“The most dangerous leadership failures aren’t the spectacular explosions everyone notices, but the subtle, persistent warning signs—the organizational equivalent of burnt toast—that we dismiss until the smoke detector finally blares. Great leaders develop a sensitivity to these early signals and act on them, not because the house is on fire, but because they recognize the pattern that leads there.” — Margaret Heffernan
When Management Breaks the System: Red Flags, Better Patterns, and a Way Forward
It started like many teams do—small, passionate, with a vision. A growing startup, an ambitious roadmap, and a headcount that doubled in a year. But somewhere along the way, things got messy. Delivery slowed. Morale dipped. Slack channels got quieter. People left.
It wasn’t a tech debt issue. It wasn’t a talent gap.
It was management.
Not abusive, not even malicious. Just… untrained. Patterned. Caught in the gravity of old habits. And the red flags were there—if you knew what to look for.
This is the story of those red flags—sh*t fans, seagulls, hero culture, and more—and what modern leadership looks like when it’s done right. With analysis, examples, and wisdom from the people who’ve shaped the craft, this post is a field guide for anyone who manages—or is managed.
The Sh*t Fan: Panic Management
The Pattern:
When something goes wrong, chaos rolls downhill. Instead of absorbing the problem, a manager escalates it—quickly, emotionally, and often without context. The team feels punished for telling the truth.
What to Watch For:
- Blame-first language: “Why didn’t I hear about this sooner?”
- Leaders who forward exec pressure without context or buffering.
- Crisis-mode emails at 10pm, scattered with exclamation points.
What Good Looks Like:
Andy Grove, in High Output Management, emphasized calm, systems-focused leadership. Good managers shield their teams during crisis, then learn and fix.
Fix It With:
- Calm, written incident reviews (see: “blameless postmortems” from Google’s SRE model).
- Explicit praise for risk flagging.
- Leadership SLAs for escalation handling.
Thought Leader Resource:
Kim Scott – Radical Candor → Teaches leaders how to challenge directly and care personally. Builds a culture where feedback and mistakes aren’t feared.
Funnel Managers: Bottleneck Bosses
The Pattern:
One person must review, approve, and comment on everything. The team’s speed is tied to their calendar.
What to Watch For:
- “Waiting on feedback” becomes the bottleneck in standups.
- Leaders hoarding knowledge, decision rights, or customer access.
What Good Looks Like:
Jeff Bezos’ “two-pizza team” principle decentralizes decisions. Netflix’s culture doc insists managers lead with context, not control.
Fix It With:
- RACI or DACI for every project.
- “You own this” declarations with psychological safety.
- Decision logs over endless debates.
Thought Leader Resource:
Julie Zhuo – The Making of a Manager → Practical, story-driven lessons on giving up control and empowering decisions at every level.
The Leaky Umbrella: No Psychological Safety
The Pattern:
In failure, managers distance themselves from their team. In success, they take the spotlight.
What to Watch For:
- No upward advocacy during resourcing or performance reviews.
- Leaders who present “lessons learned” without shared ownership.
What Good Looks Like:
Brené Brown teaches that vulnerability and accountability must coexist. The best managers admit when they’ve failed their teams.
Fix It With:
- Public credit, private feedback.
- “We statements” in exec conversations.
- Coaching managers to advocate hard, even when uncomfortable.
Thought Leader Resource:
Brené Brown – Dare to Lead → Deep dives on courage, trust, and creating cultures where people feel safe speaking up.
Seagull Management: The Executive Drive-By
The Pattern:
Execs parachute in, throw disruptive ideas into the roadmap, then disappear.
What to Watch For:
- “Why are we even doing this?” days before a launch.
- Roadmap whiplash from unaligned stakeholder interventions.
What Good Looks Like:
Satya Nadella’s Microsoft reorgs brought clarity and cadence to executive engagement. Instead of surprises, he anchored reviews to OKRs and quarterly check-ins.
Fix It With:
- Scheduled leadership reviews.
- Context primers before feedback.
- Roadmap “locking” periods to limit chaos.
Thought Leader Resource:
Ben Horowitz – The Hard Thing About Hard Things → Real talk from a founder-turned-VC about chaotic exec energy and how to create operational calm.
Fungible Resources: Humans ≠ Widgets
The Pattern:
Managers treat team members as interchangeable. “Just grab another engineer” becomes a solution.
What to Watch For:
- Resource swaps mid-project.
- Overloaded specialists because “we don’t have anyone else.”
What Good Looks Like:
Spotify (on paper) structures around stable squads with long-term ownership of domains. Tenure builds velocity. Context matters.
Fix It With:
- Maintain skills maps, not just titles.
- Let people grow into roles with mentorship, not swaps.
- Consider team stability a KPI.
Thought Leader Resource:
Lara Hogan – Resilient Management → Fantastic for recognizing how individuals grow, struggle, and need to be supported as people, not units of output.
The Headcount Fallacy
The Pattern:
A project slips. Leadership responds: “Add more people.” But more bodies = more coordination.
What to Watch For:
- Bursting teams without onboarding.
- People joining with no context, no charter, no clear role.
What Good Looks Like:
Fred Brooks’ law—“Adding people to a late project makes it later”—still holds. Great teams fix process, not just capacity.
Fix It With:
- Define onboarding cost in every hiring decision.
- Prioritize scope reduction before staff expansion.
- Adopt internal rotations before external hiring.
Thought Leader Resource:
Fred Brooks – The Mythical Man-Month → The original and still-relevant breakdown of why software projects slip and what to do about it.
Hero Culture: Rewarding Burnout
The Pattern:
The loudest, most visibly burned-out team members are treated as high performers.
What to Watch For:
- Weekend work rewarded in all-hands.
- Quiet, consistent contributors overlooked.
What Good Looks Like:
Basecamp’s culture prioritizes calm. They’ve publicly banned heroics in favor of sustainability. Leaders ask how the work was done, not just that it was.
Fix It With:
- Equal recognition for sustainable wins.
- Explicit manager praise for “boring, well-run systems.”
- Normalize PTO, unplugging, and mental health time.
Thought Leader Resource:
Jason Fried & DHH – It Doesn’t Have to Be Crazy at Work → A manifesto for calm, focused, sustainable teams—and why heroism is often a failure of planning.
PowerPoint Empires: Managing the Optics, Not the Work
The Pattern:
Teams spend more time building slides and dashboards than building products.
What to Watch For:
- Decks about decks. Meetings about metrics. KPIs that don’t map to outcomes.
What Good Looks Like:
Amazon’s six-pager memo culture pushes deep thinking and clarity over performative slides. Internal comms drive action, not optics.
Fix It With:
- Use async updates (Notion, Confluence, Linear).
- Ban status decks from internal standups.
- Focus reporting on decisions, not activity.
Thought Leader Resource:
Colin Bryar & Bill Carr – Working Backwards → Deep dive into Amazon’s internal decision-making systems and writing-first culture.
Wrapping up…
The modern workplace doesn’t fail because people are bad. It fails because systems don’t scale. Management patterns compound over time—what starts as “we’re moving fast” becomes burnout. What starts as “I’ll review this to help” becomes a bottleneck.
But every red flag is a chance to reset.
Modern management is no longer about control. It’s about leverage. It’s about clarity, context, and coaching. It’s about enabling people to be their best—not burning them out chasing quarterly goals.
So whether you’re an aspiring lead or a seasoned VP: read widely, listen closely, and fix the patterns before they break the people.
🧰 Resources for Managers at Every Stage
| Experience Level | Recommended Resources |
| First-Time Manager | The Making of a Manager – Julie Zhuo |
| Mid-Level Manager | Radical Candor – Kim Scott Resilient Management – Lara Hogan |
| Senior Leader | The Hard Thing About Hard Things – Ben Horowitz Working Backwards – Colin Bryar & Bill Carr |
| Burnout-Aware Culture Builder | It Doesn’t Have to Be Crazy at Work – Jason Fried & DHH Dare to Lead – Brené Brown |
| Engineering Org Builder | High Output Management – Andy Grove Mythical Man-Month – Fred Brooks |
