The AI-Driven Leader 9. CRIT™: Building Your Leadership Playbook for Growth
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Oct 9, 2025 In this insightful discussion, Brian Lang, CEO of UpsideCFO, shares his expertise in financial strategy for SMBs. He explores the challenges of scaling leadership and reveals how AI can be leveraged to create a robust leadership playbook. Brian discusses the Working Wealthy Operating System, emphasizing its role in aligning goals and providing clarity through metrics. Key tactics include integrating visual dashboards and strategic questions in forecasting. The conversation highlights how AI amplifies leadership capacity and transforms instinct into effective systems.
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CRIT Framework Scales Leadership
- CRIT is a four-step framework: Context, Role, Interview, Task to get better outputs from AI.
- Use CRIT to turn tacit leadership knowledge into repeatable systems with AI as a strategic operator.
AI Replaced Multiple Senior Hires
- Brian used AI to effectively add the capacity of many senior hires for a tiny recurring cost.
- He built personas (executive coach, CRO) in AI to fill leadership gaps without large hires.
Structure Prompts With Clear Headers
- When prompting, give AI rich context and tell it to speak in first person as the subject.
- Use delimiters and clear headers (Context, Role, Interview, Task) to structure the prompt.
