Professional Change: The First 90 Days

Your career will go through many changes.  How you approach the first few months of each change (a promotion, a new role, a new set of responsibilities) will disproportionately affect your trajectory.

If you knew that the base rate of executives failing to transition well was around 70% (this is the number of “external senior hires” that “don’t work out”), how would this change your approach to a new role?  This comes down to a failure to operate effectively in the first 90 days.  

Michael Watkins shares his perspective in The First 90 Days and Master Your Next Move.  He observes:

In one Silicon Valley technology company I looked at, the success rate for outside hires was close to zero.

This is a resource I wish I encountered earlier in my career.  In the rest of this post, I’ll share my thoughts on his advice and additional ways of framing dimensions of change.  This post will have less of a narrative structure and could be thought of more as a guide or reference (although the books themselves will be great references too).

Like other impactful books, these provide a mental framework for navigating career transitions.  There’s so much in life that runs on System 1 (instinct).  For those who are less familiar with the concept, System 1 could be thought of as an auto-pilot or subconscious reaction.  System 2 is the deliberate choice module.  The most helpful books are the maps that give your System 2 a chance of systematically approaching challenges when the stakes are high.  

The stakes are the highest when your career is undergoing a large shift.  

The first thing to avoid are the common traps.  Per Watkins, these traps include:

• Sticking with what you know – doing what worked in your old role uncritically.
• Action imperative – trying to do too much, too soon.  Likely due to some feeling of pressure to ‘make your mark.’
• Unrealistic expectations – failing to discuss or negotiate concrete expectations with your new stakeholders, especially your new boss.
• Attempting to do too much – similar to the action imperative, but starting more threads than you can realistically support.
• Mind made up – not learning enough (or at all) and trying to make decisions too soon.
• Wrong type of learning – for example overemphasizing technical dimensions and neglecting cultural or relationship dimensions.
• Neglecting horizontal relationships – too much focus on your boss and your team at the expense of getting to know your peers.

In The First 90 Days, the correct set of things to do are listed below.  I provide a deep dive on each in the appendix of this post.

• Prepare yourself – get ready for a large change.  Plan ahead and stay curious.
• Accelerate your learning – ramp up as quickly as you can, and be systematic and structured about your learning.
• Match your strategy to your situation – Watkins suggests there are 5 of these scenarios (STARS) and your optimal set of actions will depend on which situation you are in.
• Negotiate success – to offset the trap of unrealistic expectations, invest the time in building a productive relationship with your manager (or managers).
• Secure early wins – getting early wins build credibility and momentum.
• Achieve alignment – understand your stakeholders in relation to your expectations and start to get them aligned.
• Build your team – this has a set of sub-traps that you could fall into while trying to build up your team.  But you won’t get work done without your team being ready to support you.
• Create alliances – in many companies, there’s a limit to what you can do on your own.  There are also vetoes somewhere in the organization and you need to understand what those might be (called blocking alliances).
• Manage yourself – the change may involve a large change in your personal life.  Make sure to manage your non-work life and energy to bring your best to your new role.  This is especially true if your change involves uprooting your family.

As you think through these transitions, Watkins gives some good general advice.  He argues that by taking a business-first approach (in a relentless, deeply principled way) you can avoid some of the dimensions of appearing “political” and get more buy-in for what you’re trying to do.

You also need to keep in mind that organizations have “immune systems” and many unsuccessful executives accidentally trigger them.  You trigger them and get labeled as dangerous then it’s likely over.  These include doing things like thinking you have all of the answers, not showing a willingness to learn or adapt, and rushing to bring in “your own people” at the cost of “not seeing the good there.”  Instead, you should adapt to the culture, make connections and align expectations.

If you’re able to do all of these well, you will find that your transitions will go more smoothly.  Don’t wait for a formal job change to implement any of these either – any time your role or responsibility set changes, these dynamics could apply.

In summary, I wish I had found this book much earlier in my career.  I’ve undergone many of these transitions without the benefit of a great map of the territory.  If you find this guide helpful, including the detailed appendix, I encourage you to pick up the book itself.

Appendix with detailed, tactical advice.

Each section is roughly structured around a chapter in The First 90 Days with my own perspective added.  For the questions, I take a subset of the key questions in the book and add some of my own.

Prepare yourself

Begin with humility.  Understand that many leaders who were very successful in their old roles fail to transition well.  Come curious and ready to learn.  Understand that your credibility resets as you join a new organization.  This means a mixture of curiosity and humility will allow you to best adapt your style and approach in a way that is best suited to your new role.  Sometimes the most important things to learn are the unspoken ones and you will only learn that through curiosity and having an open mind.

At a previous company, I once witnessed a person hired at the director level only to be managed out a few months later.  Why?  Everyone quickly concluded that he was not willing to do things in the way the company expected.  Worse, the attitude caused many stakeholders to give up on him within the first 3 months.

The way things get done are different.  It’s important to re-check your expectations as you join.

Here’s a short list of things to keep in mind:

• Influence – how do people get new projects going?  Is it bottom up or top down or peer driven?  You absolutely need to understand how this works in your new environment, or you risk what happened to the aforementioned director.
• Meetings – are they where real decisions get made or mainly informational?  Mistaking one for the other means you’ll be ineffective (or abrasive).
• Execution – do you need to understand the process or know the right people?  All systems have bottlenecks and key decision makers or metrics.  Knowing which one matters will allow you to target the right path forward.
• Recognition – what does the company reward?  Stars vs quiet collaborators?  This is about outcomes, but should be thought of as a feedback loop back into what work matters and how work gets done.
• Ends vs means – is it about results or about how you get there as well?  What incentives are in place?  Does the company tolerate brilliant jerks or not?  

Questions to ask yourself:

• If you are joining a new organization, how will you orient yourself to the business, identify and connect with key stakeholders, clarify expectations, and adapt to the new culture?  The key idea is to think about your approach in advance.
• What has made you successful so far in your career? Can you succeed in your new position by relying solely on those strengths? If not, what are the critical skills you need to develop?  Do you have a system for gauging these and how they change over time?  Reflect deeply and, if needed, get others to help with this process.

Accelerate your learning

Learn deliberately.  Ideally you actually structurally lay out a learning agenda for your new role.  This will help you ramp up more quickly.  I’ve also found it helpful to write out my notes by hand during the ramp-up period and later review them on the weekend as a structured process.  By doing this, you are less likely to fall into any trap that would render you ineffective.

As discussed above, it really pays to be curious.  There are many more sample questions in the book, but here are some that stood out to me.  Use these and the rest of the ones in the book as the backbone of your learning agenda.

For performance questions, related to how the organization is currently performing:

• How has this organization performed in the past? How do people in the organization think it has performed? 
• How were goals set? Were they insufficiently or overly ambitious? 
• Were internal or external benchmarks used? 
• What measures were employed? What behaviors did they encourage and discourage? 
• What happened if goals were not met?

If you’re trying to understand root case of the previous group, these might help:

If performance has been good, why has that been the case?  What have been the relative contributions of strategy, structure, systems, talent bases, culture, and politics? 

If performance has been poor, why has that been the case? Do the primary issues reside in the organization’s strategy? Its structure? Its technical capabilities? Its culture? Its politics?

As you meet with various members of your new organization, it can pay off to ask a similar set of questions.  The reason for some standardization is to get a sense of what’s common vs what individuals are integrating into their personal perspective.  Here’s a sample I like:

• What are the biggest challenges the organization is facing (or will face in the near future)?  Why is the organization facing (or going to face) these challenges? 
• What are the most promising unexploited opportunities for growth?  What would need to happen for the organization to exploit the potential of these opportunities? 
• If you were me, what would you focus your attention on?

You should feel free to refine or come up with your own list.  Even use LLMs to augment your list–they are great for high recall tasks!  There can be product-specific or company-specific dimensions to your list.  Your list should also evolve as you go through your first 90 (or more) days.

Questions to ask yourself:

• How effective are you at learning about new organizations? 
• Do you sometimes fall prey to the action imperative or to coming in with “the” answer? If so, how will you avoid doing this?  It’s important not to problem solve from day one, unless your situation (see next section) explicitly calls for it.
• Given the questions you want to answer, who is likely to provide you with the most useful insights?  Ask your new boss for a map and suggested people to talk to.
• How might you increase the efficiency of your learning process? What are some structured ways you might extract more insight for your investment of time and energy?  I’ve found journaling and deliberate reflective time to be incredibly helpful.  Is that something you’ll need to schedule into your ramp up?  It’s good to have a mentor who can help you make sense of the wide range of information you’re learning.
• What support is available to accelerate your learning, and how might you best leverage it?  What tools might help you?

Match your strategy to your situation

I’ve found it very helpful to apply a systems lens to thinking about new organizations.

Michael Watkins offers the STARS categorization for various situations you may find yourself in.  It’s also possible you’ll have elements of more than one of the STARS.

STARS stands for 1) start-up, 2) turnaround, 3) accelerated growth, 4) realignment, and 5) sustaining success.  Each of those requires something different from you as a new leader.  

I recommend this chapter in full to really understand the nuance, especially on whether or not a “hero” or a “steward” are situationally necessary.  A brief survey from 90 Days:

• In the start-up situation, a major challenge is building the strategy, structures, and systems from scratch without a clear framework or boundaries.
• In an accelerated-growth situation, the organization has begun to hit its stride, and the hard work of scaling up has begun. This typically means you’re putting in the structures, processes, and systems necessary to rapidly expand the business (or project, product, or relationship). You also likely need to hire and onboard a lot of people while making sure they become part of the culture that has made the organization successful thus far.
• In turnarounds, leaders are often dealing with people who are hungry for hope, vision, and direction, and that necessitates a heroic style of leadership—charging against the enemy, sword in hand.
• Realignments, in contrast, demand from leaders something more akin to stewardship or servant leadership—a more diplomatic and less ego-driven approach that entails building consensus for the need for change.
• In a sustaining-success situation, you are shouldering responsibility for preserving the vitality of a successful organization and taking it to the next level. This emphatically does not mean that the organization can rest on its laurels.

Questions to ask yourself:

• What portfolio of STARS situations have you inherited?  Does your situational understanding match that of your stakeholders?  If you don’t know what your situation is, you need to understand it and understand what it takes to move forward (see next section).
• Do you need to understand only the technical side of the business, or is it critical that you understand culture and politics as well?  My guess is that many readers of this will over-index on technical.  I made this mistake in a previous role.
• What is the prevailing climate in your organization?  What psychological transformations do you need to make, and how will you bring them about?  In particular, it may make sense to get a pulse of how the organization is doing.  Are people generally energized or burnt out?  How do they feel about the direction?
• How can you best lead change given the situations you face?  It’s worth being introspective about how these align with your own strengths and weaknesses.  And this insight leads into the next big idea: negotiating success.

Negotiate success

This may be one of the most important parts of transitioning to a new role successfully.  You need to be proactive in shaping what success looks like (shaping the game) rather than passively receiving or taking the situation (just playing the game).  Many successful leaders are generally good at “playing the game” but this is the wrong way to approach a new transition.

Being proactive means that you ultimately take ownership and find a way to work with your new boss, even if they are very busy.  Watkins offers these helpful tips in working with a new boss:

Don’t run down your checklist. … You should assume she wants to focus on the most important things you’re trying to do and how she can help.

Don’t expect your boss to change. You and your new boss may have very different working styles.

As you go through your learning agenda, you should continually clarify expectations.  Additionally, you need to understand what “wins” are important to your boss and find a way to get some early wins (see later section) on those dimensions.

As you start working in your new environment, there are 5 intertwined conversations you need to have.  They are:

• The situational diagnosis conversation. This is about aligning on your current situations (STARS) and the history of the team.  Depending on which situation you are in, you may expect different levels and types of support from your boss.  You should aim to have a shared understanding of the current team’s situation when this is done.
• The expectations conversation. Your goal in this conversation is to understand and negotiate expectations. What does your new boss need you to do in the short term and in the medium term? What will constitute success? Critically, how will your performance be measured?  Try to find out what is considered proprietary (hands-off) for your boss.  Also aim to underpromise and overdeliver.
• The resource conversation. This conversation is essentially a negotiation for critical resources. What do you need to be successful? What do you need your boss to do?  This is about understanding what’s possible and what various levels of investment would look like.
• The style conversation. This is about learning how you can best work with your new boss.  Whether emails, slack messages, or live meetings are typically preferred.  What’s the best way (and time) to share good news and bad news?  When is consultation necessary vs just informing after the fact?  By approaching this deliberately and directly, you’re much more likely to avoid any misunderstanding or misattribution of intention.
• The personal development conversation. Once you’re sufficiently ramped up, you can start to explore what future growth may look like.

The theme of all of this is proactive communication with your boss.  It’s one of the most important parts of getting started well.

Questions to ask yourself:

• How effectively have you built relationships with new bosses in the past? What have you done well? Where do you need improvement? 
• Create a plan for the situational conversation. Based on what you know now, what issues will you raise with your boss in this conversation? What do you want to say up front? In what order do you want to raise issues? 
• Create a plan for the expectations conversation. How will you figure out what your new boss expects you to do? 
• Create a plan for the style conversation. How will you figure out how best to work with your boss? What mode of communication does he prefer? How often should you interact? How much detail should you provide? What types of issues should you consult with him about before deciding? 
• Create a plan for the resource conversation. Given what you need to do, what resources are absolutely needed? With fewer resources, what would you have to forgo? If you had more resources, what would the benefits be? Be sure to build the business case. 
• Create a plan for the personal development conversation. What are your strengths, and where do you need improvement? What kinds of assignments or projects might help you develop skills you need? 
• How might you use the five conversations framework to accelerate the development of your team? Where are you in terms of having the key conversations with each of your direct reports?

Secure early wins

Securing early wins is the best strategy for building credibility and getting momentum for future efforts.  It’s also a great way to build key relationships.  In the abstract, this should be your strategy for the “first wave of change.”  The second wave (later in the 90 days, or even beyond) can focus more on strategy, structure, and deeper changes.

In my personal experience, this is one of the most important things leaders can do.  The ones who I’ve observed that had the best transitions were able to do this well.  Leaders who have a visible, early win are the ones you’d want to follow and ones who are most likely going to give you a chance to grow.  It’s something I did not emphasize enough in my previous moves.  Ultimately it’ll come down to credibility and if people will want to follow you as a leader.

90 Days offers this test–”Do you have the insight and steadiness to make tough decisions? Do you have values that they relate to, admire, and want to emulate? Do you have the right kind of energy? Do you demand high levels of performance from yourself and others?”  With that in mind, the best leaders are:

• Demanding but able to be satisfied.
• Accessible but not too familiar.
• Decisive but judicious.
• Focused but flexible.
• Active without causing commotion. There’s a fine line between building momentum and overwhelming your group or unit.
• Willing to make tough calls but humane.

This sounds like a very hard bar to hit–and I think that’s why many leaders do not successfully make this leap.  Every new company or organization will have a different cultural balance along these dimensions.  Your job is to figure out where you need to move to be the most effective while delivering on your expectations.

Questions to ask yourself:

• Given your agreed-to business goals, what do you need to do during your transition to create momentum for achieving them? How do people need to behave differently to achieve these goals? Describe as vividly as you can the behaviors you need to encourage and those you need to discourage. 
• What are the most promising focal points to get some early improvements in performance and start the process of behavior change? What projects do you need to launch, and who will lead them? 
• What predictable surprises could take you off track?  This is similar to the concept of a pre-mortem for a project.

Achieve alignment 

Organizations grow and can become misaligned.  Additionally, the context around the company may change and the company itself may not have adapted.  90 Days gives examples of organizational misalignment between any of strategic direction, skill bases, processes, and structure.  Any of these being out of alignment would cause the organization to be ineffective.  For example, a gap between direction and skill may manifest in something like GE’s abortive attempt to become a software company.

As a new leader, it’s important to consider this dimension as you take on a new role in a new organization.  If you are unable to diagnose these misalignments, it’s hard to drive long term success in alignment with the long term strategy.  More recently, the market has richly rewarded GE as it has split up into 3 companies.  This is a great example of fixing alignment.  To this end, Watkins recommends reordering SWOT into TOWS to better focus on the challenges in the right order (threat first).

Questions to ask yourself:

• What are your observations about misalignments among strategic direction, structure, processes, and skills? How will you dig deeper to confirm or refine your impressions? 
• What is your current assessment of the coherence of the organization’s strategic direction?  Of its adequacy?  What are the strengths and weaknesses of the organization’s structure?  This is about how well matched the organization is to the opportunity.
• What are the core processes in your organization?  How well are they performing?  Ideally you’re able to benchmark this in some meaningful way.

Build your team

When building up your new team, there are many traps documented by Watkins in his experience working with many business leaders.  The mistakes include:

• Criticizing the previous leadership.  There’s not much to be gained by doing so and it can distract you from what needs to be done.
• Keeping the existing team too long.  Unless you’re in a start-up situation or a rapid-growth one, you’re likely inheriting a team and you’ll need to mold it.  It’s possible to do this with the same people, but they may need to grow into what is optimal for the team.  In my experience, people are usually excited to grow given the right alignment and vision.
• Not holding onto the good people.  The corollary of reshaping your team is that you also want to be careful to retain the “good people.”  It’s easy to overshoot on the previous point and try to reform the team too quickly.
• Not balancing stability and change / Not working on organizational alignment and team development in parallel – it’s a terrifically difficult balancing act.  You need to meet your team where they are but get them moving to where they need to be.
• Making implementation-dependent decisions too early  / Undertaking team building before the core is in place – a second dichotomy that’s hard to get right.  Here you need to understand which decisions need to be made when and with what level of information or ramp-up.  I like the reversible vs irreversible decision framework to help with this.

The book also offers a framework for thinking about evaluating your team:

• Competence. Does this person have the technical competence and experience to do the job effectively? 
• Judgment. Does this person exercise good judgment, especially under pressure or when faced with making sacrifices for the greater good? 
• Energy. Does this team member bring the right kind of energy to the job, or is she burned out or disengaged? 
• Focus. Is this person capable of setting priorities and sticking to them, or prone to riding off in all directions? 
• Relationships. Does this individual get along with others on the team and support collective decision making, or is he difficult to work with? 
• Trust. Can you trust this person to keep her word and follow through on commitments?

It’s often hard to answer all of these with high fidelity early on.  Take the time to get to know each person on each dimension to help you make that assessment.

There’s also a brief note on what could make for a good vision for a team.  A good vision should involve others, tap into something inspirational and even contain evocative language.  Setting a good vision is a key part in getting your team to go with you in the right direction.  A great vision provides meaning to your team.

Questions to ask yourself:

• What are your criteria for assessing the performance of members of your team? How will you go about assessing your team? 
• What personnel changes do you need to make? Which changes are urgent, and which can wait? How will you create backups and options? 
• How will you align the team? What mix of push (goals, incentives) and pull (shared vision) will you use? 
• How do you want your new team to operate? What roles do you want people to play? Do you need to shrink the core team or expand it? How do you plan to manage decision making?

Create alliances

In almost any role imaginable, you will need the support of those for whom you have very little direct authority.

When you’re new to an organization, you’ll have little relationship capital.  If you have a new role in your old organization (say a promotion or new responsibilities), you will still need the support of a new set of stakeholders.  There’s a concept from 7 Habits of Highly Effective People of a “relationship bank account” that applies here.  You want to start investing in various ones.

Instead of going by default or reactively, you should proactively think about if there are people key to your success that you don’t know yet.  An easy way of getting started is to ask your new boss about this.

When meeting new counterparts, you should approach these discussions with an open mind and a true curiosity.  This will make “active listening” happen naturally.  You’ll also gain an understanding of these stakeholders for future collaboration.  In my personal experience, I’ve met very, very few people who have bad intentions.  (Perhaps it was hidden or I was naive?).  Instead when I’ve encountered professional conflict, it’s been due to incentives – often ones that didn’t have to conflict if there was a more creative win-win solution available.

This chapter offers some persuasive techniques such as incrementalism, sequencing, and others to help you make a case.  While they could be tactically helpful, I feel more strongly that investing in good relationships wins out over tactical methods any day.  Will Larson says “With the right people, any process works, and with the wrong people, no process works.”

Questions to ask yourself:

• What are the critical alliances you need to build—both within your organization and externally—to advance your agenda? 
• What agendas are other key players pursuing? Where might they align with yours, and where might they come into conflict?  
• How does influence work in the organization? Who defers to whom on key issues of concern? 
• How should you frame your arguments? Might influence tools such as incrementalism, sequencing, and action-forcing events help?

Manage yourself

At the end of the day, you will not succeed if you are unable to bring the best version of yourself consistently.  This means taking care of your health, managing burnout, and making sure your work is in alignment with your values.  Getting the foundation right means that you can position yourself better.

I’m a big believer in thinking like a multiplier and knowing your own limits.  The impact I’ve been able to observe in my career has come from periods of deep focus with the right level of ambition.

Tactically this means:

• Operate with focus.  Find out what’s important and really go after it.
• Build in time for reflection.  Increase what you learn from each plan and outcome.
• Make use of “no.”  Learning to say no gracefully will enable you to focus on the most important things.
• Create the right support network.  Sometimes it's those closest to us that see us more clearly than we do.

This chapter emphasizes self-awareness.  It’s surprisingly hard to achieve but critically important to do so.  The best leaders manage themselves first, then step out into the world.

Questions to ask yourself:

• What are your greatest vulnerabilities in your new role? How do you plan to compensate for them? 
• What personal disciplines do you most need to develop or enhance? How will you do that? What will success look like? 
• What support relationships will you have to build? 

Summary

This is meant to be a reference doc more than a narrative review.  I hope you find it helpful, and I plan to update it over time as I learn more.  

Managing transitions in your career deliberately may be one of the highest leverage activities you end up doing.  The difference can affect you, your teams, and organizations for years to come.  It’s worth doing it well and doing it deliberately.