Have You Ever Had a Boss That…?

Succeeding in a Dysfunctional Workplace

Eric Charran, a veteran technology executive with over 25 years of leadership experience at some of the world’s largest organizations—including 18 years at Microsoft—has worked under every kind of boss imaginable. From transformational leaders to those who thrive in chaos, he has seen firsthand how leadership dynamics shape workplace culture, employee engagement, and career progression.

In Have You Ever Had a Boss That…?, Charran offers a compelling, research-backed guide for professionals at all career stages, from early-career employees to senior executives, providing actionable strategies to not just survive—but excel in dysfunctional workplaces.

Through real-world case studies, psychological insights, and practical frameworks, Charran introduces nine distinct boss archetypes, each representing a different form of unhelpful or toxic leadership. From The Firefighter, who creates emergencies just to put them out, to The Attack Sub, who operates in secrecy to undermine colleagues, these archetypes explain why so many professionals struggle with ineffective managers—and how to turn these challenges into career-building opportunities.

Workplace dysfunction can drain productivity, stall careers, and create daily stress, but professionals who understand leadership behaviors and adapt strategically can navigate even the most challenging environments. Drawing from his extensive experience leading high-impact teams, Charran reveals how to “manage up,” influence from any position, and take control of your career path—even when working for a difficult boss.

This book is an essential resource for anyone who has ever felt stuck in a frustrating workplace, struggled under poor leadership, or wondered how to turn dysfunction into success.

You may not be able to choose your boss, but you can choose how to thrive, grow, and take control of your success—no matter the workplace challenges you face.

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