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.