Funny Boss Cartoons: Leadership Fails

Bad leadership takes many shapes — micromanagers, unclear expectations, shifting priorities, ego-driven decisions, and bosses who think pressure equals performance.

These funny boss cartoons highlight the everyday leadership fails that shape corporate life: chaotic feedback, last-minute demands, inconsistent direction, and meetings that solve nothing.

If you’ve ever worked under a manager who shouldn’t be leading, these cartoons will feel painfully — and hilariously — accurate.