This document outlines important considerations and questions for conducting technical diligence on a company or product. It discusses evaluating a technology's capability, stability, expandability, security, costs, support methods, dependencies, risks, initiatives, intellectual property, vendors, and technical challenges. It provides sample questions to assess a team's management and staff capabilities, structure, skills, processes, and risks around scalability, supportability, intellectual property, partnerships, and technical difficulties handling performance, data, machine learning, various devices and languages. The document emphasizes the importance of diligence from someone familiar with the specific technology and tradeoffs, and that these questions can provide meaningful insights.