Executives must decide between upskilling internal teams or hiring external experts to advance their AI initiatives, balancing costs, organizational needs, and long-term goals. While external consultants offer immediate specialized skills, integrating them with internal teams can be challenging and may lead to dependency, whereas upskilling fosters internal growth but requires significant investment. Companies like Bitsight and Alignment Health demonstrate the benefits and challenges of both approaches, emphasizing the importance of strategic planning, knowledge transfer, and continuous development to maximize AI's potential.