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Not Sure When to Let Your Boss Know You’re Leaving? Ask Madeleine

  • A senior leader in a digital publishing organization is planning to transition into coaching and consulting by end of 2025.
  • The leader is seeking advice on when to inform their boss about the exit plan to ensure a smooth transition.
  • They have been successfully building their coaching business as a side hustle and want to avoid damaging their relationship with their boss.
  • Madeleine suggests considering the boss's appreciation for loyalty and proper planning before sharing the news.
  • She recommends assessing the company culture and identifying potential successors among the leader's direct reports.
  • The norm for senior executives is to provide 60-90 days notice for a smooth transition.
  • In case of concerns about the boss's reaction, waiting until ready to leave and offering a flexible transition period is advised.
  • Madeleine emphasizes the importance of being prepared with recommendations for replacements and maintaining professionalism throughout the process.
  • She encourages the leader to take care of themselves and be ready for different outcomes regarding their involvement in passing the baton.
  • Madeleine offers support and wishes the leader luck in their upcoming career transition.

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