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Ever find yourself bending over backward to be the cool boss? The one everyone likes, who’s fun, flexible, and super approachable — only to watch accountability tank, trust slip, and your own confidence take a nosedive?
In this quick cast, we’re breaking down the “Cool Boss Trap” — why it happens, how it drains your time and money, and the dead-simple step that gets you out of the pendulum swing between people-pleasing and micromanaging.
You'll learn:
✅ How trying too hard to be liked quietly erodes your team’s performance
✅ The role of clear expectations in keeping things fun and high performing
✅ How to handle tough conversations without turning into a jerk
If you’ve been struggling with slipping standards, second-guessing your leadership, or just want to finally build a team that respects you and enjoys working with you, this one’s for you.
By Samantha C. PrestidgeEver find yourself bending over backward to be the cool boss? The one everyone likes, who’s fun, flexible, and super approachable — only to watch accountability tank, trust slip, and your own confidence take a nosedive?
In this quick cast, we’re breaking down the “Cool Boss Trap” — why it happens, how it drains your time and money, and the dead-simple step that gets you out of the pendulum swing between people-pleasing and micromanaging.
You'll learn:
✅ How trying too hard to be liked quietly erodes your team’s performance
✅ The role of clear expectations in keeping things fun and high performing
✅ How to handle tough conversations without turning into a jerk
If you’ve been struggling with slipping standards, second-guessing your leadership, or just want to finally build a team that respects you and enjoys working with you, this one’s for you.