Level Up Your Leadership: Key Insights from "The First 90 Days"

💡Book Summary and Key Lessons

1. Preparation for a New Role

The first step is a self-assessment to determine what problems you prefer solving. This surprised me, as the exercise was supposed to reveal my blind spots—the problems I would rather neglect and rank lower. But these are the ones that could create vulnerabilities.

Once determined, the book provides ideas on how to close the gaps found and what to do. The three basic tools for compensation are self-discipline, team building, and advice and counsel from others.

Rework your network - it is important to understand your network and take a step back to analyze blind spots in current expertise. The type of advice needed might change, while moving up. It goes from more functional/technical advisers to more political counsel. They help understand how to navigate the politics of an organization. As well as personal advice - that helps navigate times of stress.

This is something I never did well in. All my meetings or 1:1s were focused on the task at hand. I rarely took the time to connect for advice. However, I was surprised by how open people are to take a mentorship position when asked.

Watkins describes two cycles of transition: vicious and virtuous. Today, let’s aim for the virtuous one.

2. Accelerate Learning About the Organization

Few leaders are trained to analyze an organization systematically. This is interesting because leaders are often brought in to improve and change things. How can they succeed systematically if they don’t know how to diagnose? The book emphasizes figuring out what you need to learn and then building a “learning agenda.”

The book provides a long list of insightful questions about the past, present and future. For example: What’s been tried before and failed? Where are we succeeding? What opportunities are untapped? Are there islands of excellence or other high-quality resources that I can leverage? What potentially damaging cultural or political missteps must you avoid?

I often find that people in the organization have yet to investigate some of these questions, but they are great conversation starters. I once triggered a series of meetings based on a question about the key processes we needed to focus on automating. Collecting all of them helped me meet all stakeholders, became an early win, and gave my work momentum.

3. Match Strategy to Situation

It’s like picking the right outfit for the weather. Just like a winter coat doesn’t fit at the beach, a scrappy startup mindset doesn’t work well in a well-oiled corporate machine… at least not for long success. I liked how the book differentiates. Watkins describes different situations with the STARS framework. Start-up, Turnaround, Accelerated growth, Realignment, and Sustaining Success.

Let me tell you, during Rivian's hypergrowth phase, we saw the situation change, and thus, our strategy needed to change. What worked when we “just” needed to get our cars out the door, did not work as we scaled.

4. Early Wins are More Strategic Than They Seem

It always seemed that early wins were just a flashy party trick a new leader uses to impress the teams. But the book points out that early wins do more than that. They set the pace, build trust, and establish the right momentum with the team for the bigger tasks to come. These are described in "Waves of Change.”

Securing early wins is part of a bigger plan. The initial period of focused learning lets leaders find areas for wins, create momentum, and build personal credibility. What follows is Stage 2 - a slower pace to allow for deeper learning about the organization. More insight enables a deeper wave of change. The final stage, named consolidation, then focuses on maximizing performance.

However, from my experience in growth companies, these waves don’t get smaller. In a company that’s in the middle of scaling, new ceilings are hit, and new challenges arise constantly. The waves of change below never lose intensity—but that’s the fun of it.