Overskill Series Part 2: Refining Your App | Coaching Corner #043

7 Oct 2026 · 32 min
31:42

In this live Coaching Corner episode, Tyson and Devin continue their Overskill series by refining a prototype roofing app built on the Overskill platform. They review the initial app, discuss the need for iterative refinement after the first generation, and demonstrate a back‑and‑forth workflow with the AI using spoken prompts (WhisperFlow) and prompt stacking. Key design concerns surface, including client‑side vs. admin‑side UI separation, lack of clear client navigation, missing calendar and timeline views, revenue/estimate fields, and the desire for weekly project updates. They ask the AI clarifying questions, adjust the prompt to add a calendar, revenue projection, and project‑stage cost fields, and observe the AI’s queue‑based processing. Throughout, they emphasize treating the AI interaction as a conversational dance, using WhisperFlow for hands‑free dictation, and iterating until the app reaches a usable state. The session ends with a call for viewer feedback, a reminder of weekly office hours, and plans to continue the series toward a marketable product.

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