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Here's an example of client intelligence across multiple sessions
Build confidence in delegation, establish healthier work-life boundaries, and develop leadership presence with the executive team.
Struggles with work-life boundaries and saying "no" to requests that don't align with strategic priorities
Building confidence to delegate high-stakes tasks to senior team members
Tension between maintaining technical involvement and stepping into executive leadership role
Recognition anxiety - feeling undervalued despite company success
Client mentioned being "always available" - explore protective structures and communication norms
Pattern of holding onto tasks - test assumptions about team capability and identify what truly requires founder attention
Explore resistance to "letting go" of technical work and what executive leadership means at this stage
Notice pattern of seeking external validation - could explore internal sources of worth and success metrics
Client explored the tension between wanting to be seen as a technical leader versus embracing the CEO role. Identified specific fears around "letting go" of code reviews and architecture decisions. Made connection between need for control in technical domain and childhood experiences of not being heard. Committed to delegating one major technical decision to VP of Engineering this week.
Delegate architecture decision for new payments system to VP of Engineering. Schedule one-on-one to discuss approach but resist urge to override. Journal about what comes up emotionally when stepping back from this decision.