The First 90 Days - Chapter Notes

Leaders are readers and with that in mind, I push myself to read as often as I can. Recently, in preparation for my new management role at Dropbox, I read “The First 90 Days” and took notes throughout. Below are my notes, takeaways, and raw thoughts from each chapter.

Table of Contents:

Introduction

  • Transitions into new roles are the most challenging times in the professional lives of leaders
  • Success or failure during the first few months is a strong predictor of overall success or failure in the job
  • Leaders average a major transition every 1.3 years
    • Each year about a quarter of managers in a Fortune 500 company change jobs
  • You goal is to reach the break-even point as rapidly as possible
    • “Break-even point”: the point in which you have contributed as much value to the new organization as you have consumed from it
    • Average time is 6.2 months. Can reduce it by following this book (sounds like a hustle, lol, like an infomercial)
  • Transition Traps:
    • Sticking with what you know
    • Falling prey to the “action imperative” - feeling like you must take action
    • Setting unrealistic expectations
    • Attempting to do too much
    • Coming in with “the” answer
    • Engaging in the wrong type of learning - e.g. learning about the technical aspects of the business, but not the culture and the people
    • Neglecting horizontal relationships
  • Make sure to create virtuous cycles
  • Transition failures happen because new leaders either misunderstand the essential demands of the situation or lack the skill and flexibility to adapt to them.
    • The key, then, is to match your strategy to the situation.
  • The first step is to diagnose the type of transitions you are going through - most leaders experience multiple transitions in parallel
    • For example, I am currently starting a new job, living through a pandemic, and preparing to be a father as my wife is pregnant
  • Spend time learning about the organization.
    • 90 day mark can start as soon as you learn you’re being considered for a new role
  • Start planning what you want to accomplish and by when
    • Plan the first day, week, month, months, 90 days
  • Identify the transition risks you face, e.g.: moving to a new company, taking on a cross-functional leadership position for the first time, moving to a new industry or profession, etc.
  • Every new leader needs to quickly:
    • Become familiar with the new organization
    • Secure early wins
    • Build supportive coalitions

Chapter 1: Prepare Yourself

  • It is a mistake to believe that you will be successful in your new job by continuing to do what you did in your previous job, only more so

    What got you here won’t get you there

  • Prepare yourself for the new position: let go of the past, embrace the imperatives of the new situation
  • Understand the types of transitions, two key ones are:
    • Being promoted
    • Onboarding into a new company
  • Getting Promoted presents core challenges (and opportunities) to be overcome
    • Balance breadth and depth
    • Rethink what you delegate
    • Influence differently
      • (Decision making becomes more political the higher you go); important to build and sustain alliances
    • Communicate more formally
    • Exhibit the right presence (what does a leader look/act like at this level)
  • Onboarding into a New Company
    • Leaders are often hired (lateral move) to do things that they have been successful at doing elsewhere (here’s looking at you kid)
    • In promotion cases, leaders understand a lot about the company…in this case, they do not and need to learn (fast)!
    • Surveys show that coming in from the outside is “much harder” than being promoted from within
    • High failure rate of leaders coming from outside (e.g. leaders not familiar with internal network of new company, not familiar with corporate structures, unknown to the organization, etc.)
    • Four pillars of effective onboarding
      • Business orientation (learn about the company as a whole, not just your specific parts)
      • Stakeholder connection (vertical as well as - importantly - horizontal); find historians, cultural interpreters
      • Expectations alignment
      • Cultural adaptation (determine the norms, shared language, values, etc.) - this is the most daunting of the pillars
        • Key check list includes: Influence; Meetings; Execution; Conflict; Recognition; Ends versus means.
    • Key ways to prepare yourself:
      • When transitioning, take time to make a clear break from the old and the new (e.g. take a weekend or a day to focus on what you need to be successful in the new role)
      • Assess your vulnerabilities
      • Watch out for your strengths
      • Relearn how to learn (and learn how to “unlearn”)
      • Rework your network
      • Watch out for people who want to hold you back
      • Get some help

Chapter 2: Accelerate Your Learning

Stop doing and start listening

  • Learn about culture and politics
  • Planning to learn: figure out in advance what the important questions are and how you can best answer them
  • Understand the history, a baseline question is “how did we get to this point?”
  • Effective leaders strike a balance between doing (making things happen) and being (observing and reflecting)
  • Display a genuine desire to learn
  • Don’t rush to take action, most of the impulse to take action comes from internal sources
  • Focus on learning and adapting to the new culture
  • Actionable insight: knowledge that helps you make better decisions earlier and helps you quickly reach the break even point
  • Effective learning: figure out what you need to learn so you can focus your efforts
  • Define your learning agenda
    • Different people inside and outside of the organization can give you insight into the business, e.g. historians, suppliers, integrators, etc. See page 55.
    • A good approach to start learning is to have 1-1s with direct reports. Page 59 has some good questions
    • Good questions on page 60 (assimilating new leaders)

Chapter 3: Match Strategy to Situation

  • Ask: what kind of change am I being called upon to lead? And…what kind of leader am I?
  • Use the STARS model, page 71, table on page 72
  • To understand the company, put on your historian hat
  • To adapt your personal leadership style you must:
    • enhance self awareness
    • exercise personal discipline
    • build complementary teams
  • Make a hard assessment of which skills will serve you well and which are likely to get you in trouble
  • Leadership is a team sport
  • For sustaining success, focus on learning, reflection, and influence

Chapter 4: Negotiate Success

  • Clearly communicate a 90 day plan
  • Proactively engage with your new boss to shape the game so that you have a fighting chance of achieving desired goals
  • Establish realistic expectations
  • Establishing a relationship with your boss dos an don’ts, page 90-93
    • Don’t run down your checklist with your boss, have at most 3 things
    • Do clarify expectations early and often
    • Figure out what your boss cares about most
      • E.g. “What are three things that are important to you?”
  • Planning for 5 conversations (page 93)
  • Under promise and over deliver
  • “What exactly do I need from my boss?”
  • Determine your boss’s working style (page 104)
  • Scope out the decision making box (104)
  • After 90 days, discuss how I am doing
  • 90 day plan creation guide on page 109

Chapter 5: Secure Early Wins

  • Keep your ends clearly in mind when you devise your plan to secure early wins
  • Build waves of change that consist of: learning, designing the changes, building support, implementing the changes, observing results
  • First wave of change is to secure early wins
  • Start with the goal in mind, that is your anchor
    • Define your goals
    • Identify and support behavioral changes
  • Page 120 had problematic behavior patterns (revisit this in 30 days)
  • Principles of wins
    • Focus on a few promising opportunities
    • Get wins that matter to your boss
    • Get wins in the right ways
    • Take STARS portfolio into account
    • Adjust for the culture
  • First 30 days, build personal credibility
  • People will form opinions on you with very little data
  • New leaders are perceived as more credible when they display the following characteristics
    • Demanding but able to be satisfied
    • Accessible but not too familiar
    • Decisive but judicious
    • Focused but flexible
    • Active without causing commotion
    • Willing to make tough calls, but humane
  • Launch early win projects (page 129); Review page 130
  • Early wins: best are problems you can tackle quickly, with modest expenditure, and will yield visible operational and financial gain
  • Align your learning agenda with early wins
  • Launch early win projects, manage these initiatives as projects targeted at chosen focal points
  • Use FOGLAMP when planning for projects, early wins
  • Identify the most important problems and issues to address
  • When changing, need to decide if better to plan or conduct collective learning (i.e. experiment and see how it goes)
  • NTS: create better, clearer benchmarks for success (outcome over output, but what is the desired outcome)
  • Ask questions to identify where potential problems may be lurking, set of questions on page 137
  • Goal: creating a virtuous cycle that reinforces wanted behaviors and contributes to helping you achieve your agreed to goals for the organization

Chapter 6: Achieve Alignment

  • Understand the organizations hierarchy, structure, and systems
  • Don’t make change for change’s sake
  • Adjust for the STARS situation
  • Four elements of organizational architecture:
    • strategic direction
    • structure
    • core processes
    • skill bases
  • Goal for the first 90 days: identify potential misalignments and design a plan for correcting them
    • Page 146 and 147 have details on how to get started (Review page 148)
  • Strategic direction encompasses mission, vision, and strategy
    • Mission: what is achieved
    • Vision: why people should feel motivation to perform at a high level
    • Strategy: how you get there
  • Assess the alignment
    • Assess coherence: look at documents that describes your groups mission, vision, and strategy
    • Assess adequacy: is what your group is working in sufficient for the group to succeed and to help the larger company succeed for 2-3 years
    • Ask probing questions, prove the history of how the strategic direction got defined
    • Assess implementation: have the mission vision and strategy been pursued energetically
  • Does the structure support the strategy?
    • NTS: Revisit page 154 and write out these areas
  • Every org structure has trade offs
    • Make the right trade offs? E.g. Innovation or flawless execution?
  • What are our core processes? Review page 159
  • Align processes with structure
  • To evaluate efficiency and effectiveness of a core process, examine for aspects: productivity, timeliness, reliability, quality (p160)
  • Treat processes like a portfolio, focus on a few at a time. Take care to factor in your organizations, capacity for change
  • Key takeaway from this chapter: it is critical to identify the mission, strategy, and core processes of your team (group, unit, etc)

Chapter 7: Build Your Team

  • Assess existing team members; Align and motivate them; establish new processes to promote team work
  • Avoid common traps:
    • Do not criticize people who led before you arrived, nothing to gain from this, evaluate the impact, concentrate on assessing current behavior;
    • Keeping the existing team too long, establish deadlines and conclusions about the team in first 90 days
    • Not balancing stability and change: find the right balance
    • Not working on organizational alignment and team development in parallel, be sure to understand the destination, route, and ship, captain 👨‍✈️.
    • Not holding on to the good people
    • Undertaking team building before the core is in place; avoid explicit team-building activities until the team you want is largely in place
    • Making implementation decisions too early
    • Trying to do it all yourself
  • Page 170 has a chart on how to synchronize architectural alignment and team restructuring
  • Between day 30 and 60, sort out who is who, what roles people have played, and how the group has worked in the past
  • Establish your evaluative criteria: competence, judgement, energy, focus, relationships, trust (refer to page 171)
  • Be sure to: factor in the STARS matrix, criticality of positions, functional experience, extent of team work…most importantly check your assumptions
  • Assess both the positions and the players
  • Get historical data on past performance (performance reviews, etc)
  • Meet 1-1 to assess team performance. Essentially I should meet and learn everyone, getting to know them personally, then understand how they work and their questions / abilities from an execution standpoint - great questions on page 176
  • Test their judgment? (Not sure if I agree with the way this one is framed. I believe this could be confrontational and maybe feel like a “gotcha” for the employee)
  • Assess the team as a whole
    • Study the data: reports of team meetings, Jira, previous release targets, morale surveys
    • Systematically ask questions: assess responses to the questions and see how they align or don’t align
    • Probe group dynamics: how do people interact? Alliances? Attitudes?
  • Evolve the team, after 30 days should be able to assign people to the following categories: (note. I think 30 days is very aggressive. Half of your first few days of onboarding, will not even be able meet with team members. So the question is “when does the clock tick on 90 days”)
    • Keep in place
    • Keep and develop
    • Move to another position
    • Replace (low priority)
    • Replace (high priority)
    • Observe for a while
  • Aligning your team
    • Ensure a combination of push (goals, performance measurement, incentives) and pull (compelling vision, inspiring people)
    • NTS: I am better at pull than I am at push. Push helps execution, need to work on this
    • Define quantifiable goals and metrics
    • Incentive equation (a bit early I think to get into this, but worth revisiting p184)
    • Articulate your vision. It should: tap into a source of inspiration, make people part of “the story”, contains evocative language (e.g. provide in graphic detail the vision, e.g. putting a man on the moon and landing them safely vs launching 10 rockets into space - this is vision vs goal respectively)
    • It is critical to live in the vision you create! You must walk the walk
    • For team building, refer to the offsite planning check list
  • Leading your team
    • Assess what worked well and did not work well before the team arrived
    • Assess existing processes: participants roles, team meetings, decision making, leadership style
    • Have a framework for deciding how decisions get made. Not all decisions should be made the same way (good insight for me)
      • E.g. We may need to alter team meetings. Make meetings smaller and more focused
    • Two key decision making approaches “consult and decide” and “build consensus”. Separating information gathering from evaluating and reaching closure, is consult and decide. When you seek both information and seek buy-in from everyone, then it’s build consensus.
      • NTS: I think I typically lean towards consult and decide, but this might be a blind spot
      • Rules of thumb:
        • Decisions that bias winners and losers, highly decisive, sharing losses and pain, are best made by the leader
        • If decision requires energetic support to implement by people whose performance you cannot adequately observe and control, build consensus
        • If team is inexperienced: consult and decide
        • If need to establish authority, consult and decide
        • However, take the STARS matrix into account. Startups may need more consult and decide. Realignment and sustaining success, leaders deal with strong intact teams, and confront cultural and political issues - typically better addressed with building consensus

Chapter 8: Create Alliances

  • Build up relationships with people you have no direct control over
  • Recognize when your new role presents you with different influence challenges from those you experienced in the past
  • Need to influence in different ways: through persuasion and alliance building
  • Identify who you need to influence, who is likely to support (or resist) your key initiatives is an integral part of 90 day plan
  • Define your include objectives
    • First step: be clear about why you need the support of others, think about the alliances you need to secure early wins
    • Consider creating an alliance-building plan for each early win project
    • Try to identify who or what might stand in your way of getting support for your direction?
  • Understand the influence landscape: who are the key decision makers? What do you need them to do and when do you need them to do it?
  • Determine decision makers for your early wins
  • Who are the winning alliances? Who are the blocking alliances
  • Map the influence networks: who influences whom on issues of concern to you
  • Strategy to map influence networks: identify key points of contact between your organization and others; get your boss to connect you to key stakeholders
  • When you identify support, solidify and nurture it
  • Take time to think about the forces acting on the people you want to influence
  • Analyze the influencer network
  • Assess people’s intrinsic motivations (the need for recognition, for control, for power, personal growth, etc)
  • There is a lot of research that suggests we overestimate personality and underestimate the impact of situational pressures in reaching conclusions about the reasons people act the way they do
  • Table for argument framing on page 215

Chapter 9: Manage Yourself

  • Take stock of yourself and note the many things that might be in transition (new job, move to a new city, new apt, baby on the way, etc)
  • Go through the guidelines for structured reflection (page 223)
  • It’s ok to have an emotional roller coaster; it’s common for leaders to go into the valley 3-6 months after starting
    • NTS: be clear to establish boundaries: what can you and what can you not do? Reflect on this. Work avoidance?
  • 3 pillars of self-management:
    • adopt a 90 day plan
    • develop personal disciplines
    • build your support systems
  • Plan to plan: at the end of each day, spend 10 minutes evaluating how well you met your goals, and then plan for the next day

    Don’t let urgent crowd out the important

  • Carve out time to focus, focus, focus
  • Defer commitment: say “let me think about it and get back to you”;
    • NTS: I think I over commit sometimes
    • Begin with “no”, if pressed, easier to say “yes” later.
  • Find time to check-in with yourself. Maybe daily or weekly? How are you doing? How are you feeling?
  • Recognize when to quit
  • Build your advice and counsel network

Chapter 10: Accelerate Everyone

  • Make a 90 day plan for the entire team
  • Identify the transitions happening on your company, team, etc.
  • Don’t stay in your comfort zone, don’t try to do too much to fast
  • Great chart that highlights some reasons for transition failure on page 245
  • Setup time with leaders to put action oriented / coaching meetings on the calendar to carve out time for them to make their 90 plans, engage in reflection, etc.
  • NTS: work to define what successful execution looks like
  • NTS: spend time, assessing the business and the new role, create / update the strategy to build momentum, create a strategy for managing myself, develop an action plan
  • Fill out the development grid on page 256

More “Chapter Notes”

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