Coaching Real Leaders Coaching Real Leaders

How Do I Help My Boss Without Doing Their Job For Them?

Apr 27, 2026

Summary

Executive coach Muriel Wilkins guides Kate, a senior leader frustrated by a mismatched dynamic with her manager. Kate feels stifled because she was hired to help build organizational structure but perceives her boss as micromanaging and unresponsive to her ideas. Wilkins helps Kate reframe the conflict by distinguishing between the "what" of their goals and the "how" of their collaboration, urging her to define what "helpful" means to her boss. The episode concludes with Kate committing to verify her assumptions about her manager’s needs and evaluating whether the role aligns with her profe…

Topics discussed

Sponsors: The RealReal and Everand Introduction: Kate's career transition and new role The disconnect: Lack of follow-through on ideas Role ambiguity: Ownership vs. Support dynamics Communication styles: Fear of appearing arrogant Sponsors: Shopify and Alma Aligning on the 'What' vs. the 'How' Reframing help: Understanding the boss's needs Defining rules of engagement and working preferences Proposing solutions: Weekly updates vs. CCing Sponsors: Stamps.com and NetSuite The 'Why': Finding motivation to adapt Action plan: Testing hypotheses with the manager Conclusion and Sponsor: Trusted House Sitters
Listen ad-free on Castria