How Do I Help My Boss Without Doing Their Job For Them?
Apr 27, 2026
Summary
In this episode, the host coaches Kate, a senior leader struggling with a mismatched dynamic with her manager. Kate feels stifled because she was hired to build organizational structure but perceives her boss as micromanaging and unresponsive to her ideas. The coaching session reveals a fundamental misalignment in expectations: Kate views her role as collaborative ownership, while her manager likely sees it as supportive execution. The discussion focuses on reframing the relationship by clarifying what "help" means to the boss, exploring Kate’s personal motivations, and deciding whether to …
Topics discussed
Intro: Evolve immersion and Coaching Real podcast overview
Kate's background and frustration with new role
Analyzing the mismatch in expectations with her boss
Sponsors: Alma therapy and Cozy Earth clogs
Identifying alignment on goals but misalignment on methods
The 'Help Me Help You' approach to understanding needs
Strategies for observing and adapting to boss's style
Sponsors: NetSuite AI and Stamps.com shipping
Kate's resistance and exploring the 'Why' vs 'Why Not'
Committing to experiments and validating hypotheses
Outro: Key takeaways, reviews, and Scribe sponsor
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