first 90 days as CIO determine whether you'll succeed or struggle for your entire tenure. This isn't hyperbole—research by Michael Watkins shows that leaders who execute their transition well are 80% more likely to achieve their objectives. For CIOs specifically, the challenge is unique: you need to build relationships across the business, assess complex technical systems, address urgent issues, and chart strategic direction simultaneously.
Most new CIOs make one of two mistakes: they either dive straight into firefighting (addressing every urgent issue but never stepping back to think strategically), or they spend months in "learning mode" (analyzing everything while urgent problems fester). The organizations that thrive under new CIO leadership get leaders who balance immediate action with strategic assessment—addressing urgent issues while systematically building understanding and setting direction.
Divide your first 90 days into three distinct phases, each with specific objectives and deliverables.
Days 1-30: Learn, Listen, and Stabilize
Primary Objective: Understand the current state, build relationships, and prevent things from getting worse.
Day 1-5: Immediate Priorities
1. Meet Your Direct Reports (Day 1-2)
Schedule 60-90 minute one-on-one meetings with each direct report in the first 48 hours.
Questions to Ask:
- What's working well in your area? What are you proud of?
- What's not working? What keeps you up at night?
- If you were CIO, what would you change first?
- What's the one thing I should know about our systems/team/vendor relationships?
- What urgent issues need my attention in the next 7 days?
What You're Assessing:
- Competence and capability of your leadership team
- Alignment (or lack thereof) on priorities and problems
- Political dynamics and relationships
- Immediate risks that need attention
Critical Move: Schedule weekly 1:1s with each direct report for at least 90 days. Building these relationships is your highest priority.
2. Identify and Address Immediate Crises (Day 2-5)
Questions to Answer:
- Are any systems at risk of failure in the next 30 days?
- Are we facing any compliance deadlines or audit findings?
- Are any critical projects about to miss major milestones?
- Are any key people about to quit?
- Are there any vendor relationships in crisis?
Action: Create a "watch list" of urgent issues and assign owners to each. You don't need to solve them all yourself—you need to ensure someone competent is handling each one.
3. Meet the C-Suite and Key Stakeholders (Day 3-7)
Don't wait for formal introductions. Proactively schedule 30-45 minute meetings with:
- CEO (most important relationship)
- CFO (controls your budget)
- COO (likely your biggest customer)
- Other C-suite members
- Key business unit leaders
- Board members (if accessible)
Questions to Ask:
- What's your top business priority for the next 12 months?
- How does technology support (or hinder) that priority?
- What's your perception of IT today? (Ask directly—you need honest feedback)
- If you could change one thing about IT, what would it be?
- What technology questions keep you awake at night?
What You're Building:
- Relationships based on understanding their needs, not defending IT
- Credibility by listening more than talking
- Intelligence about where IT has failed or succeeded previously
- Foundation for future partnership
Critical Move: Take notes in every meeting. Create a summary document of what you heard. This becomes your "Voice of the Customer" document guiding priorities.
Day 6-30: Systematic Assessment
Architecture and Technology Assessment
Understand what you own and how it works (or doesn't).
Key Activities:
- Application Portfolio Review: List all applications, their business purpose, technology stack, age, and maintenance cost
- Infrastructure Inventory: Data centers, cloud footprint, network architecture, security posture
- Integration Mapping: How systems connect, data flows, single points of failure
- Technical Debt Quantification: Aging systems, unsupported software, security vulnerabilities
Deliverable: One-page architecture overview showing major systems, their relationships, and risk hotspots
Financial Assessment
Understand where money goes and why.
Key Questions:
- What's the total IT budget? (Not just what's in the IT department—include shadow IT)
- How much is run-the-business vs. change-the-business?
- What are our largest vendor contracts and renewal dates?
- Where are we overspending? Where are we underinvesting?
- What's the actual TCO of major systems?
Red Flags to Look For:
70% of budget on maintenance (not enough for innovation)
- Large contracts with no competitive bidding in 5+ years
- "Zombie" applications that cost money but deliver no value
- Shadow IT spending that rivals official IT budget
Deliverable: IT cost structure pie chart and comparison to industry benchmarks
Project and Delivery Assessment
Understand what IT is working on and whether it's succeeding.
Key Questions:
- How many active projects? (Get the real number, not the official count)
- How many are on time and on budget?
- What's in the pipeline for the next 12 months?
- What methodology do we use? (Agile, waterfall, chaos?)
- How do we measure success?
Red Flags to Look For:
20 concurrent projects for a 50-person IT team (overcommitted)
- No projects completed in the last 6 months (delivery problems)
40% of projects significantly behind schedule
- No kill criteria (failing projects continue indefinitely)
Deliverable: Project portfolio one-pager showing status, resource allocation, and business value
People and Culture Assessment
Understand your team's capabilities and morale.
Key Activities:
- Review org structure and role definitions
- Assess skill gaps and bench strength
- Understand turnover and retention issues
- Identify flight risks (top performers considering leaving)
- Gauge morale and engagement
Assessment Methods:
- Skip-level meetings (talk to individual contributors without their managers present)
- Anonymous survey (what's working, what's not, what should change)
- Performance review history (who's succeeding, who's struggling)
- Compensation benchmarking (are we paying competitively?)
Red Flags to Look For:
- Turnover >20% annually (people are leaving)
- Cluster turnover (entire teams leaving)
- No succession planning (key person dependencies)
- Skill gaps in critical areas (cloud, security, modern development practices)
Deliverable: People assessment including high performers to retain, skill gaps to fill, and culture issues to address
Vendor and Partner Assessment
Understand external relationships and dependencies.
Key Questions:
- Who are our strategic vendors and partners?
- What's the quality of these relationships?
- Where are we vendor-dependent or locked in?
- Are we getting value for money?
- What contracts are up for renewal in the next 12 months?
Critical Meetings:
- Top 5 vendors: Introduce yourself, understand the relationship
- System integrators and consulting partners
- Managed service providers
Deliverable: Vendor relationship summary with contract values, expiration dates, and relationship health
Month 1 Deliverable: "State of IT" Document
By day 30, create a comprehensive but concise assessment document (10-15 pages maximum):
Contents:
- Executive Summary (1 page)
- What's Working Well (1 page)
- Top 10 Issues and Risks (2 pages)
- Organization and People Assessment (2 pages)
- Technology and Architecture Overview (2 pages)
- Financial Summary (1 page)
- Project Portfolio Status (1 page)
- Preliminary Recommendations (2 pages)
Audience: CEO, CFO, your boss (if not CEO), Board (if appropriate)
Purpose: Demonstrate you understand the situation and establish credibility for the changes you'll propose in month 2-3.
Days 31-60: Define Direction and Build the Plan
Primary Objective: Establish strategic direction, build alignment, and create your transformation roadmap.
Week 5-6: Strategy Definition
Based on your month 1 assessment, define where IT needs to go.
Strategic Framework Components:
1. Vision Statement (What IT Will Become)
Example: "IT will be a strategic partner enabling business growth through modern, reliable technology and exceptional service delivery."
Make it memorable, aspirational, and business-focused (not technology-focused).
2. Strategic Pillars (3-5 Major Themes)
Example pillars:
- Operational Excellence: Reliable, secure, efficient IT operations
- Business Partnership: Deep alignment with business unit priorities
- Modern Architecture: Cloud-first, API-driven, data-enabled infrastructure
- Team Development: Attract, develop, and retain top technology talent
- Innovation Culture: Safe experimentation and continuous improvement
3. Success Metrics (How We'll Measure Progress)
Choose 5-8 metrics that matter to the business:
- Business Metrics: Revenue enabled, customer satisfaction, time-to-market
- Operational Metrics: System uptime, security incidents, project delivery
- Financial Metrics: IT cost as % of revenue, ROI on technology investments
- People Metrics: Employee engagement, key talent retention, skill development
Critical Rule: Metrics must be things the business cares about, not just IT operational measures.
Week 7-8: Roadmap Development
Translate strategy into a concrete 12-18 month action plan.
Roadmap Structure:
Immediate Priorities (Next 90 Days):
- Fix critical issues identified in month 1
- Quick wins that build credibility
- Stop obvious waste (kill zombie projects, renegotiate bad contracts)
Near-Term Initiatives (3-9 Months):
- Strategic projects aligned with business priorities
- Foundation building (architecture modernization, process improvements)
- Team capability development
Strategic Investments (9-18 Months):
- Transformation initiatives
- Platform and capability building
- Competitive differentiation through technology
Resource Requirements:
- Budget: What needs funding beyond current budget?
- People: What roles/skills need to be hired or developed?
- Vendor/Partner: What external help is needed?
Week 8: Validation and Alignment
Before finalizing the strategy, validate with key stakeholders.
Validation Approach:
Individual Validation Sessions (Week 7-8)
- Meet with CEO, CFO, and key business leaders individually
- Present draft strategy and roadmap
- Ask: "What am I missing? What would you change?"
- Incorporate feedback
Leadership Team Workshop (End of Week 8)
- 3-4 hour session with your IT leadership team
- Present strategy and roadmap
- Get their input and buy-in
- Assign accountability for major initiatives
Executive Presentation (Early Month 3)
- Present to C-suite or Board
- 30-minute presentation + 30 minutes Q&A
- Goal: Get approval to proceed
Month 2 Deliverable: "IT Strategy and Roadmap" Document
Contents:
- Executive Summary (1 page)
- Strategic Context (2 pages): Business drivers, IT assessment summary
- Vision and Strategic Pillars (2 pages)
- 18-Month Roadmap (2 pages): Timeline of major initiatives
- Success Metrics (1 page): How we'll measure progress
- Resource Requirements (1 page): Budget, people, partners needed
- Governance Model (1 page): How we'll manage execution
Presentation Deck: 15-20 slides for executive presentation
Days 61-90: Execute Quick Wins and Build Momentum
Primary Objective: Demonstrate early value, build team confidence, and establish new operating rhythms.
Week 9-10: Launch Quick Wins
You can't wait 18 months to show value. Identify and execute 3-5 quick wins that build credibility.
Quick Win Characteristics:
- Delivers visible value in <90 days
- Requires modest investment (<€50K or existing resources)
- High stakeholder pain point (people notice the improvement)
- Low risk (probability of success >80%)
Example Quick Wins:
Kill Zombie Projects
- Action: Cancel 5-10 projects that have been dragging on with no clear value
- Impact: Free 15-20% of IT capacity for higher priorities
- Timeline: 2 weeks to decide, 4 weeks to wind down
- Stakeholder Impact: Business leaders appreciate decisiveness
Renegotiate Overpriced Contract
- Action: Competitively rebid a major software or service contract
- Impact: Save €200-500K annually
- Timeline: 6-8 weeks from RFP to new contract
- Stakeholder Impact: CFO appreciates cost management
Fix Persistent Pain Point
- Action: Solve a system/process issue that frustrates users daily
- Impact: Improve user satisfaction, reduce support tickets
- Timeline: 4-8 weeks from identification to fix
- Stakeholder Impact: Demonstrates IT is listening and responsive
Improve Transparency
- Action: Launch IT service status dashboard visible to all employees
- Impact: Reduce "Is email down?" questions, build trust
- Timeline: 2-3 weeks to build and deploy
- Stakeholder Impact: Shows IT is becoming more transparent
Business Value Demo
- Action: Calculate and communicate business value IT delivered last quarter
- Impact: Change perception from cost center to value driver
- Timeline: 2 weeks to analyze data and create communication
- Stakeholder Impact: Executives see IT differently
Week 11-12: Establish Operating Rhythms
Set up recurring meetings and processes that will sustain your leadership.
Key Rhythms to Establish:
Daily:
- Morning standup with key operations leaders (15 min): Any issues overnight? What's happening today?
Weekly:
- IT leadership team meeting (90 min): Performance review, issues, priorities
- 1:1s with each direct report (30-60 min each)
- Top project reviews (as needed, 30 min each)
Monthly:
- Portfolio review: Project status, resource allocation, upcoming decisions
- Financial review: Actuals vs. budget, forecast updates
- All-hands IT meeting: Communicate priorities, celebrate wins, build culture
Quarterly:
- Strategy review with C-suite: Progress on roadmap, adjustments needed
- Board update (if applicable): Strategic initiatives and business value
- IT team performance reviews and development planning
Week 12-13: Team Changes and Investments
By now you understand your team. Make the personnel moves that set you up for success.
High Performers to Retain:
- Have career conversations: What do they want? How can I help them grow?
- Compensation adjustments if they're underpaid
- Give them visibility and meaty assignments
- Make them feel valued and essential
Underperformers to Address:
- Have honest conversations about performance gaps
- Provide clear expectations and development plans
- Set 90-day improvement timeline
- Be prepared to move them out if performance doesn't improve
Key Hires to Initiate:
- Critical skill gaps identified in month 1
- Leadership roles that strengthen your team
- Specialized expertise for strategic initiatives
Organizational Changes:
- Restructure if needed (better to do it early than wait)
- Clarify roles and accountabilities
- Eliminate redundancies or inefficiencies
Critical Rule: Make people changes decisively in months 2-3. Waiting 12 months to address obvious issues wastes a year.
Day 90 Deliverable: "First 90 Days Accomplishments" Report
Create a 1-page summary showing:
- What you learned (assessment highlights)
- Where you're going (strategy summary)
- What you've accomplished (quick wins and changes made)
- What's next (roadmap preview)
Audience: CEO, CFO, Board, your IT team, key business stakeholders
Purpose: Establish credibility, demonstrate momentum, build confidence in your leadership
The Common Pitfalls to Avoid
Based on my experience and observing other CIOs, here are the failure modes to avoid:
Pitfall 1: Trying to Fix Everything at Once
You'll identify 50+ issues in month 1. You cannot fix them all simultaneously. Prioritize ruthlessly. Pick 3-5 things to tackle in the first year and execute them well.
Pitfall 2: Staying in "Learning Mode" Too Long
Analysis is comfortable. Decision-making is hard. Some new CIOs spend 6 months "assessing" to avoid making tough calls. The organization loses confidence. Assess for 30 days, decide, then act.
Pitfall 3: Ignoring the People Dimension
Technology problems are usually people problems. If your entire focus is systems and projects, you'll miss the cultural and relationship issues that determine success or failure.
Pitfall 4: Over-Committing
The business will ask you to commit to ambitious timelines and budgets. Don't overpromise to look good in month 1. Under-promise and over-deliver. Your credibility depends on keeping commitments.
Pitfall 5: Not Building Relationships Outside IT
If you spend all your time with your IT team and not enough time with business leaders, you'll build a great IT organization that the business doesn't value. CIO success is 60% relationship-building, 40% technology.
Pitfall 6: Defending the Status Quo
You inherited systems, vendors, and decisions you didn't make. Don't defend them. Be honest about what's working and what isn't. The organization is giving you permission to change things—take it.
Pitfall 7: Forgetting to Celebrate Wins
Your first 90 days will be intense. Make sure you pause to recognize team accomplishments and celebrate progress. This builds momentum and morale.
Your Action Plan: First 90 Days as CIO
Days 1-7: Foundation
- Meet every direct report within 48 hours (60-90 min each)
- Identify any immediate crises and assign owners
- Schedule meetings with CEO, CFO, COO, and key business leaders
- Set up weekly 1:1s with direct reports
- Create "Voice of the Customer" document from stakeholder meetings
Days 8-30: Assessment
- Complete architecture and technology inventory
- Analyze IT financials and cost structure
- Review project portfolio and delivery capability
- Assess team capabilities and identify flight risks
- Evaluate vendor relationships and contracts
- Produce "State of IT" document by day 30
Days 31-60: Strategy
- Define IT vision and strategic pillars (Week 5-6)
- Develop 18-month roadmap with business-aligned initiatives (Week 7-8)
- Validate strategy with CEO, CFO, and key stakeholders individually
- Hold IT leadership team workshop to align on strategy
- Prepare executive presentation of strategy and roadmap
Days 61-90: Execution
- Launch 3-5 quick wins that deliver value in <90 days
- Present strategy to C-suite or Board (get approval)
- Establish daily/weekly/monthly/quarterly operating rhythms
- Make necessary team changes (retain high performers, address underperformers)
- Produce "First 90 Days Accomplishments" report by day 90
The Bottom Line
The first 90 days as CIO determine your long-term success in the role. New CIOs who thrive use a structured approach: 30 days to learn and stabilize, 30 days to define direction and build the plan, 30 days to execute quick wins and build momentum.
This requires balancing immediate firefighting with strategic thinking, building relationships across the business while assessing technology, and addressing urgent issues while charting long-term direction. The CIOs who execute this well establish credibility early, build strong stakeholder relationships, and set themselves up for sustained success.
Most importantly, they resist the temptation to stay in learning mode or dive into firefighting exclusively. They systematically assess, decide, and act—demonstrating both strategic thinking and bias for action.
If you're stepping into a CIO role or considering a CIO transition and want guidance on navigating the first 90 days successfully, you don't have to figure it out alone.
I help new CIOs execute systematic transitions that build credibility and set strategic direction. The typical engagement involves advising through your first 90 days with weekly coaching sessions, helping you structure your assessment and strategy development, and providing feedback on your presentations to stakeholders.
→ Schedule a 30-minute CIO transition consultation to discuss your upcoming transition and how to set yourself up for success in the critical first 90 days.
→ Download the CIO First 90 Days Template - A comprehensive Excel workbook with checklists, assessment frameworks, and presentation templates to guide your transition.