Coaching Real Leaders Coaching Real Leaders

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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