The High Performer Who Can’t Perform
Your startup just hired a brilliant product manager from Spotify. She managed features for millions of users, led cross-functional teams, and delivered consistently. Six months later, she’s struggling with your 25-person company. She spends weeks on strategy documents that no one reads, gets frustrated by the lack of user research infrastructure, and seems paralyzed when asked to “just figure it out.”
Meanwhile, your scrappy startup PM who could turn customer feedback into shipped features in a week just joined Amazon. Three months in, he’s drowning in stakeholder alignment meetings, struggling with the complexity of getting basic decisions approved, and his “move fast and break things” approach is creating friction across teams.
Both are exceptional product managers. Neither is failing due to lack of skill. They’re experiencing organizational stage mismatch—being optimized for a different stage of organizational maturity than where they now work.
The Four Stages of Organizational Maturity
Stage 1: Startup Chaos (0-25 people)
What it requires: People who thrive in ambiguity and can create structure from nothing.
The Startup Engineer builds the entire backend in two weeks, deploys to production from their laptop, and debugs customer issues directly. They make architectural decisions quickly, value shipping over perfection, and are energized by wearing multiple hats.
The Startup Product Manager talks to customers daily, makes product decisions based on gut and limited data, and ships features based on a Slack conversation. They’re comfortable with incomplete information and prioritize learning over planning.
Stage 2: Early Scale (25-100 people)
What it requires: People who can build processes while maintaining speed.
The Scale Engineer introduces code reviews and basic CI/CD while keeping deployment velocity high. They document decisions, mentor junior engineers, and balance technical debt against feature velocity.
The Scale Product Manager implements basic analytics, creates lightweight processes for feature prioritization, and begins systematic customer feedback collection while maintaining rapid iteration.
Stage 3: Growth Organization (100-500 people)
What it requires: People who work effectively within established systems.
The Growth Engineer operates within architectural standards, collaborates across multiple teams, and contributes to established processes. They value consistency, quality gates, and coordinated releases.
The Growth Product Manager uses comprehensive data for decisions, manages complex stakeholder relationships, and works within established planning cycles. They value thorough analysis and coordinated execution.
Stage 4: Enterprise Scale (500+ people)
What it requires: People who excel in structured, specialized environments.
The Enterprise Engineer is a deep specialist who works within comprehensive processes, coordinates across many teams, and optimizes existing systems. They value expertise, thorough planning, and risk mitigation.
The Enterprise Product Manager manages complex requirements across multiple organizations, works with extensive data and research, and operates within formal planning processes. They value comprehensive analysis and stakeholder alignment.
When Great People Fail
The Enterprise Person in a Startup
What they expect: Clear requirements, established processes, comprehensive data, specialized teams, and structured decision-making.
What they get: Ambiguous goals, no processes, limited data, wearing multiple hats, and “figure it out” directives.
Why they struggle:
- Spend too much time planning and not enough executing
- Wait for perfect information that doesn’t exist
- Try to implement enterprise processes inappropriate for the stage
- Become paralyzed by the lack of structure and support
The Sales Example: An enterprise sales director joins a startup and spends months building a comprehensive sales process, lead scoring system, and territory management approach. Meanwhile, the startup needs someone to pick up the phone and close the three prospects in the pipeline.
The Startup Person in Enterprise
What they expect: Direct decision-making, rapid execution, minimal oversight, and ability to “just build it.”
What they get: Complex approval processes, extensive stakeholder management, quality gates, and coordinated planning cycles.
Why they struggle:
- Try to bypass established processes, creating friction
- Make decisions too quickly without proper stakeholder input
- Underestimate complexity and coordination requirements
- Become frustrated with “bureaucracy” and “red tape”
The Designer Example: A startup designer joins a large tech company and tries to redesign a key workflow over a weekend. They skip user research, don’t coordinate with other design teams, and ignore accessibility requirements. The design is brilliant but unusable because it doesn’t work within the ecosystem.
The Hidden Cost of Mismatch
Organizations often misinterpret stage mismatch as performance problems:
“They’re not strategic enough” (Enterprise person in startup who over-plans) “They’re not detail-oriented” (Startup person in enterprise who under-plans) “They don’t understand our customers” (Different data/feedback loops at different stages) “They’re not collaborative” (Different collaboration patterns at different stages)
These aren’t capability problems—they’re environmental mismatches.
Getting the Match Right
For Hiring
Ask stage-specific questions:
- “Describe a time you made a decision with incomplete information.”
- “How do you approach a problem when there’s no established process?”
- “Tell me about working on something where you didn’t have all the resources you needed.”
- “How do you handle situations where priorities change frequently?”
Be honest about your stage: Don’t oversell your process maturity or undersell your chaos level. A startup that claims to have “enterprise-grade processes” will attract the wrong people.
For Integration (M&A)
When acquiring companies, the stage mismatch problem becomes acute:
Don’t force immediate stage transitions. The startup team that made the acquisition valuable probably can’t operate immediately within enterprise processes.
Create bridge roles. Use people who have successfully transitioned between stages to help others adapt.
Preserve stage-appropriate work. Keep some startup-stage projects for startup-stage people while they adapt.
For Career Development
Help people understand their stage preference. Some people thrive in chaos, others in structure. Neither is wrong.
Plan transitions gradually. Moving from startup to enterprise (or vice versa) is a skill that requires deliberate development.
Value different stage expertise. Your organization will evolve through stages and needs people who understand different stages.
The Skills of Stage Transition
Some rare individuals can operate effectively across multiple stages. They typically:
- Consciously adapt their working style to the organizational context
- Read organizational needs and adjust their approach accordingly
- Build stage-appropriate solutions rather than imposing their preferred approach
- Help others navigate stage transitions through mentoring and example
These people become invaluable during periods of organizational change.
Conclusion
Organizational stage mismatch is one of the most common but least recognized causes of performance problems. It’s not about better or worse people—it’s about fit between individual working styles and organizational needs.
The next time you see a high performer struggling, ask: Is this a capability problem, or are they optimized for a different organizational stage?
Understanding stage mismatch helps with hiring decisions, performance evaluations, and career development. Most importantly, it helps create empathy for people who are trying their best in an environment that doesn’t match their strengths.
The goal isn’t to only hire people who fit your current stage—it’s to understand the fits and mismatches, plan for them, and help people adapt when possible. Your organization will evolve through stages, and the people who can navigate those transitions will become your most valuable assets.