Project Management is Boring

Jordon Keen

Project Management Is Boring focuses on the unglamorous work that actually makes projects succeed. We talk planning, requirements, meetings, stakeholder management, and execution—without pretending PMs are superheroes or that every problem can be solved with a new framework. Built for IT project managers, business analysts and professionals who value discipline, clarity and realism over buzzwords.

  1. PMIB Season 2: The System is Live - Season 2 Continues

    SEASON 2 TRAILER

    PMIB Season 2: The System is Live - Season 2 Continues

    The second half of Season 2 of Project Management Is Boring shifts from risk to execution—exploring how systems behave under pressure and how project management shapes detection, decision-making, and response. Through the lens of real-world failure, we break down how poor system design leads to chaos, and how strong project management builds the controls that prevent it.

    1 min
  2. Risks Without Controls Are Just Predictions

    3 DAYS AGO

    Risks Without Controls Are Just Predictions

    By this point in the season, we’ve examined the Knight Capital incident from multiple angles: deployment verification, technical debt, change classification, rollback, authority, signal recognition, and incident coordination. Each of these failures contributed to the outcome. But they all point to a deeper structural issue. The risks were not unknown. They were unmanaged. Episode 9 explores the relationship between risk identification and control implementation. In many organizations, risks are documented, discussed, and even formally tracked — but they are not always tied to specific, enforceable controls. Without that connection, risk management becomes observational rather than operational. Each segment examines a different dimension of this gap: why organizations often stop at identifying risk, how controls translate awareness into action, the role of project managers in connecting risks to delivery structures, and how governance systems fail when risks are not embedded into execution processes. Together, these segments build toward a central insight: A risk that is not tied to a control is not being managed. It is simply being described. And in fast systems, described risks do not prevent failure. Only controlled risks do.

    23 min
  3. War Rooms are a Symptom

    26 MAR

    War Rooms are a Symptom

    By the time an organization declares an incident, the problem is no longer detection. It’s coordination. Multiple teams begin investigating. Engineers search logs, leaders request updates, stakeholders ask for timelines, and communication channels fill quickly with information — and questions. This is often referred to as a “war room.” War rooms are intended to bring clarity. But in many cases, they introduce confusion. Episode 8 explores incident response coordination and why unstructured collaboration can slow down recovery instead of accelerating it. Each segment examines a different dimension of incident management: the role of centralized command, the risk of too many decision-makers, the importance of communication discipline, and how clearly defined roles allow teams to move faster under pressure. The episode connects these ideas back to the Knight Capital incident, where the system continued operating while teams worked to understand and respond to the problem. Together, these segments build toward a central insight: War rooms don’t solve incidents. Structure does. Bringing people together is not enough. Without defined roles, authority, and communication discipline, coordination becomes noise. And in fast systems, noise delays action.

    21 min
  4. The First Signal Never Looks Like Failure

    24 MAR

    The First Signal Never Looks Like Failure

    In complex systems, failure rarely announces itself clearly. It does not begin with alarms, flashing dashboards, or obvious error messages. Instead, the earliest signals of trouble often look like something ordinary: a slight change in behavior, a metric drifting out of range, or activity that can easily be explained by normal operating conditions. This ambiguity makes early detection difficult. In the Knight Capital incident, the first signs of the malfunction did not appear as a system outage. Instead, they looked like unusual market activity. Stocks were moving in ways that traders initially interpreted as volatility rather than a malfunctioning trading algorithm. By the time the pattern became clear, the system had already executed thousands of unintended trades. Episode 7 explores the discipline of recognizing early signals in complex environments. Each segment examines a different dimension of that challenge: why systems produce ambiguous signals, how cognitive bias affects incident response, why monitoring systems must be designed around interpretation rather than observation, and how organizations structure escalation procedures to respond to uncertain signals. Together, these segments build toward one central insight: The earliest signal of failure rarely looks like failure. It looks like noise. And the ability to recognize when noise might actually be a signal is one of the most important disciplines in operational governance.

    23 min
  5. Who Gets to Stop the System?

    22 MAR

    Who Gets to Stop the System?

    In the previous episode, we talked about rollback — the ability to reverse a change when something goes wrong. But rollback capability alone isn’t enough. Someone still has to decide to use it. In fast automated environments, hesitation can be just as dangerous as technical failure. When engineers see unusual behavior, stopping a system may interrupt revenue, halt operations, or create visible business impact. Because of that, people often pause. They escalate. They ask for confirmation. And while that conversation is happening, the system keeps running. Episode 6 explores the governance structures that determine who has the authority to halt a system during an incident.Each segment examines a different dimension of that discipline: why unclear authority delays containment, how escalation chains unintentionally slow incident response, the psychology behind hesitation during outages, and how project managers help define operational authority before systems go live. Together, these segments build toward one central insight: Containment requires authority. If no one is clearly empowered to stop automation when something looks wrong, the system will continue operating while people debate what to do. And in fast systems, those minutes matter.

    16 min
  6. You Don't Invent the Exit During the Fire

    17 MAR

    You Don't Invent the Exit During the Fire

    In the previous episodes, we’ve looked at several structural failures that contributed to the Knight Capital incident: incomplete deployment verification, unmanaged technical debt, and changes that were treated as routine when they carried significant systemic risk. But there’s another discipline that determines how severe a failure becomes once it begins. That discipline is rollback. In complex systems, problems will eventually occur. Software behaves in unexpected ways, integrations create unintended interactions, and automation amplifies small defects very quickly. What determines whether those problems remain small incidents or grow into catastrophic failures is often the speed with which the organization can stop the system. Episode 5 explores rollback as a core element of responsible change management. Each segment examines a different dimension of rollback discipline: why every change needs an exit strategy, how automation compresses the time available to react, why rollback procedures must be rehearsed rather than merely documented, and how governance structures determine whether a system can actually be stopped when something goes wrong. Together, these segments build toward a central insight: Rollback is not a reaction to failure. It is part of the design of responsible delivery. Organizations that plan exits before activation can stop problems quickly. Organizations that do not often end up designing their exit during the incident itself. And that is a very stressful time to start being creative.

    18 min
  7. Routine is a Dangerous Word

    12 MAR

    Routine is a Dangerous Word

    This episode explores a deceptively simple problem inside complex systems: the danger of treating high-impact changes as routine work. At Knight Capital, the deployment that triggered a $440 million loss was not classified as extraordinary. It was not handled as a high-risk event. It was treated like a normal release — something the organization had done many times before. And that’s the problem. This episode breaks down how change classification and governance determine how much scrutiny a release receives. Each segment examines a different layer of change management discipline — from the psychological risks of familiarity, to the structural mechanisms organizations use to assess risk, to the role project managers play in forcing meaningful review before activation. Together, the segments build toward one larger insight: Change management is not about paperwork. It is about ensuring that the amount of scrutiny applied to a change matches the amount of systemic risk that change introduces. When organizations label risky changes as routine, they remove the friction that protects them. And in fast systems, that friction is often the only thing standing between a routine morning… and a very expensive one.

    18 min
  8. Dormant Doesn't Mean Dead

    10 MAR

    Dormant Doesn't Mean Dead

    This episode explores a quieter but equally dangerous structural problem in complex systems: technical debt that remains in production long after it has been forgotten. At Knight Capital, the code that triggered the trading malfunction was not new. It was legacy logic called Power Peg — software originally written for an earlier trading context that had been left in the system after its operational use had ended. The code was considered dormant. But dormant code is not removed code. Episode 3 examines how technical debt accumulates in production environments and why organizations often struggle to retire legacy logic. Each segment explores a different dimension of the problem: why teams hesitate to delete old code, how dormant features remain executable inside evolving systems, and how technical debt quietly expands the risk surface of a platform over time. The episode then shifts into governance, examining how disciplined organizations track technical debt as part of their project and risk management practices. Technical debt registers, ownership assignments, retirement planning, and change reviews all serve as mechanisms that ensure legacy artifacts do not remain invisible inside active systems. The segments build toward a larger insight: Technical debt is not dangerous because it exists. It becomes dangerous when it is unmanaged. Legacy logic that remains unowned, undocumented, and unreviewed can unexpectedly re-enter execution paths when new changes interact with old assumptions. Episode 3 argues that managing technical debt is not simply an engineering cleanup task — it is a project governance responsibility. By linking technical debt to risk registers, change planning, and ownership structures, project managers help ensure that legacy systems are intentionally retired rather than quietly forgotten. Because in fast systems, anything that remains in production is part of the system. And if it is part of the system, it is part of the risk surface. Dormant doesn’t mean dead. It means waiting.

    20 min
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Project Management Is Boring focuses on the unglamorous work that actually makes projects succeed. We talk planning, requirements, meetings, stakeholder management, and execution—without pretending PMs are superheroes or that every problem can be solved with a new framework. Built for IT project managers, business analysts and professionals who value discipline, clarity and realism over buzzwords.

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