5 Career Questions Your Old Playbook Can’t Answer

The Skip Podcast · Jun 10, 2026 · 1h 8m

In today's episode, we work through five questions from leaders in the Skip community who are doing well by any measure: a director whose career keeps ending in short stints despite strong performance, a manager whose top performer turned adversarial, an exec fielding multiple outsized offers, a PM who does her best work with a great manager, and a first-time manager whose first report is more experienced than they are. In each case, the old playbook can't answer the real question.

Key topics:

• The "layoff merry-go-round": why short stints compound and what it actually takes to break the…