The First 90 Days: A Leader’s Roadmap to Success

“The actions you take during your first three months in a new role will largely determine whether you succeed or fail.” — Michael Watkins

Whether you’re stepping into a new leadership role, transitioning to a different team, or leading through change, The First 90 Days by Michael Watkins is a must-read guide. Watkins masterfully breaks down the critical period of transition—the first 90 days—into a roadmap that helps leaders hit the ground running, build credibility, and create momentum for long-term success.

Let’s unpack the key insights, simple explanations, and real-world applications that make this book an essential read for any leader.

Why the First 90 Days Matter

Watkins argues that transitions are pivotal moments in a leader’s career. Get them right, and you accelerate your impact. Miss the mark, and it’s hard to recover. This period is about learning, building relationships, and aligning quick wins with long-term goals.

Think of it as planting seeds—how you nurture them in the first 90 days determines the strength of the harvest.

Key Insights & Actionable Lessons

1. Prepare Yourself Before the Transition

Watkins calls this “promoting yourself.” Don’t just accept the new title; shift your mindset to embrace the demands of the new role. Assess what skills, behaviors, and attitudes you need to leave behind—and which ones you must strengthen.

Action: Journal or discuss with a coach: “What do I need to let go of? What do I need to embrace?”

2. Accelerate Your Learning

The faster you climb the learning curve, the sooner you can make informed decisions. Seek to understand the culture, politics, processes, and key players. Watkins calls this “diagnostic mapping.”

Action: Create a learning plan: Identify key stakeholders, internal reports, and external resources.

3. Match Strategy to the Situation (STARS Model)

Watkins introduces the STARS model:

• Start-up – Building from scratch

• Turnaround – Fixing a broken system

• Accelerated Growth – Managing rapid expansion

• Realignment – Revitalizing a once-thriving unit

• Sustaining Success – Keeping momentum in a well-functioning unit

Action: Ask yourself, “Which STARS situation am I in? How does that influence my priorities and leadership approach?”

4. Secure Early Wins

Early wins build credibility and momentum. They demonstrate that you’re a capable leader who can deliver results.

Action: Identify a few achievable goals that align with broader priorities. Communicate them clearly and celebrate progress.

5. Negotiate Success with Your Boss

Align expectations early. Define what success looks like and discuss potential pitfalls. This relationship is foundational.

Action: Schedule a “success conversation” with your boss to clarify priorities, deliverables, and communication preferences.

6. Build Your Team & Relationships

Watkins emphasizes that leadership is a relationship game. Evaluate your team’s strengths and weaknesses, build trust, and clarify roles.

Action: Hold one-on-one meetings to get to know your team’s aspirations and concerns. Use DISC or other frameworks to tailor your communication style.

7. Keep Aligned

Transitions can be stressful—Watkins calls this the “personal adaptation challenge.” He recommends managing your energy, stress, and expectations.

Action: Create a self-care routine and a support network (e.g., mentor, coach, or peer group).

“You only get one chance to make a first impression, and it’s a lasting one.” — Michael Watkins

Follow-Up Books & Resources

Your Next Five Moves by Patrick Bet-David — For strategic thinking and anticipating challenges.

Atomic Habits by James Clear — For building consistent habits that stick.

Radical Candor by Kim Scott — For building relationships and giving feedback with compassion.

The 5 Levels of Leadership by John Maxwell — For a step-by-step guide to growing as a leader.

Stepping into a new leadership role is both exciting and daunting. The First 90 Days is more than a survival guide—it’s a blueprint for thriving, building influence, and making a meaningful impact.

So, whether you’re leading a team of five or fifty, remember: Start strong, learn fast, and lead with intention. Want to learn more -- feel free to schedule a free consultation today.  

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