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Michael D. Watkins

The First 90 Days

# Introduction

Transitioning roles consumes resources before it starts to produce them. The goal is to reach break-even, which can take six months or more to accomplish. Avoiding transition traps will increase your transition speed.

# Avoid Transition Traps

  • Stuck with What You Know: failure to think start / stop / continue.
  • The "Action Imperative": too much, too early leading to failure to learn first, making bad decisions and encountering resistance.
  • Unrealistic Expectations: failure to negotiate your mandate.
  • Too Much: multiple initiatives, scattered efforts and no critical mass.
  • Starting only with The Easiest: looking for the quickest, not the highest value to effort.
  • Wrong Learning: failure to prioritize and balance technical, cultural and political learning, thus missing cultural insight, required relationships and communications channels.
  • Neglect Horizontal Relationships: focus only on vertical relationships between your boss, yourself and your direct reports.

You need to understand the history that led to the current situation. Focus on getting to know your team, both their skills and alignment. Building interpersonal relationships will help you identify opportunities and challenges that should form your early goals. You can also learn about coalitions where you will need to support. It is important to recognize that you will be completing several transitions in parallel; identify them all. Adaptive learning: What needs come first? How will you accomplish change? Who needs support your actions?

  • People
  • Structures
  • Products
  • Markets
  • Technology
  • Systems

Attempt to identify and understand the biggest situational need, then negotiate what success will look like with your boss.

Combine these into your 90-day plan:

  • Conversations
  • Expectations
  • Workstyle
  • Resources

# Chapter 1: Prepare Yourself

You need to find a balance between going wide and going deep. Coming from the outside can be much harder than being promoted internally:

  • You need to identify all the informal networks of communication and information flow.
  • Learn corporate and team culture, norms and rituals.
  • Gain credibility within the organization.
  • Overcome resistance to acceptance as an outside hire vs. promotion of an existing employee.

# How will you make an impact?

  • Operating model
  • Planning systems
  • Performance evaluation
  • Talent management

# Stakeholder Connections

Relationships with key stakeholders can be both internal to the team and cross functional. You need to map context of the relationship to your role. Horizontal relationships trump vertical, including lateral relationships with your peers and key people outside the immediate team.

# Expectations Alignment

Validate your understanding of expectations. Preexisting mandates, expected support and available resources may no longer be accurate AFTER you join.

Vertical Assumptions: How much latitude do you have to make change?

Lateral Assumptions: How much change will be accepted? How fast? When?

# Cultural Adaption

Factors include the size and age of the organization, growth rate, hierarchy.

Companies exist on a spectrum; all are political but in very different ways

authority-driven,						consensus-oriented,
process-focused							relationship-based
vertical											lateral

There is always pressure to move towards the alternative focus

Disciplined execution
"data driven"
					Strategic Focus on Big Things

The state of the organization and environment influences how good of a fit the current culture is, but this changes due to externalities.

Culture influences how people

  • think
  • communicate
  • act

Fundamental assumptions are a series of trade-offs

  • Influence: authority vs. consensus
  • Meetings: public forum for ratifying private agreements vs. dialog & debate around hard issues
  • Execution: deep understand of process vs. relationships with the right people
  • Conflict: open talk without fear of retribution vs. avoid and redirect conflict
  • Recognition: visible rock-stars who are vocally celebrated vs. team players who quietly lead collaboration
  • Ends vs. Means: positive vs. negative incentives

Does decision-making authority come from seniority, hierarchy or persuasion?

Look for "cultural interpreters" for guidance.

Evaluate adapting to the organization compared to trying to alter the environment.

# Problem Preferences

Determine where your interest lies, not necessarily your skills. Skills lead to only attempting to solve problems where you can "use your hammer".

Ask: What comes naturally (and can be taken for granted)? What doesn't (and needs focused learning)?

Imposter's Syndrome is both common and strong for new leadership roles. Use your feelings of incompetence and vulnerability to identify where you can adapt and be flexible. The goal is to avoid brittle skills and strategies.

Build and rework your network of advice and counsel to address where you most need help:

  • technical experts
  • domain experts
  • political counsel
  • personal advisors

To determine what you need:

  • Orient yourself to the business
  • Identify and connect with key stakeholders
  • Clarify expectations
  • Adapt to the new culture
  • Balance between adaptation and altering your environment

Questions to ask yourself:

  • Where has success to-date come from?
  • What new critical skills do you need to develop?
  • What are your problem preferences?
  • Are you mentally prepared for the new role?
  • Do you have a network of advisors and counsel tailored to the role?
  • Are there other resources or activities that will help you prepare?

# Chapter 2: Accelerate Your Learning

# Overcoming Learning Roadblocks

  1. Plan to learn
  2. Execute Learning Plan


# Questions to Ask
  • What does past performance and results look like?
  • Historically is goal setting cautious, ambitious or unrealistic?
  • Are there internal or external benchmarks?
  • What types of measures and methodology are used (ex: OKRs)?
  • What behaviours are encouraged or discouraged?
  • Are there consequences if goals are not met?

Look for the root cause(s) of the answers in: strategy, structure, systems, talent, culture, politics.

Examine the history of change: past efforts, people who were drivers.


  • Is the vision and strategy aligned with current actions?
  • Does it serve the stated goals?
  • Identify people who are viewed as capable, trustworthy and influencers - why are they held in this regard?
  • What key processes appear to be working to address quality, reliability, scheduling and deliverables?

What out for cultural and political missteps.

Identify early wins that support people, products and process.


  • What areas are projected to be challenging? How can you help mitigate their impact?
  • What is required to pursue identified opportunities?
  • What aspects of culture are likely to persist? What may change?

Look for barriers that could be technical, cultural or political.

Identify "Islands of Excellence"; pockets of high skill and capability

Sources of insight include:

  • Customers
  • Suppliers
  • Sales
  • Staff
  • Integrators
  • Historians

# Structured Learning

Hold 1:1 interviews with the sources you have identified and ask them the same set of questions:

  1. What are the biggest challenges for you, the team and the organization?
  2. Why?
  3. What are the most promising opportunities?
  4. What's required to pursue them?
  5. If you were in my situation, where would you focus your attention?

The results can form the focus of your learning plan.


  • Strategy, structure, people, performance
  • External assessments
  • Talk to your new boss
  • Write down your observations and hypotheses
  • Talk to your predecessor


  • 1:1s with your direct reports
  • Identify interfaces: perception, reputation, communication, visibility
  • follow strategic alignments from top to bottom
  • follow challenges and opportunities from bottom to top

At 30 days...

  • Share your findings with the team, confirm your assessments and observe group dynamics
  • Trace key interfaces inside => out, then outside => in
  • Inventory and analyze key processes around productivity, quality and delivery
  • Update your questions and hypotheses
  • Discuss with your boss

# Chapter 3: Match Strategy to Situation

Determine the make-up of your portfolio (STARS)

S - Startup:

  • building
  • greenfield
  • limited resources
  • time pressures
  • success is recognized

T - Turn Around:

  • hard decisions
  • resistance to change
  • move from a state of despair to one of hope
  • structure and motivation
  • requires hope, vision and likely hero leadership

A - Accelerated Growth:

  • integration challenges
  • scaled process
  • adding structure for predictability
  • communication and visibility

R - Realignment:

  • identify and acknowledge both success and failings
  • fight complacency, raise awareness
  • gradual vs. crisis
  • find pockets of strength
  • stewardship and servant-leadership

S - Sustained Growth

  • shadow of success
  • defense, preservation
  • strong team

Start-up and Accelerated Growth are viewed as easier, more fun and provide more recognition.

You portfolio will have different elements, so you have a basket of different challenges and opportunities.

The needs and impacts of each situation have predictable themes.

For each element of your job, identify the STARS situation and priority percentage (out of a total of 100%).

# Chapter 4: Negotiate Success

Use your STARS portfolio to identify what you can accomplish, where you should focus and what resources you need for success.

Starts with the relationship and dialog you build with your new boss.

# Focus on Fundamentals

  • Don't stay away from uncomfortable interactions, force communication.
  • Don't surprise your boss by delaying bad news.
  • Don't only take problems to your boss, present strategies and potential solutions.
  • Don't run down a checklist, focus on the most important issues.
  • Don't expect your boss to change, adapt your working style to theirs.
  • Clarify expectations early and often.
  • Take 100% responsibility for making the relationship work.
  • Negotiate timelines for diagnosis and action planning.
  • Aim for early wins in areas important to your boss.
  • Pursue good marks from those whose opinions your boss respects.

# Five Conversations

  1. The situational diagnosis conversation: learn how your boss views your STARS portfolio. Soft/hard factors in-play, organizational resources available.
  2. The expectations conversation: understand and negotiate expectations. short term vs. midterm? definition of success?
  3. The resources conversation: negotiate for critical resources. Discuss cost/benefit from viewpoint of your boss.
  4. The style conversation: Interaction optimization, communication style, decision autonomy vs. consultation vs. permission
  5. The personal development conversation: early (first few months) performance assessment. What's working? Areas of improvement? Projects & special assignments?

# Negotiate Your 90-Day Plan

  • Written, even if only bullet points
  • Specify priorities and goals
  • Set Milestones
  • Share with your boss and look for buy-in

Start with three 30-day blocks.

Block 1: learning and building personal credibility

output: diagnosis of the situation, identify key priorities and a plan for the next 30 days.

Block 2: achieve early wins

output: progress towards goals

Block 3: next goals, resourcing required for larger initiatives

output: review initial assessment of strategy & structure, discussing with your team.

# Chapter 5: Secure Early Wins

Leaders plan and implement change in four phases. After an early period of focused learning they start with a wave of changes. The pace then slows to allow for consolidation and deeper learning, then deeper waves of change and a final phase focused on fine-tuning to maximize performance. Following this most leaders move on.

  • Transition
  • Immersion
  • Reshaping
  • Consolidation

The first wave should target early wins in support of longer-term goals.

The second wave are fundamental: strategy, structure, systems, skills.

Identify business priorities, then:

  • Learn
  • Design
  • Build Support
  • Implement Change
  • Observe Results & Consolidate

Focus on promising opportunities that matter to your boss, that you can achieve in-line with current culture and politics.

Your STARS portfolio influences:

  • realign? talking and recognizing
  • turn-around? concrete acts
  • listen & learn vs. decisive actions

Adjust to culture: team, visible, individual

In the first 30 days you are trying to build personal credibility

Look for signals of value:

  • Insight
  • Energy
  • Values
  • Performance

How will you connect?

Day 1: Identify Key Audience


  • Who you are
  • Your style
  • Your goals & values
  • How you operate

Remove minor and persistent irritants

  • Strained relationships
  • Operating inefficiencies
  • Missing tools

Elevate Change Agents

Double-down on early wins

Plan vs. Learn

  • Awareness => critical mass, need for change
  • Diagnosis => What and Why
  • Vision => compelling vision, strategy
  • Plan => expertise, in-place
  • Support => alliances to execute

Planning vs. Collective Learning

Assessment vs. Action

# Chapter 6: Achieve Alignment

Align type of change with your STARS portfolio

Balance of

  • Rate of change
  • Approach to change

It is important to inventory what you will not change, to provide:

  • space to breathe
  • context of change
  • (in)capacity to absorb change

Look for misalignment in:

  • Strategic direction
  • Structure
  • Processes
  • Skills

The sequence of change is important and should include:

  • flexibility in approach & order
  • off-ramps where you can stop further change actions

SWOT is valuable, but should be viewed as TOWS because of the pairings:

  • Threats & Opportunities: external
  • Weaknesses & Strengths: internal

# Chapter 7: Build Your Team

Some of the common mistakes when starting to build and align your team are:

  • Blame previous leadership
  • Keep the existing team too long
  • No balance between stability and change
  • No organization alignment with team development in parallel
  • Losing good people

Focus on building your core team.

Define the relative importance you place on each of the following:

  • Competence
  • Judgement
  • Energy
  • Focus
  • Relationships
  • Trust

For each person on your team, evaluate if you should:

  • Keep in place
  • Keep and develop
  • Move
  • Replace (low priority)
  • Replace (high priority)
  • Observe

Develop bus capacity: parallel skill & talent pools to increase your resiliency to losing key team members.

# Alignment


Incentives				Vision
Reporting				Teamwork
Planning		==> 	Norms
Process					Culture

COMMENT: This might be backwards; should you use the PULL forces to define the PUSH levers?

# Team Process - existing

  • Participant roles
  • Meetings
  • Decision making (see below)
  • Leadership style

High stress & divisive? Consult and Decide (C&D)

Energetic support needed? Build Consensus (BC)

Inexperienced? C&D

Supervise former peers? BC

S - C&D
T - C&D
A - mix
R - BC
S - BC

If you are remote...

  • Try to meet your team physically early in onboarding.
  • Communication norms: channels, responsiveness, interaction
  • Support and follow-up on commitments: discipline
  • Rhythm of interaction: celebrate

# Chapter 8: Create Alliances

Need to secure support without direct authority.

Focus on building networks - Start early!

Define WHY you need support

WINNING: incorporate and make an active participant

BLOCKING: mitigate and make passive member of team

Map influence networks and define their support status as yes / no / undecided

Identify informal channels of communication and persuasion. This is often parallel to the formal organizational structure.

TIP: Ask your boss for key people with which you should coordinate and build relationships.

# Key People

  • Expertise (SME)
  • Information control
  • Maven (network hub)
  • Access to resources (budget, rewards)
  • Personal loyalty

# Categorization

  • Supporters: vision, small scale change, new ideas
  • Opponents: status quo, core values, power
  • Persuadables: indifferent, undecided, politicians

# Strategies

  • Consultation: appeal to expertise
  • Inclusion: put in a key role
  • Framing: personal, a few key themes
  • Logos: logical, data facts
  • Ethos: values, what is right?
  • Pathos: emotional connection
  • Choice shaping: control available options
  • Social influence: impact of other opinions & society expectations

People want consistency with what they value and believe. This includes historical reputation and treatment, reciprocity (payback) and reputation.

Preserve space between

  • Incrementalism: small steps, experiment, "just try this for a bit"
  • Sequencing: strategic order, action-forcing events (make commitments to take action)

# Chapter 9: Manage Yourself

Structured self-reflection

  • timing
  • measurement (relative)
  • topics

Excited? Confident? In-control?

Connections: key and/or missed

Troubled initiatives, meetings, communication

Interactions: good/bad

Missed Opportunities: blocked by you or others?

# Influencing Factors

  • Personal Boundaries with your life
  • Brittleness in personal processes
  • Isolation
  • Work Avoidance

# Pillars

  1. 90-day plans and strategies
    • prepare yourself
    • accelerate your learning
    • match strategy to situation
    • negotiate success
    • secure early wins
    • achieve alignment
    • build your team
    • create alliances
  2. personal discipline
    • routines
    • plan to plan
    • focus on important
    • defer commitment (default)
    • big picture reminder
    • check-in with yourself
    • no when to quit
  3. Build support systems
    • assert control locally (things you have ability to influence)
    • stabilize home
    • build advice & counsel networks: technical, cultural, political (mix of internal & external)

# Chapter 10: Accelerate Everyone

Align incentives so your success is compatible with the team and company success.

Identify your most critical transitions and how they are influenced by or impact others.

Reduce transition risk for everyone; for people this includes hired, fired, lay-offs, promotions and transfers.

Understand the products and their phase: new, growth, harvest, maintain or sunset.

Evaluate skill alignment and look for gaps using:

  • STARS portfolio
  • technical, cultural and political learnings
  • conversations about situation, expectations, style, resources and progress
  • priorities and plans (quick wins)
  • alliances and relationships