Mastering the Leadership Transition: Key Insights from "The First 90 Days"

During my 5+ years at a startup, I experienced multiple role transitions that taught me hard lessons about leadership changes. I've lived through the growing pains of agreeing to unrealistic expectations just to avoid looking incompetent in my new position. I've launched too many initiatives simultaneously, desperately trying to prove my worth. And I've failed to clearly negotiate success metrics, leaving both myself and stakeholders confused about what "good" actually looked like.

These mistakes weren't just personally stressful—they impacted team performance and company outcomes. That's why Michael Watkins' "The First 90 Days" resonates so deeply with me. Reading it feels like someone documented the pitfalls I've stumbled into and created a practical roadmap around them.

The book has helped me recognize that I've done some things right, too. My natural tendency to observe and learn before acting has served me well when I've resisted external pressure to act prematurely. And my focus on building strong horizontal relationships across departments—something I attribute partly to my Chinese cultural background that emphasizes relationship-building—has repeatedly saved projects that would have otherwise derailed. I've also approached new challenges without predetermined solutions, recognizing that every situation requires unique approaches.

Let me share the insights from Watkins' framework that have helped me make sense of my own transitions and might help you navigate yours more effectively.

Why the First 90 Days Matter

The first three months in a new role set the trajectory for everything that follows. By this point, key stakeholders form lasting impressions of your effectiveness, and you've either built momentum or created problems that will take months to unwind. I've experienced both outcomes, and the difference in stress level and impact is enormous.

Avoiding Common Transition Traps

Watkins identifies several traps that new leaders fall into:

• Sticking with what you know: When I moved from individual contributor to leading teams, I kept trying to solve technical problems myself instead of empowering others.
• Falling prey to the "action imperative": I've rushed into decisions before understanding the landscape, creating messes I had to clean up later.
• Setting unrealistic expectations: I've fallen into this trap repeatedly, agreeing to timelines I knew were impossible just to appear confident.
• Attempting too much at once: I've learned that scattering focus across too many initiatives means nothing gets done well.
• Coming in with "the" answer: I've seen how this approach shuts down the very people whose buy-in I need most.

The Critical First Steps: Prepare Yourself

Leadership transitions require a mental reset. I've found that taking even a brief period to mentally prepare for a new role makes a tremendous difference in my approach. You need to:

1. Let go of your past identity: What made you successful before might not be relevant now.
2. Embrace new competencies: Each level of leadership requires new skills and mindsets.
3. Recognize the shift in how decisions get made: At higher levels, decisions rely less on data and more on judgment, relationships, and trust networks.

Accelerate Your Learning

The faster you understand your new environment, the quicker you'll make an impact. These questions have helped me rapidly get oriented:

About the Past:

• How has the organization performed, and why?
• What change efforts have succeeded or failed, and why?

About the Present:

• What's the current strategy and vision?
• Who are the key players and influencers?
• What are the critical processes and their pain points?

About the Future:

• What challenges and opportunities are on the horizon?
• What barriers might prevent necessary changes?

This structured approach to gathering information has helped me avoid jumping to conclusions based on limited perspectives.

Negotiate Success with Your Boss

This is where I've stumbled repeatedly. I've learned (the hard way) that proactively managing relationships with leadership is critical:

• Don't stay away: Regular check-ins create alignment, even when things are going well.
• Don't surprise your boss: I've learned to flag potential issues early rather than delivering bad news after it's too late.
• Take 100% responsibility: The relationship is yours to manage, not your boss's.
• Clarify expectations early and often: I now routinely revisit expectations to prevent drift.
• Understand their priorities: What keeps your boss up at night should inform your priorities.

Secure Early Wins

Early wins build credibility and create momentum, but they must be the right wins. I've wasted energy on initiatives that impressed no one who mattered.

Focus on wins that:

• Align with your boss's priorities
• Address real business needs
• Introduce positive behavioral changes
• Build capability for longer-term transformation

Build Your Team

By roughly 30 days in, you should have a preliminary assessment of your team. I evaluate team members across six dimensions:

1. Competence
2. Judgment
3. Energy
4. Focus
5. Relationships
6. Trust

This isn't about making immediate personnel changes but developing a clear understanding of your team's strengths and gaps.

Create Coalitions

No leader succeeds alone. Your ability to influence extends far beyond your direct authority:

• Identify sources of power and influence
• Understand potential opposition and their concerns
• Build relationships before you need them
• Connect your agenda to others' interests

This approach to relationship-building has been crucial in my own experience. The stakeholders you neglect early on often become the barriers to your success later.

Maintain Your Balance

The transition period is exhausting. I've burned out by neglecting self-care during intense transitions. Establish sustainable routines from day one:

• Set aside time daily for reflection
• Prioritize ruthlessly
• Defer non-critical commitments
• Check in with yourself regularly
• Know when to step back

Putting It All Together

A 90-day plan divides naturally into three phases:

First 30 days: Focus on learning, building relationships, and personal credibility.

Days 30-60: Begin implementing early win projects, refine your team assessment, and deepen key relationships.

Days 60-90: Shift toward more fundamental changes in strategy, structure, and team composition based on your deeper understanding.

The Real Return on Investment

The principles in "The First 90 Days" aren't academic—they're practical tools that have helped me navigate complex transitions. When I've followed them, I've found my footing faster and delivered value sooner. When I've ignored them, I've created unnecessary struggles for myself and others.

Leadership transitions aren't just professional challenges—they're personal ones too. Approaching them with intention and structure doesn't just improve outcomes; it reduces the stress and anxiety that come with stepping into the unknown.