Notes and Takeaways from The First 90 Days
When I read it: August 2021
Why I read it: The First 90 Days is required reading for new employees at Windfall. I decided to take notes on it so it would be easy for everyone at the company to revisit the key points. While reading the entire book is overkill for most non-executive roles, there are some really good frameworks that anyone can benefit from employing when they start a new job or receive a promotion.
Go to the Amazon listing for the book or scroll down for my notes.
Want to get my future notes when I publish them? Subscribe to my weekly newsletter below.
My notes
About Michael Watkins
Michael Watkins is the author of The First 90 Days and the co-founder of Genesis Advisers. Michael advises C-level executives on how to succeed as they take on challenging new roles. He specializes in helping first-time CEOs work with their boards, navigate and shape external complexities, and assess and reshape their teams.
About The First 90 Days
When you accept a new leadership role, you embark on what Michael Watkins calls a "leadership transition". The First 90 Days provides strategies for getting up to speed faster in a new leadership role. In 2006, The Economist called The First 90 Days “the onboarding bible.”
Professional transitions
Transitions into new roles are the most challenging periods of a professional's life. You are vulnerable because you lack established working relations and a clear understanding of the new role. During your first 90 days, it's important to accelerate your learning, secure early wins, and create alliances.
The two most common types of transitions are 1) getting promoted within a current organization and 2) onboarding into a new organization.
When you're promoted, your responsibilities grow. This comes with increase scrutiny and requires you to rebalance your role in the organization. This includes rethinking what you are delegating and how you leverage influencer versus authority. As you rise in an organization, leveraging authority becomes less effective for getting stuff done. You’ll also need to establish new communication channels to inform you about what is happening and communicate your strategy and vision across the organization.
Joining a new company is like an organ transplant. You're the organ and the company is the body. If you don't fit, the company's immune system may reject you. When you join a new organization, you have to adjust to a new business context, political structure, and culture. You also often have to start from zero with credibility and build new working relationships. When you join a new company, you should start by getting familiar with the business. Develop a “birds-eye view” of the people, processes, and systems. Learn about the company as a whole. Understand the strategic business plan, the products and services, the industry, and the competition. Identify the cultural norms and align with them. Also, Identify your key stakeholders and develop the working relationships and trust required to succeed. Don't forget about the stakeholders who fall outside of your reporting hierarchy.
The first 90 days
In a new role, the actions you take during your first few months dictate whether you will succeed or fail. First impressions are hard to change.
Your transition begins the moment you learn you are being considered for a new role. Michael Watkins calls this the preselection phase. Once you have been selected, you enter the pre-entry phase. And once you officially start the new role, you enter the taking charge phase.
The ability to successfully transition into new roles is a critical skill.
Today, a long career at a single company in a single role is rare. If you're a high performer or aspiring leader, you should invest time and effort into getting good at role transitions. A successful career is a series of new assignments, all of which require successful transitions. According to Michael Watkins, leaders experience a major role transition every one and a half years on average.
Your transition begins the moment you learn you are being considered for a new role.
Your transition affects others and vice versa.
Your transition into a new role impacts the performance of other people including your boss, peers, direct reports, friends, and family members. And your performance is affected by others' transitions too. Even if you are not experiencing a personal transition, you are probably being affected by one right now.
The break-even point.
When you start a new role, you consume value as you learn and prepare to take action. As you get up to speed, you begin to produce value. You reach the break-even point when you have contributed as much value in your new role as you have consumed from it. The goal of every role transition is to reach this break-even point as fast as possible, ideally in the first 90 days. How long it takes to reach the break-even point varies by person and situation. Regardless of the situation, when you transition into any new role, your new stakeholders will expect you to demonstrate some traction in the first 90 days.
Avoid creating vicious cycles and focus on creating virtuous ones.
Another goal in your first 90 days is to create virtuous cycles while avoiding vicious ones. With vicious cycles, poor decision-making leads to reduced credibility. Reduced credibility leads to reduced trust. And reduced trust leads to reduced access to information and a higher risk of falling into additional traps. With virtuous cycles, good decision-making leads to increased credibility and trust which leads to access to more information that allows you to make even better decisions.
Most people fail in new roles for one of two reasons. Either they misunderstand the situation they're walking into or they fail to adapt to it.
In The First 90 Days, Michael Watkins shares some common transition traps people fall into, including:
Sticking with what you know. You fail to embrace new concepts. You assume that what made you successful in your previous role will make you successful in your new role. Sometimes the strengths that are assets in one role can become liabilities in a new one. For example, extraordinary attention to detail as an individual contributor can turn into overcontrolling micromanagement when you become a manager.
Falling prey to the “action imperative.” You try to take action too early without the necessary context.
Setting unrealistic expectations. You don't establish clear, achievable objectives.
Attempting to do too much. You don't focus enough to progress key initiatives.
Coming in with “the” answer. You make poor assumptions and reach poor conclusions about problems and solutions.
Engaging in the wrong type of learning. You don't take time to learn the culture and politics of your new role.
Neglecting horizontal relationships. You fail to build supportive alliances with key stakeholders who fall outside of your vertical reporting structure.
(Michael goes into detail on common transitions in this article and the below video.)
How to approach your first 90 days
While some situations require unique considerations (e.g. high-growth startups and turnarounds), there are some fundamental principles you can focus on to ensure your success. In the book, Michael Watkins shares ten fundamental principles for success. In my view, you only need to focus on five core concepts:
Create a plan.
Learn and align.
Develop relationships.
Establish credibility.
Assess and build your team (if applicable).
1. Create a plan
First, you need to create a plan for your first 90 days. Michael refers to this as a 90-day plan. (At Windfall, we call it a 30-60-90-day plan.) Your 90-day plan should include specific goals, priorities, and key milestones that you and your boss agree to.
Before you create your 90-day plan, make sure you identify and understand the specific types of transitions you're experiencing. There are all sorts of common transitions and we often experience multiple transitions at the same time. Some examples include moving to a new industry, joining a new company, joining a new team in the same company, receiving a promotion, moving to a new geographic location, and taking on a role you haven’t done before. (When I joined Windfall in September 2021, I faced several of these transitions in parallel. I moved to a new industry, joined a new company, had to do two jobs at the same time, took on a newly created role, and entered a high-growth startup where major change is the status quo.)
When you transition into a new role, it's important to clarify the situation you are coming into. Different situations require different strategies. Joining a company in crisis is not the same as receiving a promotion in an organization that is enjoying success. Once you understand the situation, you can then choose a transition strategy that fits it.
STARS is Michael Watkins' framework for the five common business situations leaders transition into. S stands for Startup. T stands for Turnaround. A stands for Accelerated Growth. R stands for Realignment. And S stands for Sustaining Success. It’s rare for a transition to fit perfectly into one of the five STARS situations, but it’s useful to evaluate each of your new responsibilities through the STARS lens. Knowing the STARS situation for a particular initiative can help you pick the right approach during your 90 days. (Michael goes into detail on his STARS Framework in this article.)
In a startup situation, you need to get a new business or initiative going from zero to one. The challenges are figuring out how to get everything to work, recruiting high performers amid uncertainty, and operating with constrained resources. The advantages are that you get to do things right from the beginning and you can move fast. There usually aren't rigid policies and procedures in place to slow you down.
In a turnaround situation, you need to save a business or initiative that is failing. These situations demand rapid, decisive action. The challenges are that you often have to reenergize demoralized stakeholders, make decisions under time pressure, and make deep resource cuts. The advantage is that expectations are usually lower so a little success can go a long way.
In an accelerated growth situation, you need to support rapid growth. This often requires you to hire and onboard a lot of people while making sure they become part of the culture. You also have to implement new processes and systems to enable continued growth. The advantage is that the company’s success often motivates employees to stretch themselves.
In a realignment situation, you need to reenergize a complacent business or initiative by creating a sense of urgency. The challenge is convincing employees that change is necessary to avoid future problems. The advantage is that there are often existing team members with strengths you can leverage.
In a sustaining success situation, you need to preserve the success of a successful business or initiative while you try to take it to the next level. You have to combat complacency and find new sources for growth. The challenges include living in the shadow of the former leader, prioritizing defense over offense, and discovering how you can get to the next level. The advantage is that a strong, motivated team and foundation are usually already in place.
One approach is to break your plan into three 30-day milestones:
30 Days. It often makes sense to dedicate your first 30 days to learning and building personal credibility. What’s the org chart? What’re the core systems What’re the core processes and handoffs? What’re the operating and communication cadences? Who are your key stakeholders? Consider collecting 360-degree feedback after the first month to gauge how you're doing.
60 Days. The output from your first 30 days is often a situation assessment (or diagnosis) along with a plan for how you will spend the next 30 days including how you will secure some early wins.
90 Days. At the 60-day mark, you might focus on assessing your progress toward your plan’s goals and what you're on track to achieve by the end of your first 90 days.
2. Learn and align.
When you start a new role, it often feels like you are drinking from a fire hose. There is so much information and it's unclear where you should focus. But, it’s important to identify what you need to learn and then learn it as fast as you can. You need to strike a balance between doing (taking action) and being (observing and reflecting). When you take action without investing time in learning, it can lead to poor decision-making that can undermine your credibility.
The goal of your learning plan is to help you clarify your company's strategic direction so you can align with it. To create a learning plan, start by defining what you need to learn. List out questions in the following areas to avoid surprises:
Business. What are the plans, markets, products, systems, and processes?
People. What relationships do you need to develop?
Culture. What are the cultural norms?
Politics. What land mines do you need to avoid?
Trends. What macro trends present threats or opportunities?
Competition. What is the competition and what are they doing that present a threat?
Fires. Are there problems with current processes or people that could turn into fires?
Next, identify sources of information that can aid in your learning. You can learn from both hard data (i.e. reviewing financial and operating reports, plans, and employee surveys) and soft data (i.e. talking to people).
Make sure to leverage both external and internal sources. Reviewing information from different points of view will deepen your insight. The most valuable external sources of information include customers, suppliers, distributors, and outside analysts. The most valuable internal sources include frontline team members, cross-functional staff, and the people who have been at the organization the longest.
Consider using structured learning processes to save time and avoid bias. For example, script your one-on-one conversations to ensure you ask the standard questions. You can also employ frameworks such as a SWOT (strengths, weaknesses, opportunities, and threats) analysis to guide your diagnostic work.
According to Michael Watkins, an organization's culture is the set of consistent patterns its people follow when communicating, thinking, and acting based on their shared assumptions and values. An organization’s fundamental assumptions and values are often invisible and take time to become clear. Pay attention to visible representations of culture like symbols and languages. These include things like logos, dress codes, office design, and shared language like acronyms. Also, note cultural norms. These include patterns of behavior like how people build support for initiatives, how recognition is handled, how conflict is resolved, and how meetings run. Pay special attention to areas in which how you accomplish something is more important than getting it done.
3. Develop relationships.
When you start a new role, you often have to develop new relationships to succeed.
Start by building a productive relationship with your new boss. To do this, you need to understand how you and your new boss can best interact and work together on an ongoing basis. Be sure to cover communication preferences and decision-making processes. And make sure you understand what resources you have at your disposal and the process for securing additional resources when you need them.
Make sure you have clear expectations. Even if you’re sure you know what your boss expects, you should regularly reconfirm and clarify. Ambiguous goals and expectations are dangerous. What will constitute success? It’s better to underpromise and overdeliver than to overpromise and underdeliver. Identify the areas that are important to your boss and get some quick wins.
Negotiate timelines for an initial diagnosis and follow-up action plans. Your 90-day plan is an excellent vehicle for this. For example, you could say: "Let's operate on a 90-day time frame. Give me 30 days to get on top of things. Then, I will bring you a detailed assessment and plan with goals and actions items for the next 60 days.” You should understand how your new boss sees the situation(s) you have inherited and how her view differs from your initial assessment. Once you get buy-in from your boss on your 90-day plan, it serves as a “contract” between the two of you about how you’re going to spend your time.
Once you get started, be sure your boss is aware of the issues you face. Provide regular updates and avoid surprises. Give your boss a heads-up as soon as you become aware of a problem. When you share problems, also suggest potential solutions. Meet regularly and when you meet, prioritize discussion on what's most important.
Don't expect your boss to change. It's your responsibility to adapt to your boss's preferences and make the relationship work. Make sure you understand what your doing well, what's not going well, and where you can improve. Also, remember that your new boss's opinion of you is influenced by what she hears about you from others. So, develop relationships with the people your boss respects.
Once you and your boss are on the same page, focus on developing relationships with your new direct reports if you have them. Seek their input on the biggest challenges and opportunities at the organization along with what priorities they believe deserve the most immediate attention. And get to know them personally and professionally.
You will also need support from people whom you hold no authority over. In your first 90 days, you should identify all stakeholders whose support is critical for your success and align with them. Michael Watkins refers to this as building up “relationship bank accounts”. Depending on the situation, you may find one of the following influence techniques helpful:
Consultation. Pose questions and encourage people to voice their real concerns. Then, summarize what you’ve heard.
Framing. Craft persuasive arguments on a person-by-person basis.
Choice-shaping. Make it hard for people to say no based on their perceived alternatives.
Social influence. Leverage the support of high-influence stakeholders to gain the support of others.
Incrementalism. Start small and build from there.
Sequencing. Be strategic about the order in which you influence people to build momentum.
Action-forcing events. Create forcing functions like meetings and deadlines to make it hard for people to delay decisions or avoid commitment.
Finally, start building out your third-party advice network. It should include people you can turn to when you get stuck., You need trusted advisers outside of your organization who can help you evaluate markets and strategy, adapt to the culture, and navigate politics.
4. Establish credibility.
When you start a new role, it’s critical to establish credibility. Your credibility depends on how people view your ability to make tough decisions, whether you have values they want to emulate, and the level of performance you demand from yourself and others.
According to Michael Watkins, credible leaders walk the fine line between building momentum and overwhelming. People perceive new leaders as more credible when they get people to make realistic commitments and then hold them responsible for achieving results. Credible leaders also give people the autonomy to achieve results in their own way. They’re decisive when they need to be, but they’re also comfortable delaying non-urgent decisions to ensure they make the right call. And when they do make a tough call, credible leaders are humane. They do what needs to be done in a way that preserves people's dignity.
One way to build credibility and momentum is to secure early wins. By the end of your first 90 days, you want your boss, your peers, and your direct reports to feel like something new and good is happening. Similarly, you want to avoid early losses because it's difficult to recover from them. Your early wins should help you progress your 90-day plan while also laying the groundwork for your longer-term goals. You'll achieve more substantial wins in future initiatives.
To secure wins the right way, focus on a few promising opportunities and avoid spreading yourself too thin. Also, prioritize wins that matter to your boss. Finally, make sure you get wins in a way that is consistent with your organization's culture.
5. Assess and build your team.
In your first 90 days, it's important to assess the alignment of the organization. Start with the mission, vision, and strategy. Then, dive into how people are organized and coordinate to get work done. Next, identify the core process and activity that create value. Finally, assess the capabilities of the workforce. Your goal during your first 90 days is to identify potential misalignments and design a plan for correcting them.
The most important decisions you make in your first 90 days are often about people. Building a high-performance team gives you tremendous leverage. However, you have to strike the right balance between stability and change. You want to avoid forcing too much change at once, but you also don’t want to wait too long. You should make the key changes to your team in your first 90 days.
Start by assessing your existing team members. By the end of your first 30 days, you should be able to group your people into high performers, potential high performers, and low performers.
Then, decide what changes you need to make and how you can make them without damaging short-term performance. Make sure your top performers know where they stand and retain them. You don’t want to lose your best people. Also, avoid criticizing the previous leadership. There's nothing to be gained from this and it can damage your credibility.
In your first 90 days, you'll want to identify problematic behavior patterns. You may notice a lack of focus, discipline, teamwork, urgency, or creativity. Some team members may not be able to clearly define priorities or have too many priorities. Some team members may lack self-accountability.
Hold off on team-building until you let the lower performers go. It confuses your team members when you let go of people they've begun to form bonds with. Also, when possible, wait to implement major new initiatives until you have the team in place. It's often counterproductive to commit a future team member to a course of action they did not choose.
Random anecdotes
Leadership is about influence and leverage. To succeed, you need to harness the energy of others.
The higher you rise in an organization, the more you play the role of company architect.
Recruiting is romance. Employment is marriage.
What works well in one organization or role may fail in another.
There is no one-size-fits-all approach to leading change.
Your ability to adapt and self-manage depends on both self-awareness and personal discipline.
When you transition into a role in which you have to lead your former peers, the first step is to accept that those relationships must change.
The higher you climb in an organization the more you must play the role of the organizational architect.
Effective delegation requires you to translate higher-level goals into specific jobs, fill those jobs with competent people you trust, and establish metrics to monitor their progress. How you approach delegation varies based on whether you are delegating tasks, projects, processes, or outcomes. For example, outcomes require more strategic context than tasks.
According to a study on leadership transitions, executives plan and implement change in waves. The first wave of change follows a period of focused learning. Then, the executive regroups to focus on deeper learning about the organization and to allow people to adapt to the initial changes. Armed with more actionable insight, the executive implements another wave of deeper change. From there, the executive focuses on fine-tuning to maximize performance until moving on to a new leadership transition either via a promotion with the same company or a new job with a new company. For more on this, see When a New Manager Takes Charge by John J. Gabarro.
Random quotes
"If the only tool you have is a hammer, you tend to see every problem as a nail." —Abraham Maslow