5 Career Questions Your Old Playbook Can’t Answer

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 cycle

• Why the decision to found should only stay on the table if you're obsessed with a specific problem — not just bullish on AI

• How a sponsor-to-manager dynamic turns adversarial

• "Every superpower comes with a shadow", and what that means for the manager who created the monster

• Why some management relationships reach a graduation, and how to recognize when you're there

• The mercenary vs. missionary question: and why the person asking usually already knows their answer

• Why senior product leaders should remove "great manager" from their job search criteria entirely

• The pretzel framework: how to identify the culture where you have to “bend yourself” the least

• Why being "safe" as a manager matters more than matching your direct report's experience level

Referenced:

• Anthropic

• ChatGPT

• Claude

• Copilot

• Facebook

• Google

• Meta

Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]

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• Guru—Trusted knowledge for every AI tool and team

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