How to Manage a Boss Who Is a Chronic Procrastinator episode artwork

EPISODE · May 29, 2026 · 9 MIN

How to Manage a Boss Who Is a Chronic Procrastinator

from The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival · host Fexingo

In this episode of The Difficult Boss Podcast, Lucas and Luna tackle a frustrating workplace dynamic: the boss who procrastinates on decisions, approvals, and feedback—leaving you in limbo. Using the real-world example of a product manager at a mid-sized SaaS company whose CEO kept delaying a critical feature launch, they break down why chronic procrastination happens (fear of failure, perfectionism, or overload) and offer three concrete strategies: creating a decision deadline with a default outcome, breaking requests into smaller yes/no steps, and using a 'straw man' proposal to reduce friction. They also discuss when to escalate and how to protect your own deadlines. This episode offers practical scripts and a compassionate framework for understanding your procrastinating boss without excusing the behavior. No fluff, just actionable career survival tactics. #DifficultBossPodcast #ManagingUp #Procrastination #WorkplaceSurvival #CareerAdvice #ToxicManager #BossProblems #DecisionMaking #Productivity #Leadership #CareerStrategy #WorkplaceDynamics #ManagerTips #EmployeeAdvice #FexingoBusiness #BusinessPodcast #Careers #ProcrastinatingBoss Keep every episode free: buymeacoffee.com/fexingo

In this episode of The Difficult Boss Podcast, Lucas and Luna tackle a frustrating workplace dynamic: the boss who procrastinates on decisions, approvals, and feedback—leaving you in limbo. Using the real-world example of a product manager at a mid-sized SaaS company whose CEO kept delaying a critical feature launch, they break down why chronic procrastination happens (fear of failure, perfectionism, or overload) and offer three concrete strategies: creating a decision deadline with a default outcome, breaking requests into smaller yes/no steps, and using a 'straw man' proposal to reduce friction. They also discuss when to escalate and how to protect your own deadlines. This episode offers practical scripts and a compassionate framework for understanding your procrastinating boss without excusing the behavior. No fluff, just actionable career survival tactics. #DifficultBossPodcast #ManagingUp #Procrastination #WorkplaceSurvival #CareerAdvice #ToxicManager #BossProblems #DecisionMaking #Productivity #Leadership #CareerStrategy #WorkplaceDynamics #ManagerTips #EmployeeAdvice #FexingoBusiness #BusinessPodcast #Careers #ProcrastinatingBoss Keep every episode free: buymeacoffee.com/fexingo

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How to Manage a Boss Who Is a Chronic Procrastinator

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How long is this episode of The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival?

This episode is 9 minutes long.

When was this The Difficult Boss Podcast with Fexingo: Managing Up, Toxic Managers, and Workplace Survival episode published?

This episode was published on May 29, 2026.

What is this episode about?

In this episode of The Difficult Boss Podcast, Lucas and Luna tackle a frustrating workplace dynamic: the boss who procrastinates on decisions, approvals, and feedback—leaving you in limbo. Using the real-world example of a product manager at a...

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