Mastering Your Leadership Transition: The First 90 Days

Welcome to Leadership Insights Collective, where we help leaders navigate growth with real-world examples and powerful insights. In this edition, we dive into one of the most practical and essential books for leaders stepping into new roles: The First 90 Days by Michael Watkins. Whether you're transitioning into leadership for the first time or taking on a new challenge, this book offers a framework to accelerate success and avoid common pitfalls.

Overview

In The First 90 Days, Michael Watkins outlines strategies to help leaders navigate the critical transition period when entering a new role. He explains that a leader’s performance during the first three months largely determines their long-term success. This "transition acceleration" book is designed to help leaders build credibility quickly, secure early wins, and reach the "breakeven point"—where their contributions outweigh the cost of their onboarding.

Watkins offers a roadmap with actionable strategies like accelerating learning, securing early wins, aligning expectations, and building supportive coalitions. His framework is widely adopted by leaders across industries to ensure successful role transitions.

Key Takeaways and How to Execute Them

1. Promote Yourself Transitioning into a leadership role requires you to mentally and practically separate yourself from your previous role. Watkins emphasizes making a clean break to avoid falling into the trap of continuing old habits. Leaders must adjust their thinking and approach to align with the broader strategic goals of their new role.

Execution Strategy:

• Establish a clear breakpoint between your old role and the new one. Watkins suggests using a weekend to mentally and emotionally prepare for your new responsibilities. This is the moment to let go of old tasks and focus on your new position's demands.

• Reorganize your day-to-day thinking. Ask yourself, “What must I let go of to be successful?” and “What does this new role demand that my old role did not?”

2. Accelerate Your Learning Rapid learning is critical in a new role, and Watkins advises leaders to create a structured learning plan. This means focusing on both hard data (e.g., financials and strategic reports) and soft data (e.g., culture, politics, and informal networks). Understanding the organizational dynamics quickly can help avoid common mistakes.

Execution Strategy:

• Develop a learning agenda. In your first week, set up one-on-one meetings with key stakeholders and team members to gather insights. Watkins provides a set of five key questions to guide these meetings:

  1. What are the biggest challenges facing this organization now and in the future?

  2. Why are we facing these challenges?

  3. What are the most promising opportunities for growth?

  4. What needs to happen for us to exploit these opportunities?

  5. If you were me, what would you focus on?

• Use these answers to quickly diagnose the situation and develop hypotheses that you can test and refine as you go.

3. Secure Early Wins Securing early wins is essential to build credibility and energize your team. Watkins advises focusing on visible achievements that align with your boss’s priorities and the organization’s immediate needs.

Execution Strategy:

• Identify areas where you can make immediate improvements. Look for low-hanging fruit—issues that you can address quickly with minimal resources but significant visibility.

• Ensure these early wins are aligned with your boss’s key priorities to build credibility both with your team and leadership.

4. Match Strategy to Situation Watkins introduces the STaRS model (Start-up, Turnaround, Realignment, Sustaining Success), helping leaders tailor their strategy to their specific situation. The context in which you operate (whether it’s a turnaround or sustaining success) dictates your approach to learning, decision-making, and team-building.

Execution Strategy:

• Diagnose the situation using the STaRS model. Assess whether the organization is in need of revitalization (realignment), stabilization (turnaround), or continued success.

• Match your approach to the situation. In a turnaround, for example, you’ll need to act swiftly and decisively, whereas in a sustaining success situation, you’ll focus more on building relationships and diagnosing deeper issues over time.

5. Build Your Team Assessing and realigning your team is critical. Watkins advises that new leaders carefully evaluate their team members early on to identify who can help advance the new agenda and who may need to be repositioned or replaced.

Execution Strategy:

• Use the first few weeks to evaluate your direct reports through one-on-one meetings and observation. Assess their alignment with your vision, their skill sets, and their influence within the organization.

• If necessary, make tough decisions about team composition early. Replacing key people or reassigning responsibilities can set the tone for the type of leadership and results you expect.

6. Negotiate Success with Your Boss
   Watkins emphasizes that leaders should clarify expectations and develop a strong relationship with their boss early on. This can be achieved through what Watkins calls the Five Conversations.

Execution Strategy:

• Initiate these conversations in the first few weeks to align on key expectations:

  1. Situational Diagnosis: Understand your boss’s view of the business and the challenges ahead.

  2. Expectations: Clarify what success looks like and how you’ll be evaluated.

  3. Style: Understand your boss’s preferred communication style and working approach.

  4. Resources: Discuss what you’ll need to succeed and negotiate for those resources.

  5. Personal Development: Explore how this role will support your own growth and future aspirations.

Your Next Moves

1. Promote Yourself and Make a Clean Break
   Transitioning into a new role requires a mental shift. Create a clear distinction between your old role and your new one to avoid carrying over habits that may not serve you. Watkins emphasizes the importance of breaking away from the day-to-day tasks of your previous role and embracing new, strategic responsibilities.

   Action Steps:

   • Set a breakpoint for when you officially transition out of your old role. Pick a specific time (such as the weekend) to reflect on the differences between the two roles and what will be required of you.

   • Mentally prepare by identifying what you need to leave behind and what new skills or behaviors you’ll need to embrace.

2. Create a Learning Agenda
   Develop a structured plan to learn about the organization. Focus on both formal data (e.g., financial reports) and informal networks (e.g., the organizational culture and internal politics).

   Action Steps:

   • Identify the critical areas where you need more information and set up one-on-ones with key stakeholders. Ask the Five Essential Questions to quickly diagnose challenges and opportunities.

   • Build an understanding of the organization’s culture and norms by observing behaviors, asking questions, and taking notes on areas that may need to be addressed later.

3. Identify and Pursue Early Wins
   Achieving early wins provides momentum and builds credibility with your team and leadership.

   Action Steps:

   • Identify two or three key areas where you can make visible improvements within the first few months.

   • Align your early wins with what matters most to your boss. Focus on initiatives that provide measurable results quickly.

4. Build Key Relationships
   Invest time in building relationships with your boss, peers, and team members. These connections will help you navigate challenges and drive long-term success.

   Action Steps:

   • Schedule regular check-ins with your boss to ensure alignment and manage expectations.

   • Build rapport with your peers and direct reports by actively listening and seeking their input.

5. Assess and Align Your Team
   The first 90 days are crucial for evaluating your team’s strengths and addressing any gaps.

   Action Steps:

   • Meet individually with your direct reports to assess their alignment with your vision and strategy.

   • Make adjustments where necessary—whether that means redeploying talent or replacing key roles.

Conclusion

The First 90 Days provides a comprehensive roadmap for leaders in transition. By following Watkins’ strategies, you can accelerate your success, build credibility, and set the foundation for lasting impact in your new role. Ready to explore more? Dive into Michael Watkins' additional resources on leadership transitions to continue your learning journey.

Further Reading and Resources

For more insights from Michael Watkins, visit his website or explore additional resources designed to help leaders succeed in transition. His work at Genesis Advisors and the content available on his platforms offer in-depth tools, articles, and guides for leadership development.

• Michael Watkins' Website: Genesis Advisors

• The First 90 Days Workbook: A hands-on guide that complements the book with exercises and practical applications.

• Additional Books by Michael Watkins: Explore more of Watkins’ work, including Your Next Move and Shaping the Future.

For those ready to take their leadership development further, check out leadership courses and workshops designed around The First 90 Days framework. These can help deepen your understanding and provide practical support as you navigate your transition.

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