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
What this episode covers
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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