99 Problems

Adaptability & Innovation

Business can’t change or adapt
Innovation trapped in R&D or side teams
No change management process
No experimentation with business models
No growth loops / repeatable growth engine
No process to manage experimentation
No process to support innovation
No sandbox or safe-to-fail zones
Systems that resist change
Technical debt strangling innovation
Unable to experiment
Unable to innovate
Vulnerable to supply chain disruptions

People & Culture

Burnout culture
Corrosive culture
Fear-driven culture
Inability to retain key talent
Inability to scale teams/processes
Inappropriate hiring or role design
Lack of cross-functional collaboration
Lack of psychological safety
Leadership vacuum / weak middle management
No informal collaboration
No recognition or reward system
Remote teams that don’t perform
Team conflict avoidance
Teams unable to work together effectively
Toxic silos between functions
Tribal knowledge locked in key people
Underutilized resources (people, tech, IP)

Process & Operations

Build-vs-buy decisions poorly made
Bureaucracy
Cash flow mismanagement
Inappropriate prioritization
Inappropriate process
Missing prioritization
No agreed upon decision making process
No data governance
No facilitation skills
No flow
No process
No risk management process
No standards
Platform decisions driven by hype, not need
Processes that prioritize control over learning
Too many standards
Too much process

Product & Market

Business too reliant on one customer or revenue stream
Ignoring market signals
No clear ICP (Ideal Customer Profile)
No contact with the customer
No customer discovery
No product lifecycle planning
No product management function
No understanding of customer needs
No understanding of profitability by segment/product
Overreliance on market conditions staying stable
Poor product/customer fit
Poor value proposition
Products that don’t scale
Unable to kill obsolete products

Strategy & Vision

Chasing trends without a clear thesis
Competition
Conflicting strategies across departments
Conflicts of interest go unchecked
Constant context-switching
Ethical missteps damaging brand
Feature bloat
Growth without a viable foundation
IA Ignorance
Incorrect Strategy
Increasing taxes or tariffs
Ineffective goal setting
Ineffective operating model
Ineffective retrospectives
Ineffective Strategy
Ineffectual portfolio management
Insights not shared across org
Learning happens too late
Manual workarounds that hide real issues
Micromanagement
Misalignment between vision and execution
Missing learning practices
Missing retrospectives
Missing Strategy
Missing working agreements
Misunderstood Agility
No clear positioning or differentiation
No clear theory of change
No continuous improvement mindset
No feedback loops
No growth strategy
No identified value stream
No investment in skill-building or education
No lobbying or regulatory foresight
No margin of safety
No operating model
No portfolio
No product strategy
No strategy for AI/disruption resilience
No success measures
No succession planning
No understanding of competitive landscape
No vision for the future market
No way to see what is happening (visualization)
Obsolete mindset
Out of regulatory compliance
Over-customization for individual clients
Partners outgrowing or outpacing you
Phase gates
Planning disconnected from delivery
Poor Alignment
Poor business resilience
Poor capital allocation
Poor cost-to-value ratio
Poor onboarding and offboarding practices
Poor onboarding/user activation
Poor pricing strategy
Reinventing the wheel repeatedly
Rigid budgeting cycles that block agility
Rising Expenses
Shadow IT undermining compliance
Short-termism / lack of long-term planning
Slow or defensive response to PR crises
Strategy decoupled from reality (wishful thinking)
Strategy not communicated
Strategy not understood at different levels
Suppressing new ideas
Unable to collaborate
Unable to manage the system effectively
Useless executives
Vendor lock-in
Work starts without clear outcomes

Technology & Infrastructure

Fragile infrastructure and outages
Inflexible architecture
Missing tools
Misuse of AI or automation
Misused tools
No observability into systems
No sustainability or ESG consideration
Security as afterthought
Tech not aligned with business needs
Unable to see systems
Unsustainable business model
Wrong tools