The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter

The First 90 Days by Michael D. Watkins

Overview

A comprehensive guide for leaders transitioning into new roles, providing a systematic approach to accelerate learning, build credibility, and achieve early wins. Essential reading for Principal Engineers stepping into leadership positions.

Key Concepts

The STARS Model

Watkins introduces five business situations requiring different leadership approaches:

• Start-up: Building from scratch
• Turnaround: Saving a failing situation
• Accelerated growth: Managing rapid expansion
• Realignment: Revitalizing a successful but stagnating organization
• Sustaining success: Maintaining momentum

Critical Transition Periods

• First 30 days: Learning and building relationships
• Days 30-60: Developing strategy and securing early wins
• Days 60-90: Executing plans and building momentum

Practical Takeaways

1. Accelerate Your Learning

• Conduct systematic learning across technical, cultural, and political dimensions
• Use the “learning plan” framework with structured questions
• Avoid “action imperative” trap - resist urge to act before understanding
• Schedule learning conversations with stakeholders, team members, and customers

2. Match Strategy to Situation

• Diagnose your STARS situation accurately (often hybrid scenarios)
• Turnarounds require fast, decisive action and visible wins
• Realignments need careful messaging - people may resist change when “things are fine”
• Sustaining success focuses on continuous improvement and avoiding complacency

3. Secure Early Wins

• Build credibility through small, visible improvements in first 90 days
• Choose wins that are: achievable, meaningful to stakeholders, and align with strategy
• Avoid “playing it safe” or “going for broke” extremes
• Early wins create momentum and political capital for larger initiatives

4. Negotiate Success

• Clarify expectations with your boss early and often
• Create a “90-day plan” and get alignment
• Establish preferred communication style and meeting cadence
• Understand what success looks like from your boss’s perspective

5. Build Your Team

• Assess inherited team members systematically (avoid snap judgments)
• Restructure if needed, but timing matters based on STARS situation
• Make people decisions quickly once you have sufficient data
• Balance keeping continuity with making necessary changes

6. Create Coalitions

• Map stakeholders and influence networks early
• Identify “winning alliances” - supporters who can help you succeed
• Build bridges with skeptics through listening and small collaborative wins
• Understand informal power structures, not just org charts

7. Achieve Alignment

• Ensure strategy, structure, systems, and skills support each other
• Look for misalignments causing organizational friction
• Fix critical misalignments early to prevent recurring problems
• Architecture metaphor: Strong foundation enables everything else

Quick Facts

• Transition risk: 40-50% of executives fail in transitions (research cited)
• Break-even time: Takes 6+ months for leaders to reach break-even point of value creation
• Critical window: First 90 days set trajectory for tenure in new role
• Most common failure: Acting before learning (action imperative)
• Hidden trap: What made you successful before may not work in new role

For Principal Engineers

Especially relevant when:

• Joining a new company or team
• Promoted to Staff/Principal role with broader scope
• Taking on technical leadership of critical initiative
• Transitioning from IC to people management
• Leading architectural transformation or modernization

Key adaptations for technical leaders:

• Your early wins should demonstrate technical judgment, not just management skill
• Balance “deep dive” technical learning with organizational/political learning
• Build coalitions across engineering, product, and business stakeholders
• Technical credibility buys you time, but organizational credibility sustains you
• Architecture decisions are long-lasting - invest time in learning before committing

Application to technical transitions:

• Use STARS model to diagnose technical situations (legacy modernization = turnaround/realignment)
• Early technical wins: Fix critical bugs, improve CI/CD, reduce toil, clarify architecture
• Negotiate success: Align on technical metrics, architectural principles, and delivery expectations
• Team assessment: Evaluate technical skills, growth mindset, and collaborative capability

Reflection Questions

1. What STARS situation am I in? (Be honest - likely hybrid)
2. What are the 3-5 things I most need to learn in my first 30 days?
3. Who are the key stakeholders I need to build relationships with?
4. What early wins would build credibility with my team and leadership?
5. What worked in my last role that might NOT work here?

Bottom Line

Transitions are vulnerable periods requiring intentional strategy. Success isn’t about working harder - it’s about accelerating learning, building relationships, and creating virtuous cycles of credibility and momentum. The first 90 days set the trajectory for your entire tenure.