Learnings from Michael D. Watkins’ The First 90 Days

The First 90 Days by Michael D. Watkins is a strategic playbook for leaders navigating new roles. It highlights that the first three months in a new position are critical for establishing credibility, building relationships, and securing early wins. Watkins introduces key frameworks like the STARS model, which helps leaders assess their organizational landscape—whether they are stepping into a start-up, turnaround, or a well-functioning team. The book stresses the importance of learning before acting, aligning goals, and adapting leadership style to fit the situation. Leaders must also build alliances, engage stakeholders, and avoid common pitfalls like rushing decisions or ignoring company culture. By following a structured 90-day transition plan, leaders can accelerate their effectiveness and lay the foundation for long-term success in their new role. The first 90 days in any new leadership role are a critical window of opportunity—a time when first impressions are made, credibility is established, and key relationships are formed. During this period, a leader is under intense observation. Team members, peers, and senior executives are all watching closely, assessing whether the new leader understands the organization, can make sound decisions, and has the ability to drive results. Research shows that leaders who transition successfully during this time are far more likely to achieve long-term success, while those who struggle early on may find it difficult to recover. Michael D. Watkins emphasizes that leaders should approach this period with a clear strategy, focusing on learning, adapting, and delivering early wins rather than rushing into drastic changes without a full understanding of the organization’s landscape. One of the most common mistakes new leaders make is trying to impose their own ways of working too quickly, without considering the existing company culture or team dynamics. While it's natural to want to prove oneself, acting too fast without proper insight can alienate employees, disrupt workflows, and create resistance. Instead, Watkins advocates for a “learn before you act” approach, where leaders take the time to observe, ask questions, and identify patterns before making major decisions. This involves understanding the team’s strengths, weaknesses, and key pain points while also assessing the broader company strategy and expectations from senior leadership. By approaching the first 90 days as a structured transition rather than a rushed takeover, leaders can build trust, establish credibility, and ensure that their actions are well-informed and aligned with the organization's goals. Equally important is the need to secure early wins, which help to build momentum and signal to the team that progress is happening under new leadership. Early wins don’t have to be massive changes—they can be small, meaningful improvements that directly address team challenges or inefficiencies. Whether it’s improving communication, streamlining a process, or resolving a long-standing issue, these quick successes serve as confidence boosters for both the leader and the team. They help demonstrate capability, create buy-in, and set a positive tone for the rest of the leader’s tenure. Leaders who fail to achieve early wins may struggle to gain traction, while those who secure them earn trust and support that will serve as a foundation for long-term success. Thus, the first 90 days should be a well-balanced mix of learning, relationship-building, and strategic action, ensuring that a new leader is seen as a valuable asset rather than a disruptor. The STARS Model: Understanding Your Situation as a Leader Stepping into a leadership role is never a one-size-fits-all experience. Every organization is at a different stage, facing unique challenges, opportunities, and expectations. This is where Michael D. Watkins’ STARS Model comes into play—helping leaders assess the kind of environment they are entering and adapt their approach accordingly. STARS stands for Start-Up, Turnaround, Accelerated Growth, Realignment, and Sustaining Success—five distinct business situations that require different leadership strategies. A leader stepping into a Start-Up must be visionary, innovative, and willing to build from the ground up, often with limited resources and high uncertainty. In contrast, a Turnaround demands quick decision-making, problem-solving, and bold action to rescue a struggling organization from crisis. Leaders who misread their situation—perhaps treating a realignment like a startup or assuming a turnaround is just about sustaining success—often struggle to gain credibility and make the right impact. Understanding where the organization stands allows a leader to set realistic expectations, identify priorities, and choose the right leadership approach. For instance, if a company is in Accelerated Growth, the focus should be on scaling teams, improving efficiency, and maintaining quality while expanding rapidly. On the other hand, Sustaining Success requires a more measured approach—continuing what already works while finding ways to innovate and stay ahead of competitors. Perhaps the most challenging situation is Realignment, where an organization isn’t in crisis, but it’s stagnant or losing its edge. Here, the leader’s job is to help the team see the need for change before things start falling apart—a task that requires diplomacy, vision, and strong communication skills. Watkins stresses that leaders who fail to recognize their environment risk making the wrong moves—either acting too aggressively in a stable situation or hesitating when decisive action is needed. By using the STARS Model as a guide, new leaders can better navigate their first 90 days, avoiding missteps and ensuring they adapt their leadership style to the unique challenges and opportunities of their organization. Learn Before Acting: The Key to Leadership Success One of the biggest mistakes new leaders make is rushing into action before fully understanding their new environment. The pressure to prove oneself and make an immediate impact often leads to hasty decisions, premature changes, and misplaced priorities. However, Michael D. Watkins emphasizes that effective leadership starts with learning, not action. Before making any big decisions, leaders need to deeply understand the company’s culture, power dynamics, key players, and operational challenges. A leader who skips this crucial learning phase risks disrupting well-functioning systems, alienating team members, and making changes that don’t align with the company’s true needs. Instead of assuming that what worked in their previous role will work here, great leaders approach their first 90 days with curiosity, humility, and a strategic learning mindset. The best way to learn? Ask questions, listen intently, and observe how things work. Watkins advises new leaders to conduct structured listening sessions with employees at all levels. What challenges do they face? What changes would they like to see? What’s working well and shouldn’t be disrupted? Engaging with people in one-on-one conversations, team meetings, and informal settings helps leaders gain unfiltered insights into the organization’s strengths, weaknesses, and unspoken norms. Additionally, studying company reports, past performance data, customer feedback, and market trends gives a fact-based perspective on where the company stands. Observing decision-making processes, internal politics, and team interactions also helps leaders decode the organization's culture and understand how influence truly works. By committing to learning before acting, leaders build trust, credibility, and informed strategies. Employees respect leaders who listen before making changes rather than imposing their own assumptions. A leader who takes the time to learn first is more likely to make decisions that are thoughtful, aligned with company goals, and welcomed by the team. Conversely, leaders who jump into action too quickly often face resistance, struggle to gain support, and risk making costly mistakes. Watkins’ core message is simple but powerful: before leading a company forward, take the time to understand where it has been, what makes it work, and what truly needs to change. Secure Early Wins: Building Momentum and Credibility in the First 90 Days One of the most powerful ways to establish credibility as a new leader is by securing early wins—visible, meaningful achievements that demonstrate competence and create momentum. Employees, colleagues, and senior executives are all observing how a new leader handles the transition, and early wins set the tone for their confidence in you. Michael D. Watkins emphasizes that these initial victories don’t have to be massive overhauls or groundbreaking innovations; in fact, small but impactful improvements can have an outsized effect on morale and trust. The key is to identify pain points that matter to the organization and address them quickly. Whether it’s streamlining an inefficient process, resolving a lingering issue, or making a symbolic gesture that reinforces company values, these small but meaningful actions signal to the team that progress is being made under new leadership. The best early wins are strategic, visible, and meaningful to employees. A common mistake new leaders make is focusing on high-level initiatives that may take months to materialize, leaving employees frustrated and uncertain about their direction. Instead, successful leaders listen to their teams and pinpoint quick, achievable goals that boost morale and productivity. For example, if employees are struggling with outdated tools that slow down workflow, prioritizing a quick fix—like upgrading a system or providing better resources—can immediately demonstrate responsiveness and commitment to improvement. Likewise, if a company has communication challenges, initiating weekly check-ins or an open-door policy can create an immediate, positive shift in workplace culture. Early wins should not only solve immediate problems but also align with the broader goals of the organization, reinforcing the leader’s vision while gaining trust from employees. However, securing early wins isn’t just about fixing problems—it’s about uniting people around a shared sense of progress. A leader who celebrates small victories, recognizes employee contributions, and builds momentum step by step creates an energized and motivated team. It’s also important to communicate these wins effectively, ensuring that employees and stakeholders see the positive changes taking place. People want to feel that they are part of a winning team, and early successes generate optimism, enthusiasm, and a sense of shared purpose. On the other hand, failing to establish early credibility can result in skepticism, disengagement, and missed opportunities for influence. Watkins makes it clear: the first 90 days are about proving yourself—not through grand promises, but through tangible results that set the stage for long-term success. Build Key Relationships: Earning Trust and Influence as a New Leader Stepping into a leadership role isn’t just about strategy and execution—it’s about people. One of the most critical success factors in the first 90 days is building strong, trusting relationships with key stakeholders. No leader can succeed in isolation, and without a supportive network, even the best strategies will struggle to gain traction. Michael D. Watkins emphasizes that leaders who fail to establish relationships early risk misalignment, resistance, and a lack of credibility. People don’t just follow leaders because of their title; they follow those they trust, respect, and believe in. That’s why a new leader must prioritize relationships from day one—connecting with their boss, peers, direct reports, and influencers across the organization. The ability to read personalities, understand motivations, and align expectations is as important as any business strategy. One of the most important relationships a leader must navigate is the one with their boss or direct supervisor. Many new leaders make the mistake of assuming that their boss will automatically support them, but Watkins warns against this mindset. Instead, he advises leaders to take charge of this relationship by clarifying expectations, understanding their boss’s priorities, and ensuring alignment on goals. A strong leader doesn’t just take orders—they manage up, proactively communicating progress, seeking feedback, and demonstrating their ability to solve problems before they escalate. At the same time, leaders must also focus on peer relationships, as colleagues at the same level can be powerful allies or obstacles. Building trust with fellow leaders creates a collaborative, supportive environment rather than one driven by competition or conflict. When peers see a new leader as someone who listens, adds value, and respects existing expertise, they are more likely to offer support, insight, and partnership in return. Equally important is building relationships with the team—the people who will be executing plans, driving initiatives, and determining day-to-day success. Employees are often cautious when a new leader arrives, wondering, “Will this person respect our work? Will they understand our challenges? Will they listen?” New leaders who take time to meet with employees, ask questions, and show genuine interest in their experiences foster a culture of openness, trust, and respect. This can be as simple as scheduling one-on-one meetings, engaging in casual conversations, or recognizing the contributions of team members. Leaders who prioritize human connection before making demands create an engaged, motivated team that is willing to follow and support new initiatives. In contrast, leaders who remain distant, dismissive, or overly authoritative risk alienating their teams and facing silent resistance. Watkins’ advice is clear: success is built on relationships, and Avoid Common Pitfalls: Navigating Leadership Traps in the First 90 Days Taking on a new leadership role comes with immense pressure to deliver results quickly. However, in their eagerness to prove themselves, many leaders fall into predictable traps that can damage their credibility, alienate their teams, and slow down their progress. Michael D. Watkins identifies several common pitfalls that new leaders must consciously avoid. One of the biggest mistakes is trying to do too much, too soon—a new leader might feel the need to immediately implement sweeping changes without first understanding the organization's history, challenges, or unspoken cultural norms. While taking decisive action can be important, acting too aggressively can disrupt what’s already working, create resistance from employees, and make leadership seem disconnected or reckless. A more effective approach is to observe, listen, and strategically prioritize actions that align with the company’s long-term success rather than rushing to make an impression. Another common mistake is failing to build key relationships early on. Leadership isn’t just about strategy and decision-making—it’s also about earning trust and fostering collaboration. New leaders who isolate themselves, avoid feedback, or dismiss existing team dynamics often struggle to gain support, which can hinder their ability to drive meaningful change. Some leaders also make the mistake of aligning too quickly with one group or individual, unknowingly creating internal conflicts. For example, if a new executive builds a strong relationship with one department while ignoring or sidelining others, it can create resentment and weaken cross-functional teamwork. Watkins advises leaders to take a balanced approach, making an effort to connect with people at all levels of the organization and remaining open to diverse perspectives. One of the most damaging pitfalls is ignoring company culture and assuming that what worked in a previous role will work in a new environment. Leaders who impose their old ways of working without adapting to the existing culture often face resistance from employees who feel undervalued or misunderstood. Watkins stresses that leaders must take time to learn how decisions are made, what behaviors are rewarded, and what unspoken rules shape the company’s operations. A leader who ignores these cultural nuances risks alienating their team and struggling to gain influence. Instead, successful leaders blend their expertise with an understanding of the organization's unique culture, introducing changes in a way that feels aligned, rather than imposed. The key takeaway? Avoiding leadership pitfalls isn’t just about avoiding failure—it’s about setting yourself up for long-term success by being intentional, adaptive, and deeply aware of the people and systems around you. Adapt Your Leadership Style: Leading with Flexibility and Awareness One of the biggest challenges new leaders face is adapting their leadership style to fit their new organization. Many assume that what worked in their previous role will work again, but every company, team, and situation is different. Michael D. Watkins emphasizes that leadership is not about rigidly sticking to a single approach, but about having the flexibility to adjust based on the environment, culture, and people you are leading. A leader stepping into a fast-growing startup, for example, must embrace agility, innovation, and risk-taking, while a leader taking over a well-established corporate division must focus on stability, long-term strategy, and incremental improvements. Those who fail to recognize these differences risk coming across as out of touch, ineffective, or even disruptive in a negative way. Leadership is not just about having a vision—it’s about knowing how to execute that vision in a way that aligns with the organization’s unique structure and needs. Great leaders understand that different teams and individuals require different leadership approaches. Some employees thrive under high levels of autonomy, while others perform best with structured guidance. A strong leader reads the situation, identifies what each team member needs, and adapts accordingly. For example, a leader in a realignment situation, where a company is struggling to regain its direction, may need to be direct, challenge old ways of thinking, and drive cultural shifts. However, in a sustaining success situation, where the company is performing well, a leader’s role is more about encouraging innovation while respecting the processes that have already made the company successful. The mistake many leaders make is assuming their default leadership style is the best one without considering whether it actually suits their new environment. The best leaders are chameleons—they remain true to their values but adapt their approach to get the best results. Another critical aspect of adapting leadership style is understanding the unspoken rules and power structures within an organization. Some companies value collaboration and consensus-building, where leaders must work through influence rather than authority. Others have a top-down structure, where decision-making is expected to be quick and directive. Leaders who fail to recognize these dynamics often struggle to gain traction, as their leadership approach clashes with the company’s norms. Watkins advises new leaders to spend time observing, listening, and understanding how decisions are made before making major changes. Those who adapt earn trust, build stronger teams, and set themselves up for long-term success. The key takeaway? Leadership is not about being rigid in your approach—it’s about being self-aware, adaptable, and attuned to the unique challenges and opportunities of your new role. Align Strategy and Goals: Creating Clarity and Direction One of the most important responsibilities of a leader in their first 90 days is to align their strategy with the company’s goals and priorities. Without clear alignment, even the most talented leaders can find themselves working hard but making little meaningful progress. Michael D. Watkins stresses that many leaders step into their roles with big ambitions and personal visions, but fail to recognize that their success depends on how well their plans fit into the organization’s larger mission. The key to alignment isn’t just about understanding the company’s stated objectives—it’s about identifying what truly matters to senior leadership, key stakeholders, and the teams responsible for execution. New leaders should ask the right questions, analyze existing goals, and ensure that their initiatives contribute to the broader success of the company. Without this strategic alignment, leaders risk pursuing changes that may seem valuable but ultimately don’t move the needle in the areas that leadership and employees truly care about. Strategic alignment also requires balancing short-term and long-term priorities. New leaders often face pressure to deliver immediate results, but Watkins warns against focusing on short-term wins at the expense of long-term sustainability and growth. The best approach is to identify a few key areas where early impact can be made, while simultaneously laying the groundwork for long-term success. For example, if a company’s broader goal is to improve customer satisfaction, a new leader might start by resolving existing complaints and inefficiencies (short-term impact) while also building systems that prevent future issues and enhance the customer experience (long-term impact). Leaders who only focus on quick wins may gain short-lived popularity, but those who take a balanced approach earn lasting credibility and set the company up for enduring success. Another crucial aspect of aligning strategy is ensuring that teams are fully engaged and committed to the vision. It’s not enough for a leader to have a well-defined strategy—the people responsible for executing it must understand, believe in, and support it. One of the biggest mistakes leaders make is assuming that because they have a clear plan, their teams will naturally follow. But employees need to see how their work connects to the bigger picture—how their efforts contribute to the company’s goals and why the strategy matters. Effective leaders communicate their vision consistently, seek feedback, and create a culture of ownership, where team members feel that they are not just following orders but are active participants in achieving success. When leaders align strategy with goals and gain buy-in from their teams, they create a powerful, unified force that drives meaningful change and long-term impact. Create a 90-Day Plan: A Roadmap for Leadership Success Stepping into a new leadership role without a clear plan is like embarking on a journey without a map. The first 90 days are a critical window where a leader must establish credibility, learn the organization’s dynamics, and begin driving results. Michael D. Watkins stresses the importance of having a structured transition plan that keeps a leader focused, intentional, and on track. Without a roadmap, leaders often get caught up in day-to-day firefighting, reacting to challenges instead of proactively shaping their leadership approach. A well-designed 90-day plan ensures that new leaders are not just surviving in their role but actively making progress in learning, relationship-building, and strategic decision-making. A strong 90-day plan consists of four key elements: 1. A Learning Agenda – Before making big decisions, a leader should focus on gathering insights about the company’s culture, structure, key players, and pain points. 2. Early Wins – Identifying and achieving small but impactful successes helps build trust and momentum. 3. A Strategic Roadmap – Setting clear goals and aligning them with the company’s broader mission ensures long-term success. 4. Stakeholder Engagement – Building relationships with employees, peers, and senior leadership ensures that the leader has the support and influence needed to execute plans effectively. The best 90-day plans are flexible yet structured, allowing leaders to adapt while maintaining focus. They serve as a guiding framework, preventing leaders from getting overwhelmed or lost in the chaos of transition. Watkins emphasizes that leaders who have a clear plan gain confidence, reduce uncertainty, and make a stronger impact than those who approach the role without a roadmap. However, a 90-day plan is only effective if it is shared, refined, and executed with the team in mind. Leadership is not a solo effort—it’s about engaging employees, seeking feedback, and ensuring alignment. Leaders should continuously assess their progress, remain open to adjustments, and make sure that their vision is understood by those who will help implement it. Many leaders fail because they either keep their plans to themselves or assume employees will automatically follow their direction. Instead, great leaders communicate their strategy openly, invite collaboration, and inspire their teams to take ownership of the plan’s success. By combining clarity, adaptability, and teamwork, a well-crafted 90-day plan becomes a powerful tool for navigating leadership transitions and setting the foundation for long-term impact. Sustain Long-Term Success: Leadership Beyond the First 90 Days While the first 90 days are crucial for establishing credibility, learning the organization, and achieving early wins, true leadership is about long-term success, not just short-term impact. Many leaders focus intensely on their transition period but fail to think beyond it, leaving them unprepared for the challenges that come after the initial momentum fades. Michael D. Watkins emphasizes that the habits, relationships, and strategies built in the first three months should serve as the foundation for sustained leadership growth. A great leader doesn’t just step into a role, make a few changes, and then settle into a routine—they continuously adapt, innovate, and evolve to ensure long-term success. Leadership is a journey, not a one-time event, and those who remain engaged, proactive, and forward-thinking are the ones who truly make a lasting impact. Sustaining success requires ongoing learning and adaptability. The business world is constantly changing, and what works today may not work six months or a year from now. Leaders must stay curious, seek new perspectives, and challenge their own assumptions to remain effective. This means staying connected to industry trends, maintaining open communication with employees, and being willing to adjust strategies based on new data and feedback. Leaders who become complacent risk stagnation—not just for themselves, but for their teams and organizations as well. Watkins encourages leaders to develop a long-term mindset, where learning never stops, and where feedback is seen as a tool for growth rather than criticism. The best leaders embrace change rather than resist it, ensuring they remain relevant and effective long after their transition period has ended. Another critical aspect of long-term success is building a strong team and empowering others to lead. Leadership is not about doing everything alone—it’s about creating an environment where others can succeed, innovate, and take ownership of their roles. Leaders who hoard decision-making power or fail to develop their teams often find themselves overwhelmed, leading to burnout and decreased effectiveness. Instead, Watkins emphasizes the importance of delegation, mentorship, and fostering a culture of accountability and growth. A leader’s legacy isn’t just measured by their personal achievements—it’s reflected in the strength and success of the people they lead. By investing in talent, building a culture of continuous improvement, and keeping a clear vision for the future, leaders ensure that their impact extends far beyond the first 90 days, creating lasting value for their organization and their team.